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Vacation Rentals in Anna Maria Island, Florida

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about Anna Maria Island

Anna Maria Island, Florida Vacation Rentals and Tourism

Looking for Anna Maria Island rentals? Anna Maria Island is probably one of Florida’s most beloved tourist destinations. Just south of Tampa Bay, Anna Maria Island is part of Florida's many barrier islands. That means that if you rent one of the Anna Maria Island vacation rentals listed here, you will be surrounded by water! From the Gulf of Mexico to Sarasota Bay, your Anna Maria Island beach house rental will most likely be located no more than a few blocks from Florida’s inviting sandy shores. It doesn’t matter what time of year you travel here, as Anna Maria island vacation rentals see lots of sunshine every month.

So whether you’re interested in a casual Anna Maria Island beach rental or a more upscale Anna Maria Island luxury condominium, it’s always a good time to plan your vacation. But what else is there to do besides enjoy the beach? Make sure to tour the Powel Crosley Museum, eat at the island’s many fine restaurants, go fishing, get lost among the dozens and dozens of unique shops, or participate in a festival – there likely is something going on somewhere on the island.

But what makes a trip to this area of Florida such a good idea? It’s not just the attractions and the gorgeous gulf views, but of course, Anna Maria Island beach vacation rentals. No longer do you have to resign yourself to a small, overpriced, uncomfortable hotel room. Hotel resorts are out and vacation homes are in. No matter what type of vacation you are looking for or what kinds of amenities you are seeking, you can certainly find the ideal setting for you and your fellow travelers. From a relaxing Anna Maria Island beach house rental to an Anna Maria Island condo rental that has all the bells and whistles, you can find exactly what you’re looking for. Maybe you want to escape the cold weather of the North East. Maybe you want to escape the daily grind. Whatever the case, the sooner you book one of the Anna Maria Island beach rentals found here, the better.

Sites and tours to see

Powel Crosley Museum 

You are sure to have a fabulous time at Anna Maria Island with bird watching, beautiful nightly sunsets, biking, and kayaking, or even just relaxing; there are plenty of attractive things about this place.  One thing you don't want to miss out on is the affordable Anna Maria Island vacation rentals, particularly the last-minute and low-budget vacation rental deals.  We can accommodate any sized group or any sized budget.  With our wide variety of cheap Anna Maria Island rental town homes, beach houses, condos, and villas, we're sure you'll find something that's perfect for your next vacation. While stressing about money may be something you do at home, you can leave that all behind if you choose a good deal on Anna Maria Island vacation rentals!

 

Deals on Anna Maria Island Rentals

If you're looking for Anna Maria Island rentals, you're probably looking to save a buck. Vacation Rentals.com features condos, homes, and villas all over Florida, and Anna Maria Island is no exception. Enjoy ocean views, the option to bring your pets along, loads of amenity and space, and more, with rentals in Anna Maria Island. Just check out our current deals and other special offers. So, what are you waiting for? Book one of our affordable Anna Maria Island vacation rentals today!

more destinations

Check out more areas which feature homes, villas, cabins, cottages, or condos.

Anna Maria Island things to do

 

Stay Anna Maria Island

AMI is where I like to spend my winters. Beautiful uncrowded beaches, good restaurants good shopping and great house rentals all over the island. Close...read more

 

Fort De Soto Park

I love this beach! We live in Orlando so it took about 2 hours to get there but was well worth the drive. We will probably only go to this dog beach from...read more

 

Anna Maria Beach

Such a gorgeous beach it makes you understand how someone could truly be a beach bum. Not someone who loves sun worshiping or hanging out at the beach - I...read more

 

Robinson Preserve

Beautiful park in West Bradenton. Excellent trails for bikers or walkers which include paved roads, shell roads, and small bridges. The main path is 3...read more

 

Banana Cabana Caribbean Restaurant

Banana Cabana was a welcome change after several days of eating cookie-cutter combinations of fish, steak, and french fries. This restaurant is exactly what...read more

 

Beach Bums

A little disorganized for a well established business, but sturdy stable of cruiser bikes and golf carts. Very willing to swap out bikes at any time. Loved...read more

 

Desoto National Memorial

Hubs, pup and I stopped in this past weekend - we loved that dogs were welcome, and provided mutt mitts/appropriate trash cans. This attraction is small,...read more

 

Surferbus

Our kayaking trip was my favorite part about our recent trip to Florida. Four of us rented two tandem sit-on-top Ocean Kayak Malibu XLs and after a brief...read more

 

Egmont Key State Park

We've visited the St. Pete Beach area each of the past three years now and enjoy exploring the area. Egmont Key Park is one of the best areas we've found....read more

 

Coquina Beach

Sometimes when I read reviews, I can't believe we've all gone to the same place. Coquina Beach is at the southern end of Santa Maria Island. I like the...read more

 

Arts & Eats Restaurant & Gallery

Eclectic restaurant with chef driven menu. We drove here from Anna Maria because of the good yelp reviews. It's located in an interesting area in an old...read more

 

Bradenton Beach City Pier

Went here for a the 4th of July dinner and wow! Great service, amazing view, unbelievable food, and fair prices. What else can you ask for?! This place is a...read more

 

Holmes Beach

Very beautiful and great sand. Has restrooms and an eatery right on the beach. A playground for small kids and volleyball for big kids. Lifeguards on duty....read more

 

South Florida Museum

This place is enormous! Definitely worth going. We have 4 kids ages 2 to 6 and they had a great time with the exhibits. We are members of "Friends of the...read more

 

Longboat Key Beaches

This is by far worst beach... Not sure why people like it. There is no parking, water so shallow u literally have to go like miles from shore to get past...read more

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DEAL!! Light, Bright, Sure to Delight! Fall Special
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $850 per week
  • bedrooms 2
  • community Gulf Watch
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $1,050 - $2,450 /wk
    $3,200 - $6,800 /mth
 
 
 
 
 

6 reviews write a review

DEAL!! Vista Grande # 3 -- Penthouse Direct Views
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $150 off = $449 per night
  • bedrooms 3
  • community
  • rental type Condo
  • sleeps 6
  • baths 3
  • rates (USD) $549 - $749 /nt
    $3,843 - $5,243 /wk
 
 
 
 
 

1 reviews write a review

DEAL!! Terraces 1 - Beautiful End Unit Townhome w/Garage near Beach
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $50 off = $700 per week
  • bedrooms 2
  • community Terraces
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,100 /wk
    $2,600 - $3,600 /mth
 
 
 
 
 

10 reviews write a review

DEAL!! Ground Floor-Sea Pirate 6
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $100 off = $625 per week
  • bedrooms 2
  • community Sea Pirate Condo
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $95 - $125 /nt
    $665 - $875 /wk
    $2,200 - $3,000 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Shell Cove Unit #1 Direct Gulf Front Condo Bradenton Beach
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $150 off = $875 per week
  • bedrooms 1
  • community Shell Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $145 - $170 /nt
    $1,000 - $1,050 /wk
    $3,800 - $4,100 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Songbird
Anna Maria Island Cottage Rental Picture
  • Cottage Rental Deals and Discounts $15 off = $510 per week
  • bedrooms 2
  • community Holmes Beach
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $525 - $1,000 /wk
    $1,650 - $3,000 /mth
 
 
 
 
 

55 reviews write a review

DEAL!! Seagrape Cottage - Wonderful Gulf and Sunset Views!
Anna Maria Island House Rental Picture
  • House Rental Deals and Discounts $75 off = $825 per week
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $130 - $185 /nt
    $900 - $1,100 /wk
    $3,200 - $4,200 /mth
 
 
 
 
 

8 reviews write a review

DEAL!! Florida Beach Rentals, Anna Maria Island, Florida
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $400 off = $1,000 per week
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $250 /nt
    $1,400 - $1,800 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

12 reviews write a review

DEAL!! Seagrape II-charming & steps to the beach
Anna Maria Island Cottage Rental Picture
  • Cottage Rental Deals and Discounts $30 off = $550 per week
  • bedrooms 1
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $85 - $110 /nt
    $580 - $700 /wk
    $2,100 - $2,700 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Gulf Front Luxury Condo
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $300 off = $900 per week
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,100 - $1,700 /wk
 
 
 
 
 

88 reviews write a review

DEAL!! 174 Runaway Bay
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $100 off = $750 per week
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,300 /wk
 
 
 
 
 

3 reviews write a review

DEAL!! Condo in quiet complex
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $100 off = $700 per week
  • bedrooms 2
  • community Sandy Pointe
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $800 - $900 /wk
 
 
 
 
 

1 reviews write a review

DEAL!! Ground Floor Condo ON THE BAY!
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Specials Save $450 in rent and $100 in cleaning... ($550)
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $800 - $1,500 /wk
    $3,850 - $4,200 /mth
 
 
 
 
 

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DEAL!! Sandy Beach Access
Anna Maria Island House Rental Picture
  • House Rental Deals and Discounts $150 off = $550 per week
  • bedrooms 2
  • community Holmes Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $700 - $850 /wk
    $2,500 - $3,000 /mth
 
 
 
 
 

11 reviews write a review

DEAL!! Anna Maria Island Beach Paradise
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $400 off = $1,000 per week
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $250 /nt
    $1,400 - $1,800 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

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DEAL!! The Anna Maria Isalnd Beach Palms
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $400 off = $1,000 per week
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $250 /nt
    $1,400 - $1,800 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

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DEAL!! The Anna Maria Island Beach Breeze
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $400 off = $1,000 per week
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $250 /nt
    $1,400 - $1,800 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

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DEAL!! 2312 Gulf Drive North-Beachfront Condo w/ Pool!
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $100 off = $1,150 per week
  • Condo Rental Deals and Specials Wi-Fi ($39)
  • bedrooms 2
  • community Sunset Terrace
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,250 - $1,450 /wk
    $3,600 - $5,000 /mth
 
 
 
 
 

1 reviews write a review

DEAL!! Tradewinds Resort-Vacation Cottage Rental-Daily/ Wkly Specal
Anna Maria Island Cottage Rental Picture
  • Cottage Rental Deals and Discounts 25% off = $116 per night
  • Cottage Rental Deals and Specials this price reflects a 4 night stay with... ($155)
  • bedrooms 1
  • community Tradewinds Resort
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $155 - $265 /nt
    $851 - $1,364 /wk
    $3,500 - $4,640 /mth
 
 
 
 
 

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LaCasa #8 - Partial Views & Steps to Sand
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community La Casa Costiera
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $329 - $499 /nt
    $2,363 - $3,493 /wk
 
 
 
 
 

2 reviews write a review

Runaway Bay Stunning 2BD / 2BA Condo
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $750 - $1,200 /wk
    $2,400 - $3,600 /mth
 
 
 
 
 

4 reviews write a review

By The C- Condo Directly on Beach with Pool and Elevator
Anna Maria Island Studio Rental Picture
  • bedrooms 0
  • community Club Bamboo South
  • rental type Studio
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $89 - $157 /nt
    $600 - $1,125 /wk
 
 
 
 
 

11 reviews write a review

Gulf Views From Every Room!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $219 - $499 /nt
    $1,883 - $3,143 /wk
    $6,132 - $8,932 /mth
 
 
 
 
 

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Sea Crest Condos II, Unit 3
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $805 - $1,559 /wk
 
 
 
 
 

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Anthony Beach Cottages-302 Holmes Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $800 - $1,200 /wk
 
 
 
 
 

1 reviews write a review

Island Retreat - 4 bedroom with water view
Anna Maria Island House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,200 - $1,800 /wk
 
 
 
 
 

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Gulfview Condo - Gulf front with heated pool
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $1,200 - $1,900 /wk
    $3,000 - $5,400 /mth
 
 
 
 
 

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Best Newer House On The Beach!!!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • community Bradenton Beach, Fl
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,300 - $1,500 /wk
    $4,800 - $5,500 /mth
 
 
 
 
 

21 reviews write a review

Gorgeous Island 2BD/2BA, walk to beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,400 /wk
    $2,400 - $3,995 /mth
 
 
 
 
 

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Anna Maria Island 3 Bedroom Rental
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $111 - $185 /nt
    $775 - $1,300 /wk
 
 
 
 
 

42 reviews write a review

Sandy Pointe II Holmes Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Sandy Pointe
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $450 - $650 /wk
    $1,700 - $2,600 /mth
 
 
 
 
 

4 reviews write a review

Anna Maria Island Beach Palace
Anna Maria Island House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $400 - $450 /nt
    $2,500 - $2,900 /wk
    $9,000 - $10,600 /mth
 
 
 
 
 

9 reviews write a review

Gulf View Luxury Condo
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Bradenton Beach
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $850 - $1,400 /wk
    $2,750 - $4,300 /mth
 
 
 
 
 

6 reviews write a review

Water water everywhere
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Gated community
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $125 - $225 /nt
    $850 - $1,250 /wk
    $1,800 - $3,500 /mth
 
 
 
 
 

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LaCasa Costiera Unit 1 Beach. Aug/sept $2700./wk.
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • community La Casa Costiera
  • rental type Villa
  • sleeps 5
  • baths 2
  • rates (USD) $2,800 - $4,200 /wk
 
 
 
 
 

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Sea Breeze Retreat
Anna Maria Island Townhome Rental Picture
  • bedrooms 2
  • community
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $120 - $150 /nt
    $675 - $995 /wk
    $2,500 - $3,750 /mth
 
 
 
 
 

1 reviews write a review

Coquina Cottage at the Beach: Newly Renourished Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community Cortez Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $275 - $300 /nt
    $800 - $1,500 /wk
 
 
 
 
 

2 reviews write a review

Seaside Beach House
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • community Seaside Beach House
  • rental type Condo
  • owner badgeowner badge
  • sleeps 3
  • baths
  • rates (USD) $1,200 /nt
    $1,200 /wk
    $4,000 /mth
 
 
 
 
 

11 reviews write a review

Cindy's Beach House & Bass Cottage on Anna Maria Island
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $125 - $175 /nt
    $750 - $1,225 /wk
    $2,800 - $4,200 /mth
 
 
 
 
 

4 reviews write a review

Beachfront Bungalow on Gulf of Mexico
Anna Maria Island Studio Rental Picture
  • bedrooms 0
  • community Dream Inn
  • rental type Studio
  • sleeps 4
  • baths 1
  • rates (USD) $150 - $200 /nt
    $900 - $1,400 /wk
 
 
 
 
 

1 reviews write a review

Shady Pines - Gulf-front Home
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,690 - $2,100 /wk
 
 
 
 
 

2 reviews write a review

Anna Maria Island Townhome: Simply Beautiful
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • community
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $850 - $1,200 /wk
    $3,900 /mth
 
 
 
 
 

16 reviews write a review

Runaway Bay Lovely 2-Bed condo by the beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $110 - $170 /nt
    $750 - $1,300 /wk
    $2,400 - $4,200 /mth
 
 
 
 
 

3 reviews write a review

Lay-Z-Liv-N
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Lay-z Liv-n
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $450 - $800 /wk
    $1,500 - $2,500 /mth
 
 
 
 
 

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Fabulous Rates at the Beautiful Cove
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Sandy Pointe
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $600 - $800 /wk
    $2,400 - $3,200 /mth
 
 
 
 
 

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Gulf Front Luxury Condo - La Plage-Unit 9 (3 BR)
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community La Plage
  • rental type Condo
  • sleeps 6
  • baths 3
  • rates (USD) $3,295 - $4,890 /wk
 
 
 
 
 

2 reviews write a review

LaPlage (4 BR) Luxurious,Largest Beachfront
Anna Maria Island Condo Rental Picture
  • bedrooms 4
  • community La Plage
  • rental type Condo
  • sleeps 8
  • baths 3
  • rates (USD) $3,295 - $4,890 /wk
 
 
 
 
 

1 reviews write a review

Luxury Gulf Front Condo - Tropical Europa (2 BR)
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Island Paradise
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,995 - $3,595 /wk
 
 
 
 
 

1 reviews write a review

Luxury Gulf Front Condo - Bradenton Beach Club (3 BR)
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community Bradenton Beach
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $2,995 - $3,595 /wk
 
 
 
 
 

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Luxury Gulf Front Condo - La Casa Costiera (3 BR)
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community La Casa Costiera
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $3,095 - $3,595 /wk
 
 
 
 
 

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Runaway Bay - one bedroom / bathroom - perfect for couples
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $650 /wk
    $2,200 /mth
 
 
 
 
 

7 reviews write a review

Affordable One Bedroom Island Condo in Runaway Bay Resort
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $725 - $995 /wk
    $2,100 - $3,100 /mth
 
 
 
 
 

14 reviews write a review

Bay Views and Short 5 Minute walk to Beach!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community Bradenton Beach
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $840 - $1,085 /wk
    $2,900 - $3,300 /mth
 
 
 
 
 

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Anna Maria Island Beach Paradise 10
Anna Maria Island Studio Rental Picture
  • bedrooms 1
  • community
  • rental type Studio
  • sleeps 4
  • baths 1
  • rates (USD) $150 /nt
    $600 - $800 /wk
    $2,850 /mth
 
 
 
 
 

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Gulf Watch!! from Every Room / Super Deals!
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $990 - $1,395 /wk
 
 
 
 
 

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Coconut Vacations - 104 N. 23rd - Bradenton Beach, FL
Anna Maria Island Cottage Rental Picture
  • bedrooms 5
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 18
  • baths 4
  • rates (USD) $90 - $143 /nt
    $700 - $910 /wk
    $2,520 - $3,276 /mth
 
 
 
 
 

5 reviews write a review

Pelican Landing at the Terraces
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Terraces
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,200 /wk
 
 
 
 
 

2 reviews write a review

Beaches, fishing, and family fun in the tropics
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community Coquina Moorings
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $215 /nt
    $1,200 - $1,500 /wk
    $3,600 - $4,500 /mth
 
 
 
 
 

1 reviews write a review

Gulf Front Beach House
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $6,700 /mth
 
 
 
 
 

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Beach View Condos - Last minute discounts!
Anna Maria Island Condo Rental Picture
  • bedrooms 6
  • community Gulf Beach Place
  • rental type Condo
  • sleeps 6
  • baths 6
  • rates (USD) $300 - $749 /nt
    $2,700 - $4,989 /wk
    $9,000 - $15,000 /mth
 
 
 
 
 

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Anna Maria Island Bungalow just a few steps from the Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community Bradenton Beach, Fl
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $700 - $1,000 /wk
 
 
 
 
 

6 reviews write a review

Beach Front Living on Anna Maria Island
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • community Bradenton Beach, Fl
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $175 - $188 /nt
    $735 - $1,417 /wk
 
 
 
 
 

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Steps to the Beautiful Gulf of Mexico
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 5
  • baths 2
  • rates (USD) $850 - $950 /wk
    $3,000 - $3,500 /mth
 
 
 
 
 

1 reviews write a review

Pelican Cove 15
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $700 - $1,470 /wk
    $2,891 - $4,641 /mth
 
 
 
 
 

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Holmes Beach Gem - unit #205
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Sandy Pointe
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $110 - $145 /nt
    $800 - $1,050 /wk
    $2,200 - $3,300 /mth
 
 
 
 
 

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Gulf Dream
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $700 - $1,050 /wk
    $2,400 - $4,000 /mth
 
 
 
 
 

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Sandy Pointe II
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • community Sandy Pointe
  • rental type Townhome
  • sleeps 6
  • baths 3
  • rates (USD) $900 - $1,500 /wk
    $2,500 - $3,500 /mth
 
 
 
 
 

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Waterfront Gulf & Bay Condo with Pool & Spectacular Views
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community Coquina Moorings
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 - $1,800 /wk
 
 
 
 
 

1 reviews write a review

Sandyislegetaway
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $600 - $800 /wk
    $1,800 - $2,900 /mth
 
 
 
 
 

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Gulf View- Don't Miss our Deal
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Pelican Cove
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $850 - $1,250 /wk
    $3,000 - $4,000 /mth
 
 
 
 
 

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Bradenton Beach House
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community Bradenton Beach
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $825 - $1,082 /wk
    $2,640 - $3,462 /mth
 
 
 
 
 

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Beach Barn
Anna Maria Island House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $1,350 - $1,550 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

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Golden Dolphin - Gulf front pool home that sleeps 14!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $5,500 - $7,000 /wk
 
 
 
 
 

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Anna Maria Beach Cottage
Anna Maria Island Cottage Rental Picture
  • bedrooms 3
  • community
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $1,250 - $2,050 /wk
    $4,000 - $8,200 /mth
 
 
 
 
 

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Absolutely Perfect Gulf front 5 bedroom home
Anna Maria Island House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $3,800 - $4,400 /wk
 
 
 
 
 

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Bay and Beach Breezes Mobile Home; Steps to Water Views
Anna Maria Island House Rental Picture
  • bedrooms 1
  • community Sandpiper Resort
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $400 - $500 /wk
    $900 - $1,600 /mth
 
 
 
 
 

1 reviews write a review

Palm Cottage on Anna Maria
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $250 /nt
    $875 - $975 /wk
    $2,700 - $3,200 /mth
 
 
 
 
 

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Flamingo Condo-Gulf Front
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,350 - $1,650 /wk
    $4,400 - $5,400 /mth
 
 
 
 
 

6 reviews write a review

Executive 6 bed 4 bath private pool home,v near beach
Anna Maria Island House Rental Picture
  • bedrooms 6
  • community Holmes Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 4
  • rates (USD) $500 - $700 /nt
    $3,200 - $4,000 /wk
    $10,000 - $12,000 /mth
 
 
 
 
 

5 reviews write a review

All the Comforts of Home and More!
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • community North Beach Village
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $1,350 - $1,750 /wk
    $3,700 - $5,000 /mth
 
 
 
 
 

1 reviews write a review

Bay Rest - On Sarasota Bay - Yards to Gulf of Mexico Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $500 - $1,000 /nt
    $1,500 - $2,000 /wk
    $3,500 - $5,000 /mth
 
 
 
 
 

1 reviews write a review

Sandcastle Rent 3 or 6 BR Lg. Family Home Across from Beach!
Anna Maria Island House Rental Picture
  • bedrooms 6
  • community
  • rental type House
  • sleeps 16
  • baths 4
  • rates (USD) $1,600 - $5,000 /wk
 
 
 
 
 

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Hacienda del Mar -- Beachfront Luxury Home, Incredible Views
Anna Maria Island House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $2,500 - $5,200 /wk
 
 
 
 
 

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Coquina Beach Condos
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $800 - $1,200 /wk
    $2,500 - $3,800 /mth
 
 
 
 
 

5 reviews write a review

Seconds From The Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $150 - $220 /nt
    $850 - $1,350 /wk
 
 
 
 
 

2 reviews write a review

Tiffany Place "See the porpoise while you eat"
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Condominium
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $190 /nt
 
 
 
 
 

1 reviews write a review

Alecassandra Vacation Villas Of Anna Maria Island
Anna Maria Island Villa Rental Picture
  • bedrooms 11
  • community
  • rental type Villa
  • sleeps 30
  • baths 10
  • rates (USD) $250 /nt
    $1,200 /wk
 
 
 
 
 

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Sunset Terrace
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Bradenton Beach
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $1,120 - $2,187 /wk
    $3,808 - $7,436 /mth
 
 
 
 
 

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Sunset Terrace condo 207
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Bradenton Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,120 - $2,187 /wk
    $3,808 - $7,436 /mth
 
 
 
 
 

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**50 steps to the sand!** Aug/Sep special $550 for any week
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community neighborhood
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $295 /nt
    $750 - $1,450 /wk
 
 
 
 
 

2 reviews write a review

Beachcomber - Gulf front pool home
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $3,400 - $4,000 /wk
 
 
 
 
 

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Serenity - Gulf Side Pool Home
Anna Maria Island House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $1,500 - $3,000 /wk
 
 
 
 
 

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$350.00 per week plus cleaning and tx Anna Maria /September
Anna Maria Island Villa Rental Picture
  • bedrooms 1
  • community
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (VEF) Bs.100 - Bs.140 /nt
    Bs.499 - Bs.900 /wk
    Bs.2,000 - Bs.3,400 /mth
 
 
 
 
 

3 reviews write a review

Coconuts Gulf Front Condo
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • community
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,000 - $1,450 /wk
 
 
 
 
 

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Sea Isle motel
Anna Maria Island Hotel Rental Picture
  • bedrooms 1
  • community
  • rental type Hotel
  • sleeps 4
  • baths 1
  • rates (USD) $99 - $149 /nt
    $599 - $890 /wk
 
 
 
 
 

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Blue Dolphin Inn Flamingo unit
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community Blue Dolphin Inn
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $1,190 - $1,400 /wk
 
 
 
 
 

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Lake by the Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,260 - $1,750 /wk
 
 
 
 
 

1 reviews write a review

Breakers of Beautiful Anna Maria Island
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,995 - $2,995 /wk
 
 
 
 
 

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Sans Souci Duplex
Anna Maria Island House Rental Picture
  • bedrooms 6
  • community
  • rental type House
  • sleeps 14
  • baths 4
  • rates (USD) $1,400 - $4,933 /wk
    $4,760 - $16,772 /mth
 
 
 
 
 

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Allegria by the Sea ~ RA43580
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $245 - $545 /nt
    $1,700 - $3,800 /wk
 
 
 
 
 

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Anna Maria - Tarpon, Canal front, Dock, Saltwater Pool
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $243 - $371 /nt
    $1,700 - $2,600 /wk
    $5,950 - $7,800 /mth
 
 
 
 
 

5 reviews write a review

Hurry! Last Minute 25% Discount for Labor Day (August 30-September 6)
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $186 - $250 /nt
    $1,400 - $1,750 /wk
    $4,680 - $6,300 /mth
 
 
 
 
 

61 reviews write a review

Whispering Palms: Hurry... Fall Special $1800 Between Sept. 6 - October 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 9
  • baths 3
  • rates (USD) $2,000 - $3,200 /wk
 
 
 
 
 

1 reviews write a review

Seahorse Paradise: Dont Miss Fall Special $1200/wk Now Through Oct. 21, 2014!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,400 - $1,950 /wk
 
 
 
 
 

1 reviews write a review

Mar y Sol: Fall Special Dont Miss It $1400/wk Through October 23 , 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,550 - $2,250 /wk
 
 
 
 
 

5 reviews write a review

Island Memories: Perfect North End Home,Heated Pool/Hot Tub,Short Block to Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,700 - $2,100 /wk
 
 
 
 
 

1 reviews write a review

$1699 Aug Deal ~ Resort Style Luxury Waterfront Heated Pool/Dock Steps to Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,699 - $3,700 /wk
 
 
 
 
 

6 reviews write a review

Island Place Cottage: 1BR/1BA Quaint Pet-Friendly Cottage
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $121 - $143 /nt
    $850 - $1,000 /wk
 
 
 
 
 

21 reviews write a review

Happy Heron: 1BR/1BA Newly Renovated and Block from Beach
Anna Maria Island House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 2
  • baths 1
  • rates (USD) $107 - $129 /nt
    $750 - $900 /wk
 
 
 
 
 

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BON AMI: 3BR/2BA Family- and Pet-Friendly Less than Block from Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $189 - $251 /nt
    $1,320 - $1,760 /wk
 
 
 
 
 

2 reviews write a review

2 Bedroom, Poolside, Steps from the White Sand Beach of the Gulf of Mexico
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $175 /nt
    $1,145 /wk
    $4,499 /mth
 
 
 
 
 

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Luxury Gulf Front 3bd Condo --- La Casa 8 with Special Pricing!
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $339 - $399 /nt
    $2,373 - $2,793 /wk
 
 
 
 
 

2 reviews write a review

Latitude Adjustment, 2BR. 1BA., Quiet North End Location, Close To Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $585 - $970 /wk
 
 
 
 
 

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BoatHouse Cottage - N. end Anna Maria- steps to beach - Private Pool
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $200 - $225 /nt
    $1,050 - $1,225 /wk
    $3,920 /mth
 
 
 
 
 

17 reviews write a review

Brand New 4 Bed/3 Bath Fully Loaded Bungalow W Heated Pool Near Beach
Anna Maria Island Bungalow Rental Picture
  • bedrooms 4
  • rental type Bungalow
  • sleeps 13
  • baths 3
  • rates (USD) $475 - $600 /nt
    $2,500 - $4,200 /wk
 
 
 
 
 

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Fabulous Home with Outstanding Location and HEATED POOL!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $250 - $275 /nt
    $1,575 - $1,750 /wk
    $6,000 - $6,750 /mth
 
 
 
 
 

20 reviews write a review

Elegant Gulf Front Condo Overlooking Both Beach and Pool
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $4,134 - $5,094 /wk
 
 
 
 
 

8 reviews write a review

Sandpail: Adorable Duplex, Heated Pool, Tropical Landscaping, 75 Yards to Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $800 - $975 /wk
 
 
 
 
 

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Hurry...Last Minute Special Deal: $1400/wk for the Week of May 17 - May 24, 2014
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,600 - $2,400 /wk
 
 
 
 
 

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North Beach Condo Villa & Large Pool - Steps to Beach
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $2,200 /wk
    $4,853 /mth
 
 
 
 
 

14 reviews write a review

late season availability for this cute 3 bedroom 1 bath apartment
Anna Maria Island Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $115 - $143 /nt
    $805 - $1,001 /wk
    $3,450 - $4,004 /mth
 
 
 
 
 

4 reviews write a review

Private 3 Bedroom house with new Pool
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

8 reviews write a review

New 3 bedroom, private pool and close to the sandy beach
Anna Maria Island Rental Picture
  • bedrooms 3
  • rental type
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

7 reviews write a review

20% off wk - Sat to Sat - Aug, Sept, Oct, Nov - 4Bd 3Ba- Shared Heated Poo
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

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Luxury Beach House with Spectacular Views -Beach,3BR & Loft
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,200 - $2,500 /wk
 
 
 
 
 

9 reviews write a review

Tranquil, Island Rental Home - Serendipity I
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $400 - $650 /nt
    $2,500 - $4,000 /wk
 
 
 
 
 

13 reviews write a review

Great August rates for late summer vacation! Own pool, walk to beach, private
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $211 - $257 /nt
    $1,525 - $1,700 /wk
    $4,900 - $5,400 /mth
 
 
 
 
 

19 reviews write a review

Direct Beachfront 2 Br Condo On Florida’s Beautiful Gulf Coast!
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $125 - $279 /nt
    $3,750 - $5,950 /mth
 
 
 
 
 

1 reviews write a review

ANNA MARIA ISLAND *SALE ALL FALL* Canal Front Heated Pool 3 Bed 3 Bath Home
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths 0
  • rates (USD) $1,195 - $8,365 /wk
 
 
 
 
 

1 reviews write a review

ANNA MARIA ISLAND *SALE ALL FALL* THIS 3B/3B POOL HOME IN THE VILLAGE!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 0
  • rates (USD) $1,295 - $3,795 /wk
 
 
 
 
 

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North Beach Village Unit 27 ~ RA43576
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $125 - $265 /nt
    $885 - $1,825 /wk
 
 
 
 
 

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Holmes Beach Holiday Home ~ RA43516
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $260 - $675 /nt
    $1,810 - $4,720 /wk
 
 
 
 
 

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Island Oasis ~ RA43515
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $405 - $1,310 /nt
    $2,820 - $9,180 /wk
 
 
 
 
 

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Sea Glass ~ RA43513
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $230 - $375 /nt
    $1,590 - $2,625 /wk
 
 
 
 
 

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Bikini Bottom ~ RA43486
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $175 - $360 /nt
    $1,225 - $2,525 /wk
 
 
 
 
 

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Casa Del Sol - Holmes Beach ~ RA43479
Anna Maria Island Townhome Rental Picture
  • bedrooms 4
  • rental type Townhome
  • sleeps 10
  • baths 4
  • rates (USD) $255 - $585 /nt
    $1,790 - $4,095 /wk
 
 
 
 
 

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Turtle Trax: Fall Special Dont Miss it $750 Now Through October 4, 2014!!!
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $825 - $1,125 /wk
 
 
 
 
 

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Ground Floor 3 Bedroom 2.5 Bath Duplex with Private Pool
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD)
 
 
 
 
 

12 reviews write a review

Sept Deal $1999/wk ~ Resort Style Luxury Waterfront Htd Pool Dock/Steps to Beach
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 5
  • rates (USD) $2,099 - $4,600 /wk
 
 
 
 
 

11 reviews write a review

Large and elegant canal home,Heated pool,fish from your backyard,walk to beach.
Anna Maria Island House Rental Picture
  • bedrooms 7
  • rental type House
  • owner badgeowner badge
  • sleeps 16
  • baths
  • rates (USD) $2,500 - $4,900 /wk
 
 
 
 
 

44 reviews write a review

Listen to the Mermaids Sing at Sunset Cottage - A Luxury Property
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD)
 
 
 
 
 

17 reviews write a review

Unexpected Blessings One house from beach
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $175 /nt
    $1,095 /wk
 
 
 
 
 

11 reviews write a review

Emerald Seas, New, Luxury 6-bdrm House, Tropical Pool/Spa, Beach, Lake
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 16
  • baths
  • rates (USD) $2,520 - $6,500 /wk
 
 
 
 
 

18 reviews write a review

15% off wk - Sat to Sat- Sept & Oct -Banyan Treehouse-2BD/2.5BA-Upscale Condo
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths
  • rates (USD)
 
 
 
 
 

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Luxurious Two Bedroom Home with Heated Pool at North End of Island
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $229 - $286 /nt
    $1,600 - $1,800 /wk
 
 
 
 
 

30 reviews write a review

BRAND NEW 4 Bed/3 Bath Fully Loaded BUNGALOW w Heated Pool Near Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $457 - $621 /nt
    $3,600 - $4,350 /wk
 
 
 
 
 

18 reviews write a review

The Perfect Gulf Front Vacation, Directly on the Beach!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,650 - $2,250 /wk
 
 
 
 
 

7 reviews write a review

Tropical Oasis: Dont Miss Fall Special $3800/month Now Through October 14, 2014!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $264 /nt
 
 
 
 
 

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Mermaid's Purse: Adorable, Comfortable, Unique Cottage, 2 Houses to Gulf Beach!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $775 - $975 /wk
 
 
 
 
 

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Plum Cottage 324 with Beautiful & Peaceful Tropical Garden ~ RA43477
Anna Maria Island Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $145 - $325 /nt
    $1,000 - $2,245 /wk
 
 
 
 
 

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The Sassy Seahorse, Much, Much More than a Vacation Rental
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,436 - $2,764 /wk
 
 
 
 
 

2 reviews write a review

Private Heated Pool, Single Story, Minutes To Gulf Beach & Shops, North End
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $170 - $257 /nt
    $1,000 - $1,800 /wk
 
 
 
 
 

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Brand New Custom Anna Maria Island Vacation Home With Pool!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,450 - $1,850 /wk
    $5,220 - $6,660 /mth
 
 
 
 
 

10 reviews write a review

Newly Remodeled 2 BR/2 BA with Pool - 1.5 Blocks to Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $1,150 - $1,600 /wk
    $3,225 - $4,050 /mth
 
 
 
 
 

41 reviews write a review

Surf's Up: Dont Miss This Fall Special $1500/wk Through October 4, 2014!!!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,800 - $2,800 /wk
 
 
 
 
 

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Beautiful and private 3 bedroom home centrally located on Anna Maria Island.
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $171 - $271 /nt
    $1,200 - $1,900 /wk
 
 
 
 
 

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Beautiful pool home located just steps to the Gulf of Mexico.
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $257 - $800 /nt
    $1,800 - $5,600 /wk
 
 
 
 
 

4 reviews write a review

Newly Remodeled with specatacular outdoor pool space! Near new construction, 10% discount!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 5
  • baths 2
  • rates (USD) $200 - $293 /nt
    $1,400 - $2,050 /wk
    $4,200 - $6,150 /mth
 
 
 
 
 

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Luxury finishes, private backyard with heated pool! Steps to the beach!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 5
  • baths
  • rates (USD) $175 - $275 /nt
    $1,225 - $1,925 /wk
    $3,675 - $5,775 /mth
 
 
 
 
 

1 reviews write a review

Newly Remodeled Duplex! Steps to the beach, luxury finishes!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 2
  • rates (USD) $189 - $279 /nt
    $1,325 - $1,950 /wk
    $3,975 - $5,850 /mth
 
 
 
 
 

1 reviews write a review

Aloha Home - Beach Getaway 2 Minute Walk from Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

7 reviews write a review

Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,950 - $2,100 /wk
 
 
 
 
 

22 reviews write a review

4 Bedroom w/ Lagoon pool/spa & golf cart- comes w/ all the Toys!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $1,475 - $2,650 /wk
    $5,800 - $8,900 /mth
 
 
 
 
 

13 reviews write a review

Two Pina Coladas: Tropical Heated Pool, Hot Tub, Tiki Bar, Short Block to Beach,
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $3,000 - $4,800 /wk
 
 
 
 
 

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TRIPLE PLAY: Triple Paradise - Pool/Spa/Dock - Walk To Beach On North End!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,300 - $1,700 /wk
 
 
 
 
 

3 reviews write a review

Suz's Seabreeze: Great Beach House, Heated Pool, Short Block to Beach!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,725 - $2,325 /wk
 
 
 
 
 

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SUNDAZE: Very Short Block to Beach, West of Gulf Drive, Adorable Villa, Private Heated Pool!
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $1,100 - $1,500 /wk
 
 
 
 
 

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Summer Breeze: Cottage in Peaceful Setting, Dock and Kayaks, 250 Steps to Beach
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $700 - $975 /wk
 
 
 
 
 

2 reviews write a review

SIMPLY CHIC: Beautiful, Remodeled, Heated Pool, Waterfall, 1.5 Block to Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,700 - $2,400 /wk
 
 
 
 
 

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Serendipity: Very Private Tropical Pool Area with Rockin Tiki Bar,Close to Beach
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $1,375 - $1,825 /wk
 
 
 
 
 

1 reviews write a review

Sea Turtle: Fall Special Dont Miss It $1050/wk Through September 26, 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,300 - $1,650 /wk
 
 
 
 
 

2 reviews write a review

Sea Oats: Fall Special Dont Miss It $2400/wk Through October 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 13
  • baths
  • rates (USD) $3,125 - $5,125 /wk
 
 
 
 
 

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Sand Castle: Fall Special Dont Miss $1600/wk Through October 5, 2014
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $1,900 - $3,200 /wk
 
 
 
 
 

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Sand 'n Sea Beach Flats 113B: Large Heated Pool, Only 50 Steps To The Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $700 - $1,250 /wk
 
 
 
 
 

4 reviews write a review

Sand 'n Sea Beach Flats 113A: Large Heated Pool, Only 50 Steps To The Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 7
  • baths 1
  • rates (USD) $700 - $1,250 /wk
 
 
 
 
 

3 reviews write a review

Sand 'n Sea Beach Flats 111B: Large Heated Pool, Only 50 Steps To The Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 7
  • baths 1
  • rates (USD) $700 - $1,350 /wk
 
 
 
 
 

5 reviews write a review

Sand 'n Sea Beach Flats 109B: Large Heated Pool, Only 50 Steps To The Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $700 - $1,250 /wk
 
 
 
 
 

4 reviews write a review

Sand 'n Sea Beach Flats 109A: Large Heated Pool, Only 50 Steps To The Beach
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $700 - $1,250 /wk
 
 
 
 
 

3 reviews write a review

Poseidon's Palace: Fall Special Dont Miss $3900/wk Through October 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 8
  • rental type House
  • sleeps 18
  • baths
  • rates (USD) $4,100 - $8,250 /wk
 
 
 
 
 

2 reviews write a review

PERFECTION IN PARADISE: Immaculate, Deep Water Canal Front, with Heated Pool!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,495 - $1,995 /wk
 
 
 
 
 

1 reviews write a review

Pelican Place: Close To Beach, Heated Pool, Beautiful North End Location!!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,275 - $1,675 /wk
 
 
 
 
 

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PEACH BELLINI: Adorable, Eye-popping Renovated Villa,Heated Pool, Close To Beach
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $1,100 - $1,550 /wk
 
 
 
 
 

1 reviews write a review

Palm Paradise: Fall Special $1500/wk for Available Weeks Through Oct. 4, 2014!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $1,800 - $2,400 /wk
 
 
 
 
 

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OUR PLACE BY THE SEA: Tropical Retreat, Spacious Pool Home, North End!!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,500 - $1,950 /wk
 
 
 
 
 

4 reviews write a review

NORTH END CHIC:Gorgeous Ground Level, Perfectly Remodeled, Heated Pool,waterfall
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,700 - $2,300 /wk
 
 
 
 
 

1 reviews write a review

My Big Fat Beach House: Fall Special Dont Miss $1900/wk Through Sept. 23, 2014
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $2,100 - $3,600 /wk
 
 
 
 
 

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Mermaid Tales: Adorable 2 Bed/ 2 Bath, Canalfront Home with Large Heated Pool
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 - $1,600 /wk
 
 
 
 
 

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MELLOW YELLOW: Gorgeous with Tropical Heated Pool, Elevator, Short Block to Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $1,800 - $2,400 /wk
 
 
 
 
 

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MARGARITA-VILLE: Tropical Heated Pool, Hot Tub, Tiki Bar, Short Block to Beach,
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $3,000 - $4,800 /wk
 
 
 
 
 

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Manatee Watch: Fall Special Dont Miss It $1200/wk Through Sept. 20, 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,550 - $2,250 /wk
 
 
 
 
 

2 reviews write a review

Luana:Awesome Ground Level, Heated Pool & Hot Tub, Very Close to Beach!!!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,800 - $2,500 /wk
 
 
 
 
 

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LOGGERHEAD: Fall Special $800/wk Now Through October 18. 2014!!!
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $925 - $1,225 /wk
 
 
 
 
 

1 reviews write a review

Lazy Daze: Dont Miss Fall Special $900/wk Now Through October 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,075 - $1,625 /wk
 
 
 
 
 

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La Hacienda: Relax In Style In This Gorgeous Mediterranean Pool Home (Heated)
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $2,000 - $3,200 /wk
 
 
 
 
 

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Island Time:Great Gulf Views, 3 Houses to Beach, Tropical Heated Pool, Ping-Pong
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,950 - $3,500 /wk
 
 
 
 
 

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HURRICANE HOUSE: Awesome Home with Heated Pool and Steps to the Beach!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,475 - $1,775 /wk
 
 
 
 
 

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Hawaiian Punch: Dont Miss Fall Special $1300/wk Now Through Sept. 22 2014!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,600 - $2,000 /wk
 
 
 
 
 

2 reviews write a review

Hav'Anna Hideaway: Dont Miss Fall Special $1400/wk Now Through Oct. 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 11
  • baths 4
  • rates (USD) $2,000 - $2,900 /wk
 
 
 
 
 

1 reviews write a review

Hav'Anna Daydreamin: Fall Special $1100/wk Through October 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,425 - $1,775 /wk
 
 
 
 
 

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Going Coastal: Super Deal....$795/wk Now Through September 27, 2014
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,400 /wk
 
 
 
 
 

2 reviews write a review

FAIRWINDS: Amazingly Perfect Island Home with Everything, Heated Pool, Hot Tub +
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $1,800 - $2,600 /wk
 
 
 
 
 

3 reviews write a review

Endless Summer: Dont Miss This... $1300/wk Now Through October 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,600 - $2,400 /wk
 
 
 
 
 

3 reviews write a review

Dancing Dolphin: Awesome Heated Pool, Hot Tub, Short 1.5 Blocks to Beach!!!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,700 - $2,500 /wk
 
 
 
 
 

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CRESCENT WAVE: Dont Miss Fall Special $1300/wk Now Through October 4, 2014!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,600 - $2,400 /wk
 
 
 
 
 

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Coral Castle: Fall Special Dont Miss It $1600/wk through September 13, 2014
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $1,800 - $3,300 /wk
 
 
 
 
 

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COCONUT COTTAGE: Gorgeous, Spacious, Close to Beach, With Heated Pool!!!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,375 - $1,875 /wk
 
 
 
 
 

1 reviews write a review

Champagne Shores: Dont Miss Fall Special $995/wk Now Through October 4, 2014!!!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,300 - $1,600 /wk
 
 
 
 
 

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CASA CON VISTA: Perfectly Adorable Canalfront Home, Heated Pool, Hot Tub, Dock!!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,300 - $1,700 /wk
 
 
 
 
 

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CARIBBEAN SOUL:Fall Special $1100/wk for Available Weeks Through October 4, 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths
  • rates (USD) $1,650 - $1,850 /wk
 
 
 
 
 

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Canario Cottage: Awesome North End Location, 3 Blocks to Gulf, 1 Block to Bay
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $1,550 - $1,800 /wk
 
 
 
 
 

1 reviews write a review

Camp Tarpon: Waterfront On Deep Canal Brand New Heated Pool And Large Tiki Hut!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,500 - $2,100 /wk
 
 
 
 
 

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Calypso:Awesome Villa with Private Heated Pool, Swim-Up Tiki Table and Waterfall
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 8
  • baths 2
  • rates (USD) $1,100 - $1,550 /wk
 
 
 
 
 

2 reviews write a review

Blue Sky: Blue Sky: Pristine,Close to Beach and Trolley,Heated Pool and Hot Tub
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,425 - $1,875 /wk
 
 
 
 
 

2 reviews write a review

BLUE MERMAID: Amazing Gulf Views, One House to the Beach, Cool Coastal Living!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,800 - $4,000 /wk
 
 
 
 
 

1 reviews write a review

BLUE MARTINI:Tropical Setting, Heated Pool, No Busy Streets To Cross To Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,500 - $2,100 /wk
 
 
 
 
 

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BLUE MARLIN: Large Heated Lap Pool, Hot Tub, Outdoor Dining, Close To Beach!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,200 - $1,600 /wk
 
 
 
 
 

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BEACH WALK:Steps to Beach, Heated Pool & Waterfall in Very Tropical Setting
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,600 - $1,950 /wk
 
 
 
 
 

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Beachside Paradise: Dont Miss Fall Special $1250/wk Now Through October 4, 2011
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $1,600 - $2,400 /wk
 
 
 
 
 

5 reviews write a review

Beach Daze: Awesome Villa with Private Heated Pool and Just a Block to Beach!!!
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 - $1,400 /wk
 
 
 
 
 

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Beach Breezes: Dont Miss - Fall Special $1100/wk Now Through October 11, 2014!!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $1,425 - $1,875 /wk
 
 
 
 
 

5 reviews write a review

BEACH RETREAT 206: Private Heated Pool, Very Spacious Villa, Short Block to Beac
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 8
  • baths 2
  • rates (USD) $1,350 - $1,950 /wk
 
 
 
 
 

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BEACH RETREAT 204:Private Heated Pool, Very Spacious Villa, Short Block to Beach
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 8
  • baths 2
  • rates (USD) $1,350 - $1,950 /wk
 
 
 
 
 

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BAREFOOT BLISS:Coastal Living in a Tropical Setting, Heated Pool, Short Stroll t
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,375 - $1,775 /wk
 
 
 
 
 

4 reviews write a review

ANOTHER PARADISE: Beautiful Home, Only 7 Houses to Beach with Heated Pool!!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,495 - $2,395 /wk
 
 
 
 
 

1 reviews write a review

Anna Banana: Dont Miss Fall Special $1100/wk Now Through October 4, 2011
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,400 - $1,800 /wk
 
 
 
 
 

1 reviews write a review

Angelfish: North End, Ground Level, Heated Pool, 2 Houses to the Gulf Beach!!!
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $1,250 - $4,250 /wk
 
 
 
 
 

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Anchors Away: Fall Special Dont Miss It $800/wk Through October 4, 2014
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $975 - $1,425 /wk
 
 
 
 
 

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Ahoy Matey: Fall Special Dont Miss It $800/wk Through October 4, 2014
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $975 - $1,425 /wk
 
 
 
 
 

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3 Bedroom beachfront condo. Enjoy the Gulf of Mexico from your porch.
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 7
  • rates (USD) $214 - $346 /nt
    $1,500 - $2,420 /wk
 
 
 
 
 

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Brand new 5 bedroom, 4 bath home, steps to the Gulf beaches.
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $321 - $929 /nt
    $2,250 - $6,500 /wk
 
 
 
 
 

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Large pool home located just steps to the Gulf of Mexico.
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $400 - $786 /nt
    $2,800 - $5,500 /wk
 
 
 
 
 

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Completely Renovated Beach Home, Stunning, Unobstructed Bayview, Heated Pool
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $357 - $643 /nt
    $2,500 - $4,500 /wk
 
 
 
 
 

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Mangoes on Magnolia: 3BR/2BA Classic Elevated Beach Home with Pool
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $171 - $229 /nt
    $1,200 - $1,600 /wk
 
 
 
 
 

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Beautiful Villa by the Sea: 4BR/3BA Family- and Pet-Friendly Pool Home
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $236 - $321 /nt
    $1,650 - $2,250 /wk
 
 
 
 
 

3 reviews write a review

797 NS - Villa Marisol - DIRECTLY ON THE BEACH OF ANNA MARIA ISLAND !
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 8
  • rates (USD) $500 - $786 /nt
    $3,500 - $4,950 /wk
    $14,000 - $19,800 /mth
 
 
 
 
 

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WATERFRONT - POOL HOME, Island vacation rental sleeps 5-6,
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $1,470 - $3,200 /wk
 
 
 
 
 

5 reviews write a review

North End Location-Luxury, Private, Spacious 4 Bedroom, 3 Bath Pool & Canal Home
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,750 - $2,775 /wk
 
 
 
 
 

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Starfish Dreams: 2BR/2BA Canal-Front Home with Dock and Pool
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $229 /nt
    $1,400 - $1,600 /wk
 
 
 
 
 

2 reviews write a review

Simpatico: 2BR/2.5BA Pet-Friendly Canal Home with Dock/Kayaks
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $171 - $229 /nt
    $1,200 - $1,600 /wk
 
 
 
 
 

1 reviews write a review

Seahorse Cove: 5BR/6BA Family-Friendly Pool Home with Dock
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 5
  • rates (USD) $568 - $643 /nt
    $3,975 - $4,500 /wk
 
 
 
 
 

7 reviews write a review

Pineapple Cottage: 2BR/1BA Quaint Family- and Pet-Friendly Cottage
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $157 - $186 /nt
    $1,100 - $1,300 /wk
 
 
 
 
 

31 reviews write a review

15% off wk - Sat to Sat - Aug, Sept, Oct, Nov - 4 Bed/3 Bath Home-Private Pool
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $2,000 - $2,250 /wk
 
 
 
 
 

2 reviews write a review

Brand New 5 Bed/3 Bath Fully Loaded Home W Heated Pool Spa. 1 minute to Beach!!
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $429 - $629 /nt
    $3,200 - $4,400 /wk
 
 
 
 
 

2 reviews write a review

$700 wk NOW!!! 3 Bedroom, 2 Bath; Private Upscale Home! Heated Jet Pool!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $700 - $1,610 /wk
    $5,474 /mth
 
 
 
 
 

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Charming Beach Home-99 Steps to the Beach!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $200 - $486 /nt
    $2,100 - $3,400 /wk
 
 
 
 
 

50 reviews write a review

Beautiful Beach Views! Steps to gulf access. Easy Walk To Shops And Restaurants
Anna Maria Island Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • sleeps 8
  • baths
  • rates (USD) $320 - $600 /nt
    $2,250 - $3,250 /wk
    $7,250 /mth
 
 
 
 
 

8 reviews write a review

City of ANNA MARIA!LOCATION! Northshore Beach Villa,Anna Maria Island, Pine Ave
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $114 - $164 /nt
    $850 - $1,150 /wk
 
 
 
 
 

22 reviews write a review

The Anna Maria Island Beach Retreat
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $250 /nt
    $1,100 /wk
    $3,600 /mth
 
 
 
 
 

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Beach Bound: Awesome Ground Level Beach House,Heated Pool,Hot Tub, Close 2 Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $1,850 - $3,150 /wk
 
 
 
 
 

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Ainsley Beach House: Fall Special Dont Miss It $1000/wk Through November 1, 2014
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 8
  • baths 2
  • rates (USD) $1,300 - $1,750 /wk
 
 
 
 
 

8 reviews write a review

Addisons Beach House: Fall Special Dont Miss It $1250/wk Through October 4, 2014
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 8
  • baths 2
  • rates (USD) $1,300 - $1,900 /wk
 
 
 
 
 

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Tip of the Island! 3BR+Den, Heated Pool, Canal/Dock, Walk to Beaches & Dining
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $200 - $257 /nt
    $1,350 - $1,800 /wk
    $4,300 - $5,750 /mth
 
 
 
 
 

18 reviews write a review

4 bedroom home just steps to the beach and Pine Ave.
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $229 - $321 /nt
    $1,600 - $2,250 /wk
 
 
 
 
 

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Cherryfish is part of a very unique group of rental properties called Pineapplefish.
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $400 - $519 /nt
    $2,800 - $3,630 /wk
 
 
 
 
 

1 reviews write a review

Happy Island Cottage with heated private Pool
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $170 - $427 /nt
 
 
 
 
 

14 reviews write a review

BRAND NEW 3/2 Luxury Home with Garage Heated Pool & Spa Close to Beach!
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $300 /nt
    $1,400 - $2,000 /wk
 
 
 
 
 

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ISLAND TIME PRIVATE PARADISE!Heated Pool&Spa,Boat Slip
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,850 /wk
 
 
 
 
 

25 reviews write a review

The Shady Mango - Anna Maria's Most Charming Coastal Cottage!
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,750 - $2,450 /wk
 
 
 
 
 

6 reviews write a review

Spoil yourself! Pool-spa-dock-sea+only steps to sugar-white-sand. GEM!
Anna Maria Island Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $357 - $729 /nt
    $5,100 /wk
 
 
 
 
 

27 reviews write a review

ANGELFISH: Northshore 3/2- Great Location- Walk everywhere!!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 /wk
 
 
 
 
 

12 reviews write a review

3 Bedroom / 2 Bath Ground Level Unit. 5 minute walk to the beach!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $220 - $286 /nt
    $1,400 - $2,000 /wk
 
 
 
 
 

8 reviews write a review

2 Bedroom / 2 Bath Ground Level Cottage Near The Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $195 - $257 /nt
    $1,200 - $1,800 /wk
 
 
 
 
 

10 reviews write a review

Beach House on Anna Maria Island-Rental Openings
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 16
  • baths
  • rates (USD)
 
 
 
 
 

5 reviews write a review

Peaceful Island Rental Home - Serendipity II
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $400 - $650 /nt
    $2,500 - $4,000 /wk
 
 
 
 
 

11 reviews write a review

Ohana Hale Island Retreat on Anna Maria Island
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $125 - $157 /nt
    $750 - $1,100 /wk
    $4,100 /mth
 
 
 
 
 

8 reviews write a review

Anna Marie 2 Family Home w/pool, beach/3 blocks. Fall Special $950wk thru 10/4
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $950 - $2,075 /wk
    $4,500 /mth
 
 
 
 
 

2 reviews write a review

15% off wk- Sat to Sat- Aug, Sept, Oct, Nov-2bd, 2ba-tiki & waterfall in pool
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,150 - $1,455 /wk
 
 
 
 
 

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Anna Marie Hideaway!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $200 - $350 /nt
    $1,780 - $2,350 /wk
    $6,960 /mth
 
 
 
 
 

4 reviews write a review

Bahama Mama's - 3bd/2ba-Private Pool-2 Blks to Beach-single family home
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD)
 
 
 
 
 

3 reviews write a review

4 bed 3 bath BRAND NEW fully loaded duplex heated pool & spa near beach
Anna Maria Island Townhome Rental Picture
  • bedrooms 4
  • rental type Townhome
  • sleeps 9
  • baths 3
  • rates (USD) $264 - $357 /nt
    $2,200 - $2,500 /wk
 
 
 
 
 

3 reviews write a review

Huge Beach Front Condo - 3 Bedrooms, 2.5 Baths, Million Dollar View
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths
  • rates (USD) $200 /nt
 
 
 
 
 

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Real Gulf-Front Home: Step Out the Backdoor and Onto the Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,850 - $2,100 /wk
    $7,200 - $7,900 /mth
 
 
 
 
 

14 reviews write a review

The ultimate family vacation home
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,325 - $2,195 /wk
 
 
 
 
 

16 reviews write a review

Stunning Brand New 5 Bed, 3 Bath home w/ Heated Pool and Spa Near BEACH!
Anna Maria Island Townhome Rental Picture
  • bedrooms 5
  • rental type Townhome
  • sleeps 12
  • baths 3
  • rates (USD) $400 - $571 /nt
    $2,500 - $4,000 /wk
 
 
 
 
 

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Beach & Boaters Island Family Retreat
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 5
  • rates (USD) $2,200 - $3,000 /wk
 
 
 
 
 

6 reviews write a review

SUNNYSIDE - $1050 per week in August, September, October 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,050 - $1,700 /wk
    $3,450 - $5,450 /mth
 
 
 
 
 

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Extremely Close to Nicest GULF Beach, LARGE Heated Pool
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,820 - $2,730 /wk
 
 
 
 
 

10 reviews write a review

Best Location on Island - Read Our Guest Reviews!
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $693 - $1,266 /wk
    $4,573 - $5,606 /mth
 
 
 
 
 

35 reviews write a review

Sept special $999.00 Beautiful Classy Gulf Coast Anna Maria, beach, private poo
Anna Maria Island Bungalow Rental Picture
  • bedrooms 3
  • rental type Bungalow
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $1,400 - $1,750 /wk
 
 
 
 
 

4 reviews write a review

Beautiful Beach Escape Home - Four Houses from the Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,600 - $2,100 /wk
 
 
 
 
 

21 reviews write a review

Heated Pool, Canal/Dock, Single Story, Minutes to Gulf Beach & Shops, North End
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $286 /nt
    $1,000 - $2,000 /wk
 
 
 
 
 

5 reviews write a review

LAST MINUTE SPECIALS FOR AUG/SEP: Gorgeous home,Great Location
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $900 - $2,200 /wk
    $6,000 /mth
 
 
 
 
 

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Seaglass Cottage, 3 houses from Bean Point beach, Heated Pool
Anna Maria Island Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 5
  • baths 2
  • rates (USD) $1,300 - $1,750 /wk
 
 
 
 
 

12 reviews write a review

OUTRAGEOUS FALL SPECIALS!!!! OCT/NOV are the BEST months to enjoy Paradise!!!
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $150 - $175 /nt
    $750 - $850 /wk
    $2,800 - $3,200 /mth
 
 
 
 
 

34 reviews write a review

3bd, 2ba remodeled luxury private home! Across the street from Bean's Point!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,020 - $1,650 /wk
 
 
 
 
 

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$800wk Aug, Sept, Oct, Nov!! - 3 bedroom, 2 bath; pool home
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $800 - $1,610 /wk
    $5,474 /mth
 
 
 
 
 

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25% off wk - Sat to Sat - Aug, Sept, Oct, Nov - 2 Bedroom, 2 Bath; Private Pool
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,150 - $1,475 /wk
    $3,910 - $5,015 /mth
 
 
 
 
 

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August/September Island Getaways - Private Pool -Screened Lanai -Close to Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,000 - $2,000 /wk
    $3,600 - $5,400 /mth
 
 
 
 
 

18 reviews write a review

Newly Remodled / 100 Yards to Spectacular Beach / West of Gulf Blvd
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $250 - $300 /nt
    $1,250 /wk
    $2,800 /mth
 
 
 
 
 

10 reviews write a review

3 bed 2 bath BRAND NEW fully loaded 1 level home - heated pool & spa near beach
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $236 - $307 /nt
    $1,750 - $2,150 /wk
 
 
 
 
 

2 reviews write a review

Luxury home, pool, 600ft from sandy gulf beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,610 - $2,450 /wk
    $6,750 - $8,700 /mth
 
 
 
 
 

21 reviews write a review

Sapphire Surf - Private Heated Pool, North End, Ground Level,
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $171 - $275 /nt
    $1,100 - $1,825 /wk
 
 
 
 
 

31 reviews write a review

Beautiful Beach Front Gulf of Mexico 3 bedroom NOW ON SALE!!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $343 - $750 /nt
    $2,400 - $4,567 /wk
    $8,340 - $13,050 /mth
 
 
 
 
 

5 reviews write a review

Luxurious Cottage with Private Pool, Steps to Beach and MORE!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $257 - $293 /nt
    $1,700 - $2,050 /wk
 
 
 
 
 

11 reviews write a review

Anna Maria Rental Steps to Gulf Beach with Private Pool!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,400 - $1,700 /wk
    $3,600 /mth
 
 
 
 
 

6 reviews write a review

Family and pet friendly! A boater and beachcomber's paradise!
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $950 - $1,200 /wk
 
 
 
 
 

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Anna Maria, BRAND NEW HOME, GULF VIEWS 6 BR
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $3,900 - $5,500 /wk
 
 
 
 
 

6 reviews write a review

Townhouse/ 100 Steps to the Gulf of Mexico/ NO POOL
Anna Maria Island Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Anna Maria Island Beach House! Sleeps 10 -Heated Pool- across street from beach!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $2,100 - $3,900 /wk
 
 
 
 
 

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Unexpected Blessings II One house from beach, great views
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $2,800 /wk
 
 
 
 
 

5 reviews write a review

Beach Getaway, One Minute Walk from the Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD)
 
 
 
 
 

8 reviews write a review

ANNA MARIA 'In The Heart Of The Village' 2 Bed 2 Bath Pool Home, Canal Front!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $1,300 - $2,000 /wk
    $5,200 - $8,000 /mth
 
 
 
 
 

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A 3 bedroom tropical paradise 1/2 block to the beach with a private pool
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $243 - $357 /nt
    $1,700 - $2,500 /wk
    $5,464 /mth
 
 
 
 
 

2 reviews write a review

Anna Maria Island Cottage
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,000 - $1,260 /wk
    $3,500 - $4,350 /mth
 
 
 
 
 

3 reviews write a review

Come & Enjoy Our Island Paradise
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $2,000 - $2,400 /wk
    $5,600 - $7,000 /mth
 
 
 
 
 

19 reviews write a review

Anna Maria Island Beach Front Property - Warren Spahn's Vacation Home
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $335 /nt
    $2,205 - $2,303 /wk
    $6,804 - $7,000 /mth
 
 
 
 
 

1 reviews write a review

Exotic Private Island Waterfront Polynesian Pod-Style Home with Boat
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 18
  • baths 5
  • rates (USD) $1,100 - $3,000 /nt
    $6,650 - $7,700 /wk
    $26,400 - $30,000 /mth
 
 
 
 
 

8 reviews write a review

Swim Up Tiki Bar Pool Exclusively for your use
Anna Maria Island Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $193 - $275 /nt
    $1,350 - $1,925 /wk
 
 
 
 
 

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Paradisaical Enclave-5*WaterFront Home-Pool/Canal-Dock/Kayak/Bikes/Hammocks
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,750 - $2,550 /wk
 
 
 
 
 

6 reviews write a review

Anna Maria 'New Listing' 3 Bed 2 Bath Sleeps 10! Directly On The Beach!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $2,400 - $4,567 /wk
 
 
 
 
 

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ANNA MARIA SALE! *FALL SPECIALS STARTING 8/16 BOOK NOW* BRING YOUR BOAT!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,640 - $3,200 /wk
 
 
 
 
 

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ANNA MARIA BEACHFRONT HOME! *FILL IN THE CALENDAR GAPS AND LET'S MAKE A DEAL!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $3,750 /wk
    $6,000 - $15,000 /mth
 
 
 
 
 

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Stunning Luxury Newly Constructed Beachfront House W/Pool &Spa
Anna Maria Island Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $543 - $786 /nt
    $3,400 - $5,500 /wk
 
 
 
 
 

14 reviews write a review

ANNA MARIA ISLAND *SALE* $5500 TOTAL for any 90 days between 7/10-11/8!
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,582 - $3,220 /mth
 
 
 
 
 

3 reviews write a review

ANNA MARIA *SALE, FILL UP THE CALENDAR* 2 BED 2 FULL BATH HEATED POOL & HOT TUB!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $142 - $257 /nt
    $995 - $1,800 /wk
    $3,580 - $6,800 /mth
 
 
 
 
 

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Steps to the Beach-North Point of Anna Maria Island
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $990 - $1,350 /wk
 
 
 
 
 

8 reviews write a review

La Plage 02: 4 BR / 3.0 BA condo in Holmes Beach, Sleeps 8
Anna Maria Island Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • sleeps 8
  • baths 3
  • rates (USD) $3,295 - $4,890 /wk
 
 
 
 
 

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Beach/Gulf Front Three Bedroom Condominium.
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $1,800 /wk
    $4,500 - $5,500 /mth
 
 
 
 
 

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Luxury gulf-front 3-bedroom home on pristine beach!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Beachfront Home, Super Views, Dogs stay free, Walking Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $375 /nt
    $2,300 /wk
 
 
 
 
 

7 reviews write a review