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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!

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DEAL!! Coquina Cottage at the Beach: A Newly Renourished Beach
Anna Maria Island House Rental Picture
  • House Rental Deals and Specials Free Wireless Internet ($70)
  • bedrooms 3
  • community Cortez Beach
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $275 - $300 /nt
    $800 - $1,500 /wk
 
 
 
 
 

1 reviews write a review

DEAL!! Anna Maria Island Beach Palace
Anna Maria Island House Rental Picture
  • House Rental Deals and Discounts $300 off = $2,200 per week
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $357 - $450 /nt
    $2,500 - $2,900 /wk
    $9,000 - $10,600 /mth
 
 
 
 
 

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DEAL!! Anna Maria Island Beach Paradise 10
Anna Maria Island Studio Rental Picture
  • Studio Rental Deals and Discounts $100 off = $700 per week
  • bedrooms 1
  • community
  • rental type Studio
  • sleeps 4
  • baths 1
  • rates (USD) $150 /nt
    $600 - $800 /wk
    $2,850 /mth
 
 
 
 
 

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DEAL!! The Anna Maria Isalnd Beach Palms
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $250 off = $1,550 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 $300 off = $1,500 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!! Florida Beach Rentals, Anna Maria Island, Florida
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $250 off = $1,550 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!! May Special - Live Your Dreams Today- Island Living
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $700 off = $750 per week
  • bedrooms 2
  • community Gulf Watch
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $950 - $2,495 /wk
 
 
 
 
 

11 reviews write a review

DEAL!! Paradise Full Gulf Views - On the SAND
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $1,450 per week
  • bedrooms 1
  • community Sunset Terrace
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $995 - $2,495 /wk
    $4,000 - $6,000 /mth
 
 
 
 
 

41 reviews write a review

DEAL!! Seagrape II-charming & steps to the beach
Anna Maria Island Cottage Rental Picture
  • Cottage Rental Deals and Discounts $40 off = $600 per week
  • bedrooms 1
  • community
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $85 - $110 /nt
    $560 - $700 /wk
    $2,100 - $2,700 /mth
 
 
 
 
 

1 reviews write a review

DEAL!! Runaway Bay Stunning 2BD / 2BA Condo
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Specials $750 All inclusive, we pay FST, cleaning... ($130)
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $750 - $1,200 /wk
    $2,400 - $3,600 /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 $50 off = $975 per week
  • bedrooms 1
  • community Shell Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $135 - $165 /nt
    $900 - $1,050 /wk
    $3,300 - $4,000 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Light, Bright, Sure to Delight 300 Feet of Renourished Beach
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $400 off = $850 per week
  • bedrooms 2
  • community Gulf Watch
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $850 - $2,450 /wk
    $3,200 - $6,800 /mth
 
 
 
 
 

6 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 $200 off = $900 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
 
 
 
 
 

9 reviews write a review

DEAL!! Songbird
Anna Maria Island Cottage Rental Picture
  • Cottage Rental Deals and Discounts $30 off = $555 per week
  • bedrooms 2
  • community Holmes Beach
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $76 - $143 /nt
    $535 - $1,000 /wk
    $1,770 - $2,700 /mth
 
 
 
 
 

48 reviews write a review

DEAL!! Gulf View- Don't Miss our Deal
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $650 per week
  • bedrooms 2
  • community Pelican Cove
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $850 - $1,250 /wk
 
 
 
 
 

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DEAL!! May Special Beautiful Beach Front Paradise
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $600 off = $850 per week
  • bedrooms 2
  • community Gulf Watch
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $950 - $2,495 /wk
    $4,000 - $6,000 /mth
 
 
 
 
 

53 reviews write a review

DEAL!! Runaway Bay re-modelled one bedroom ground floor condo
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Specials $700 per week all inclusive ($110)
  • bedrooms 1
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $650 - $1,000 /wk
    $2,200 - $3,200 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Gulf Front Luxury Condo
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $250 off = $1,150 per week
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,100 - $1,700 /wk
 
 
 
 
 

86 reviews write a review

DEAL!! Seagrape Cottage - Wonderful Gulf and Sunset Views!
Anna Maria Island House Rental Picture
  • House Rental Deals and Discounts $50 off = $900 per week
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $140 - $180 /nt
    $925 - $1,100 /wk
    $3,200 - $4,200 /mth
 
 
 
 
 

8 reviews write a review

DEAL!! Sandy Beach Access
Anna Maria Island House Rental Picture
  • House Rental Deals and Discounts $200 off = $500 per week
  • bedrooms 2
  • community Holmes Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $400 - $850 /wk
    $2,500 - $3,000 /mth
 
 
 
 
 

11 reviews write a review

DEAL!! Gulf Front Luxury Condo - La Plage-Unit 9 (3 BR)
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $650 off = $4,240 per week
  • bedrooms 3
  • community La Plage
  • rental type Condo
  • sleeps 6
  • baths 3
  • rates (USD) $3,295 - $4,890 /wk
 
 
 
 
 

2 reviews write a review

DEAL!! LaPlage (4 BR) Luxurious,Largest Beachfront
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $650 off = $4,240 per week
  • bedrooms 4
  • community La Plage
  • rental type Condo
  • sleeps 8
  • baths 3
  • rates (USD) $3,295 - $4,890 /wk
 
 
 
 
 

1 reviews write a review

DEAL!! Luxury Gulf Front Condo - La Casa Costiera (3 BR)
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $3,145 per week
  • bedrooms 3
  • community La Casa Costiera
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $2,495 - $3,595 /wk
 
 
 
 
 

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DEAL!! Luxury Gulf Front Condo - Tropical Europa (2 BR)
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $3,055 per week
  • bedrooms 2
  • community Island Paradise
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,595 - $3,395 /wk
 
 
 
 
 

1 reviews write a review

DEAL!! Luxury Gulf Front Condo - Bradenton Beach Club (3 BR)
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $3,145 per week
  • bedrooms 3
  • community Bradenton Beach
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $2,595 - $3,495 /wk
 
 
 
 
 

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DEAL!! Ground Floor Condo ON THE BAY!
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $400 off = $1,100 per week
  • 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!! 2312 Gulf Drive North-Beachfront Condo w/ Pool!
Anna Maria Island Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $1,050 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
 
 
 
 
 

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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 the 4th night FREE -... ($155)
  • bedrooms 1
  • community Tradewinds Resort
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $155 - $265 /nt
    $867 - $1,364 /wk
    $3,500 - $4,640 /mth
 
 
 
 
 

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Ground Floor-Sea Pirate 6
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Sea Pirate Condo
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $90 - $125 /nt
    $665 - $875 /wk
    $2,000 - $3,000 /mth
 
 
 
 
 

3 reviews write a review

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

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Sirenia Beach House Luxury Htd Pool/Spa Steps to beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • community Anna Maria
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $2,950 - $4,300 /wk
 
 
 
 
 

31 reviews write a review

Vista Grande # 3 -- Penthouse Direct Views
Anna Maria Island Condo Rental Picture
  • bedrooms 3
  • community
  • rental type Condo
  • sleeps 6
  • baths 3
  • rates (USD) $449 - $749 /nt
    $3,143 - $5,243 /wk
 
 
 
 
 

1 reviews write a review

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

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) $1,000 - $1,200 /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 - $1,400 /wk
 
 
 
 
 

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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
 
 
 
 
 

40 reviews write a review

Anna Maria Island Beach Paradise
Anna Maria Island Condo Rental Picture
  • 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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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

Anthony Beach Cottages-302 Holmes Beach
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $700 - $1,100 /wk
    $1,900 - $3,000 /mth
 
 
 
 
 

1 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

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
 
 
 
 
 

8 reviews write a review

174 Runaway Bay
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,300 /wk
 
 
 
 
 

2 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

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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Beachfront Bungalow on Gulf of Mexico- April 12-19 available
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

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
 
 
 
 
 

9 reviews write a review

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

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

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

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

Shady Palms; Gulf-Front House on the Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,650 - $2,100 /wk
    $6,500 - $7,800 /mth
 
 
 
 
 

11 reviews write a review

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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Condo in quiet complex
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Sandy Pointe
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $800 - $900 /wk
 
 
 
 
 

1 reviews write a review

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
 
 
 
 
 

20 reviews write a review

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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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

Palms of Cortez 5 miles to IMG Academy and Anna Maria Island
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • community The Palms of Cortez
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $950 - $1,700 /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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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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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
 
 
 
 
 

4 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 - $1,300 /wk
    $2,400 - $3,850 /mth
 
 
 
 
 

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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

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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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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Pelican Cove 15
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $875 - $1,400 /wk
    $2,891 - $4,641 /mth
 
 
 
 
 

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"La Coconut" Two minute walk to beach-Private Heated Pool
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,250 - $1,800 /wk
 
 
 
 
 

1 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) $900 - $1,200 /wk
 
 
 
 
 

2 reviews write a review

Shell Point Condominium Flotilla Drive
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Shell Point
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $3,000 - $3,500 /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
 
 
 
 
 

5 reviews write a review

Shell Point Condominium
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Shell Point
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,000 - $3,000 /mth
 
 
 
 
 

1 reviews write a review

Runaway Bay 1-2 Bedroom Condos and 2 Bedroom Apartment
Anna Maria Island Condo Rental Picture
  • bedrooms 2
  • community Runaway Bay
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $649 - $1,750 /wk
    $2,200 - $5,400 /mth
 
 
 
 
 

28 reviews write a review

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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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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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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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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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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Sandy Pointe II
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • community Sandy Pointe
  • rental type Townhome
  • sleeps 6
  • baths 3
  • rates (USD) $900 - $1,200 /wk
    $3 - $3,500 /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) $1,095 - $1,500 /wk
    $4,250 - $4,950 /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

Luxurious Tropical Oasis! Steps to Beach, Heated Pool
Anna Maria Island Cottage Rental Picture
  • bedrooms 3
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $200 - $280 /nt
    $1,400 - $1,950 /wk
 
 
 
 
 

3 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) $75 - $175 /nt
    $600 - $1,000 /wk
    $1,600 - $3,000 /mth
 
 
 
 
 

3 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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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

LaCasa Costiera Unit 1 Beach June $3000./wk.
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • community La Casa Costiera
  • rental type Villa
  • sleeps 5
  • baths 2
  • rates (USD) $2,800 - $4,000 /wk
 
 
 
 
 

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Beautiful 2 Bedroom Family Home in Bradenton Beach
Anna Maria Island House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $120 /nt
    $700 - $800 /wk
    $2,900 - $3,200 /mth
 
 
 
 
 

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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
 
 
 
 
 

4 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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Gulf Views From Every Room!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $2,583 - $3,483 /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!**
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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$599.00 per week: April at "Beachside Paradise"/
Anna Maria Island Villa Rental Picture
  • bedrooms 1
  • community
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (VEF) Bs.120 - Bs.140 /nt
    Bs.500 - Bs.850 /wk
    Bs.2,000 - Bs.3,200 /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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Anna Maria 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
 
 
 
 
 

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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
    $3,900 - $8,000 /mth
 
 
 
 
 

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ANNA MARIA EASTER SPECIAL $2900 4/19-4/26 ALL IN!
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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ANNA MARIA EASTER WEEK SPECIAL$1200 ALL IN!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • 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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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 - $4,600 /mth
 
 
 
 
 

4 reviews write a review

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
  • sleeps 10
  • baths 3
  • rates (USD) $257 - $800 /nt
    $1,800 - $5,600 /wk
 
 
 
 
 

4 reviews write a review

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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3 bed 2 bath BRAND NEW fully loaded duplex heated pool & spa near beach *EASTER*
Anna Maria Island Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $243 - $307 /nt
    $1,850 - $2,150 /wk
 
 
 
 
 

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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) $1,030 - $1,450 /wk
 
 
 
 
 

8 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
 
 
 
 
 

15 reviews write a review

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) $1,100 - $2,100 /wk
    $4,667 /mth
 
 
 
 
 

13 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)
 
 
 
 
 

7 reviews write a review

ANNA MARIA ISLAND 90 DAY SUMMER SPECIALS MARTINIQUE SOUTH CONDO ON THE BEACH!
Anna Maria Island Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $57 - $115 /nt
    $1,582 - $3,220 /mth
 
 
 
 
 

3 reviews write a review

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
 
 
 
 
 

7 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
    $1,175 - $1,825 /wk
 
 
 
 
 

26 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) $157 - $229 /nt
    $3,600 - $4,500 /mth
 
 
 
 
 

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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
 
 
 
 
 

16 reviews write a review

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

14 reviews write a review

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

4 reviews write a review

Anna Maria New Listing! Water Front Heated Pool & Hot Tub Home 2/2 Sleeps 6.
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 - 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 - $300 /nt
    $1,700 - $2,100 /wk
    $6,650 - $7,800 /mth
 
 
 
 
 

4 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
 
 
 
 
 

9 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)
 
 
 
 
 

11 reviews write a review

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

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
 
 
 
 
 

16 reviews write a review

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

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
 
 
 
 
 

10 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)
 
 
 
 
 

5 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) $2,000 - $4,500 /wk
    $8,000 - $18,000 /mth
 
 
 
 
 

40 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
    $4,802 - $5,103 /wk
 
 
 
 
 

21 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
 
 
 
 
 

8 reviews write a review

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) $229 - $457 /nt
    $1,800 - $3,200 /wk
 
 
 
 
 

38 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
    $2,000 - $2,500 /wk
 
 
 
 
 

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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

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
 
 
 
 
 

34 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
 
 
 
 
 

5 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
  • sleeps 6
  • baths 1
  • rates (USD) $115 - $143 /nt
    $805 - $1,001 /wk
    $3,450 - $4,004 /mth
 
 
 
 
 

4 reviews write a review

SPECIAL PRICE: $1500/WK FOR AVAILABLE WEEKS BETWEEN JAN.8 - FEB.1, 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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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
 
 
 
 
 

6 reviews write a review

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
 
 
 
 
 

5 reviews write a review

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) $200 - $316 /nt
    $1,275 - $1,925 /wk
    $3,825 - $5,775 /mth
 
 
 
 
 

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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) $220 - $337 /nt
    $1,400 - $2,050 /wk
    $4,200 - $6,150 /mth
 
 
 
 
 

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Hurry...Very Special Pricing: $3000/wk for the week of May 10 - May 17, 2014
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $2,625 - $4,125 /wk
 
 
 
 
 

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SUZ'S SEABREEZE: Perfect for Large Families, Heated Pool in Very Tropical Setting!
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 - $1,400 /wk
 
 
 
 
 

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SUMMER BREEZE: Adorable 1 Bed/1 Bath Cottage, With Dock And 250 Steps To Beach
Anna Maria Island Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $700 - $975 /wk
 
 
 
 
 

1 reviews write a review

SERENDIPITY: Special Pricing of $1350/wk for Available Weeks Between May 10 - May 31,2014
Anna Maria Island Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $1,375 - $1,825 /wk
 
 
 
 
 

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Hurry...Special Pricing: $2200/wk for Available Weeks Between May 3-May 31, 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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Hurry...Very Special Pricing: $4250/wk for Available Weeks Between May 3 - May 17, 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

Hurry...Special Pricing:$1200/wk between May 8 - May 17, 2014
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

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, Elevator
Anna Maria Island House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $2,625 - $4,125 /wk
 
 
 
 
 

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Hurry...Special Pricing: $1350/wk for Available Weeks Between May 10-May 31,2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,550 - $2,250 /wk
 
 
 
 
 

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Hurry...Special Pricing: $1600/wk for the week of May 3-May 10, 2014
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: Adorable Villa with Private Heated Pool, Only 2 Blocks to the Beach
Anna Maria Island Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $925 - $1,225 /wk
 
 
 
 
 

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Hurry...Special Pricing: $1100/wk for Available Weeks Between May 10-May 24,2014
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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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: Canal Front, Heated Pool And Only 3 Blocks To The Incredible Gulf Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,600 - $2,000 /wk
 
 
 
 
 

1 reviews write a review

Hurry...Special Pricing:$1600/wk for Available Weeks Between May 17-May 31, 2014
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 11
  • baths 4
  • rates (USD) $2,000 - $2,900 /wk
 
 
 
 
 

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Hurry...Special Pricing:$1200/wk for Available Weeks Between Apr.30-May 31, 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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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: Perfect Ground Level Pool Home, Excellent Location, Very Close to Beach!!!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,600 - $2,400 /wk
 
 
 
 
 

2 reviews write a review

CRESCENT WAVE: Great Ground Level Home, New Heated Pool, Hot Tub, Close to Beac
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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Hurry...Special Pricing: $2500/wk for Available Weeks Between May 11-May 17,2014
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

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: Private Tropical Heated Pool, Short Walk to Bean Pointe and Beach
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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Hurry...Special Pricing:$1200/wk for Available Weeks Between Apr.26-May 24, 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $1,550 - $1,800 /wk
 
 
 
 
 

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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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BAREFOOT BLISS:Coastal Living in a Tropical Setting, Heated Pool, Short Stroll to Beach!
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

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

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 2
  • rates (USD) $214 - $346 /nt
    $1,500 - $2,420 /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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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

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

$1800 WK FEB&JAN!4Bd 3Ba-Luxury Home w Large Shared Heated Pool-2 Blks To Beach
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

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New 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) $1,400 - $1,800 /wk
 
 
 
 
 

3 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) $1,200 - $1,600 /wk
 
 
 
 
 

6 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 - $1,750 /wk
    $2,800 - $3,750 /mth
 
 
 
 
 

10 reviews write a review

Allegria by the Sea ~ RA43580 ~ RA43580
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $225 - $505 /nt
    $1,575 - $3,515 /wk
 
 
 
 
 

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May Deal $2499* ~ 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) $2,499 - $4,600 /wk
 
 
 
 
 

10 reviews write a review

May Deal $1999* Sirenia Cove - Waterfront Heated Pool/Dock Steps to Beaches
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $171 - $571 /nt
    $1,999 - $4,000 /wk
 
 
 
 
 

2 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
  • sleeps 10
  • baths 2
  • rates (USD) $1,890 - $2,780 /wk
    $7,000 /mth
 
 
 
 
 

9 reviews write a review

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
 
 
 
 
 

12 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

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) $111 - $164 /nt
    $850 - $1,150 /wk
 
 
 
 
 

19 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

Heated Pool, Canal/Dock, Single Story, Minutes to Gulf Beach & Shops, North End
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $275 /nt
    $1,200 - $1,900 /wk
 
 
 
 
 

2 reviews write a review

Paradise is Waiting! Steps to Beach, Luxury Cottage with Heated Pool, and More!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $257 - $279 /nt
    $1,600 - $1,950 /wk
 
 
 
 
 

5 reviews write a review

Big Savings in May!! 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) $1,395 - $1,850 /wk
    $5,000 - $6,660 /mth
 
 
 
 
 

2 reviews write a review

Champagne Shores: Adorable, Great Location, Heated Pool, Short Block to Beach
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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My Big Fat Beach House: A Premier Island Home, Heated Pool, Hot Tub, Waterfall
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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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) $221 /nt
 
 
 
 
 

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5 Bedroom, 3 Baths Ground Level, Private Home w/private Heated Pool, Near Beach
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,400 - $3,500 /wk
 
 
 
 
 

3 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

4 Bed 3.5 Bath Keywest Style Home - Pool, Hot Tub And Game Room Too!
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 13
  • baths 3
  • rates (USD) $217 - $450 /nt
    $2,000 - $3,000 /wk
    $6,000 - $9,750 /mth
 
 
 
 
 

2 reviews write a review

3 bedroom, 2 bath; private upscale pool home. Ping pong!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,300 - $1,850 /wk
    $4,420 - $6,290 /mth
 
 
 
 
 

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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
 
 
 
 
 

20 reviews write a review

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

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) $2,795 - $5,190 /wk
 
 
 
 
 

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Walk to beach and private pool! bikes, quiet street. slice of AMI paradise!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $214 - $257 /nt
    $1,700 - $1,800 /wk
    $5,400 /mth
 
 
 
 
 

16 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 - $507 /nt
    $2,250 - $3,550 /wk
    $8,000 /mth
 
 
 
 
 

4 reviews write a review

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
 
 
 
 
 

20 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

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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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) $1,300 - $1,850 /wk
    $4,420 - $6,290 /mth
 
 
 
 
 

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Spacious 2bd, 2ba-tiki & waterfall in pool-private location-2blks to beach
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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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

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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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

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

Sea Turtle: Great Gound Level Home with Private Heated Pool, Two Blocks 2 Beach!
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,300 - $1,650 /wk
 
 
 
 
 

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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
 
 
 
 
 

3 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

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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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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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) $186 - $214 /nt
    $1,300 - $1,500 /wk
 
 
 
 
 

1 reviews write a review

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

1 reviews write a review

Seahorse Cove: 4BR/5.5BA Family-Friendly Pool Home with Dock
Anna Maria Island House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 6
  • rates (USD) $496 - $571 /nt
    $3,475 - $4,000 /wk
 
 
 
 
 

7 reviews write a review

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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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) $171 - $229 /nt
    $1,200 - $1,600 /wk
 
 
 
 
 

2 reviews write a review

Beautiful Villa by the Sea: 3BR/3BA Family- and Pet-Friendly Pool Home
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $200 - $286 /nt
    $1,400 - $2,000 /wk
 
 
 
 
 

1 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
 
 
 
 
 

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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 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
 
 
 
 
 

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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
 
 
 
 
 

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Hurry...Special Pricing: $1200/wk for Available Weeks Between May 10-May 24, 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,400 - $1,800 /wk
 
 
 
 
 

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ANCHORS AWAY: Adorable 2 Bed/2 Bath Villa, Private Heated Pool, Block To Beach
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: Adorable Villa with PRIVATE Heated Pool, Very Short Block to Beach!
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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Hurry...Special Pricing: $3300/wk for Available Weeks Between April 26-May 17, 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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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

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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Hurry...Very Special Pricing: $2500/wk for the week of April 26 - May 3, 2014
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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Hurry...Special Pricing: $1600/wk for Available Weeks Between Apr.26-May 17,2014
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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Hurry...Special Pricing: $1350/wk for Available Weeks Between May 3-May 31, 2014
Anna Maria Island House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,425 - $1,875 /wk
 
 
 
 
 

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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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BEACH WALK: Steps to Beach, Heated Pool with Waterfall in a 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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BEACH DAZE: Awesome Villa with Private Heated Pool and Just a Block to the Gorgeous Gulf 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 RETREAT 206: 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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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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Hurry...Special Price: $2200/wk for Available Weeks Between May 17-May 31, 2014
Anna Maria Island House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $1,750 - $4,250 /wk
 
 
 
 
 

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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) $115 - $157 /nt
    $750 - $1,100 /wk
 
 
 
 
 

8 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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2 Bedroom, 2 Bath; Private Pool; 8 Houses To The North End Beaches!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,150 - $1,575 /wk
    $3,910 - $5,355 /mth
 
 
 
 
 

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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
 
 
 
 
 

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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
 
 
 
 
 

2 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
 
 
 
 
 

1 reviews write a review

Anna Maria Island/Holmes Beach/Berry Dune
Anna Maria Island Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • sleeps 8
  • baths 4
  • rates (USD) $3,500 /wk
 
 
 
 
 

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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
 
 
 
 
 

18 reviews write a review

Palm Paradise: Great Ground Level Heated Pool Home, 5 Houses to Beach, Remodeled
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
 
 
 
 
 

3 reviews write a review

GOING COASTAL: Adorable Canalfront With Dock And Private Heated Pool, North End!
Anna Maria Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,400 /wk
 
 
 
 
 

1 reviews write a review

August/Autumn 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) $1,250 - $2,100 /wk
    $3,600 - $5,400 /mth
 
 
 
 
 

16 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 - $6,500 /mth
 
 
 
 
 

19 reviews write a review

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 - $2,497 /wk
 
 
 
 
 

5 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
 
 
 
 
 

16 reviews write a review

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) $2,625 - $3,500 /wk
 
 
 
 
 

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
 
 
 
 
 

6 reviews write a review