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Vacation Rentals in Longboat Key, Florida

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about Longboat Key

Longboat Key, Florida Vacation Rentals and Tourism

When you want your next vacation to be peaceful, scenic, and utterly refreshing, check into Longboat Key vacation rentals. Combining a charming town with a laid-back atmosphere means that vacation success is virtually assured – that is if you choose wisely and give Longboat Key Florida rentals a chance to shine.

  • Need help planning your travels? Then look no further than Vacation Rentals.com comprehensive and free Longboat Key Travel Guide.

Longboat Key FL vacation rentals outfitted with washer/dryers, kitchens, closets and views of the Gulf will win you over in no time; be careful of getting too used to such a sweet lifestyle. In addition to enjoying nature you can also shop, dine and tour the top-notch nearby aquarium, so if you do decide to stay for longer than you had originally planned, you’ll find yourself wanting for nothing.

Longboat Key vacation home rentals will suit families, big groups of friends and couples, too. Multi-faceted destinations can only be considered truly welcoming if they have something along the lines of Longboat Key cottage rentals intertwined in their landscape, so feel confident that this upcoming Florida vacation has true potential.

Make this potential a reality by carefully browsing the Longboat Key, FL condo rentals found here and finding the one that stands out. Your biggest problem will likely be that there's more than just one Longboat Key condo rental that you like, but what a good problem to have! 

You are sure to have a fabulous time at Longboat Key on your next vacation, and you don't want to miss out on Longboat Key vacation rental last-minute and low-budget deals. Longboat Key discount vacation rentals can accommodate any sized group or any sized budget.  With our wide variety of Longboat Key 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 Longboat Key vacation rental deals! With all the tennis you can play down there, we thought we'd serve you an ace of a deal.

 

more destinations

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

Longboat Key things to do

 

The Ringling

Un incontournable dans la région. Il y en a pour toute la famille. Le domaine en soi vaut le détour avec ses points de vue remarquables, sa vue imprenable...read more

 

Lido Beach

Absolutely loved it here. What's not to love about the gulf?!!! What sets this beach apart from others in the area is that it has a concession stand...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

 

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

 

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

 

Mote Marine Laboratory & Aquarium

This place is great, and I love love love it. What not to expect: Tampa Aquarium, Shedd Aquarium, the Chattanooga Aquarium, etc. If you've visited the...read more

 

Sea Life Kayak Adventures

Sea Life Kayak Adventures in Sarasota. Tom was our guide. Highlight of our trip! We just returned from the wildlife exploration with Tom. We had a great...read more

 

Stay Anna Maria Island

Anna Maria Island has to have one of the best beaches I have been to during my 13+ years of living in Florida. I just visited this past weekend and 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

 

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

 

Siesta Key Beach

Most beautiful beach you'll see, travel the world & come back. You'll appreciate what I mean. The sand is the consistency of powder. It never feels hot to...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

 

Sarasota Jungle Gardens

I was very excited about Jungle Gardens. According to TripAdvisor, it is "an Old Florida attraction since 1939. Sarasota Jungle Gardens allows visitors to...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

 

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

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DEAL!! Dec Deal Gulf Beach Front & View 2 Pools Spa, 8 Tennis Crts
Longboat Key Condo Rental Picture
  • Condo Rental Deals and Discounts $1,000 off = $3,000 per month
  • bedrooms 2
  • community Club Longboat
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,200 /wk
    $2,500 - $6,500 /mth
 
 
 
 
 

7 reviews write a review

DEAL!! Direct Gulf Front Large Private Balcony with 180 Degree View
Longboat Key Condo Rental Picture
  • Condo Rental Deals and Discounts $56 off = $119 per night
  • bedrooms 1
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $170 - $240 /nt
    $910 - $1,505 /wk
 
 
 
 
 

5 reviews write a review

DEAL!! Longboat Key - Beachcomber - Unit 505
Longboat Key Condo Rental Picture
  • Condo Rental Deals and Discounts $36 off = $99 per night
  • bedrooms 1
  • community Beachcomber
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $190 /nt
 
 
 
 
 

1 reviews write a review

DEAL!! ~New Direct Ocean Front Condo~1 Bedroom & Studio~
Longboat Key Condo Rental Picture
  • Condo Rental Deals and Discounts $51 off = $99 per night
  • bedrooms 1
  • community The Beach on Longboat Key
  • rental type Condo
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $110 - $240 /nt
    $770 - $1,610 /wk
 
 
 
 
 

4 reviews write a review

DEAL!! New Beach Condo, Short Stays, Specials, Free WiFi!!
Longboat Key Condo Rental Picture
  • Condo Rental Deals and Discounts $15 off = $125 per night
  • bedrooms 1
  • community Silver Sands
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $250 /nt
    $875 - $1,750 /wk
 
 
 
 
 

21 reviews write a review

DEAL!! On The Beach. Unit 303 completely renovated in 2014
Longboat Key Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $990 per week
  • bedrooms 1
  • community Beachcomber
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $135 - $190 /nt
    $945 - $1,330 /wk
    $2,600 - $4,250 /mth
 
 
 
 
 

8 reviews write a review

DEAL!! Gulf Front One Bedroom Awesome View On The Beach End Unit
Longboat Key Condo Rental Picture
  • Condo Rental Deals and Discounts 15% off = $161 per night
  • bedrooms 1
  • community The Beach on Longboat Key
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $175 - $295 /nt
    $1,200 - $2,065 /wk
 
 
 
 
 

4 reviews write a review

3 Bedroom Luxury Gulf Front Condo
Longboat Key Condo Rental Picture
  • bedrooms 3
  • community La Playa
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,100 - $2,915 /wk
 
 
 
 
 

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Bayside condo steps from the Gulf
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Portobello
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,000 - $4,500 /mth
 
 
 
 
 

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Condo On The Beach
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $1,000 - $2,200 /wk
    $3,500 - $5,000 /mth
 
 
 
 
 

2 reviews write a review

Bayfront Longboat Key House with Pool and Beach Access
Longboat Key House Rental Picture
  • bedrooms 3
  • community Covert II and III
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,300 - $1,800 /wk
 
 
 
 
 

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Sunset Beach House on the BEACH
Longboat Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 7
  • baths 3
  • rates (USD) $2,000 - $3,200 /wk
 
 
 
 
 

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Beautiful Pool Home steps from Beach or Bay
Longboat Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,400 /wk
    $4,200 /mth
 
 
 
 
 

4 reviews write a review

Luxury Home private pool, dock & walk to beach in Longboat
Longboat Key House Rental Picture
  • bedrooms 5
  • community Sleepy Lagoon
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $3,800 - $3,900 /wk
    $9,700 - $9,950 /mth
 
 
 
 
 

12 reviews write a review

January Available, Amazing View/sunsets
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Covert II and III
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,250 /wk
    $5,000 /mth
 
 
 
 
 

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Spacious condo - Beach and bay - Covert I
Longboat Key Condo Rental Picture
  • bedrooms 1
  • community Covert I
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $675 - $850 /wk
 
 
 
 
 

2 reviews write a review

Family friendly FL Oasis- walk to beach, bring boat
Longboat Key House Rental Picture
  • bedrooms 3
  • community Sleepy Lagoon
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $1,500 - $1,700 /wk
    $4,900 - $5,900 /mth
 
 
 
 
 

5 reviews write a review

Secluded Beachfront on Serene Gulf of Mexico
Longboat Key Villa Rental Picture
  • bedrooms 2
  • community Cabana Beach Club
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $230 - $360 /nt
    $1,595 - $2,495 /wk
 
 
 
 
 

1 reviews write a review

Stunning Waterfront 3 bedroom home with pool/boat dock
Longboat Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $4,000 - $7,500 /mth
 
 
 
 
 

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LongBoat Key Country Club with pool boat dock and beach
Longboat Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $150 /nt
    $950 - $1,150 /wk
    $3,900 - $4,500 /mth
 
 
 
 
 

7 reviews write a review

Gulf Beachfront at Whitney Beach, LBK
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Whitney Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $300 /nt
    $1,400 - $1,800 /wk
    $3,500 - $5,900 /mth
 
 
 
 
 

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Adorable Beach Cottage
Longboat Key Cottage Rental Picture
  • bedrooms 1
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,000 - $1,150 /wk
 
 
 
 
 

4 reviews write a review

Cottage on sailboat water, walk to beach, bring the family!
Longboat Key House Rental Picture
  • bedrooms 3
  • community Sleepy Lagoon
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths
  • rates (USD) $200 - $315 /nt
    $1,400 - $2,200 /wk
    $3,950 - $6,000 /mth
 
 
 
 
 

2 reviews write a review

Historic Village Cottage for One or for All
Longboat Key House Rental Picture
  • bedrooms 3
  • community Longbeach Village
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $950 - $1,050 /wk
    $2,900 - $3,200 /mth
 
 
 
 
 

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Beach time at Cedars, great deal.....
Longboat Key House Rental Picture
  • bedrooms 2
  • community Cedars
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $825 - $1,600 /wk
 
 
 
 
 

1 reviews write a review

Beautiful Gulf View Condo on White Sandy Beach
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Sand Cay Beach Resort
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $199 - $314 /nt
    $1,393 - $2,195 /wk
    $4,500 - $8,500 /mth
 
 
 
 
 

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2 bedroom beachfront villa
Longboat Key House Rental Picture
  • bedrooms 2
  • community Turtle Crawl
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $999 - $2,199 /wk
 
 
 
 
 

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Longboat Key Mid Century Modern Beach House Rental
Longboat Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $1,800 - $2,200 /wk
    $4,000 - $6,000 /mth
 
 
 
 
 

1 reviews write a review

Pristine Gulffront Complex: Fall '14 Available
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Club Longboat
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 - $4,800 /mth
 
 
 
 
 

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Whitney Beach Condo-Just Renovated-Steps from Beach & Bay
Longboat Key Condo Rental Picture
  • bedrooms 1
  • community Whitney Beach
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,800 - $3,200 /mth
 
 
 
 
 

1 reviews write a review

Sand Cay: Small beach resort!
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Sand Cay Beach Resort
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $91 - $250 /nt
    $950 - $1,750 /wk
 
 
 
 
 

4 reviews write a review

Sea Pines - Incredible natural beauty with simply amazing vi
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Sea Pines
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $4,700 - $5,700 /mth
 
 
 
 
 

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Inviting and serene getaway on Longboat Key
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Whitney Beach
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $2,500 - $3,600 /mth
 
 
 
 
 

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Covert II
Longboat Key Condo Rental Picture
  • bedrooms 1
  • community Covert II and III
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $900 - $1,200 /wk
    $3,000 - $4,200 /mth
 
 
 
 
 

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Whitney Beach Villa - Steps from the Beach, Docks & Pool!
Longboat Key Villa Rental Picture
  • bedrooms 2
  • community Whitney Beach
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $2,000 - $3,500 /mth
 
 
 
 
 

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Little Gull Cottages
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Little Gull
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $120 - $375 /nt
    $700 - $2,500 /wk
 
 
 
 
 

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Covert Two
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $1,250 - $1,500 /wk
    $4,500 - $4,900 /mth
 
 
 
 
 

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Gulf Tides of Longboat Key
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Gulf Tides
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $100 - $300 /nt
    $600 - $2,000 /wk
 
 
 
 
 

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Gulfside Villa on North Longboat Key
Longboat Key Villa Rental Picture
  • bedrooms 2
  • community
  • rental type Villa
  • sleeps 4
  • baths 2
  • rates (USD) $800 - $1,480 /wk
    $2,000 - $3,700 /mth
 
 
 
 
 

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Breathtaking Sunrises Over Buttonwood Cove
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Buttonwood Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $2,750 - $4,000 /mth
 
 
 
 
 

2 reviews write a review

Sea Pines
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $2,000 - $5,250 /mth
 
 
 
 
 

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Welcome to Paradise: Charming Condo with Spectacular Views
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Longboat Harbour
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $2,500 - $3,200 /mth
 
 
 
 
 

4 reviews write a review

Beautiful One Bedroom Beachfront Condo on the Gulf
Longboat Key Condo Rental Picture
  • bedrooms 1
  • community Covert II and III
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $2,400 - $3,200 /mth
 
 
 
 
 

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Direct Beachfront Condominium - Spectacular Sunsets
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Portobello
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $5,500 - $6,500 /mth
 
 
 
 
 

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Beachside Ground Floor Corner Unit Steps to the Beach
Longboat Key Condo Rental Picture
  • bedrooms 3
  • community Covert II and III
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,100 - $1,300 /wk
    $2,900 - $4,500 /mth
 
 
 
 
 

1 reviews write a review

Whitney Beach condo in Longboat Key
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Whitney Beach
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $3,500 - $4,200 /mth
 
 
 
 
 

1 reviews write a review

Secluded Beachfront Condo On The Gulf!
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Sea PInes
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $1,600 - $2,000 /wk
    $4,000 - $5,800 /mth
 
 
 
 
 

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Gulf-Front Condo-New Bths+Kitchen.Will discount 10% for 4 mo
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Longboat Harbour
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $3,750 - $4,800 /mth
 
 
 
 
 

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La Playa Beach Resort - Special!
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $159 - $213 /nt
    $1,110 - $1,490 /wk
 
 
 
 
 

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Longboat Bay Club Condo in Sarasota 3/28/15 - 4/4/15
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Longboat Bay Club
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 /wk
 
 
 
 
 

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3 Bedroom Beachfront Condo!!!
Longboat Key Condo Rental Picture
  • bedrooms 3
  • community La Playa
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,800 - $2,500 /wk
 
 
 
 
 

1 reviews write a review

Beautiful oceanfront condo
Longboat Key House Rental Picture
  • bedrooms 1
  • community Beachcomber
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $600 - $1,100 /wk
 
 
 
 
 

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Beach Castle Resort Gulf to Bay 1st Floor Condo
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Beach Castle Resort
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,750 /wk
 
 
 
 
 

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Longboat Bay Club
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Longboat Bay Club
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $285 /nt
    $950 - $1,900 /wk
 
 
 
 
 

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Beautiful island, gorgeous condo
Longboat Key Condo Rental Picture
  • bedrooms 2
  • community Longboat Harbour
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,400 - $3,200 /mth
 
 
 
 
 

1 reviews write a review

!1st Floor Unit Steps from the Beach. $100 Visa Gift Card last minute specials
Longboat Key Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $139 - $192 /nt
    $970 - $1,342 /wk
 
 
 
 
 

31 reviews write a review

7 nights for the price of 6 for each week's stay! Spectacular Beachfront Condo
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,400 - $1,785 /wk
 
 
 
 
 

2 reviews write a review

Turtle Crawl Unit 204, Enjoy the spectacular view from this condo at Turtle Crawl, a beach lover's paradise
Longboat Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $195 - $260 /nt
    $1,365 - $1,820 /wk
    $3,675 - $5,460 /mth
 
 
 
 
 

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FB144 - Fairway Bay 144 - Enjoy a terrific holiday at Fairway Bay, one of south Longboat Key's most coveted addresses!
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $3,750 - $5,500 /mth
 
 
 
 
 

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Direct Gulf Access - White Sandy Beach - Heated Pool - Tennis
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $160 - $239 /nt
    $1,050 - $1,670 /wk
    $3,980 /mth
 
 
 
 
 

8 reviews write a review

Rent the Historic and Famous Longboat Key Beach House Weekly.
Longboat Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $3,000 - $4,000 /wk
 
 
 
 
 

53 reviews write a review

Beautiful home situated on prestine Longboat Key beach!
Longboat Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $2,000 - $3,200 /wk
 
 
 
 
 

3 reviews write a review

Beautiful Complex on the Beach. Family-friendly And Family Fun
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $183 - $239 /nt
    $1,281 - $1,670 /wk
    $4,395 - $6,475 /mth
 
 
 
 
 

2 reviews write a review

Charming Beach House Private Pool, Dock, Beach Access in Longboat Key
Longboat Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 - $1,700 /wk
    $4,000 - $5,300 /mth
 
 
 
 
 

35 reviews write a review

Charming Canal Home With Private Dock, Enclosed Pool And Short Walk To Beach
Longboat Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,400 /wk
    $4,000 /mth
 
 
 
 
 

19 reviews write a review

PREMIER BEACHFRONT HOUSE - THE ULTIMATE IN LUXURY
Longboat Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

12 reviews write a review

Totally Redone & Upgraded Condo Directly on Sandy Beach
Longboat Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $186 - $258 /nt
    $1,172 - $1,625 /wk
 
 
 
 
 

7 reviews write a review

Home On The Water just off the Gulf of Mexico With Large Pool
Longboat Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $4,200 - $7,000 /wk
 
 
 
 
 

1 reviews write a review

Pet Friendly with Gulf Views
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $125 /nt
 
 
 
 
 

35 reviews write a review

Longboat Key Gulf-Front Paradise Condominium
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $179 - $239 /nt
    $1,199 - $1,499 /wk
 
 
 
 
 

21 reviews write a review

Outstanding Beachfront Resort - 2014/2015 Award of Excellence Winner
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $159 - $232 /nt
    $1,115 - $1,625 /wk
 
 
 
 
 

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Luxury Single Family Beach House (Movie Theatre and Gym)
Longboat Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $3,150 - $4,200 /wk
    $11,200 - $16,800 /mth
 
 
 
 
 

5 reviews write a review

Beachfront Property Longboat Key
Longboat Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,750 - $2,765 /wk
    $7,500 /mth
 
 
 
 
 

2 reviews write a review

Beach & Boater's Paradise
Longboat Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $2,300 - $3,000 /wk
    $6,200 - $8,000 /mth
 
 
 
 
 

6 reviews write a review

Gulf Breezes, Soft Sand-Your Place on the Beach
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Luxury Single Family Tranquil Beach House
Longboat Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $200 /nt
 
 
 
 
 

3 reviews write a review

Beautiful Ocean View Condos on Soft White Sandy Beach
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $177 - $314 /nt
    $1,179 - $2,195 /wk
 
 
 
 
 

3 reviews write a review

Tropical Warmth Awaits You -Sept/Oct/Nov Special- 25% Off!
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $159 - $232 /nt
    $4,300 - $6,475 /mth
 
 
 
 
 

33 reviews write a review

Updated Condo in Serene Setting with Beach and Bay Access
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $5,000 /mth
 
 
 
 
 

1 reviews write a review

Luxurious, fully renovated, first floor condo with Golf Course view.
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $130 - $230 /nt
 
 
 
 
 

1 reviews write a review

Lovely, Updated And Convenient
Longboat Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $200 /nt
    $950 - $1,400 /wk
    $2,750 /mth
 
 
 
 
 

3 reviews write a review

Gulf Front, luxury condominium - Long Boat Key, FL
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $3,500 - $6,000 /mth
 
 
 
 
 

6 reviews write a review

Waterfront Home In Country Club Shores With Private Dock/Pool
Longboat Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $4,000 /wk
    $8,000 - $8,500 /mth
 
 
 
 
 

8 reviews write a review

Top floor with breathtaking views of the beach
Longboat Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $150 - $250 /nt
    $995 - $1,750 /wk
    $3,980 - $6,600 /mth
 
 
 
 
 

2 reviews write a review

3 Bedroom/3bath Vacation Rental in Private Gated Community
Longboat Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 3
  • rates (USD) $6,000 /mth
 
 
 
 
 

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Perfect Beach Getway!
Longboat Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $300 - $416 /nt
    $2,100 - $2,915 /wk
 
 
 
 
 

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Freshly renovated condo just on the Beach with hotel service
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $300 /nt
    $2,000 /wk
    $5,000 /mth
 
 
 
 
 

3 reviews write a review

Spectacular Gulf View (2 month minimum)
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $5,063 - $6,200 /mth
 
 
 
 
 

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Gated Luxury in Gulfside Paridise
Longboat Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,616 - $4,650 /mth
 
 
 
 
 

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Beautiful Ground-floor Beachfront Condo On The Gulf
Longboat Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $129 - $143 /nt
    $3,000 - $3,200 /mth
 
 
 
 
 

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Luxury Family Friendly Italian Villa With Private Beach On Longboat Key
Longboat Key Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 6
  • baths
  • rates (USD) $2,500 - $4,000 /wk
    $4,800 - $8,000 /mth
 
 
 
 
 

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Waterfront Country Club Shores With Heated Pool And Private Dock
Longboat Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $6,000 /wk
    $12,000 /mth
 
 
 
 
 

2 reviews write a review

Sea Grape Inn in Longboat Key
Longboat Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

1 reviews write a review