Longboat Key Vacation Rentals

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Craig House with Heated Pool
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Craig House with Heated Pool

2 Bedrooms
2 Bathrooms
4.84IconIconIconIconIcon
83 reviews
$151 - $205 / night
(excl. fees & taxes)
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Anna Maria Island - Azure Bliss Vacation Home
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Anna Maria Island - 3Bed 2Bath Home - Private Heated Pool - Walk to Beach

3 Bedrooms
2 Bathrooms
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49 reviews
$500 / night
(excl. fees & taxes)
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Beach Downtown Pet-friendly 1 BD @ The Park
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Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.

1 Bedroom
1 Bathroom
4.86IconIconIconIconIcon
14 reviews
$95 - $263 / night
(excl. fees & taxes)
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Poolside paradise LillyBug Lane LLC
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Poolside paradise LillyBug Lane LLC

4 Bedrooms
4 Bathrooms
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1 review
$300 - $550 / night
(excl. fees & taxes)
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Beach, Bay, Food, Fun - 2BD/2BA
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Beach, Bay, Food, Fun - 2BD/2BA

2 Bedrooms
2 Bathrooms
4.67IconIconIconIconIcon
9 reviews
$174 - $250 / night
(excl. fees & taxes)
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Tropical Beach Condo!
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Peaceful and Serene

1 Bedroom
1 Bathroom
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11 reviews
$200 - $300 / night
(excl. fees & taxes)
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Gulf-to-Bay Living on Longboat Key
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Waterfront condo paradise. Island living. Ground floor. 2 Bd, 2 Ba. Private harbour community, 4 heated pools, Gulf-front pavilion.

2 Bedrooms
2 Bathrooms
$180 / night
(excl. fees & taxes)
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Panoramic Gulf View with Amazing Sunset.
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Spacious Condo, 1 huge Bedroom, 2 very comfortable Queen beds. One Sofa sleeper in the living room. What you see is what you get to view every day.

1 Bedroom
1 Bathroom
4.84IconIconIconIconIcon
188 reviews
$229 - $390 / night
(excl. fees & taxes)
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Turtle Crawl Inn 64
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Beach Front One Bedroom Condo Paradise. Fully Remodeled.

1 Bedroom
1 Bathroom
4.88IconIconIconIconIcon
73 reviews
$229 - $389 / night
(excl. fees & taxes)
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Turtle Crawl Inn 63
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Beach Front Condo Paradise. Ground Floor. Studio.

0 Bedroom
1 Bathroom
4.74IconIconIconIconIcon
88 reviews
$198 - $275 / night
(excl. fees & taxes)
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Condo with a View on Longboat Key
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Kick Back and Relax

0 Bedroom
1 Bathroom
4.98IconIconIconIconIcon
122 reviews
$225 - $275 / night
(excl. fees & taxes)
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The Surof House
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Anna Maria Island Direct Beach/ Gulf Views

2 Bedrooms
1 Bathroom
$550 - $1035 / night
(excl. fees & taxes)
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Merry Mermaid Tree House
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Almost Beachfront, private pool/spa backyard oasis, Gulf views!

3 Bedrooms
3 Bathrooms
$1000 - $1300 / night
(excl. fees & taxes)
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Making Waves
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Heated Pool/Walk to Anna Maria Beaches/Restaurants

3 Bedrooms
3 Bathrooms
$603 - $900 / night
(excl. fees & taxes)
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Welcome to Paradise
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6 miles from Anna Maria Island Beaches

3 Bedrooms
2 Bathrooms
$170 / night
(excl. fees & taxes)
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Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub
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Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

3 Bedrooms
2 Bathrooms
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50 reviews
$500 - $650 / night
(excl. fees & taxes)
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Bradenton Boho Bungalow
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NO CLEANING FEE-Heated Pool-Completely Remodeled-King Beds-Close to IMG, restaurants & beaches-2GB Fiber Internet-10% off 7+ nights

3 Bedrooms
2 Bathrooms
$300 - $365 / night
(excl. fees & taxes)
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Heated Saltwater Pool+Private Yard+AMI in 5 Miles!
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Prime location+Private HTD Saltwater Pool+Spacious Master Suite w/private pool access. New Furniture, Appliances, Quartz Countertops, Travertine Patio

4 Bedrooms
2 Bathrooms
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3 reviews
$274 - $834 / night
(excl. fees & taxes)
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2 Neighboring Homes with Pools! Close to AMI/IMG!
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Rent 2 homes right next to each other! Perfect for multiple families and friends. Both homes are 3BR/2 bath with pools.

6 Bedrooms
4 Bathrooms
$798 - $1143 / night
(excl. fees & taxes)
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Gulf Coast Home w/Private Pool  Near AMI & Beaches
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Updated two stories home with private pool, pool table, ping pong table and games. Only 5 miles to Anna Maria Island and 23 miles to Siesta Key.

4 Bedrooms
3 Bathrooms
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13 reviews
$399 - $629 / night
(excl. fees & taxes)
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Gorgeous Beach Home with heated pool and dock
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Gorgeous Beach Home with dock

3 Bedrooms
3 Bathrooms
$300 - $500 / night
(excl. fees & taxes)
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New 1 BD Downtown Beach-town Apartment Nov 2023
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Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.

1 Bedroom
1 Bathroom
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2 reviews
$95 - $263 / night
(excl. fees & taxes)
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Beachtown Pet-Friendly Downtown Home @ The Park
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Beach-town Pet-Friendly Downtown Sarasota Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.

3 Bedrooms
3½ Bathrooms
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26 reviews
$213 - $566 / night
(excl. fees & taxes)
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Beach Downtown Pet-friendly @ The Park Home
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Beach Downtown Sarasota Pet-friendly Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.

3 Bedrooms
3½ Bathrooms
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22 reviews
$213 - $566 / night
(excl. fees & taxes)
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Tropical Escape Sarasota
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Real Florida Up Close!

3 Bedrooms
2 Bathrooms
$135 - $274 / night
(excl. fees & taxes)
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