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276 villas

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Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

2 bedrooms
2 bathrooms

sleeps 6

Match: Rental types Bicycles available Safe

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Price per night from

$273

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$160

Port Charlotte 3 bedroom, 2 bathroom heated pool villa

Port Charlotte villa

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$99

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$193

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$262

River Strand Luxury Condo-Tennis & Golf Community

Bradenton condo

2 bedrooms
2 bathrooms

sleeps 5

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$86

Enjoy our pool and prime location for beach, downtown and bike trail.

Venice house

2 bedrooms
2 bathrooms

sleeps 4

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$149

Heritage Oaks

Heritage Oaks Golf and Country Club condo

2 bedrooms
2 bathrooms

sleeps 5

Responds fast! avg. 3 hours 56 minutes

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$98

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$434

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

2 bedrooms
2 bathrooms

sleeps 4

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$1,026

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$177

Beautiful Longboat Key Home!

Bradenton Beach house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 27 minutes

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$514

White Sand Beaches- Bayfront Park

Anna Maria house

3 bedrooms
2 bathrooms

sleeps 8

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$628

Beach Get-Away Downtown Pet-Friendly 1 bedroom apartment at a 10 acre park-633

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$137

Cloud 9

Anna Maria house

5 bedrooms
5 bathrooms

sleeps 8

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$1,940

Once Upon a Tide: By Beachside Management

Siesta Key apartment

3 bedrooms
2 bathrooms

sleeps 8

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$399

A Tide That Binds Us - 602: By Beachside Management

Siesta Key townhouse

3 bedrooms
3 bathrooms

sleeps 9

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$490

Beach Walk: By Beachside Management

Siesta Key townhouse

3 bedrooms
3 bathrooms

sleeps 8

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$513

Buena Vida: By Beachside Management

Siesta Key house

4 bedrooms
5 bathrooms

sleeps 10

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Price per night from

$513

A Somewhere Is Here - Changes in Attitude: By Beachside Management

Siesta Key apartment

3 bedrooms
3 bathrooms

sleeps 9

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$410

A Somewhere is Here - Changes in Latitude: By Beachside Management

Siesta Key apartment

3 bedrooms
3 bathrooms

sleeps 9

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Price per night from

$456

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$189

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 1 minutes

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$265

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

3 bedrooms
3 bathrooms

sleeps 8

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$741

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$117

Florida Ocean Front Condo

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$620

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

3 bedrooms
2 bathrooms

sleeps 8

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$627

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

2 of 3 match: Rental types, Bicycles available, Safe

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Price per night from

$114