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Siesta Key Vacation Homes and Villas with Pools

Find Luxury Places to Stay Near Siesta Key with a Swimming Pool. Find pool in Siesta Key, Florida.

Pool

Only stays with pool access are shown on this page

129 stays

a living room with a couch and a table at Beach Cottage with heated pool just off Siesta Key in Sarasota

From US $263

Beach Cottage with heated pool just off Siesta Key Pool available

9.5 (62 Reviews) Apartment

The entire place is yours • 70 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.7km from Siesta Beach

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a living room with a couch and a fireplace at Fantastic Island House 1 mile to the beach with heated pool in Sarasota

From US $278

Fantastic Island House 1 mile to the beach with heated pool Pool available

8.6 (20 Reviews) Holiday_home

The entire place is yours • 116 m² size • Free on-site parking

Siesta Key Siesta Beach • 2.8km from Siesta Beach

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a swimming pool with lounge chairs and palm trees at Siesta Key Beach Resort and Suites in Sarasota

From US $310

Siesta Key Beach Resort and Suites Pool available

8.8 (556 Reviews) Villa

Houses • Private parking • Outdoor swimming pool

Siesta Key Siesta Beach • 1.5km from Siesta Beach

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a view of a beach from a balcony at Crescent Arms Condominiums in Siesta Key

From US $615

Crescent Arms Condominiums Pool available

9.1 (11 Reviews) Holiday_home

The entire place is yours • 84 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.9km from Siesta Beach

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a large blue swimming pool with a white fence at Florinda 3bdr/2bth 2car garage with New Pool in Sarasota

From US $453

Florinda 3bdr/2bth 2car garage with New Pool Pool available

8.9 (67 Reviews) Holiday_home

The entire place is yours • 130 m² size • Kitchen

Siesta Key Siesta Beach • 3.6km from Siesta Beach

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a swimming pool in front of a house at Siesta Key Beachside Villas in Sarasota

From US $352

Siesta Key Beachside Villas Pool available

8.7 (359 Reviews) Villa

Houses • Private parking • Outdoor swimming pool

Siesta Key Siesta Beach • 1.8km from Siesta Beach

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a tennis court with palm trees in the background at Tranquil Court Oasis in Sarasota

From US $723

Tranquil Court Oasis Pool available

10.0 (5 Reviews) Villa

The entire place is yours • 372 m² size • Kitchen

Siesta Key Siesta Beach • 3.8km from Siesta Beach

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a wooden deck with a chair and a table on a river at Siesta Heron Suites & Villas in Siesta Key

From US $350

Siesta Heron Suites & Villas Pool available

8.8 (168 Reviews) Holiday_home

Houses • Free on-site parking • Outdoor swimming pool

Siesta Key Siesta Beach • 4.9km from Siesta Beach

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a swimming pool with two lounge chairs in it at Luxury 3BD house, Siesta Key Beach in Sarasota

From US $486

Luxury 3BD house, Siesta Key Beach Pool available

9.9 (29 Reviews) Holiday_home

The entire place is yours • 158 m² size • Kitchen

Siesta Key Siesta Beach • 3.8km from Siesta Beach

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a bedroom with a bed with a bottle of wine at Luxury Zen Den with heated pool just off Siesta Key in Sarasota

From US $201

Luxury Zen Den with heated pool just off Siesta Key Pool available

9.0 (33 Reviews) Apartment

The entire place is yours • 60 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.7km from Siesta Beach

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a group of people on a beach at sunset at Siesta Key Beach House in Siesta Key

From US $360

Siesta Key Beach House Pool available

8.4 (67 Reviews) Villa

The entire place is yours • 131 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.3km from Siesta Beach

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a white house with a porch and patio at Beautiful property on Siesta Key in Siesta Key

From US $370

Beautiful property on Siesta Key Pool available

7.8 (62 Reviews) Villa

The entire place is yours • 100 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.3km from Siesta Beach

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a living room with a couch and a sliding glass door at Heat of Siesta Village Walk to Beach w heated Pool in Siesta Key

From US $282

Heat of Siesta Village Walk to Beach w heated Pool Pool available

9.6 (19 Reviews) Holiday_home

The entire place is yours • 71 m² size • Kitchen

Siesta Key Siesta Beach • 1.8km from Siesta Beach

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a swimming pool with two chairs and a tent at New England 3bd 2bt Home Heated Pool Close to Siesta in Sarasota

From US $298

New England 3bd 2bt Home Heated Pool Close to Siesta Pool available

9.2 (23 Reviews) Holiday_home

The entire place is yours • 130 m² size • Kitchen

Siesta Key Siesta Beach • 4.1km from Siesta Beach

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a living room with a couch and a tv at Our House at the Beach 502E By Beachside Management in Siesta Key

From US $425

Our House at the Beach 502E By Beachside Management Pool available

8.8 (35 Reviews) Apartment

The entire place is yours • 112 m² size • Kitchen

Siesta Key Siesta Beach • 305m from Siesta Beach

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a swimming pool in a house with a tent at Bernice 3bd2bth With Heated Pool Near Siesta Key! in Sarasota

From US $453

Bernice 3bd2bth With Heated Pool Near Siesta Key! Pool available

8.2 (34 Reviews) Holiday_home

The entire place is yours • 153 m² size • Kitchen

Siesta Key Siesta Beach • 5.5km from Siesta Beach

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a view of a lake from a balcony at Sienna Park Apartments in Sarasota

From US $136

Sienna Park Apartments Pool available

9.0 (21 Reviews) Apartment

The entire place is yours • 52 m² size • Free on-site parking

Siesta Key Siesta Beach • 5.0km from Siesta Beach

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a bedroom with a large bed with flowers on it at Heated pool just 1.7 mi to beach The Ocean Pearl in Sarasota

From US $249

Heated pool just 1.7 mi to beach The Ocean Pearl Pool available

8.8 (16 Reviews) Apartment

The entire place is yours • 74 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.7km from Siesta Beach

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a large swimming pool with an open roof at Rowena House 2bd Den 2bth Heated Pool Near Siesta Key in Sarasota

From US $292

Rowena House 2bd Den 2bth Heated Pool Near Siesta Key Pool available

8.1 (28 Reviews) Holiday_home

The entire place is yours • 232 m² size • Kitchen

Siesta Key Siesta Beach • 4.8km from Siesta Beach

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an aerial view of aominium complex with a body of water at Siesta Key Beach - 2 Bedroom - 3 Beds - 3 Bathroom Duplex with Heated Swimming Pool in Siesta Key

From US $372

Siesta Key Beach - 2 Bedroom - 3 Beds - 3 Bathroom Duplex with Heated Swimming Pool Pool available

9.5 (18 Reviews) Apartment

The entire place is yours • 111 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.6km from Siesta Beach

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a swimming pool with a pergola over it at Comfortable home, heated salt-cell pool, 10 min to beach in Sarasota

From US $207

Comfortable home, heated salt-cell pool, 10 min to beach Pool available

9.1 (14 Reviews) Holiday_home

The entire place is yours • 139 m² size • Free on-site parking

Siesta Key Siesta Beach • 4.5km from Siesta Beach

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a sign for the new calidian sign in front of a building at Siesta Key Escape Ground Floor Steps to Heated Pool and Free Trolley in Siesta Key

From US $289

Siesta Key Escape Ground Floor Steps to Heated Pool and Free Trolley Pool available

7.6 (25 Reviews) Apartment

The entire place is yours • 101 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.5km from Siesta Beach

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a living room with a white couch and a table at Modern beachfront condo in Sarasota

From US $695

Modern beachfront condo Pool available

9.9 (8 Reviews) Apartment

The entire place is yours • 102 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.6km from Siesta Beach

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a white house on the beach with palm trees at Lookout in Siesta Key

From US $1300

Lookout Pool available

9.2 (9 Reviews) Holiday_home

The entire place is yours • 292 m² size • Free on-site parking

Siesta Key Siesta Beach • 617m from Siesta Beach

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a table and chairs on a balcony with a view at Sarasota -Walk to Siesta Key Beach in Sarasota

From US $122

Sarasota -Walk to Siesta Key Beach Pool available

8.9 (9 Reviews) Apartment

The entire place is yours • 600 m² size • Free on-site parking

Siesta Key Siesta Beach • 2.5km from Siesta Beach

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a white house with a red door and a palm tree at Canal Lower-Gorgeous 3 bed 3 bath near SK Village in Siesta Key

From US $523

Canal Lower-Gorgeous 3 bed 3 bath near SK Village Pool available

9.4 (7 Reviews) Holiday_home

The entire place is yours • 1000 m² size • Hot tub

Siesta Key Siesta Beach • 1.6km from Siesta Beach

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a view from a window of a yard with buildings at Crescent Arms 105N in Sarasota

From US $198

Crescent Arms 105N Pool available

7.7 (14 Reviews) Holiday_home

The entire place is yours • 111 m² size • Private parking

Siesta Key Siesta Beach • 1.9km from Siesta Beach

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an aerial view of a building and the beach at A Somewhere is Here by Beachside Management in Siesta Key

From US $525

A Somewhere is Here by Beachside Management Pool available

7.8 (13 Reviews) Apartment

Apartments • Kitchen • Swimming pool

Siesta Key Siesta Beach • 585m from Siesta Beach

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a pool at a resort with palm trees and condos at Our House at the Lake House C117 by Beachside in Siesta Key

From US $420

Our House at the Lake House C117 by Beachside Pool available

8.9 (6 Reviews) Holiday_home

The entire place is yours • 126 m² size • Free on-site parking

Siesta Key Siesta Beach • 577m from Siesta Beach

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a swimming pool in front of a house at Beautiful 3 BR pool home minutes from Siesta Key - Blue Dolphin in Sarasota

From US $213

Beautiful 3 BR pool home minutes from Siesta Key - Blue Dolphin Pool available

8.6 (6 Reviews) Holiday_home

The entire place is yours • 191 m² size • Free parking

Siesta Key Siesta Beach • 4.6km from Siesta Beach

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an aerial view of a small town with palm trees at Canal Upper-Gorgeous 3 bed 3 bath near SK Village in Siesta Key

From US $578

Canal Upper-Gorgeous 3 bed 3 bath near SK Village Pool available

8.6 (6 Reviews) Holiday_home

The entire place is yours • 1000 m² size • Hot tub

Siesta Key Siesta Beach • 1.6km from Siesta Beach

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an aerial view of houses and the beach at Coastal Surfside By Beachside Management in Siesta Key

From US $488

Coastal Surfside By Beachside Management Pool available

8.4 (6 Reviews) Apartment

The entire place is yours • 140 m² size • Kitchen

Siesta Key Siesta Beach • 1.4km from Siesta Beach

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a bedroom with a bed and a ceiling fan at Beachside Bliss 1 miles to the beach with heated pool in Sarasota

From US $195

Beachside Bliss 1 miles to the beach with heated pool Pool available

7.6 (8 Reviews) Apartment

The entire place is yours • 70 m² size • Free on-site parking

Siesta Key Siesta Beach • 2.8km from Siesta Beach

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a wellness room with a hot tub and a mural at MERMAID HOUSE WITH POOL JACUZZI STEPS to SIESTA KEY BEACH in Sarasota

From US $538

MERMAID HOUSE WITH POOL JACUZZI STEPS to SIESTA KEY BEACH Pool available

9.0 (4 Reviews) Holiday_home

The entire place is yours • 93 m² size • Free on-site parking

Siesta Key Siesta Beach • 1.6km from Siesta Beach

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a view of a parking lot and the ocean at Our House at the Beach 604E By Beachside Management in Siesta Key

From US $425

Our House at the Beach 604E By Beachside Management Pool available

7.8 (4 Reviews) Apartment

The entire place is yours • 112 m² size • Kitchen

Siesta Key Siesta Beach • 348m from Siesta Beach

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a bedroom with a white bed and blue walls at Siesta Key Island Rentals in Siesta Key

From US $275

Siesta Key Island Rentals Pool available

9.0 (60 Reviews) Holiday_home

Houses • Free on-site parking • 6 swimming pools

Siesta Key Siesta Beach • 926m from Siesta Beach

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About Siesta Key Vacation Rentals with Pools on NearbyHoliday

Looking for pool in Siesta Key? Compare top options in Florida.

Find Siesta Key Rentals, Hotels, and Resorts with Swimming Pools.

Discover 129 places to stay, including hotel waterparks, vacation homes, resorts, private villas, and condos in Siesta Key that feature indoor, outdoor, or private pools.

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Vacation Rentals with Pools: Explore Top Destinations

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Frequently Asked Questions About Vacation Rentals With Pools in Siesta Key

There are a lot of vacation rentals with pools in Siesta Key. If you plan on staying in the Siesta Key area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals with Pools in Siesta Key: