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2026-11-03
2026-11-04
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Holiday Homes in Siesta Key

Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1 Mile And Crescent Beach 2 Miles, 1Bdr

8212 Midnight Pass Rd, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

The 1-bedroom Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1 Mile And Crescent Beach 2 Miles, 1Bdr villa hosts up to 3 guests and is nestled 3.2 km from natural sites such as the shaped… More

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Crescent Royale Condominiums 502

757 Beach Road, Unit 502, Siesta Key, United States Show map

Offering a heated pool, the 2-bedroom Crescent Royale Condominiums 502 Siesta Key villa is located merely 6 minutes' walk from Siesta Key Beach and is ideal for up to 5 guests. This accommodation… More

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Crescent Royale Condominiums 4D

777 Beach Road, Unit 4D, Siesta Key, United States Show map

At the 2-bedroom Crescent Royale Condominiums 4D Siesta Key villa, guests can enjoy snorkelling, billiard, and fisheries as well as a location just 6 minutes' walk from Siesta Key Beach. The… More

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Retreat Half-Mile To Beachandsiesta Key Village

605 Calle De Peru, Siesta Key, United States Show map

Nestled 10 minutes' drive from the friendly Edson Keith Estate Park, Retreat Half-Mile To Beachandsiesta Key Village villa entices guests to explore various tourist destinations nearby. More

From US$ 203 Book Now

Siesta Sunset - 524

524 Beach Rd (Ph), Siesta Key, United States Show map

The 3-bedroom Siesta Sunset - 524 Villa Siesta Key is situated just 5 minutes' stroll from Siesta Key Beach Access 7, featuring such comforts as Wi-Fi and a private parking lot. The accommodation… More

From US$ 502 Book Now

The Nautilus

1028-30 Point Of Rocks Road, Siesta Key, United States Show map

The 8-bedroom The Nautilus Villa Siesta Key hosts up to 24 guests and provides proximity to Siesta Key Marina, situated only a 7-minute walk away. The holiday home boasts an aqua park and a golf… More

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1 Block To The Beach On Siesta Key Vacation Rental Home With Swimming Pool

5545 Cape Aqua Drive, Siesta Key, United States Show map

Staying at 3-bedroom 1 Block To The Beach On Siesta Key Vacation Rental Home With Swimming Pool, guests can visit Crescent Arms, which is nearly a 25-minute walk away. The Siesta Key holiday home is… More

From US$ 325 Book Now

1017 - Premium - Beach Front

1017 West Peppertree Drive, Siesta Key, United States Show map

The 2-bedroom 1017 - Premium - Beach Front Siesta Key villa is located about 25 minutes' walk from Siesta Key Beach and provides fisheries for active guests. Providing guests with Wi-Fi and a car… More

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Harbor Towers 2Nd Fl Dock Views

5855 Midnight Pass Rd, Siesta Key, United States Show map

Located only 6 minutes' walk from Jamaica Royale, the 2-bedroom Harbor Towers 2Nd Fl Dock Views Villa Siesta Key offers a heated pool for guests to relax by. Providing guests with Wi-Fi and parking… More

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Paradise Palms!

710 Birdsong Ln, Siesta Key, United States Show map

Along with proximity to Grand Canal, merely 0.7 km away, the 3-bedroom Paradise Palms! Siesta Key villa offers opportunities for snorkelling, cycling, and fisheries in the area. This Siesta Key… More

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Spacious 2Br Siesta Key Condo 2 Heated Pools, Tennis And Pickleball, Beach Access - Gbb 1327

1327 Siesta Bayside Drive, Siesta Key, United States Show map

Located a mere 5 minutes' walk from Jamaica Royale, Spacious 2Br Siesta Key Condo 2 Heated Pools, Tennis And Pickleball, Beach Access - Gbb 1327 villa is suitable for 4 guests and provides an outdoor… More

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Southern Exposure

91 Avenida Veneccia, Us, Siesta Key, United States Show map

Southern Exposure Siesta Key villa offers proximity to nearby tourist spots, such as Siesta Key Craft Festival Museum, situated approximately 5 minutes' walk away. More

From US$ 1323 Book Now

Golden Set

1142 Windsong Lane, Unit B, Siesta Key, United States Show map

Located just a 6-minute walk from Jamaica Royale, the 5-bedroom Golden Set Villa Siesta Key features an outdoor swimming pool and can accommodate up to 14 guests. Offering a Jacuzzi, this 5-bathroom… More

From US$ 3074 Book Now

Unveiling Joyful Beachside Moments - Aloha Kai #62 - Roelens

6020 Midnight Pass Road Unit 62, Siesta Key, United States Show map

The 1-bedroom Unveiling Joyful Beachside Moments - Aloha Kai #62 - Roelens Siesta Key villa hosts up to 4 guests and provides proximity to Jamaica Royale, situated only a 9-minute walk away. This… More

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A Spacious Condo In Beautiful Siesta Key, Heated Pool, Tennis, Waterfront Picnic

6157 Midnight Pass Road, Siesta Key, United States Show map

Offering a swimming pool, the 2-bedroom A Spacious Condo In Beautiful Siesta Key, Heated Pool, Tennis, Waterfront Picnic villa is situated approximately a 5-minute walk from the shaped Crescent Beach… More

From US$ 166 Book Now

Siesta Villa Whispering Palms

1331 Moonmist Dr, Siesta Key, United States Show map

Located 700 metres from the shaped Crescent Beach, Siesta Villa Whispering Palms Siesta Key is suitable for 6 guests and provides a heated pool to relax in. This 3-bedroom villa features… More

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5177 Saint Albans

5177 Saint Albans Avenue, Siesta Key, United States Show map

Located just an 8-minute walk from Grand Canal, the 3-bedroom 5177 Saint Albans Villa Siesta Key features a swimming pool and can accommodate up to 10 guests. Located 3.4 km from Siesta Key Beach… More

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Crescent Royale Condominiums 412

757 Beach Road, Unit 412, Siesta Key, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Crescent Royale Condominiums 412 Siesta Key villa is situated merely 6 minutes' walk from Siesta Key Beach and can accommodate up to 4 guests. The… More

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Recently Updated Cozy Siesta Key Beach Villa

1269 Moonmist Circle, Siesta Key, United States Show map

Located just a 6-minute walk from the shaped Crescent Beach, the 2-bedroom Recently Updated Cozy Siesta Key Beach Villa features a swimming pool and can accommodate up to 7 guests. Located within a… More

From US$ 230 Book Now

Crescent 305

6512 Midnight Pass Road, Siesta Key, United States Show map

During the stay at Crescent 305 Villa Siesta Key, guests can indulge in cycling and fisheries or visit Siesta Key Beach, located a 25-minute walk away. Located 3.4 km from Grand Canal, the 2-bedroom… More

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Ocean Beach Gleason Home

4638 Gleason Ave, Siesta Key, United States Show map

The 4-bedroom Ocean Beach Gleason Home Siesta Key is located about 20 minutes on foot from Grand Canal and provides a hot tub. The Siesta Key villa boasts grill and a golf course, while Sarasota… More

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Midnight Cove II - 137

6327 Midnight Pass Rd, Bldg 1, Unit 137, Siesta Key, United States Show map

Midnight Cove II - 137 Villa Siesta Key, located just a 5-minute walk from Siesta Harbour Condominium Apt Harbor, can host up to 5 guests. This 2-bedroom villa features opportunities for fisheries in… More

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Walk To Siesta Key Beach And Village

544 Canal Road, Siesta Key, Fl 34242, Siesta Key, United States Show map

The 1-bedroom Walk To Siesta Key Beach And Village villa entices active guests with access to a fitness centre and is located around a 5-minute ride from Siesta Key Beach Access 2. Offering an… More

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Bay Oaks - E01

6157 Midnight Pass Road, Siesta Key, United States Show map

Located about 25 minutes' walk from Siesta Beach Pavillion, the 2-bedroom Bay Oaks - E01 Villa Siesta Key gives access to various tourist sites in the vicinity. With a maximum capacity of 4 guests… More

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Bay Oaks B-22

6157 Midnight Pass Road, Siesta Key, United States Show map

The 2-bedroom Bay Oaks B-22 Villa Siesta Key hosts up to 6 guests and provides proximity to Crescent Arms, situated a mere 0.7 km away. This Siesta Key villa boasts an aqua park and a golf course… More

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Crescent Royale Condominiums 6C

777 Beach Road Unit 6C, Siesta Key, United States Show map

The 2-bedroom Crescent Royale Condominiums 6C Siesta Key villa boasts a location within 5 minutes' walk of Siesta Beach Pavillion and offers guests to enjoy a games room. Offering a lift and a tour… More

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Crescent Royale Condominiums 309

797 Beach Rd Unit 309, Siesta Key, United States Show map

Located merely a 5-minute stroll from Siesta Key Beach, the 1-bedroom Crescent Royale Condominiums 309 Siesta Key villa provides an outdoor swimming pool as well as windsurfing, snorkelling, and… More

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Sunkissed Pool Home

5005 Commonwealth Dr, Siesta Key, United States Show map

Sunkissed Pool Home Siesta Key is located just around the corner from Grand Canal and invites guests to enjoy guided snorkelling trips. The 3-bedroom holiday home features opportunities for… More

From US$ 368 Book Now

Gulf View Paradise

1140 Seaside Dr #301, Siesta Key, United States Show map

Located merely an 8-minute walk from Crescent Arms, Gulf View Paradise Siesta Key villa features an outdoor swimming pool and can accommodate up to 16 guests. Located in the vicinity of the shaped… More

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Midnight Cove II 731F

1300 Cove II Place, Unit 731F, Siesta Key, United States Show map

Overlooking the pool, Midnight Cove II 731F Villa Siesta Key enjoys a convenient setting 5 minutes' walk from crescent arms private beach. Located in the immediate vicinity of Siesta Harbour… More

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Crescent Royale Condominiums 104

757 Beach Road, Unit 104, Siesta Key, United States Show map

Located merely a 6-minute walk from Siesta Key Beach, the 1-bedroom Crescent Royale Condominiums 104 Siesta Key villa features an outdoor swimming pool and can accommodate up to 4 guests. The holiday… More

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Blu Sky Cottage - 5037

5037 Higel Ave, Siesta Key, United States Show map

Featuring a swimming pool, the 3-bedroom Blu Sky Cottage - 5037 Siesta Key is suitable for up to 8 people and is located approximately 25 minutes on foot from Jamaica Royale. The Siesta Key holiday… More

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Siesta Sun Sets

6536 Peacock Rd., Siesta Key, United States Show map

Siesta Sun Sets Villa Siesta Key with a convenient location 750 metres from Crescent Arms entices guests with a Jacuzzi. Located 10 minutes by car from Siesta Key Village, this 7-bedroom villa… More

From US$ 5341 Book Now

Crescent Royale Condominiums 7A

777 Beach Road Unit 7A, Siesta Key, United States Show map

During the stay at Crescent Royale Condominiums 7A Siesta Key villa, guests can indulge in windsurfing, snorkelling, and billiard or visit Siesta Key Beach Access 7, located a 13-minute walk away. More

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Bay Oaks G-22

6157 Midnight Pass Road, Siesta Key, United States Show map

Located just 9 minutes' walk from Crescent Arms, the 2-bedroom Bay Oaks G-22 Villa Siesta Key offers a swimming pool for guests to relax by. Providing guests with Wi-Fi and a private parking lot… More

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Sea Escape - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach!

104 Avenida Veneccia, Siesta Key, United States Show map

Located just a 5-minute walk from Siesta Key Beach Access 2, Sea Escape - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach! villa offers windsurfing, snorkelling, and mini golf… More

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Crystal Sands 905

6300 Midnight Pass Road, Siesta Key, United States Show map

Situated 5 minutes' walk from Crescent Arms, Crystal Sands 905 Siesta Key villa offers guests to relax by a swimming pool. Located 3.9 km from Gulf Gate Public Library, the 2-bedroom holiday home… More

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Crescent Royale Condominiums 505

797 Beach Road, Unit 505, Siesta Key, United States Show map

The 2-bedroom Crescent Royale Condominiums 505 Siesta Key villa hosts up to 4 guests and provides proximity to Siesta Key Beach, situated just a 5-minute walk away. This Siesta Key holiday home… More

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Exclusive Complex - Private Heated Pool - 100 Steps To Beach - Village 5 Minute Walk

5316 Calle De La Siesta, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

The 5-bedroom Exclusive Complex - Private Heated Pool - 100 Steps To Beach - Village 5 Minute Walk Siesta Key villa offers easy access to such tourist spots as Sarasota Beach, located merely a 5… More

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Bay View Siesta Key Condo - Two Pools - Tennis And Pickleball - Beach Access - Gbb 1343

1343 Siesta Bayside Drive, Siesta Key, United States Show map

Located merely a 6-minute walk from Jamaica Royale, Bay View Siesta Key Condo - Two Pools - Tennis And Pickleball - Beach Access - Gbb 1343 villa is suitable for 4 guests and provides an outdoor… More

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New Listing - Dates Available Now! Beach & Village

544 Canal Rd., Siesta Key, United States Show map

Offering a patio and playground for guests' leisure, the 1-bedroom New Listing - Dates Available Now! Beach & Village Siesta Key villa is situated 16 minutes' walk from Siesta Key Beach Access 2. More

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Moonmist Circle-Steps To Heated Pool

1223 Moonmist Cir, Siesta Key, United States Show map

Offering a heated pool, the 2-bedroom Moonmist Circle-Steps To Heated Pool Villa Siesta Key is situated only a 9-minute walk from Crescent Arms and can accommodate up to 4 guests. This holiday home… More

From US$ 192 Book Now

Siesta Avenida

5208 Avenida De Cortez, Siesta Key, United States Show map

The 2-bedroom Siesta Avenida Villa Siesta Key offers proximity to such city sites as the co-op Gallery on Siesta Key, located only a 5-minute walk away. Providing guests with Wi-Fi and a car park… More

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Tidal Wave - In Siesta Key Village, Pet Friendly, Private Pool!

303/305 Canal Rd, Siesta Key, United States Show map

Featuring an outdoor swimming pool, the 4-bedroom Tidal Wave - In Siesta Key Village, Pet Friendly, Private Pool! villa is located nearly a 5-minute walk from Siesta Key Craft Festival Museum and is… More

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Beachside Haven - 650C

650 Calle Del Ontono #C, Siesta Key, United States Show map

Featuring an aqua park and a golf course, the 3-bedroom Beachside Haven - 650C Siesta Key villa offers guests to enjoy a prime location just a 9-minute walk from Siesta Key Beach. Offering horse… More

From US$ 754 Book Now

Siesta Dreamin

5536 Contento Dr, Siesta Key, United States Show map

The 3-bedroom Siesta Dreamin Villa Siesta Key entices guests to enjoy fisheries and offers proximity to Siesta Key Village, located about a 5-minute stroll away. Offering a swimming pool, the… More

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Siesta Sands 212

1001 Point Of Rocks Rd, #212, Siesta Key, United States Show map

Offering access to entertainment venues such as Siesta Key Marina, situated a mere 1.3 km away, the 2-bedroom Siesta Sands 212 Siesta Key villa can host up to 6 guests. More

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Vista Hermosa - 302C

116 Vista Hermosa Circle, Siesta Key, United States Show map

Nestled around a 25-minute walk from Jamaica Royale, the 2-bedroom Vista Hermosa - 302C Siesta Key villa is boasting an aqua park, a patio, and a golf course for guests' enjoyment. Located 2.8 km… More

From US$ 540 Book Now