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

New Listing! Pool Jacuzzi, 3-Min To Beach Bars & Entertainment!

1020 Sun And Sea Dr #206B, Siesta Key, Fl 34242, Siesta Key, United States Show map

Located merely 7 minutes on foot from Siesta Key Marina, the 2-bedroom New Listing! Pool Jacuzzi, 3-Min To Beach Bars & Entertainment! Siesta Key villa can accommodate up to 5 guests, providing them… More

From US$ 1089 Book Now

Hemingway House - 117

117 Pierson Lane, Siesta Key, United States Show map

Providing guests with an aqua park and a golf course to ensure a memorable stay, the 3-bedroom Hemingway House - 117 Villa Siesta Key is approximately a 5-minute walk from Shell Beach. Located within… More

From US$ 753 Book Now

Full Beachfront Condo - Gulf View- Sunsets - Pool - Chairs

6312 Midnight Pass Road 404S, Siesta Key, United States Show map

The 2-bedroom Full Beachfront Condo - Gulf View- Sunsets - Pool - Chairs Siesta Key villa, located nearly a 5-minute walk from Siesta Harbour Condominium Apt Harbor, can host up to 6 guests. This… More

From US$ 485 Book Now

Private Heated Pool - 100 Steps To Beach Access - 5-Min Walk To Siesta Key Village

5316 Calle De La Siesta Unit#3, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

The 3-bedroom Private Heated Pool - 100 Steps To Beach Access - 5-Min Walk To Siesta Key Village villa offers swift access to various city sites, such as Siesta Key Beach Access 7, situated nearly a… More

From US$ 2153 Book Now

Villa Castile - 5204

5204 Avenida De Cortez, Siesta Key, United States Show map

Located nearly a 25-minute walk from Beach Club, the 3-bedroom Villa Castile - 5204 Siesta Key has a swimming pool and is ideal for up to 8 guests. Guests can enjoy snorkelling, horseback riding, and… More

From US$ 360 Book Now

Monarch Villa - 5542 W

5542 Calle Del Invierno, Siesta Key, United States Show map

Offering an aqua park and a golf course for guests' leisure, the 3-bedroom Monarch Villa - 5542 W Siesta Key is situated 16 minutes' walk from Siesta Key Beach Access 2. This villa features… More

From US$ 596 Book Now

Our House At Turtle Gate

1087 Lake House Cir, Siesta Key, United States Show map

The 2-bedroom Our House At Turtle Gate Villa Siesta Key hosts up to 6 guests and provides proximity to Siesta Key Village, situated merely 400 metres away. The Siesta Key villa boasts a patio and a… More

From US$ 175 Book Now

Fanta-Sea 55 By Beachside Management

55 Beach Road, Siesta Key, United States Show map

The 4-bedroom Fanta-Sea 55 By Beachside Management Siesta Key villa offers proximity to such city sites as Siesta Key Craft Festival Museum, located just a 5-minute walk away. Providing guests with… More

From US$ 720 Book Now

The 19Th Hole

459 Beach Road, Unit A, Siesta Key, United States Show map

The 1-bedroom The 19Th Hole Villa Siesta Key hosts up to 14 guests and provides proximity to Siesta Key Beach Access 7, situated only 250 metres away. Providing guests with Wi-Fi and private car… More

From US$ 2443 Book Now

Sandy Cabana - 1104N

1104 Crescent St, Siesta Key, United States Show map

Offering an aqua park and a golf course for guests' leisure, Sandy Cabana - 1104N Siesta Key is situated a 17-minute walk from the shaped Crescent Beach. The 3-bedroom holiday home features… More

From US$ 529 Book Now

Beach Front And Walking Distance To Village

652 Beach Road, Siesta Key, United States Show map

The 3-bedroom Beach Front And Walking Distance To Village Siesta Key villa offers easy access to such tourist spots as Sarasota Beach, located only a 5-minute walk away. The Siesta Key holiday home… More

From US$ 593 Book Now

Sandy Seahorse Cottage

1104-1106 Crescent St, Siesta Key, United States Show map

Located a mere 7 minutes' stroll from Siesta Key Marina, the 6-bedroom Sandy Seahorse Cottage Siesta Key provides a swimming pool as well as snorkelling, horseback riding, and fisheries to diversify… More

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100 Steps To Beach Access - 5 Minute Walk To The Village - Private Porch

5316 Calle De La Siesta #1, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

Staying at the 1-bedroom 100 Steps To Beach Access - 5 Minute Walk To The Village - Private Porch Siesta Key villa, guests can visit Siesta Key Beach, which is only 1.4 km away. The Siesta Key… More

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Mimosa - 5251B

5251 Calle Menorca, Siesta Key, United States Show map

Featuring an aqua park and a golf course for added enjoyment, the 1-bedroom Mimosa - 5251B Villa Siesta Key is located about 5 minutes' walk from Siesta Key Beach Access 7. Hosting up to 4 guests… More

From US$ 145 Book Now

The Upper Deck

329 Beach Road, Unit B, Siesta Key, United States Show map

The Upper Deck Villa Siesta Key is located 17 minutes' walk from Siesta Key Beach and invites guests to enjoy a terrace. Suitable for up to 16 people, this 6-bedroom villa provides a hot tub, as well… More

From US$ 724 Book Now

Serenity Cottage - 1028

1028 Crescent St., Siesta Key, United States Show map

Situated about a 5-minute drive from Siesta Key Marina, the 3-bedroom Serenity Cottage - 1028 Siesta Key is suitable for 8 guests and provides a swimming pool to relax in. The Siesta Key villa is 2.8… More

From US$ 961 Book Now

Fanta-Sea 53 By Beachside Management

53 Beach Road, Siesta Key, United States Show map

Situated a few steps from Siesta Key Beach Access 2, the 4-bedroom Fanta-Sea 53 By Beachside Management Siesta Key villa is ideal for up to 12 guests. Located 3.6 km from the Diverse South Lido… More

From US$ 1149 Book Now

Siesta Bayside Pretty Fountain View

1273 Siesta Bayside Dr, Siesta Key, United States Show map

Situated within 5 minutes' walk of Siesta Key, the 2-bedroom Siesta Bayside Pretty Fountain View Villa Siesta Key entices guests to explore various tourist attractions in the area. Offering guided… More

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1081 Pd

1081 Peppertree Drive, Siesta Key, United States Show map

Located merely 10 minutes' walk from the shaped Crescent Beach, the 2-bedroom 1081 Pd Villa Siesta Key is suitable for 6 guests and provides an outdoor swimming pool to relax in. Located 4.2 km from… More

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6415 Midnight Pass #606

6415 Midnight Pass Road, Siesta Key, United States Show map

Welcoming guests with a Jacuzzi, the 2-bedroom 6415 Midnight Pass #606 Villa Siesta Key is located merely 8 minutes' walk from Siesta Key Marina and can host up to 6 guests. This villa features… More

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Luxury Home W/ Heated Pool And Private Beach Access

1216 Derby Lane, Siesta Key, United States Show map

Located nearly 20 minutes' walk from Siesta Key Beach, the 4-bedroom Luxury Home W/ Heated Pool And Private Beach Access Siesta Key has an outdoor swimming pool and is ideal for up to 10 guests. More

From US$ 865 Book Now

Private Beach House

5950 Midnight Pass Rd, Unit 315, Us, Siesta Key, United States Show map

Private Beach House Siesta Key villa is located 15 minutes' walk from Siesta Beach Pavillion and invites guests to join fisheries. The 2-bedroom holiday home hosts up to 8 guests and provides them… More

From US$ 398 Book Now

Fanta-Sea 47 By Beachside Management

47 Beach Road, Siesta Key, United States Show map

Fanta-Sea 47 By Beachside Management Siesta Key villa, located 5 minutes' walk from Siesta Key Craft Festival Museum, can host up to 4 guests. Located just steps from Beach Club, the 2-bedroom… More

From US$ 609 Book Now

Siesta Key Waterfront Home

6535 Sabal Drive, Siesta Key, United States Show map

Staying at Siesta Key Waterfront Home, guests can easily reach the friendly Edson Keith Estate Park, located nearly 25 minutes' walk away. More

From US$ 809 Book Now

Siesta Key Sanctuary

445 Reid Street, Siesta Key, United States Show map

Nestled a 10-minute drive from Siesta Key Beach, Siesta Key Sanctuary Villa entices guests to explore various tourist destinations nearby. More

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Fins Up

110 Avenida Veneccia, Unit 279, Us, Siesta Key, United States Show map

Fins Up Villa Siesta Key provides easy access to various city attractions, such as Siesta Key Craft Festival Museum, situated around 5 minutes' walk away. More

From US$ 684 Book Now

Jellyfish Unit, Walk To Beach & Siesta Key Village, Pet-Friendly

527 Beach Road, Siesta Key, United States Show map

Jellyfish Unit, Walk To Beach & Siesta Key Village, Pet-Friendly villa, located merely a 5-minute walk from Sarasota Beach, can host up to 10 guests. More

From US$ 568 Book Now

Crescent Royale Condominiums 508

757 Beach Road, Unit 508, Siesta Key, United States Show map

The 1-bedroom Crescent Royale Condominiums 508 Siesta Key villa accommodates up to 4 guests and offers proximity to Siesta Key Beach, located merely 500 metres away. This property features… More

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Cozy Home Near The Beach - Aloha Kai #37 - Roelens

6020 Midnight Pass Road Unit 37, Siesta Key, United States Show map

Located approximately 25 minutes' walk from Siesta Key Village, Cozy Home Near The Beach - Aloha Kai #37 - Roelens Siesta Key has an outdoor swimming pool and is ideal for up to 6 guests. Guests can… More

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Hyatt Residences On Siesta Key Beach - A Premier Hotel Experience! - Residences Of Siesta Key

915 Seaside Drive, Siesta Key, United States Show map

Hyatt Residences On Siesta Key Beach - A Premier Hotel Experience! - Residences Of Siesta Key with a convenient location 700 metres from Siesta Key Marina entices guests with a Jacuzzi and a sauna. More

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Casa Tranquila - Private Patios, Beach, Village, 100 Steps To Best Views On Siesta Key!

303 Givens Street, Siesta Key, Florida 34242, United States, Siesta Key, United States Show map

The 3-bedroom Casa Tranquila - Private Patios, Beach, Village, 100 Steps To Best Views On Siesta Key! entices guests to enjoy windsurfing, snorkelling, and mini golf and is located within 25 minutes'… More

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Siesta Key - Beach Access - Two Pools - Gbb 1260

1260 Siesta Bayside Drive, Siesta Key, United States Show map

Situated nearly a 5-minute stroll from Jamaica Royale, the 2-bedroom Gbb 1260 Beach Access - Tennis - Two Pools - Fishing Dock Siesta Key villa can welcome up to 4 guests and boasts a sauna for a… More

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Admirals Watch - 673

673 Beach Rd, Siesta Key, United States Show map

The 3-bedroom Admirals Watch - 673 Villa Siesta Key entices guests to enjoy snorkelling and fisheries and offers proximity to Siesta Key Beach Access 7, located just 5 minutes' stroll away. The… More

From US$ 506 Book Now

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

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

Nestled 4.6 km from Historic Spanish Point, the 6-room Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1-Mile And Crescent Beach 2-Miles, 1-Bdr villa is boasting a sunbathing terrace and a… More

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Lulu'S Key House Green 1/1 Upstairs

5249 Calle Menorca, Siesta Key, United States Show map

Located around 700 metres from Siesta Key Drum Circle, the 1-bedroom Lulu'S Key House Green 1/1 Upstairs Siesta Key villa offers opportunities for snorkelling, cycling, and fisheries in the area. The… More

From US$ 211 Book Now

Siesta Soul - 334

334 Canal Road, Siesta Key, United States Show map

Up to 8 guests can stay at the 3-bedroom Siesta Soul - 334 Villa Siesta Key and enjoy Siesta Key Beach Access 7, located only a 5-minute walk away. This Siesta Key holiday home boasts an aqua park… More

From US$ 642 Book Now

Charming Siesta Key Condo With Private Beach Access - Gbb 1269

1269 Siesta Bayside Drive, Siesta Key, United States Show map

Gbb 1269 Updated 2Br Siesta Key Condo With Private Beach Access villa with a convenient location a 5-minute walk from Jamaica Royale entices guests with a sauna. Located 1.7 km from Crescent Arms… More

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Gbb 1338 Charming 2Br Siesta Key Condo With Beach Access

1338 Siesta Bayside Drive, Siesta Key, United States Show map

Charming 2Br Siesta Key Condo With Beach Access villa with a convenient location just a 5-minute walk from Jamaica Royale entices guests with a sauna. Located 4.3 km from Bee Ridge Park, the 2… More

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Bay Oaks C Second Floor

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

Situated approximately 5 minutes' walk from the shaped Crescent Beach, the 2-bedroom Bay Oaks C Second Floor Villa Siesta Key is ideal for up to 6 guests. This accommodation features opportunities… More

From US$ 213 Book Now

Casa Bella Vita - 1021

1021 Crescent Street, Siesta Key, United States Show map

Along with proximity to Siesta Key Marina, merely 500 metres away, the 3-bedroom Casa Bella Vita - 1021 Siesta Key offers opportunities for snorkelling, horseback riding, and fisheries in the area. More

From US$ 1251 Book Now

Crescent Cottage - 1034

1034 Crescent St, Siesta Key, United States Show map

Providing guests with an aqua park and a golf course to ensure a memorable stay, the 4-bedroom Crescent Cottage - 1034 Siesta Key is just a 7-minute walk from Siesta Key Marina. Located 2.9 km from… More

From US$ 711 Book Now

Siesta Bayside Bliss

1243 Siesta Bayside Drive, Siesta Key, United States Show map

Located a mere 9 minutes' walk from the friendly Edson Keith Estate Park, the 2-bedroom Siesta Bayside Bliss Villa Siesta Key offers an outdoor swimming pool for guests to relax by. This holiday home… More

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Plumbago - 5251C

5251 Calle Menorca, Siesta Key, United States Show map

During the stay at Plumbago - 5251C Villa Siesta Key, guests can indulge in snorkelling, horseback riding, and fisheries or visit Siesta Key Drum Circle, located a 14-minute walk away. The 2-bedroom… More

From US$ 2075 Book Now

Fiesta Playa - 1027

1027 Crescent St, Siesta Key, United States Show map

Located merely 1.4 km from the shaped Crescent Beach, the 3-bedroom Fiesta Playa - 1027 Villa Siesta Key has an outdoor swimming pool and is ideal for up to 8 guests. More

From US$ 454 Book Now

Spacious Siesta Key Condo With Beach Access - Gbb 1241

1241 Siesta Bayside Drive, Siesta Key, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Spacious 2Br Siesta Key Condo With Private Beach Access villa is situated approximately a 5-minute walk from Jamaica Royale and can accommodate up to… More

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Coastal Comfort Steps From Crescent Beach Paradise - Aloha Kai #63 - Roelens

6020 Midnight Pass Road Unit 63, Siesta Key, United States Show map

Located only a 9-minute walk from Jamaica Royale, Coastal Comfort Steps From Crescent Beach Paradise - Aloha Kai #63 - Roelens Siesta Key villa offers an outdoor swimming pool for guests to relax by.… More

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Gbb 1385 Extraordinary Bay Views - Siesta Key

1385 Siesta Bayside Drive, Siesta Key, United States Show map

Situated just a 6-minute walk from Jamaica Royale, the 2-bedroom Extraordinary Bay Views - Siesta Key Villa offers a sauna and can accommodate up to 4 guests. The holiday home features opportunities… More

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Casita Sun Star - 1135

1135 Crescent Street, Siesta Key, United States Show map

Casita Sun Star - 1135 Villa Siesta Key is located 25 minutes' walk from Jamaica Royale and invites guests to join snorkelling, horseback riding, and fisheries. Offering horse riding tours, the 3… More

From US$ 478 Book Now

Bali Hai House - 5041

5041 Sandy Shore Avenue, Siesta Key, United States Show map

The 3-bedroom Bali Hai House - 5041 Siesta Key villa is located around 10 minutes' drive from the upscale Saint Armands Circle Outdoor Mall and provides snorkelling, horseback riding, and fisheries… More

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Gbb 1382 Bayfront 2Br Siesta Key Condo With Private Beach Access

1382 Siesta Bayside Drive, Siesta Key, United States Show map

Bayfront 2Br Siesta Key Condo With Beach Access - Gbb 1382 villa is situated merely a 5-minute walk from Jamaica Royale and provides a sauna for a relaxing stay. The 2-bedroom holiday home features… More

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