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

Crescent Arms 101S

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

The 2-bedroom Crescent Arms 101S Villa Siesta Key is nestled about a 5-minute walk from Crescent Arms and can accommodate up to 6 guests. Located 2.6 km from Siesta Key Drum Circle, this 2-bathroom… More

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Siesta Sands 512

1001 Point Of Rocks Rd, #512, Siesta Key, United States Show map

Nestled around 4 km from Grand Canal, the 2-bedroom Siesta Sands 512 Siesta Key villa is boasting a patio and barbecue for guests' enjoyment. Located within a 10-minute drive of Siesta Key Drum… More

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Crabby Bungalow - 1136-1

1136A Seaside Drive, Siesta Key, United States Show map

The 2-bedroom Crabby Bungalow - 1136-1 Siesta Key accommodates up to 6 guests and offers proximity to Siesta Key Marina, located only an 8-minute walk away. More

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Peacock Villa - 5540 E

5540 Calle Del Invierno, Siesta Key, United States Show map

Up to 8 guests can stay at the 3-bedroom Peacock Villa - 5540 E Siesta Key and enjoy Public Beach Access 10, located around 5 minutes' walk away. This villa features opportunities for snorkelling… More

From US$ 728 Book Now

Excelsior 302

6265 Midnight Pass Road, Siesta Key, United States Show map

The 2-bedroom Excelsior 302 Villa Siesta Key offers easy access to such tourist spots as Siesta Harbour Condominium Apt Harbor, located only a 5-minute walk away. This Siesta Key holiday home… More

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The Abalone

1032-34 Point Of Rocks Road, Siesta Key, United States Show map

The 8-bedroom The Abalone Villa Siesta Key hosts up to 24 guests and provides proximity to Siesta Key Marina, situated merely 7 minutes' stroll away. The Siesta Key holiday home boasts an aqua park… More

From US$ 3994 Book Now

Siesta Time

5353 Shadow Lawn Drive, Siesta Key, United States Show map

Staying at Siesta Time Villa Siesta Key, guests can easily reach Big Sarasota Pass, located approximately 3 km away. More

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Palm Island Paradise

311 Island Circle, Siesta Key, United States Show map

The 4-bedroom Palm Island Paradise Siesta Key villa is located around a 10-minute walk from Public Beach Access 10 and welcomes its guests to enjoy lawn tennis. This property hosts up to 10 guests… More

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Crescent Royale Condominiums 1B

777 Beach Road Unit 1B, Siesta Key, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Crescent Royale Condominiums 1B Siesta Key villa is located merely 6 minutes' walk from Siesta Key Beach and is ideal for up to 4 guests. The property… More

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Crescent Royale Condominiums 210

757 Beach Road, Unit 210, Siesta Key, United States Show map

Located merely a 6-minute stroll from Siesta Key Drum Circle, the 2-bedroom Crescent Royale Condominiums 210 Siesta Key villa provides an outdoor swimming pool as well as windsurfing, snorkelling… More

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Crescent Royale Condominiums 107

797 Beach Road, Unit 107, Siesta Key, United States Show map

Offering a heated pool, the 2-bedroom Crescent Royale Condominiums 107 Siesta Key villa is located approximately a 5-minute walk from Siesta Key Beach and is ideal for up to 6 guests. This… More

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Bayside Pointe 3 - 1302

1302 Siesta Bayside Drive, Siesta Key, United States Show map

The 2-bedroom Bayside Pointe 3 - 1302 Villa Siesta Key offers proximity to such city sites as Siesta Key, located only a 6-minute walk away. Providing guests with Wi-Fi and parking, this Siesta Key… More

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New Listing! Onyx Penthouse - Siesta Key Vacation Rental

1144 Windsong Ln, Siesta Key, United States Show map

Offering a heated pool, the 3-bedroom New Listing! Onyx Penthouse - Siesta Key Vacation Rental villa is located just 550 metres from Jamaica Royale and is ideal for up to 10 guests. This Siesta Key… More

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Siesta Bayside Condo 3 Bedroom

1334 Siesta Bayside Dr, Siesta Key, United States Show map

Offering a swimming pool, the 3-bedroom Siesta Bayside Condo 3 Bedroom Siesta Key villa is located nearly 5 minutes' walk from Jamaica Royale and is ideal for up to 8 guests. This Siesta Key holiday… More

From US$ 352 Book Now

Casa Leone - 3446

3446 W Anglin Drive, Siesta Key, United States Show map

At the 4-bedroom Casa Leone - 3446 Villa Siesta Key, guests can enjoy snorkelling, horseback riding, and fisheries as well as a location around 5 minutes' walk from Bay Island. Boasting an aqua park… More

From US$ 484 Book Now

High Tide - Pool, Grill, Pet Friendly, Located In The Heart Of Sk!

305 Canal Rd, Siesta Key, United States Show map

The 2-bedroom High Tide - Pool, Grill, Pet Friendly, Located In The Heart Of Sk! Villa Siesta Key offers easy access to such tourist spots as Siesta Key Craft Festival Museum, located a mere 5… More

From US$ 287 Book Now

Siesta Sands 208

1001 Point Of Rocks Rd, #208, Siesta Key, United States Show map

Situated just 0.9 km from Green Turtle Shell & Gift City, the 1-bedroom Siesta Sands 208 Siesta Key villa provides access to numerous tourist attractions in the area. More

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The Siesta Waterfront Estate

5440 Azure Way, Siesta Key, United States Show map

Featuring a swimming pool for guests' relaxation, The Siesta Waterfront Estate Villa Siesta Key is located just 0.8 km from Siesta Key Beach. More

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Blue Paradise

5234 Avenida Navarra, Us, Siesta Key, United States Show map

Located just 550 metres from Siesta Key Beach Access 2, the 6-bedroom Blue Paradise Siesta Key villa is suitable for 18 guests and offers a Jacuzzi to relax in. This Siesta Key holiday home is about… More

From US$ 2574 Book Now

Crescent 204

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

The 3-bedroom Crescent 204 Villa Siesta Key is located around a 25-minute walk from Jamaica Royale and provides a swimming pool, ensuring a relaxing stay. This 2-bathroom villa hosts up to 6 guests… More

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456 Canal Rd

456 Canal Road, Siesta Key, United States Show map

The 5-bedroom 456 Canal Rd Siesta Key villa offers proximity to such city sites as Sarasota Beach, located only a 5-minute walk away. The Siesta Key holiday home features an outdoor swimming pool and… More

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Honeysuckle - L

5251 Calle Menorca, Siesta Key, United States Show map

The 3-bedroom Honeysuckle - L Villa Siesta Key is located approximately 5 minutes' walk from Sarasota Beach and has an aqua park and a golf course to ensure a memorable stay. Staying at the villa… More

From US$ 1171 Book Now

Our House At The Beach C-114

1131 Lakehouse Cir, C114, Siesta Key, United States Show map

The 2-bedroom Our House At The Beach C-114 Siesta Key villa is situated only 6 minutes' walk from Siesta Key Public Beach, featuring such comforts as Wi-Fi and parking. This Siesta Key holiday home… More

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The Pool House

98 Avenida Messina, Us, Siesta Key, United States Show map

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

From US$ 1327 Book Now

Siesta Sunset Sanctuary

156 Givens St, Siesta Key, United States Show map

During the stay at Siesta Sunset Sanctuary Villa Siesta Key, guests can indulge in a Jacuzzi or visit the Diverse South Lido County Waterfront Park, located 2.8 km away. This 1-bedroom holiday home… More

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6415 Midnight Pass #903

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

Located 0.6 km from Crescent Arms, 6415 Midnight Pass #903 Villa Siesta Key is suitable for 4 guests and provides an outdoor swimming pool to relax in. This 2-bedroom villa features opportunities for… More

From US$ 277 Book Now

Crescent Royale Condominiums 409

797 Beach Road, Unit 409, Siesta Key, United States Show map

Located merely 8 minutes on foot from Siesta Key Village, the 1-bedroom Crescent Royale Condominiums 409 Siesta Key villa provides a heated pool as well as windsurfing, snorkelling, and billiard to… More

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Siesta Beach 3 Min Walk To Village And Patio

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

Public Beach Access 10 is just 5 minutes' walk from the 4-bedroom Siesta Beach 3 Min Walk To Village And Patio Siesta Key villa, offering a Jacuzzi for guests' relaxation. This property features… More

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Majestic Coastal Escape

5206 Cape Leyte Dr, Siesta Key, United States Show map

Majestic Coastal Escape Siesta Key villa is located around 10 minutes' drive from Siesta Key Beach Access 2 and provides a swimming pool, ensuring a relaxing stay. More

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Villa 63 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Siesta Key, United States Show map

Located nearly 25 minutes' walk from Public Beach Access 10, Villa 63 - Aloha Kai Vacation Villas Siesta Key provides access to various tourist attractions in the vicinity. More

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4931 Oxford Drive

4931 Oxford Drive, Siesta Key, United States Show map

Featuring an outdoor swimming pool, the 3-bedroom 4931 Oxford Drive Villa Siesta Key is suitable for up to 6 people and is located nearly a 25-minute walk from Siesta Key Beach Access 7. Providing… More

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Beach Rd, 300Ft To Beach Access, 500Ft To Siesta Key Village, Studio

319 Beach Rd, Unit #3, Siesta Key, Fl 34242, Siesta Key, United States Show map

The 1-bedroom Beach Rd, 300Ft To Beach Access, 500Ft To Siesta Key Village, Studio villa, located approximately a 5-minute walk from Sarasota Beach, can host up to 2 guests. Providing guests with Wi… More

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Palm Island Life - Heated Pool, Canal Front, Fire Pit, Walk To Siesta Beach

208 Island Circle, Siesta Key, United States Show map

Palm Island Life - Heated Pool, Canal Front, Fire Pit, Walk To Siesta Beach Siesta Key villa is located just 1.5 km from Siesta Beach Pavillion and welcomes its guests to enjoy snorkelling, canyoning… More

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A Shell House Compound

1108 Windsong Lane, Siesta Key, United States Show map

Staying at the 4-bedroom A Shell House Compound Villa Siesta Key, guests can visit Grand Canal, which is nearly a 25-minute walk away. The Siesta Key villa is suitable for up to 8 guests and features… More

From US$ 2881 Book Now

Crescent Royale Condominiums 5A

777 Beach Road, Unit 5A, Siesta Key, United States Show map

Crescent Royale Condominiums 5A Siesta Key villa is located 5 minutes' walk from Siesta Key Drum Circle, and offers guided tour service to provide an entertaining experience. The 2-bedroom holiday… More

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Beachside Escape With Pool & Steps To Crescent Beach - Aloha Kai #51

6020 Midnight Pass Road Unit 51, Siesta Key, United States Show map

The 1-bedroom Beachside Escape With Pool & Steps To Crescent Beach - Aloha Kai #51 Siesta Key villa is located around 25 minutes' walk from Siesta Key Beach Access 7 and welcomes its guests to enjoy… More

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Crescent Royale Condominiums 511

797 Beach Road, Unit 511, Siesta Key, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Crescent Royale Condominiums 511 Siesta Key villa is located around 5 minutes' walk from Siesta Key Beach and is ideal for up to 5 guests. The… More

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

104 Avenida Veneccia, Siesta Key, United States Show map

Sea Angel - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach! villa, located 6 minutes' walk from Seaside Vacation Villas, can host up to 4 guests. The 1-bedroom holiday home… More

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338 Canal Rd

338 Canal Road, Siesta Key, United States Show map

Situated nearly a 5-minute walk from Siesta Key Craft Festival Museum, the 4-bedroom 338 Canal Rd Siesta Key villa offers easy access to numerous tourist spots in the area. The property boasts an… More

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The Big Kahuna

5235-37 Calle Menorca, Siesta Key, United States Show map

The 8-bedroom The Big Kahuna Siesta Key villa offers proximity to such city sites as Beach Club, located approximately a 5-minute walk away. Providing guests with Wi-Fi and a private parking lot… More

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Crescent Royale Condominiums 404

757 Beach Road, Unit 404, Siesta Key, United States Show map

Located approximately a 5-minute drive from Siesta Key Beach, the 1-bedroom Crescent Royale Condominiums 404 Siesta Key villa provides a heated pool as well as windsurfing, snorkelling, and billiard… More

From US$ 285 Book Now

The Oasis

105 Columbus Blvd., Siesta Key, United States Show map

Staying at the 7-bedroom The Oasis Villa Siesta Key, guests can visit the co-op Gallery on Siesta Key, which is only 400 metres away. The Siesta Key holiday home is suitable for up to 18 guests and… More

From US$ 2013 Book Now

Siesta Beach House - 105

5950 Midnight Pass Road, Siesta Key, United States Show map

Located 25 minutes' walk from Sarasota Beach, Siesta Beach House - 105 Siesta Key villa gives access to various tourist sites in the vicinity. The 1-bedroom holiday home hosts up to 2 guests and… More

From US$ 972 Book Now

The Salt & Sand Beach Shack

4959 Commonwealth Dr, Siesta Key, United States Show map

During the stay at The Salt & Sand Beach Shack Siesta Key villa, guests can indulge in snorkelling, ping-pong, and fisheries or visit Siesta Key Drum Circle, located 10 minutes away by car. Located 3… More

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Siesta Beach House 203 Sunny Daze

5950 Midnight Pass Road, Siesta Key, United States Show map

The 2-bedroom Siesta Beach House 203 Sunny Daze Siesta Key villa hosts up to 4 guests and provides proximity to Jamaica Royale, situated merely 7 minutes' walk away. More

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Beachside Bliss Awaits - Aloha Kai #55- Roelens

6020 Midnight Pass Rd. Unit 55, Siesta Key, United States Show map

Beachside Bliss Awaits - Aloha Kai #55- Roelens Siesta Key villa is located 25 minutes' walk from Siesta Key Beach and provides an outdoor swimming pool, ensuring a relaxing stay. Suitable for 4… More

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'Sea- Esta' Winds 209

6703 Midnight Pass Road #209, Siesta Key, United States Show map

Located only 10 minutes' walk from Green Turtle Shell & Gift City, the 1-bedroom 'Sea- Esta' Winds 209 Villa Siesta Key has an outdoor swimming pool and is ideal for up to 4 guests. Guests can enjoy… More

From US$ 218 Book Now

Beach Road - Tropea

665 Beach Road, Siesta Key, United States Show map

The 1-bedroom Beach Road - Tropea Siesta Key villa accommodates up to 2 guests and offers proximity to Siesta Key Beach, located merely 0.6 km away. Providing guests with Wi-Fi and a car park, the… More

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Beach Way 314

5600 Beach Way Drive, Siesta Key, United States Show map

Located around 5 minutes' walk from Siesta Key Village, the 2-bedroom Beach Way 314 Siesta Key villa features an outdoor swimming pool and can accommodate up to 6 guests. The holiday home boasts an… More

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Gertrudes Siesta Village Properties - Short Walk To Best Beaches!

5233 Avenida Navarra, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

Featuring an aqua park and playground for added enjoyment, the 4-bedroom Gertrudes Siesta Village Properties - Short Walk To Best Beaches! Siesta Key villa is located around 5 minutes' walk from the… More

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