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

Sunset

1138 Sun N Sea Dr, Siesta Key, United States Show map

The 2-bedroom Sunset Villa Siesta Key is located around a 10-minute walk from Green Turtle Shell & Gift City and welcomes its guests to enjoy fisheries. With a maximum capacity of 6 guests, this… More

From US$ 256 Book Now

Gulf View Suite - 301

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

Offering an outdoor swimming pool, the 4-bedroom Gulf View Suite - 301 Siesta Key villa is located merely 7 minutes' walk from Siesta Key Marina and is ideal for up to 10 guests. The property… More

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Edgemere

738 Edgemere Lane, Siesta Key, United States Show map

Edgemere Siesta Key villa offers proximity to nearby tourist spots, such as Nora Patterson Bay Island Park, situated 2.9 km away. The 4-bedroom holiday home hosts up to 8 guests and provides them… More

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Terrace On Ocean - 2

5400 Ocean Blvd, 15-2, Siesta Key, United States Show map

Nestled within 5 minutes' walk of Siesta Key Beach Access #5, the 2-bedroom Terrace On Ocean - 2 Villa Siesta Key comes with a patio and a golf course for added enjoyment. Located a short way from… More

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Summer House

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

Nestled a 10-minute drive from the Diverse South Lido County Waterfront Park, Summer House Siesta Key villa entices guests to explore various tourist destinations nearby. More

From US$ 1826 Book Now

Gbb 1340 Updated 2Br, 2Nd Floor Condo On Siesta Key - Tennis And Pickleball, Private Beach Access

1340 Siesta Bayside Drive, Siesta Key, United States Show map

Located merely a 5-minute walk from Jamaica Royale, Updated 2Br, 2Nd Floor Condo On Siesta Key - Tennis And Pickleball, Private Beach Access villa is suitable for 5 guests and provides a sauna for a… More

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Walk To Siesta Key Beach And Village W Pool

544 Canal Rd., Siesta Key, Fl 34242, Siesta Key, United States Show map

The 1-bedroom Walk To Siesta Key Beach And Village W Pool villa, located only a 5-minute walk from Public Beach Access 10, can host up to 4 guests. More

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Crescent Royale Condominiums 208

757 Beach Road, Unit 208, Siesta Key, United States Show map

Located merely a 6-minute walk from Siesta Key Beach, Crescent Royale Condominiums 208 Siesta Key villa offers windsurfing, snorkelling, and billiard to diversify guests' leisure. Located 4.4 km from… More

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Siesta Sands 412

1001 Point Of Rocks Rd, #412, Siesta Key, United States Show map

The 2-bedroom Siesta Sands 412 Siesta Key villa can host up to 6 guests, boasting a beachfront location nearly a 10-minute ride from iconic cultural attractions such as Gulf Gate Public Library. More

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6415 Midnight Road #709

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

Offering a Jacuzzi, 6415 Midnight Road #709 Villa Siesta Key is situated 7 minutes' walk from Siesta Key Beach Access 2 and can accommodate 6 people. The 2-bedroom holiday home features opportunities… More

From US$ 302 Book Now

Blue Mermaid On Siesta Key

Siesta Key, United States Show map

Staying at the 3-bedroom Blue Mermaid On Siesta Key villa, guests can visit Jamaica Royale, which is approximately 3 km away. With a maximum capacity of 6 guests, the Siesta Key holiday home offers a… More

From US$ 239 Book Now

Harbor Towers 2Nd Fl Renovated Suite

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

The 3-bedroom Harbor Towers 2Nd Fl Renovated Suite Siesta Key villa is nestled merely 6 minutes' walk from Jamaica Royale and can accommodate up to 8 guests. Located not far from Siesta Key Beach… More

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Crescent Royale Condominiums 501

797 Beach Road, Unit 501, Siesta Key, United States Show map

Offering Wi-Fi, a lift and a tour desk, Crescent Royale Condominiums 501 Siesta Key villa is located a 5-minute walk from Siesta Key Drum Circle. Suitable for 8 guests, the 3-bedroom holiday home… More

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Walk To Siesta Key Beach And Village, Pool, Dock, Game Room

544 Canal Rd., Siesta Key, Fl 34242, Siesta Key, United States Show map

The 1-bedroom Walk To Siesta Key Beach And Village, Pool, Dock, Game Room villa, located about a 5-minute walk from Public Beach Access 10, can host up to 4 guests. Featuring a Jacuzzi, this… More

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1055-106 - Premium

1055 West Peppertree Drive, #106, Siesta Key, United States Show map

The 1-bedroom 1055-106 - Premium Villa Siesta Key is located around 25 minutes' walk from Siesta Key Beach and provides fisheries for active guests. Providing guests with Wi-Fi and parking, the… More

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Crescent Royale Condominiums 111

797 Beach Road, Unit 111, Siesta Key, United States Show map

Situated nearly a 5-minute stroll from Siesta Key Beach, the 2-bedroom Crescent Royale Condominiums 111 Siesta Key villa ensures a great leisure experience by offering windsurfing, snorkelling, and… More

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Changing Channels

441 Beach Rd, #F, Siesta Key, United States Show map

The 4-bedroom Changing Channels Siesta Key villa, located just a 6-minute walk from Seaside Vacation Villas, can host up to 10 guests. This accommodation features opportunities for fisheries in the… More

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Palm Bay Club #146

5964 Midnight Pass Road, Siesta Key, United States Show map

The 2-bedroom Palm Bay Club #146 Villa Siesta Key accommodates up to 6 guests and offers proximity to Jamaica Royale, located merely 500 metres away. Providing guests with Wi-Fi and a private parking… More

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Walk To Siesta Key Beach And Village, Pool, Dock

544 Canal Road, Siesta Key, United States Show map

Walk To Siesta Key Beach And Village, Pool, Dock villa is 5 minutes' walk from Public Beach Access 10, offering guests to unwind at a Jacuzzi. The 2-bedroom holiday home features opportunities for… More

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Over The Top

1060 Windsong Lane, Siesta Key, United States Show map

The 1-bedroom Over The Top Siesta Key villa hosts up to 22 guests and provides proximity to Jamaica Royale, situated only a 7-minute walk away. Featuring a Jacuzzi, this Siesta Key holiday home is… More

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Sunset Gulf

551 Beach Rd, Us, Siesta Key, United States Show map

Featuring a heated pool, Sunset Gulf Villa Siesta Key is suitable for up to 23 people and is located 3.1 km from Siesta Key Marina. Providing guests with Wi-Fi and private parking, this 8-bedroom… More

From US$ 2276 Book Now

100 Percent Private - Pool, Oceanviews, Village, Beaches!

113 Columbus Blvd, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

The 8-bedroom 100 Percent Private - Pool, Oceanviews, Village, Beaches! Siesta Key villa is situated approximately 5 minutes' walk from Beach Club, featuring such comforts as Wi-Fi and parking. More

From US$ 3923 Book Now

Siesta Key Oasis W/ Outdoor Pool + Screened Lanai!

623 Avenida Del Norte, Siesta Key, United States Show map

Siesta Key Oasis W/ Outdoor Pool + Screened Lanai! villa is 5 minutes' walk from Siesta Key Beach Access 7, offering guests to unwind at a Jacuzzi. Located 2.6 km from Big Sarasota Pass, the 4… More

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Luxe Lagoon - 119

119 Avenida Messina, Siesta Key, United States Show map

Suitable for 22 guests, Luxe Lagoon - 119 Siesta Key villa offers a location within 500 metres of Seaside Vacation Villas and features an aqua park and a golf course. Located a 10-minute drive from… More

From US$ 3121 Book Now

Family-Friendly Beach Escape With Pool, Porch & Sun-Filled Fun - Aloha Kai #24

6020 Midnight Pass Road Unit 24, Siesta Key, United States Show map

The 2-bedroom Family-Friendly Beach Escape With Pool, Porch & Sun-Filled Fun - Aloha Kai #24 Siesta Key villa is located nearly a 20-minute walk from Siesta Key Drum Circle and provides diving… More

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6415 Midnight Pass #304

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

Located about 25 minutes' walk from Siesta Key Beach, the 2-bedroom 6415 Midnight Pass #304 Villa Siesta Key boasts an outdoor swimming pool with a hot tub. Staying at the holiday home, within easy… More

From US$ 180 Book Now

Sandy Cove Sanctuary

121 Pass Key Rd, 121, Siesta Key, United States Show map

The 1-bedroom Sandy Cove Sanctuary Siesta Key villa accommodates up to 2 guests and offers a beachfront location around a 10-minute drive from shopping venues such as the upscale Saint Armands Circle… More

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112 Columbus Blvd

112 Columbus Boulevard, Siesta Key, United States Show map

Located nearly 5 minutes' walk from Siesta Key Craft Festival Museum, the 3-bedroom 112 Columbus Blvd Villa Siesta Key offers quick access to various city attractions in the vicinity. Providing… More

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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

Nestled 4.4 km from the friendly Edson Keith Estate Park, the 1-bedroom Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1 Mile And Crescent Beach 2 Miles, 1Bdr villa features an outdoor… More

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Sandy Cove - Unit 401

4900 Ocean Boulevard, Siesta Key, United States Show map

Located merely 1.2 km from Siesta Key Beach Access 2, the 2-bedroom Sandy Cove - Unit 401 Siesta Key villa provides access to various tourist attractions in the vicinity. With a maximum capacity of 4… More

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1/2 Mi To Beach! Siesta Key Home W/ Lanai

Siesta Key, FL, 34242, Siesta Key, United States Show map

Located only a 7-minute walk from Turtle Beach, the 2-bedroom 1/2 Mi To Beach! Siesta Key Home W/ Lanai boasts a swimming pool and can accommodate up to 4. Providing guests with Wi-Fi and a private… More

From US$ 295 Book Now

Double Your Beachside Fun - Aloha Kai #34 & #55 - Roelens

6020 Midnight Pass Road Unit 34 & 55, Siesta Key, United States Show map

Double Your Beachside Fun - Aloha Kai #34 & #55 - Roelens Siesta Key villa is located nearly 20 minutes' walk from Siesta Key Beach, giving access to various tourist spots nearby. The accommodation… More

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Sunburst Courtyard - 430

430 Givens Street, Siesta Key, United States Show map

The 4-bedroom Sunburst Courtyard - 430 Villa Siesta Key is located approximately 25 minutes on foot from Siesta Beach Pavillion and provides snorkelling, horseback riding, and fisheries for active… More

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Crystal Sands 1106

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

Offering a swimming pool, the 2-bedroom Crystal Sands 1106 Siesta Key villa is located nearly a 5-minute walk from Crescent Arms and is ideal for up to 6 guests. Located not far from Siesta Key… More

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Walk To Siesta Key Beach & Village, Pool, Dock

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

Located only 1.3 km from Siesta Key Beach Access 2, the 2-bedroom Walk To Siesta Key Beach & Village, Pool, Dock villa boasts a year-round outdoor swimming pool with a Jacuzzi. The Siesta Key holiday… More

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The Plaza

5458 Plaza De Las Palmas, Siesta Key, United States Show map

The 1-bedroom The Plaza Villa Siesta Key is situated about a 5-minute walk from Siesta Key Beach Access 7, featuring such comforts as Wi-Fi and a private parking lot. Staying at this holiday home… More

From US$ 5540 Book Now

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

Nestled 3.2 km from the shaped Crescent Beach, the 1-bedroom Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1 Mile And Crescent Beach 2 Miles, 1Bdr villa is boasting a sun deck and a picnic… More

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Gulf And Bay Club- B408

5780 Midnight Pass, Siesta Key, United States Show map

Boasting a Jacuzzi, the 2-bedroom Gulf And Bay Club- B408 Villa Siesta Key is located just a 7-minute walk from Jamaica Royale and can accommodate 5 guests. This 2-bathroom villa features… More

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6415 Midnight Pass #805

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

Located nearly 25 minutes' walk from Siesta Key Beach, the 2-bedroom 6415 Midnight Pass #805 Villa Siesta Key boasts an outdoor swimming pool with a hot tub. Staying at this Siesta Key villa, within… More

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Sea Winds Beachside Retreat

6703 Midnight Pass Rd, 208, Siesta Key, United States Show map

Situated about a 25-minute walk from the friendly Edson Keith Estate Park, Sea Winds Beachside Retreat Siesta Key villa provides access to numerous tourist attractions in the area. More

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Sol Y Mar

1137 Sun N Sea Dr, Siesta Key, United States Show map

Situated only 7 minutes' walk from Siesta Key Marina, the 4-bedroom Sol Y Mar Villa Siesta Key is ideal for up to 8 guests. This accommodation boasts an aqua park and a golf course, while Sarasota… More

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Siesta Key Paradise

1020 Glebe Lane, Siesta Key, United States Show map

Situated a mere 9 minutes' walk from Siesta Key Village, the 1-bedroom Siesta Key Paradise villa is ideal for up to 8 guests. More

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Excelsior Beach To Bay-Bayside

6263 Midnight Pass Rd, Siesta Key, United States Show map

Located nearly 5 minutes' walk from the shaped Crescent Beach, Excelsior Beach To Bay-Bayside Siesta Key villa provides a heated pool, a Jacuzzi for additional comfort. More

From US$ 297 Book Now

Tropical Sk Villa Private Patio & Pool Access

1386 Moonmist Drive, Siesta Key, United States Show map

The 3-bedroom Tropical Sk Villa Private Patio & Pool Access Siesta Key is situated nearly 5 minutes' walk from Siesta Harbour Condominium Apt Harbor, featuring such comforts as Wi-Fi and parking. The… More

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Crystal Sands 1101

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

Offering a swimming pool, the 2-bedroom Crystal Sands 1101 Siesta Key villa is situated nearly a 5-minute walk from Crescent Arms and can accommodate up to 6 guests. The holiday home boasts an aqua… More

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Crescent Royale Condominiums 303

797 Beach Road, Unit 303, Siesta Key, United States Show map

Crescent Royale Condominiums 303 Siesta Key villa is located 8 minutes' walk from Public Beach Access 10 and invites guests to join windsurfing, snorkelling, and hiking. The 2-bedroom holiday home… More

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Siesta Treasure

1140 Sun And Sea Drive, Siesta Key, United States Show map

Offering a heated pool, the 4-bedroom Siesta Treasure Villa Siesta Key is located just 8 minutes' walk from Siesta Key Marina and is ideal for up to 8 guests. This villa features opportunities for… More

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6415 Midnight Pass #202

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

Located merely 7 minutes' walk from Crescent Arms, the 2-bedroom 6415 Midnight Pass #202 Villa Siesta Key offers an outdoor swimming pool for guests to relax by. Featuring a Jacuzzi, the villa is… More

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Dockside Getaway On Avenida

615 Avenida Del Norte, Siesta Key, United States Show map

The 2-bedroom Dockside Getaway On Avenida Villa Siesta Key is situated nearly 5 minutes' walk from Sarasota Beach, featuring such comforts as Wi-Fi and parking. More

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Siesta Beach House - 202

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

Situated just a 7-minute walk from Jamaica Royale, the 2-bedroom Siesta Beach House - 202 Siesta Key villa is ideal for up to 4 guests. Located 4.6 km from Bee Ridge Park, the holiday home provides… More

From US$ 1106 Book Now