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2026-11-03
2026-11-04
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Extended Stay in Siesta Key

Siesta Royale 54

6334 Midnight Pass Rd, #54, Siesta Key, United States Show map

The 1-bedroom Siesta Royale 54 Villa Siesta Key is nestled around a 5-minute walk from Crescent Arms and can accommodate up to 4 guests. Located a few steps from the shaped Crescent Beach, this villa… More

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Midnight Cove II 433F

1600 Cove II Place, Unit 433F, Siesta Key, United States Show map

Featuring a swimming pool, the spacious Midnight Cove II 433F Apartment Siesta Key is a 6-minute walk from crescent arms private beach. 1.7 km from Jamaica Royale, this apartment welcomes guests with… More

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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

Villa A10 - Siesta Vacation Villa | Free Cancellation

6154 Midnight Pass Rd, #A10, Siesta Key, United States Show map

Situated merely an 8-minute walk from Crescent Arms, Villa A10 - Siesta Key Vacation Villa | Free Cancellation* offers guests to relax by a swimming pool. More

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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

Gulf And Bay Club- C201

5770 Midnight Pass Rd, Unit C201, Siesta Key, United States Show map

The 124 m² Gulf And Bay Club- C201 Apartment Siesta Key is located in Siesta Key, around a 20-minute walk from Crescent Arms, and boasts a Jacuzzi. Wi-Fi and parking are also available at this 2… More

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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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Newly Remodeled Apt! Key-West Victorian With Beach Access, To Siesta Key Beach!

6905 Point Of Rocks Road, Sarasota, Florida 34242, United States, Siesta Key, United States Show map

Located 500 metres from Siesta Key Marina, the 111 m² Newly Remodeled Apt! Key-West Victorian With Beach Access, To Siesta Key Beach! accommodates up to 12 guests. At the spacious apartment, Wi-Fi… More

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Our House At The Beach W-701

1001 Beach Rd, Unit W-701, Siesta Key, United States Show map

The spacious Our House At The Beach W-701 Siesta Key is a 6-minute walk from Siesta Key Beach and can accommodate up to 6 guests. Situated right near Siesta Key Beach Access #10, this apartment will… More

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Beach Way 110

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

Offering an outdoor swimming pool, the spacious Beach Way 110 Siesta Key apartment is situated 7 minutes' walk from Siesta Key Village. Wi-Fi and parking are among the essentials at guests' disposal. 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

Walk To #1 Siesta Beach, Htd Pool, Covered Parking

5635 Midnight Pass Road #1016, Siesta Key, United States Show map

The spacious Walk To #1 Siesta Beach, Htd Pool, Covered Parking Siesta Key apartment lies in a prime location in Siesta Key, around a 5-minute walk from Siesta Key. Guests can make use of Wi-Fi for… More

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Villa C07 - Siesta Key Sanctuary | Free Cancellation

6154 Midnight Pass Rd, C07, Siesta Key, United States Show map

Situated just 0.7 km from the shaped Crescent Beach, the 2-bedroom Villa C07 - Siesta Key Sanctuary | Free Cancellation is ideal for up to 5 guests. Providing guests with Wi-Fi and parking, this… More

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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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Villa A06 - Good Vibes & High Tides | Free Cancellation

6154 Midnight Pass Rd, #A06, Siesta Key, United States Show map

The 2-bedroom Villa A06 - Good Vibes & High Tides | Free Cancellation* Siesta Key entices guests to enjoy billiard and offers proximity to the shaped Crescent Beach, located just 9 minutes' stroll… 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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Jamaica Royale 704

5830 Midnight Pass Rd, Unit 704, Siesta Key, United States Show map

The 2-bedroom Jamaica Royale 704 Apartment Siesta Key boasts a prime setting and in just 7 minutes' walk from Jamaica Royale. Featuring spa therapy and a golf course, this spacious apartment has an… 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 Royale 25

6334 Midnight Pass Rd, #25, Siesta Key, United States Show map

Siesta Royale 25 Villa Siesta Key is nestled 8 minutes' walk from Siesta Key Marina and can accommodate up to 6 guests. More

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Island Time East - 355

355 Calle Miramar, Siesta Key, United States Show map

Featuring barbecue and a golf course for added enjoyment, the 3-bedroom Island Time East - 355 Villa Siesta Key is located about 5 minutes' walk from Sarasota Beach. Featuring a swimming pool, this… More

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Spacious 1 Br1 Bath, Renovated Ground Floor Unit, 03 Mile To Siesta Beach

5683 Midnight Pass Road #109, Siesta Key, United States Show map

Spacious 1 Br1 Bath, Renovated Ground Floor Unit, 03 Mile To Siesta Beach Siesta Key apartment is located 2.5 km from Siesta Key Beach Access 2 and about a 5-minute walk from Siesta Key. While… More

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Two-Level, Heated Pool, Trolley To Beach & Village

6157 Midnight Pass Road C32, Siesta Key, United States Show map

Two-Level, Heated Pool, Trolley To Beach & Village Siesta Key apartment is located merely 0.6 km from Siesta Harbour Condominium Apt Harbor and approximately a 20-minute walk from Siesta Key Drum… More

From US$ 178 Book Now

Gulf And Bay Club- A205

5790 Midnight Pass Rd, Unit A205, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Gulf And Bay Club- A205 Apartment Siesta Key, which is 4.4 km from South Lido Key Beach Park on the Gulf and approximately 20… 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 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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Siesta Royale 18

6334 Midnight Pass Rd, #18, Siesta Key, United States Show map

The 1-bedroom Siesta Royale 18 Apartment Siesta Key boasts a beachfront location a mere 150 metres from Crescent Arms. The 58 m² apartment offers modern facilities, such as Wi-Fi and essentials like… 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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Midnight Cove II 512F

1500 Cove II Place, Unit 512F, Siesta Key, United States Show map

Located just a 5-minute walk from Crescent Arms and Siesta Harbour Condominium Apt Harbor, the spacious Midnight Cove II 512F Apartment Siesta Key features views of the pool. 2.8 km from Nontando… 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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Walk To Siesta Key Beach 2 Br2 Bath Washerdryer Heated Pool Gas Grills

5649 Midnight Pass Road #804, Siesta Key, United States Show map

The spacious Walk To Siesta Key Beach 2 Br2 Bath Washerdryer Heated Pool Gas Grills apartment boasts a prime location within 5 minutes' walk of Jamaica Royale. Guests can relax in a private garden at… More

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Jamaica Royale 016

5830 Midnight Pass Rd, Unit 016, Siesta Key, United States Show map

Located only 1.1 km from Siesta Key Public Beach, the spacious 63 m² Jamaica Royale 016 Apartment Siesta Key features parking for those who travel by car. The 1-bedroom apartment boasts a convenient… More

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Gulf And Bay Club- A609

5790 Midnight Pass Rd, Unit A609, Siesta Key, United States Show map

Situated 20 minutes' walk from Siesta Key Village, the spacious Gulf And Bay Club- A609 Apartment Siesta Key offers a hot tub for 6 visitors. Wi-Fi and a car park are also available at this apartment. More

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Siesta Royale 22

6334 Midnight Pass Rd, #22, Siesta Key, United States Show map

The 1-bedroom Siesta Royale 22 Villa Siesta Key offers swift access to various city sites, such as Green Turtle Shell & Gift City, situated just 6 minutes' walk away. More

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Villa D15 - Siesta Key Paradise | Free Cancellation

6154 Midnight Pass Rd, D15, Siesta Key, United States Show map

Located only 1.1 km from Jamaica Royale, the 2-bedroom Villa D15 - Siesta Key Paradise | Free Cancellation* provides access to various tourist attractions in the vicinity. This Siesta Key villa is… More

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Village West Unit 101

5224 Avenida Navarra, Unit 101, Siesta Key, United States Show map

The 1-bedroom Village West Unit 101 Siesta Key apartment features a convenient location approximately 5 minutes' walk from the co-op Gallery on Siesta Key and hosts up to 4 guests. The apartment is… More

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Gulf And Bay Club- B307

5780 Midnight Pass Rd, Unit B307, Siesta Key, United States Show map

The 2-bedroom Gulf And Bay Club- B307 Apartment Siesta Key enjoys a convenient location a mere 6 minutes' walk from Jamaica Royale. Boasting a hot tub, this 124 m² apartment, suitable for 4 guests… More

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Siesta Royale 34

6334 Midnight Pass Rd, 34, Siesta Key, United States Show map

The 1-bedroom Siesta Royale 34 Villa Siesta Key offers proximity to such city sites as the shaped Crescent Beach, located only a 6-minute walk away. More

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Siesta Royale 35

6334 Midnight Pass Rd, #35, Siesta Key, United States Show map

Located a mere 5 minutes' walk from Crescent Arms, Siesta Royale 35 Villa Siesta Key features a swimming pool and can accommodate up to 4 guests. Located within reach of Christopher Wheeler Park… 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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Jamaica Royale 303

5830 Midnight Pass Rd, Unit 303, Siesta Key, United States Show map

The 2-bedroom Jamaica Royale 303 Apartment Siesta Key boasts a convenient setting and in merely 7 minutes' walk from Jamaica Royale. The spacious 119 m² apartment features Wi-Fi, along with a car… More

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Sunset Royale - 114

711 Beach Rd, Unit 114, Siesta Key, United States Show map

Sunset Royale - 114 Apartment Siesta Key is located a mere 1.8 km from Siesta Key Beach Access 2 and 25 minutes' walk from the friendly Edson Keith Estate Park. This spacious 86 m² apartment can hold… More

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