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

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

Villa B03 - Forever Starts On Siesta Key | Free Cancellation

6154 Midnight Pass Rd, #B03, Siesta Key, United States Show map

Located 9 minutes' walk from the shaped Crescent Beach, Villa B03 - Forever Starts On Siesta Key | Free Cancellation* is suitable for 2 guests and provides a swimming pool to relax in. The 1-bedroom… More

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Blue Ocean Suites By Beachside Management

632 Calle Del Otono, Siesta Key, United States Show map

Blue Ocean Suites By Beachside Management Siesta Key is located 3.3 km from Shell Beach and about a 20-minute walk from Siesta Key Beach Access 2. Wi-Fi and parking are also available at the… More

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2 Bed 2 Bath Condo! 14 Mile To #1 Siesta Beach Ground Floor With Garden View

5637 Midnight Pass Road #1019, Siesta Key, United States Show map

Featuring a prime location, the spacious 2 Bed 2 Bath Condo! 14 Mile To #1 Siesta Beach Ground Floor With Garden View Siesta Key offers views of the garden, about 25 minutes' walk from Escape Room… More

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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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Siesta Royale 23

6334 Midnight Pass Rd, #23, Siesta Key, United States Show map

Situated nearly a 5-minute stroll from Siesta Harbour Condominium Apt Harbor, the 1-bedroom Siesta Royale 23 Villa Siesta Key offers quick access to numerous city landmarks nearby. More

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Gulf And Bay Club- E204

5750 Midnight Pass Rd, Unit E204, Siesta Key, United States Show map

Gulf And Bay Club- E204 Apartment Siesta Key is located around a 20-minute walk from Siesta Key Village and about 4 km from Big Sarasota Pass. Boasting a prime location, within reach of Jamaica… 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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Midnight Cove II 533F

1500 Cove II Place, Unit 533F, Siesta Key, United States Show map

The spacious Midnight Cove II 533F Apartment Siesta Key is located about 2 km from Siesta Beach Pavillion and about a 25-minute walk from Siesta Key Beach. While staying in the apartment, guests can… More

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Midnight Cove II 912C

1100 Cove II Place, Unit 912C, Siesta Key, United States Show map

Located a mere 9 minutes' stroll from Siesta Key Marina, the spacious 130 m² Midnight Cove II 912C Apartment Siesta Key accommodates up to 6 guests. Enjoying a convenient setting, the 2-bedroom… More

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Jamaica Royale 602

5830 Midnight Pass Rd, Unit 602, Siesta Key, United States Show map

The spacious Jamaica Royale 602 Apartment Siesta Key is a 7-minute walk from Jamaica Royale and can accommodate up to 6 guests. Featuring spa therapy and a golf course, this apartment has an area of… More

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Gulf And Bay Club- B308

5780 Midnight Pass Rd, Unit B308, Siesta Key, United States Show map

Located around 5 minutes on foot from Jamaica Royale, the spacious 126 m² Gulf And Bay Club- B308 Apartment Siesta Key accommodates up to 4 guests. The 2-bedroom apartment enjoys a convenient… More

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Midnight Cove II 810F

1200 Cove II Place, Unit 810F, Siesta Key, United States Show map

The 84 m² Midnight Cove II 810F Apartment Siesta Key features a convenient location only a 10-minute walk from Christopher Wheeler Park and hosts up to 6 guests. Wi-Fi and a car park are also… More

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Jamaica Royale 081

5830 Midnight Pass Rd, Unit 081, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the 2-bedroom Jamaica Royale 081 Apartment Siesta Key, which is 19 minutes' walk from the shaped Crescent Beach and approximately 7 km from the upscale… 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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Harbor Towers 722

5855 Midnight Pass Road #722, Siesta Key, United States Show map

The 1-bedroom Harbor Towers 722 Apartment Siesta Key is also located approximately a 5-minute walk from Jamaica Royale. This 113 m² apartment features Wi-Fi, along with parking for guests travelling… 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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Harbor Towers 530

5855 Midnight Pass Road #530, Siesta Key, United States Show map

Situated about 25 minutes' walk from Siesta Key Beach Access 7, the spacious 1-bedroom Harbor Towers 530 Apartment Siesta Key provides guests with Wi-Fi for either business or leisure. Various sport… More

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Aloha Kai Villa 59 - Check In To Coastal Bliss

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

Located nearly 10 minutes' walk from the shaped Crescent Beach, the 1-bedroom Aloha Kai Villa 59 - Check In To Coastal Bliss Siesta Key offers a heated pool for guests to relax by. Providing guests… More

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Jamaica Royale 603

5830 Midnight Pass Rd, Unit 603, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Jamaica Royale 603 Apartment Siesta Key, which is just 1.5 km from Siesta Key Beach and approximately 15 minutes' drive from Edson… More

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Gulf & Bay Club By Beachside Management

5730 Midnight Pass Road, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the 2-room Gulf & Bay Club By Beachside Management Siesta Key apartment, which is around a 10-minute ride from Escape Room Sarasota and just 1.9 km from… More

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Jamaica Royale 076

5830 Midnight Pass Rd, Unit 076, Siesta Key, United States Show map

Located 7 minutes' walk from Jamaica Royale, the spacious Jamaica Royale 076 Apartment Siesta Key accommodates up to 6 guests. Wi-Fi and parking are also available at the apartment. 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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Jamaica Royale 082

5830 Midnight Pass Rd, Unit 082, Siesta Key, United States Show map

The spacious Jamaica Royale 082 Apartment Siesta Key features a prime location an 18-minute walk from Siesta Key Beach and hosts up to 6 guests. Wi-Fi and parking are also available at this apartment. 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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Siesta Royale 17

6334 Midnight Pass Rd, #17, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the 1-bedroom Siesta Royale 17 Apartment Siesta Key, which is 4.2 km from Turtle Beach and approximately 25 minutes' walk from Nontando. Guests can use… 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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Beach Rd, 300Ft To Beach Access & 500Ft To Siesta Key Village, Studio

323 Beach Rd, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

Situated nearly 5 minutes' walk from Sarasota Beach, the 1-bedroom Beach Rd, 300Ft To Beach Access & 500Ft To Siesta Key Village, Studio villa offers guests to take advantage of a sundeck and a… 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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Spacious 1 Br1 Bath, Renovated Ground Floor Unit, 03 Mile To Siesta Beach

5631 Midnight Pass Road #1003, Siesta Key, United States Show map

Spacious 1 Br1 Bath, Renovated Ground Floor Unit, 03 Mile To Siesta Beach Siesta Key apartment is located 5 minutes' walk from Siesta Key and looks out onto the pool. Wi-Fi is available for guests'… 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 Royale 01

6334 Midnight Pass Rd, #01, Siesta Key, United States Show map

The 2-bedroom Siesta Royale 01 Villa Siesta Key accommodates up to 6 guests and offers proximity to Crescent Arms, located just a 5-minute walk away. Providing guests with Wi-Fi and a private parking… 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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Sole Retreat

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

The 102 m² Sole Retreat Apartment Siesta Key is located around a 25-minute walk from Bay Island and 3.2 km from Sarasota Square. Providing a Jacuzzi and a sauna, this 2-bedroom apartment ensures a… More

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Gulf And Bay Club- E108

5750 Midnight Pass Rd, Unit E108, Siesta Key, United States Show map

Gulf And Bay Club- E108 Apartment Siesta Key is located about 10 minutes by car from Siesta Key Beach Access 7 and 4.3 km from Bay Island. Boasting a prime location, within a few blocks of Jamaica… 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

Jamaica Royale 022

5830 Midnight Pass Rd, Unit 022, Siesta Key, United States Show map

The 1-bedroom Jamaica Royale 022 Apartment Siesta Key enjoys a convenient location only a 7-minute walk from Jamaica Royale. At this spacious apartment, Wi-Fi and a car park are also provided. More

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