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2026-11-03
2026-11-04
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Siesta Key Vacation Rentals

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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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 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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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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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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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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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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Midnight Cove II 943C

1100 Cove II Place, Unit 943C, Siesta Key, United States Show map

The spacious Midnight Cove II 943C Apartment Siesta Key is located 0.6 km from Green Turtle Shell & Gift City and 25 minutes' walk from Siesta Key Drum Circle. Providing a golf course and a dining… More

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Midnight Cove II 214F

1800 Cove II Place, Unit 214F, Siesta Key, United States Show map

Situated within 25 minutes' walk of Escape Room Sarasota, the spacious 84 m² Midnight Cove II 214F Apartment Siesta Key provides guests with Wi-Fi for either business or leisure. The 2-bedroom… More

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Jamaica Royale T23

5830 Midnight Pass Rd, Unit T23, Siesta Key, United States Show map

The 111 m² Jamaica Royale T23 Apartment Siesta Key is located a mere 1.5 km from Siesta Key Beach and about a 20-minute walk from Siesta Key Village. Wi-Fi and parking are also available at this 2… More

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Bay Oaks E-93

6157 Midnight Pass Rd, Unit E-93, Siesta Key, United States Show map

Located within 25 minutes' walk of Siesta Key Beach, the spacious 102 m² Bay Oaks E-93 Apartment Siesta Key features private parking for those who travel by car. Popular points of interest close to… More

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Super 2 Bed2 Bath Ground Floor,#1 Siesta Beach

5647 Midnight Pass Road #807, Siesta Key, United States Show map

Super 2 Bed2 Bath Ground Floor,#1 Siesta Beach Siesta Key apartment is located only 1.7 km from the shaped Crescent Beach and offers Wi-Fi for either business or leisure. The spacious apartment has a… More

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Harbor Towers 520

5855 Midnight Pass Road #520, Siesta Key, United States Show map

The 98 m² Harbor Towers 520 Apartment Siesta Key is located approximately a 25-minute walk from Sarasota Beach and 2.9 km from Siesta Key Beach Access 2. This spacious apartment features Wi-Fi, along… More

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Harbor Towers 401

5855 Midnight Pass Road #401, Siesta Key, United States Show map

Located 6 minutes' walk from Jamaica Royale, the spacious Harbor Towers 401 Apartment Siesta Key accommodates up to 4 guests. Wi-Fi and a car park are also available at this apartment. More

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Midnight Cove II 620D

1400 Cove II Place, Unit 620D, Siesta Key, United States Show map

Featuring a prime location, the 3-bedroom Midnight Cove II 620D Apartment Siesta Key offers views of the pool, approximately a 10-minute walk from Siesta Key Marina. Situated a stone's throw from… More

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Gertrude'S Siesta | Beach-Views, Pool, 1 Min Walk To Beach, Balconies!

450 Beach Road #3, Siesta Key, United States Show map

Featuring a heated pool, the spacious 3-bedroom Gertrude Apartment Siesta Key is approximately 5 minutes' walk from Sarasota Beach. Windsurfing, snorkelling, and diving provide great entertainment… More

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Jamaica Royale 401

5830 Midnight Pass Rd, Unit 401, Siesta Key, United States Show map

The spacious 2-bedroom Jamaica Royale 401 Apartment Siesta Key features a prime location a mere 1.5 km from Siesta Key Beach and hosts up to 6 guests. This 119 m² apartment is situated within reach… More

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Midnight Cove II 733F

1300 Cove II Place, Unit 733F, Siesta Key, United States Show map

Located approximately 5 minutes' walk from Crescent Arms and Siesta Harbour Condominium Apt Harbor, the spacious 2-bedroom Midnight Cove II 733F Apartment Siesta Key features views of the pool. This… More

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Bay Oaks 75

Siesta Key, United States Show map

Bay Oaks 75 Apartment Siesta Key is located 2.8 km from Grand Canal and a 10-minute ride from Siesta Key Beach Access 7. More

From US$ 170 Book Now

Siesta Royale 05

6334 Midnight Pass Rd, #05, Siesta Key, United States Show map

Located 650 metres from Siesta Key Marina, Siesta Royale 05 Apartment Siesta Key accommodates up to 6 guests. Wi-Fi and private parking are also available at this spacious 67 m² apartment. More

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Midnight Cove II 911C

1100 Cove II Place, Unit 911C, Siesta Key, United States Show map

The 2-bedroom Midnight Cove II 911C Apartment Siesta Key boasts a prime setting and in approximately a 5-minute walk from Crescent Arms. Situated in close proximity to Siesta Harbour Condominium Apt… More

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Midnight Cove II 221D

1800 Cove II Place, Unit 221D, Siesta Key, United States Show map

Located merely 5 minutes' stroll from Crescent Arms, the spacious 195 m² Midnight Cove II 221D Apartment Siesta Key accommodates up to 6 guests. Enjoying a prime setting, the 3-bedroom apartment lies… More

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Harbor Towers 312

5855 Midnight Pass Road #312, Siesta Key, United States Show map

The spacious 70 m² Harbor Towers 312 Apartment Siesta Key is a good choice for accommodating up to 4 guests, offering a convenient setting about 25 minutes on foot from Grand Canal. Featuring a golf… More

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Bay Oaks A51, Ground Floor Condo With Bay View, Heated Pool

6157 Midnight Pass Rd Apt A51, Siesta Key, United States Show map

The spacious 64 m² Bay Oaks A51, Ground Floor Condo With Bay View, Heated Pool Siesta Key is located in Siesta Key, approximately a 10-minute ride from Nontando, and offers guests an outdoor swimming… More

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Gulf And Bay Club- F503

5740 Midnight Pass Rd, Unit F503, Siesta Key, United States Show map

The spacious Gulf And Bay Club- F503 Apartment Siesta Key is situated in Siesta Key, 17 minutes' walk from Siesta Beach Pavillion, and offers spa amenities such as a Jacuzzi. Wi-Fi and parking are… More

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Midnight Cove II 220D

1800 Cove II Place, Unit 220D, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 195 m² Midnight Cove II 220D Apartment Siesta Key, which is within 1 km of Christopher Wheeler Park and about 10 minutes on foot from Green… More

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Our House At The Beach W-702

1001 Beach Rd, Unit W-702, Siesta Key, United States Show map

The spacious 2-bedroom Our House At The Beach W-702 Siesta Key offers a convenient location, around 25 minutes' walk from Siesta Key Marina. This 112 m² apartment is situated just around the corner… More

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Harbor Towers 317

5855 Midnight Pass Road #317, Siesta Key, United States Show map

The spacious 98 m² Harbor Towers 317 Apartment Siesta Key is just 200 metres from Jamaica Royale and can accommodate up to 4 guests. Siesta Key is within reach of the 2-bedroom apartment, while… More

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Gulf And Bay Club- B604

5780 Midnight Pass Rd, Unit B604, Siesta Key, United States Show map

Situated just 1.1 km from Siesta Beach Pavillion, the spacious 126 m² Gulf And Bay Club- B604 Apartment Siesta Key provides guests with Wi-Fi for either business or leisure. Nearly 20 minutes' walk… More

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Gulf And Bay Club- B601

5780 Midnight Pass Rd, Unit B601, Siesta Key, United States Show map

The spacious 3-bedroom Gulf And Bay Club- B601 Apartment Siesta Key is located in Siesta Key, within a 7-km distance of the upscale Saint Armands Circle Outdoor Mall, and pampers guests with a hot… More

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Upgraded 1 Bed1 Bath Ground Flr, #1 Siesta Beach

5625 Midnight Pass Road #605, Siesta Key, United States Show map

Upgraded 1 Bed1 Bath Ground Flr, #1 Siesta Beach Siesta Key apartment is located a 5-minute walk from Siesta Key and overlooks the pool. Offering access to a swimming pool, this apartment is in the… More

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Our House At The Beach W-602

1001 Beach Rd, Unit W-602, Siesta Key, United States Show map

The 2-bedroom Our House At The Beach W-602 Siesta Key is located around a 25-minute walk from Crescent Arms and offers Wi-Fi for either business or leisure. Guests can benefit from a prime location… More

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Renovated 2Nd Floor, Easy Walk To #1 Siesta Beach, Heated Pool, Free Wifi

5649 Midnight Pass Road #802, Siesta Key, United States Show map

Located approximately 5 minutes' walk from Jamaica Royale and Siesta Key, the spacious Renovated 2Nd Floor, Easy Walk To #1 Siesta Beach, Heated Pool, Free Wifi Siesta Key apartment features views of… More

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Gulf And Bay Club- A106

5790 Midnight Pass Rd, Unit A106, Siesta Key, United States Show map

The spacious Gulf And Bay Club- A106 Apartment Siesta Key is located in Siesta Key, 20 minutes' walk from Siesta Key Village, and pampers guests with a hot tub. Wi-Fi and a car park are also… More

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Gulf Holiday Unit 3

73 Avenida Messina, #3, Siesta Key, United States Show map

Featuring a swimming pool, the spacious 38 m² Gulf Holiday Unit 3 Siesta Key apartment is only 6 minutes' walk from Beach Club. The 1-bedroom apartment is situated just near Siesta Key Beach Access 2… More

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Harbor Towers 226

5855 Midnight Pass Road #226, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Harbor Towers 226 Apartment Siesta Key, which is 4.5 km from Bee Ridge Park and around 15 minutes' drive from Lido Key Sandy Beach… More

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

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

The 8-bedroom Newly Remodeled Apt! Key-West Victorian With Beach Access, To Siesta Key Beach! boasts a prime setting and in a mere 7 minutes' walk from Siesta Key Marina. This spacious apartment… More

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Our House At The Beach E-404

1055 Beach Rd, Unit E-404, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Our House At The Beach E-404 Siesta Key, which is within 7 km of the upscale Saint Armands Circle Outdoor Mall and a mere 650… More

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Jamaica Royale 504

5830 Midnight Pass Rd, Unit 504, Siesta Key, United States Show map

Located just a 7-minute stroll from Jamaica Royale, the spacious 119 m² Jamaica Royale 504 Apartment Siesta Key accommodates up to 6 guests. Enjoying a prime setting, the 2-bedroom apartment lies… More

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Siesta Royale 08

6334 Midnight Pass Rd, #08, Siesta Key, United States Show map

The 58 m² Siesta Royale 08 Apartment Siesta Key is located 3.2 km from Siesta Key Beach Access 7 and about a 25-minute walk from Siesta Key Beach. Offering access to a heated pool, the apartment is… More

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New Listing! The Village Breeze 6Br With Heated Pool, Near Beach, 250Ft To Siesta Key Village!

5116 Calle Minorga, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at spacious 6-bedroom The Village Breeze 6Br With Heated Pool, Near Beach, 250Ft To Siesta Key Village! apartment, which is 3.8 km from Siesta Key Beach and… More

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Jamaica Royale 057

5830 Midnight Pass Rd, Unit 057, Siesta Key, United States Show map

The spacious Jamaica Royale 057 Apartment Siesta Key is located 2.3 km from Grand Canal and about a 20-minute walk from Siesta Key Drum Circle. Wi-Fi and parking are provided for guests' utmost… More

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Jamaica Royale 502

5830 Midnight Pass Rd, Unit 502, Siesta Key, United States Show map

The 119 m² Jamaica Royale 502 Apartment Siesta Key is located within a 15-minute drive of the friendly Edson Keith Estate Park and 4.7 km from Red Bug Slough Preserve. Guests can benefit from a prime… More

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Gulf And Bay Club- A207

5790 Midnight Pass Rd, Unit A207, Siesta Key, United States Show map

The 124 m² Gulf And Bay Club- A207 Apartment Siesta Key is just a 7-minute walk from Jamaica Royale and welcomes guests with a Jacuzzi. Offering spa therapy and a golf course, this 2-bedroom… More

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