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

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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A Spacious Condo In Beautiful Siesta Key, Heated Pool, Tennis, Waterfront Picnic

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

Offering a swimming pool, the 2-bedroom A Spacious Condo In Beautiful Siesta Key, Heated Pool, Tennis, Waterfront Picnic villa is situated approximately a 5-minute walk from the shaped Crescent Beach… More

From US$ 166 Book Now

Siesta Villa Whispering Palms

1331 Moonmist Dr, Siesta Key, United States Show map

Located 700 metres from the shaped Crescent Beach, Siesta Villa Whispering Palms Siesta Key is suitable for 6 guests and provides a heated pool to relax in. This 3-bedroom villa features… 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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5177 Saint Albans

5177 Saint Albans Avenue, Siesta Key, United States Show map

Located just an 8-minute walk from Grand Canal, the 3-bedroom 5177 Saint Albans Villa Siesta Key features a swimming pool and can accommodate up to 10 guests. Located 3.4 km from Siesta Key Beach… More

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Crescent Royale Condominiums 412

757 Beach Road, Unit 412, Siesta Key, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Crescent Royale Condominiums 412 Siesta Key villa is situated merely 6 minutes' walk from Siesta Key Beach and can accommodate up to 4 guests. The… More

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Recently Updated Cozy Siesta Key Beach Villa

1269 Moonmist Circle, Siesta Key, United States Show map

Located just a 6-minute walk from the shaped Crescent Beach, the 2-bedroom Recently Updated Cozy Siesta Key Beach Villa features a swimming pool and can accommodate up to 7 guests. Located within a… More

From US$ 230 Book Now

Crescent 305

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

During the stay at Crescent 305 Villa Siesta Key, guests can indulge in cycling and fisheries or visit Siesta Key Beach, located a 25-minute walk away. Located 3.4 km from Grand Canal, the 2-bedroom… 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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Villa D04 - Coastal Comfort On Siesta Key | Free Cancellation

6154 Midnight Pass Rd, #D04, Siesta Key, United States Show map

Located just a 9-minute walk from the shaped Crescent Beach, the 2-bedroom Villa D04 - Coastal Comfort On Siesta Key | Free Cancellation* boasts a heated pool and can accommodate up to 6. More

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Ocean Beach Gleason Home

4638 Gleason Ave, Siesta Key, United States Show map

The 4-bedroom Ocean Beach Gleason Home Siesta Key is located about 20 minutes on foot from Grand Canal and provides a hot tub. The Siesta Key villa boasts grill and a golf course, while Sarasota… 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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Villa D06 - Tropical Retreat You Can'T Beat | Free Cancellation

6154 Midnight Pass Rd, #D06, Siesta Key, United States Show map

The 2-bedroom Villa D06 - Tropical Retreat You Can'T Beat | Free Cancellation Siesta Key accommodates up to 5 guests and offers proximity to Crescent Arms, located merely 0.7 km away. Providing… 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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Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities

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

Staying at the 2-bedroom Stay At Sarasota County Villa 1005: Gulf Views Resort Amenities Siesta Key, guests can visit Green Turtle Shell & Gift City, which is only 0.8 km away. More

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Siesta Royale 10

6334 Midnight Pass Rd, #10, Siesta Key, United States Show map

Situated only an 8-minute walk from Siesta Key Marina, the 1-bedroom Siesta Royale 10 Villa Siesta Key is ideal for up to 2 guests. Located 3.6 km from Gulf Gate Public Library, this villa provides… 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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Heated Pool-Short Walk To Beach, Free Trolley Around Siesta Key!

6157 Midnight Pass Road Unit E32, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 102 m² Heated Pool-Short Walk To Beach, Free Trolley Around Siesta Key! apartment, which is 4.9 km from Nora Patterson Bay Island Park and… More

From US$ 194 Book Now

Jamaica Royale 089

5830 Midnight Pass Rd, Unit 089, Siesta Key, United States Show map

The spacious Jamaica Royale 089 Apartment Siesta Key is located a mere 1.2 km from Siesta Beach Pavillion and an 18-minute walk from Siesta Key Beach. Wi-Fi and a car park are provided for guests'… More

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Our House At The Beach E-302

1055 Beach Rd, Unit E-302, Siesta Key, United States Show map

The 112 m² Our House At The Beach E-302 Siesta Key is located about 6 km from Edson Keith Estate Park and merely a 14-minute walk from St. Boniface Episcopal Church Labyrinth. Guests can benefit from… More

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Our House At The Beach W-302

1001 Beach Rd, Unit W-302, Siesta Key, United States Show map

The spacious 112 m² Our House At The Beach W-302 Siesta Key is just a 6-minute stroll from Siesta Key Beach and can accommodate up to 6 guests. Grand Canal is in the vicinity of the 2-bedroom… More

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Villa D02 - Seaside Retreat | Free Cancellation

6154 Midnight Pass Rd, #D02, Siesta Key, United States Show map

The 2-bedroom Villa D02 - Seaside Retreat | Free Cancellation* Siesta Key is nestled only an 8-minute walk from Crescent Arms and can accommodate up to 6 guests. Located 2.7 km from Sarasota Beach… More

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Midnight Cove II 423F

1600 Cove II Pl, Unit 423F, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious Midnight Cove II 423F Apartment Siesta Key, which is 2.8 km from Nontando and around 25 minutes' walk from Siesta Key Beach. Wi-Fi is… More

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Gulf And Bay Club- C310

5770 Midnight Pass Rd, Unit C310, Siesta Key, United States Show map

Located just 300 metres from Jamaica Royale, the spacious 2-bedroom Gulf And Bay Club- C310 Apartment Siesta Key accommodates up to 6 guests. The apartment is approximately 5 minutes' drive from St. More

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Midnight Cove II - 137

6327 Midnight Pass Rd, Bldg 1, Unit 137, Siesta Key, United States Show map

Midnight Cove II - 137 Villa Siesta Key, located just a 5-minute walk from Siesta Harbour Condominium Apt Harbor, can host up to 5 guests. This 2-bedroom villa features opportunities for fisheries in… More

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Midnight Cove II 414F

1600 Cove II Place, Unit 414, Siesta Key, United States Show map

The spacious 84 m² Midnight Cove II 414F Apartment Siesta Key boasts a prime location about a 5-minute ride from Crescent Arms. Providing a golf course and a dining table, the 2-bedroom apartment is… More

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Harbor Towers 121

5855 Midnight Pass Road #121, Siesta Key, United States Show map

Located about a 5-minute stroll from Jamaica Royale, the spacious 107 m² Harbor Towers 121 Apartment Siesta Key accommodates up to 6 guests. The 2-bedroom apartment enjoys a prime location, within a… More

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Walk To Siesta Key Beach And Village

544 Canal Road, Siesta Key, Fl 34242, Siesta Key, United States Show map

The 1-bedroom Walk To Siesta Key Beach And Village villa entices active guests with access to a fitness centre and is located around a 5-minute ride from Siesta Key Beach Access 2. Offering an… More

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Villa A18 - Florida Sunkissed | Free Cancellation

6154 Midnight Pass Rd, #A18, Siesta Key, United States Show map

Located 9 minutes' walk from the shaped Crescent Beach, Villa A18 - Florida Sunkissed | Free Cancellation Siesta Key is suitable for 4 guests and provides a swimming pool to relax in. The 2-bedroom… More

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Siesta Royale 03

6334 Midnight Pass Rd, #03, Siesta Key, United States Show map

The 58 m² Siesta Royale 03 Apartment Siesta Key is located only 500 metres from Green Turtle Shell & Gift City and offers Wi-Fi for either business or leisure. Guests can reach the centre of Siesta… More

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Gulf And Bay Club- C207

5770 Midnight Pass Rd, Unit C207, Siesta Key, United States Show map

Situated just 450 metres from Siesta Key, the spacious 125 m² Gulf And Bay Club- C207 Apartment Siesta Key offers a Jacuzzi for up to 6 guests. Boasting a prime location within 5 minutes' walk of… More

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Bay Oaks - E01

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

Located about 25 minutes' walk from Siesta Beach Pavillion, the 2-bedroom Bay Oaks - E01 Villa Siesta Key gives access to various tourist sites in the vicinity. With a maximum capacity of 4 guests… More

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Jamaica Royale 605

5830 Midnight Pass Rd, Unit 605, Siesta Key, United States Show map

Jamaica Royale 605 Apartment Siesta Key features a beachfront location a 17-minute walk from Siesta Beach Pavillion and hosts up to 6 guests. Wi-Fi and a car park are also available at this apartment. More

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Aloha Kai Villa 05 - Your Little Corner Of Paradise

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

Located 750 metres from Crescent Arms, Aloha Kai Villa 05 - Your Little Corner Of Paradise Siesta Key is suitable for 4 guests and provides an outdoor swimming pool to relax in. Located 25 minutes'… More

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Bay Oaks B-22

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

The 2-bedroom Bay Oaks B-22 Villa Siesta Key hosts up to 6 guests and provides proximity to Crescent Arms, situated a mere 0.7 km away. This Siesta Key villa boasts an aqua park and a golf course… More

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Crescent Royale Condominiums 6C

777 Beach Road Unit 6C, Siesta Key, United States Show map

The 2-bedroom Crescent Royale Condominiums 6C Siesta Key villa boasts a location within 5 minutes' walk of Siesta Beach Pavillion and offers guests to enjoy a games room. Offering a lift and a tour… More

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Crescent Royale Condominiums 309

797 Beach Rd Unit 309, Siesta Key, United States Show map

Located merely a 5-minute stroll from Siesta Key Beach, the 1-bedroom Crescent Royale Condominiums 309 Siesta Key villa provides an outdoor swimming pool as well as windsurfing, snorkelling, and… More

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Sunkissed Pool Home

5005 Commonwealth Dr, Siesta Key, United States Show map

Sunkissed Pool Home Siesta Key is located just around the corner from Grand Canal and invites guests to enjoy guided snorkelling trips. The 3-bedroom holiday home features opportunities for… More

From US$ 368 Book Now

Gulf View Paradise

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

Located merely an 8-minute walk from Crescent Arms, Gulf View Paradise Siesta Key villa features an outdoor swimming pool and can accommodate up to 16 guests. Located in the vicinity of the shaped… More

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Midnight Cove II 731F

1300 Cove II Place, Unit 731F, Siesta Key, United States Show map

Overlooking the pool, Midnight Cove II 731F Villa Siesta Key enjoys a convenient setting 5 minutes' walk from crescent arms private beach. Located in the immediate vicinity of Siesta Harbour… More

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Crescent Royale Condominiums 104

757 Beach Road, Unit 104, Siesta Key, United States Show map

Located merely a 6-minute walk from Siesta Key Beach, the 1-bedroom Crescent Royale Condominiums 104 Siesta Key villa features an outdoor swimming pool and can accommodate up to 4 guests. The holiday… More

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Blu Sky Cottage - 5037

5037 Higel Ave, Siesta Key, United States Show map

Featuring a swimming pool, the 3-bedroom Blu Sky Cottage - 5037 Siesta Key is suitable for up to 8 people and is located approximately 25 minutes on foot from Jamaica Royale. The Siesta Key holiday… More

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Siesta Royale 57

6334 Midnight Pass Rd, #57, Siesta Key, United States Show map

The 1-bedroom Siesta Royale 57 Villa Siesta Key offers proximity to such city sites as Green Turtle Shell & Gift City, located only a 6-minute walk away. More

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Harbor Towers 302

5855 Midnight Pass Road #302, Siesta Key, United States Show map

Harbor Towers 302 Apartment Siesta Key is located a mere 1.3 km from the shaped Crescent Beach and a 19-minute walk from Siesta Key Beach. Wi-Fi and parking are also available at this spacious 108 m²… More

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