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

Siesta Key Waterfront Oasis - Heated Pool, Dock, Walk To Village & Beach

329 Avenida Leona, Siesta Key, United States Show map

Located nearly 25 minutes' walk from Shell Beach, Siesta Key Waterfront Oasis - Heated Pool, Dock, Walk To Village & Beach villa features an outdoor swimming pool, a hot tub, ensuring a relaxing stay… More

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Our House At The Beach W-Tower 5Th Floor

1001 Beach Rd, Siesta Key, United States Show map

Located 400 metres from Siesta Key Village, Our House At The Beach W-Tower 5Th Floor Siesta Key villa is suitable for 6 guests and provides a swimming pool to relax in. Located 25 minutes' walk from… More

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Gulf And Bay Club- C202

5770 Midnight Pass Rd, Unit C202, Siesta Key, United States Show map

Located just a 5-minute stroll from Jamaica Royale, the spacious 124 m² Gulf And Bay Club- C202 Apartment Siesta Key accommodates up to 6 guests. The 2-bedroom apartment is within a few blocks of… More

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The Big Dipper

3810 Flamingo Ave, Siesta Key, United States Show map

The Big Dipper Villa Siesta Key with a convenient location within a 600-metre distance of Bay Island entices guests with a Jacuzzi. Located 10 minutes' drive from Sarasota Farmers Market, the 1… More

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Our House At The Beach C-122

1169 Lake House Cir, #122, Siesta Key, United States Show map

The 126 m² Our House At The Beach C-122 Siesta Key is located about a 20-minute walk from Sarasota Beach and offers Wi-Fi for either business or leisure. This 2-bedroom apartment can host up to 6… More

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Gulf And Bay Club- C702

5770 Midnight Pass Rd, Unit C702, Siesta Key, United States Show map

The 2-bedroom Gulf And Bay Club- C702 Apartment Siesta Key lies in a prime location in Siesta Key, just a 6-minute walk from Siesta Key. Offering a Jacuzzi, this spacious apartment is located just a… More

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Villa D11 - Florida Sunshine Getaway | Free Cancellation

6154 Midnight Pass Rd, D11, Siesta Key, United States Show map

Staying at the 2-bedroom Villa D11 - Florida Sunshine Getaway | Free Cancellation* Siesta Key, guests can visit Jamaica Royale, which is only 1.1 km away. The Siesta Key villa is suitable for up to 4… More

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Villa A05 - Lost On Siesta Key | Free Cancellation

6154 Midnight Pass Rd, A05, Siesta Key, United States Show map

Featuring a heated pool, Villa A05 - Lost On Siesta Key | Free Cancellation is suitable for up to 6 people and is located 13 minutes' walk from Jamaica Royale. Providing guests with Wi-Fi and a car… More

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Harbor Towers 4Th Fl Pool & Bay Views End Unit

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

The 3-bedroom Harbor Towers 4Th Fl Pool & Bay Views End Unit Villa Siesta Key is located about 25 minutes' walk from Siesta Key Village and provides a heated pool, ensuring a relaxing stay. The villa… More

From US$ 165 Book Now

Siesta Sands 206

1001 Point Of Rocks Rd, #206, Siesta Key, United States Show map

Offering access to entertainment venues such as Siesta Key Marina, situated only 1.3 km away, Siesta Sands 206 Siesta Key villa can host up to 6 guests. Providing guests with Wi-Fi and private car… More

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The Hideaway

320 Calle Miramar, Us, Siesta Key, United States Show map

The 4-bedroom The Hideaway Villa Siesta Key, located within 5 minutes' walk of Seaside Vacation Villas, can host up to 10 guests. The holiday home features opportunities for fisheries in the area, in… More

From US$ 1446 Book Now

2Br Siesta Key Downtown Condo Walk Everywhere

5108 Calle Minorga, Siesta Key, United States Show map

2Br Siesta Key Downtown Condo Walk Everywhere villa is located 25 minutes' walk from Siesta Key Beach and provides fisheries for active guests. Located a short way from Sarasota Beach, the 2-bedroom… More

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Gulf And Bay Club- B205

5780 Midnight Pass Rd, Unit B205, Siesta Key, United States Show map

The 124 m² Gulf And Bay Club- B205 Apartment Siesta Key enjoys a prime location only a 6-minute walk from Jamaica Royale. Boasting a Jacuzzi, this 2-bedroom apartment, suitable for 6 guests, is 2.6… More

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Gulf And Bay Club- D506

5760 Midnight Pass Rd, Unit D506, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Gulf And Bay Club- D506 Apartment Siesta Key, which is 4.3 km from South Lido Key Beach Park on the Gulf and around 10 minutes by… More

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Pink Mango Cottage

5302 Avenida Navarra, Siesta Key, United States Show map

Pink Mango Cottage Siesta Key is located within 400 metres of Siesta Key Beach Access #5 and a 6-minute walk from the co-op Gallery on Siesta Key. Wi-Fi and a private parking lot are provided for… More

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The Midnight Turtle

8825 Midnight Pass Rd, Siesta Key, United States Show map

Situated about 5 minutes' walk from Turtle Beach, the 4-bedroom The Midnight Turtle Villa Siesta Key entices guests with fisheries in the area. Providing guests with Wi-Fi and a car park, the holiday… More

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The Sea Jewel On Siesta

615 Calle Del Otono, Siesta Key, Fl 34242, Siesta Key, United States Show map

Staying at The Sea Jewel On Siesta Villa Siesta Key, guests can visit Siesta Key Marina, which is nearly a 10-minute ride away. More

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Siesta Springs

1142 Windsong Lane, Unit A, Siesta Key, United States Show map

Suitable for 14 guests, the 5-bedroom Siesta Springs Villa Siesta Key is located a mere 6 minutes' walk from Jamaica Royale and provides a Jacuzzi for a relaxing stay. This 5-bathroom villa features… More

From US$ 1855 Book Now

Jamaica Royale 801

5830 Midnight Pass Rd, Unit 801, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Jamaica Royale 801 Apartment Siesta Key, which is approximately 20 minutes' walk from Siesta Key Beach and merely 1.4 km from… More

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Jamaica Royale 035

5830 Midnight Pass Rd, Unit 035, Siesta Key, United States Show map

Located merely 9 minutes' stroll from Crescent Arms, Jamaica Royale 035 Apartment Siesta Key accommodates up to 2 guests. Enjoying a prime setting, the apartment lies only 1.7 km from Siesta Beach… More

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Salty Oak

6540 Peacock Rd., Siesta Key, United States Show map

Featuring an outdoor swimming pool as well as views of the pool, Salty Oak Villa Siesta Key offers a prime location 5 minutes' walk from Siesta Key Marina. Located right near Christopher Wheeler Park… More

From US$ 3779 Book Now

Gulf And Bay Club- B507

5780 Midnight Pass Rd, Unit B507, Siesta Key, United States Show map

The 124 m² Gulf And Bay Club- B507 Apartment Siesta Key enjoys a convenient location only a 6-minute walk from Jamaica Royale. 4.7 km from Red Bug Slough Preserve, this 2-bedroom apartment for 4… More

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Villa D09 - Siesta Key Beachside Paradise | Free Cancellation

6154 Midnight Pass Rd, #D09, Siesta Key, United States Show map

Offering a location about 25 minutes' walk from Siesta Key Beach, the 1-bedroom Villa D09 - Siesta Key Beachside Paradise | Free Cancellation* gives access to various tourist spots in the area. With… More

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Jamaica Royale 075

5830 Midnight Pass Rd, Unit 075, Siesta Key, United States Show map

The spacious Jamaica Royale 075 Apartment Siesta Key features a prime location an 18-minute walk from Siesta Key Beach and hosts up to 6 guests. Wi-Fi and a car park are also available at this… More

From US$ 411 Book Now

Palm Shade Cottage - 606A

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

Offering an aqua park and a golf course to ensure a memorable stay, the 1-bedroom Palm Shade Cottage - 606A Siesta Key is located merely 5 minutes on foot from Siesta Key Beach Access 7. Hosting up… More

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Jamaica Royale 060

5830 Midnight Pass Rd, Unit 060, Siesta Key, United States Show map

The spacious Jamaica Royale 060 Apartment Siesta Key features a convenient location a 17-minute walk from Crescent Arms and hosts up to 4 guests. This apartment is situated right around the corner… More

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2 Bedroom Condo On Siesta Key, Walk To The Beach, Free Parking, Free Wifi, Ac

5657 Midnight Pass Road #712, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at 2 Bedroom Condo On Siesta Key, Walk To The Beach, Free Parking, Free Wifi, Ac, which is nearly a 5-minute drive from Escape Room Sarasota and within a 6… More

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Jamaica Royale 090

5830 Midnight Pass Rd, Unit 090, Siesta Key, United States Show map

The spacious Jamaica Royale 090 Apartment Siesta Key is located 4.3 km from the friendly Edson Keith Estate Park and about a 25-minute walk from Siesta Key Marina. Wi-Fi and parking are provided for… More

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Tiki Bar, Balcony, Patio, 250 Steps Beach Village!

360 Canal Rd, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

The 3-bedroom Tiki Bar, Balcony, Patio, 250 Steps Beach Village! Siesta Key apartment offers easy entry to such city sights as Beach Club, situated a mere 5 minutes' walk away. 3.4 km from Bay Island… More

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Crescent Royale 402

757 Beach Road, Unit 402, Siesta Key, United States Show map

The 2-bedroom Crescent Royale 402 Villa Siesta Key hosts up to 4 guests and is nestled within 25 minutes' walk of natural sites such as Edson Keith Estate Park. This Siesta Key holiday home features… More

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Harbor Towers 501

5855 Midnight Pass Road #501, Siesta Key, United States Show map

The spacious 1-bedroom Harbor Towers 501 Apartment Siesta Key is also located just 6 minutes' walk from Jamaica Royale. This 70 m² apartment offers modern facilities, such as Wi-Fi and essentials… More

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Jamaica Royale 002

5830 Midnight Pass Rd, Unit 002, Siesta Key, United States Show map

Situated about 25 minutes' walk from Crescent Arms, the 1-bedroom Jamaica Royale 002 Apartment Siesta Key provides guests with Wi-Fi for either business or leisure. An array of activities, including… More

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Aloha Kai Villa 26 - Soak Up The Sun On Siesta Key W&D

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

Located only 10 minutes' walk from the shaped Crescent Beach, 2-bedroom Aloha Kai Villa 26 - Soak Up The Sun On Siesta Key W&D boasts a heated pool and can accommodate up to 6. Providing guests with… More

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Casa Mar - 42 Relax, Recharge & Stay In Paradise

6006 Midnight Pass Rd, #42, Siesta Key, United States Show map

Located merely an 8-minute walk from Jamaica Royale, Casa Mar Villa Siesta Key is suitable for 6 guests and provides a swimming pool to relax in. Located 4.5 km from Shell Beach, this 2-bedroom villa… More

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Luxury, Exclusive Building, Ocean Views, And Private Rooftop Sundeck

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

The 6-bedroom Luxury, Exclusive Building, Ocean Views, And Private Rooftop Sundeck Siesta Key villa is located nearly 5 minutes' walk from Siesta Key Beach Access 7 and provides guests with a sundeck… More

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Ground Floor Upgraded 2 Bed 2 Bath, Washerdryer, Short Walk To #1 Siesta Beach!

5667 Midnight Pass Road #303, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious Ground Floor Upgraded 2 Bed 2 Bath, Washerdryer, Short Walk To #1 Siesta Beach! Siesta Key apartment, which is just 550 metres from St. More

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Siesta Royale 16

6334 Midnight Pass Rd, #16, Siesta Key, United States Show map

The 58 m² Siesta Royale 16 Apartment Siesta Key boasts a beachfront setting and in around a 5-minute walk from Crescent Arms. This 1-bedroom apartment features Wi-Fi in the rooms. More

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Siesta Royale 55

6334 Midnight Pass Rd, #55, Siesta Key, United States Show map

Located within 5 minutes' walk of Siesta Harbour Condominium Apt Harbor, the 1-bedroom Siesta Royale 55 Villa Siesta Key gives easy access to various tourist attractions in the area. More

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Villa B05

6154 Midnight Pass Rd, #B05, Siesta Key, United States Show map

Located just an 8-minute walk from Crescent Arms, the 2-bedroom Villa B05 Siesta Key boasts a swimming pool and can accommodate up to 4. Providing guests with Wi-Fi and parking, this 2-bathroom villa… More

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Upgraded Stunning 2 Bed 2 Bath Condo! Water View

5663Midnight Pass Road #407, Siesta Key, United States Show map

Upgraded Stunning 2 Bed 2 Bath Condo! Water View Siesta Key boasts a prime location approximately a 5-minute stroll from Jamaica Royale. Guests can relax in a private garden at the spacious apartment. More

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Villa A11 - Siesta Key Sunshine Society - Wd | Free Cancellation

6154 Midnight Pass Rd, #A11, Siesta Key, United States Show map

During the stay at Villa A11 - Siesta Key Sunshine Society - Wd | Free Cancellation, guests can indulge in billiard or visit Siesta Beach Pavillion, located a 25-minute walk away. Located 1.1 km from… More

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Jamaica Royale 078

5830 Midnight Pass Rd, Unit 078, Siesta Key, United States Show map

The spacious 2-bedroom Jamaica Royale 078 Apartment Siesta Key is just 500 metres from Jamaica Royale and can accommodate up to 6 guests. Nontando is 2.9 km away, and Siesta Key Beach Access 2 is… More

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Midnight Cove II 514F

1500 Cove II Place, Unit 514F, Siesta Key, United States Show map

The 84 m² Midnight Cove II 514F Apartment Siesta Key overlooks the pool and is situated just a 5-minute walk from Siesta Harbour Condominium Apt Harbor. In the vicinity of Green Turtle Shell & Gift… More

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Harbor Towers 603

5855 Midnight Pass Road #603, Siesta Key, United States Show map

Featuring views of the pool, the 2-bedroom Harbor Towers 603 Apartment Siesta Key is located about 25 minutes' walk from Siesta Key Marina. Guests staying at this 98 m² apartment, which is within… More

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Jamaica Royale T51

5830 Midnight Pass Rd, Unit T51, Siesta Key, United States Show map

The spacious 2-bedroom Jamaica Royale T51 Apartment Siesta Key is a good choice for accommodating up to 6 guests, offering a convenient setting approximately 25 minutes' walk from the shaped Crescent… More

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4Br Spacious Paradise

349 Avenida Madera, Siesta Key, United States Show map

Featuring an outdoor swimming pool, 4Br Spacious Paradise Siesta Key villa is suitable for up to 8 people and is located 2.6 km from Siesta Key Beach Access 7. Providing guests with Wi-Fi and private… More

From US$ 713 Book Now

Jamaica Royale T41

5830 Midnight Pass Rd, Unit T41, Siesta Key, United States Show map

The 111 m² Jamaica Royale T41 Apartment Siesta Key is located a mere 1.9 km from Crescent Arms and 17 minutes' walk from Siesta Key Drum Circle. Wi-Fi and parking are also available at this 2-bedroom… More

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Siesta Sands 609

1001 Point Of Rocks Rd, #609, Siesta Key, United States Show map

Nestled 3.5 km from Turtle Beach, the 2-bedroom Siesta Sands 609 Siesta Key villa is boasting a patio, barbecue, and a dining table for guests' enjoyment. More

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Our House At The Beach C-120

1159 Lake House Cir, #120, Siesta Key, United States Show map

The 2-bedroom Our House At The Beach C-120 Siesta Key enjoys a convenient location only a 9-minute walk from Siesta Key Drum Circle. At the spacious 126 m² apartment, Wi-Fi and parking are also… More

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Midnight Cove II 521F

1500 Cove II Place, Unit 521F, Siesta Key, United States Show map

Midnight Cove II 521F Apartment Siesta Key overlooks the pool and is situated 300 metres from Siesta Harbour Condominium Apt Harbor. Wi-Fi and a car park are also available at this spacious 84 m²… More

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