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

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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The Palm Bay Club Unit 311

5960 Midnight Pass Rd Unit #311, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at The Palm Bay Club Unit 311 Apartment Siesta Key, which is only 1.5 km from Siesta Key Beach and nearly a 10-minute drive from Shell Beach. More

From US$ 456 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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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

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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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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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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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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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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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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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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Midnight Cove II 822F

1200 Cove II Place, Unit 822F, Siesta Key, United States Show map

The 84 m² Midnight Cove II 822F Apartment Siesta Key is located 2.6 km from Nontando and merely a 7-minute walk from Green Turtle Shell & Gift City. While staying in this 2-bedroom apartment, guests… More

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Midnight Cove 1-831

6730 Midnight Cove Road, Siesta Key, United States Show map

The spacious 80 m² Midnight Cove 1-831 Apartment Siesta Key is just 500 metres from Siesta Key Marina and can accommodate up to 6 guests. Siesta Key Beach Access 7 is in proximity to the 2-bedroom… More

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Midnight Cove II 920B

1100 Cove II Place, Unit 920B, Siesta Key, United States Show map

Featuring a prime location, the 159 m² Midnight Cove II 920B Apartment Siesta Key offers views of the pool, and is about a 25-minute walk from Siesta Key Village. Situated a stone's throw from the… More

From US$ 262 Book Now

Midnight Cove II 931C

1100 Cove II Place, Unit 931C, Siesta Key, United States Show map

The spacious Midnight Cove II 931C Apartment Siesta Key is located 5 minutes' walk from Siesta Harbour Condominium Apt Harbor and looks out onto the pool. 2.8 km from Edson Keith Estate Park, the… More

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Siesta Key Pool Home 5239 Winding Way

5239 Winding Way, Siesta Key, United States Show map

The spacious 3-bedroom Siesta Key Pool Home 5239 Winding Way apartment is located 2.9 km from Big Sarasota Pass and approximately 10 minutes by car from Sarasota Beach. Featuring an aqua park and a… More

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Walk To Siesta Beach, Heated Pool, Wifi, Renovated Ground Floor Condo

5649 Midnight Pass Rd #801, Siesta Key, United States Show map

Located about 5 minutes' walk from Jamaica Royale and Siesta Key, the spacious Walk To Siesta Beach, Heated Pool, Wifi, Renovated Ground Floor Condo Siesta Key features views of the garden. More

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Jamaica Royale 028

5830 Midnight Pass Rd, Unit 028, Siesta Key, United States Show map

Featuring a convenient location merely 6 minutes' walk from Siesta Key, the spacious 1-bedroom Jamaica Royale 028 Apartment Siesta Key accommodates up to 4 guests. The apartment offers modern… More

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Jamaica Royale T64

5830 Midnight Pass Rd, Unit T64, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 111 m² Jamaica Royale T64 Apartment Siesta Key, which is within 20 minutes' walk of Siesta Key Village and within a 7-km distance of the… More

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Siesta Royale 15

6334 Midnight Pass Rd, #15, Siesta Key, United States Show map

The 1-bedroom Siesta Royale 15 Apartment Siesta Key offers easy entry to such city sights as Siesta Harbour Condominium Apt Harbor, situated nearly a 5-minute walk away. Guests can make use of Wi-Fi… More

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Walk To #1 Siesta Beach, 2 Bedroom, 2 Baths, Heated Pool, Wifi, Covered Parking

5635 Midnight Pass Road #1015, Siesta Key, United States Show map

The spacious Walk To #1 Siesta Beach, 2 Bedroom, 2 Baths, Heated Pool, Wifi, Covered Parking Siesta Key apartment enjoys a prime location about a 5-minute walk from Jamaica Royale. More

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Jamaica Royale T24

5830 Midnight Pass Rd, Unit T24, Siesta Key, United States Show map

The 2-bedroom Jamaica Royale T24 Apartment Siesta Key boasts a convenient setting and in just 7 minutes' walk from Jamaica Royale. This 111 m² apartment features Wi-Fi, along with a car park for… More

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Parrot Beach Cottages Suite #3

60 Avenida Veneccia  Suite # 3, Siesta Key, United States Show map

Featuring a convenient location approximately 5 minutes' walk from Siesta Key Craft Festival Museum, the 1-bedroom Parrot Beach Cottages Suite #3 Siesta Key accommodates up to 4 guests. This 32 m²… More

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Siesta Royale 12A

6334 Midnight Pass Rd, #12-A, Siesta Key, United States Show map

The 58 m² Siesta Royale 12A Apartment Siesta Key boasts a beachfront setting and in merely 8 minutes' walk from Siesta Key Marina. At this 1-bedroom apartment, Wi-Fi and private parking are also… More

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Gertrude

5963 Midnight Pass Rd #355, Siesta Key, United States Show map

The 2-bedroom Gertrude Apartment Siesta Key is just 7 minutes on foot from Jamaica Royale and welcomes guests with a hot tub. Siesta Key Beach is only 1.6 km away, and the shaped Crescent Beach is… More

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Upgraded 1 Br1 Bath Condo, Renovated Ground Floor Unit

5631 Midnight Pass Road #1007, Siesta Key, United States Show map

Located about a 20-minute walk from the shaped Crescent Beach, the spacious Upgraded 1 Br1 Bath Condo, Renovated Ground Floor Unit Siesta Key overlooks the garden. Wi-Fi is available for guests'… More

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E62 - Amazing Siesta Key Condo On The Water!

6157 Midnight Pass Road E62, Siesta Key, United States Show map

Spacious E62 - Amazing Siesta Key Condo On The Water! is a 10-minute walk from the shaped Crescent Beach and can accommodate up to 4 guests. Wi-Fi and private car parking are also available at this… More

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Sunset Royale - 314

711 Beach Rd, Unit 314, Siesta Key, United States Show map

Situated around 5 minutes' walk from Public Beach Access 10, the spacious 2-bedroom Sunset Royale - 314 Apartment Siesta Key offers guests easy access to various tourist attractions nearby. This 86… More

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Harbor Towers 632

5855 Midnight Pass Road #632, Siesta Key, United States Show map

The spacious 1-bedroom Harbor Towers 632 Apartment Siesta Key features a convenient location merely 1.3 km from Siesta Beach Pavillion and hosts up to 4 guests. Offering access to a swimming pool… More

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Midnight Cove II 117F

1900 Cove II Place, Unit 117F, Siesta Key, United States Show map

The spacious 84 m² Midnight Cove II 117F Apartment Siesta Key is only 9 minutes on foot from the shaped Crescent Beach and can accommodate up to 4 guests. Turtle Beach is 4.3 km from the 2-bedroom… More

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Harbor Towers 614

5855 Midnight Pass Road #614, Siesta Key, United States Show map

A convenient location of the 70 m² Harbor Towers 614 Apartment Siesta Key provides easy access to Crescent Arms 18 minutes' walk away. Wi-Fi and a car park are also available at this 1-bedroom… More

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Jamaica Royale 703

5830 Midnight Pass Rd, Unit 703, Siesta Key, United States Show map

Situated approximately a 20-minute walk from the shaped Crescent Beach, the 119 m² Jamaica Royale 703 Apartment Siesta Key can host up to 6 guests in Siesta Key. At this 2-bedroom apartment, Wi-Fi… More

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Private Patio, Remodel, Steps To Village & Beach

430 Canal Rd #11, Siesta Key, Fl 34242, Usa, Siesta Key, United States Show map

Situated a mere 14 minutes' walk from Siesta Key Beach, the 2-bedroom Private Patio, Remodel, Steps To Village & Beach Siesta Key apartment can host up to 8 guests in Siesta Key. Featuring an aqua… More

From US$ 562 Book Now

2Br Siesta Key Getaway Near Beach With Shared Pool

1138 Sun N Sea Dr, Siesta Key, United States Show map

Situated around a 25-minute walk from Escape Countdown, the spacious 2Br Siesta Key Getaway Near Beach With Shared Pool apartment provides guests with Wi-Fi for either business or leisure. 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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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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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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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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