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

Gulf And Bay Club- C209

5770 Midnight Pass Rd, Unit C209, Siesta Key, United States Show map

Gulf And Bay Club- C209 Apartment Siesta Key is situated in Siesta Key, 14 minutes' walk from Siesta Key Drum Circle, and offers spa amenities such as a Jacuzzi. At this spacious 125 m² apartment, Wi… More

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Sunset Royale - 200

711 Beach Rd, Unit 200, Siesta Key, United States Show map

The 86 m² Sunset Royale - 200 Apartment Siesta Key is located 0.7 km from Siesta Key Beach Access #10 and 17 minutes' walk from Jamaica Royale. At this 2-bedroom apartment, Wi-Fi and a car park are… More

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Gulf And Bay Club- C101

5770 Midnight Pass Rd, Unit C101, Siesta Key, United States Show map

The spacious 2-bedroom Gulf And Bay Club- C101 Apartment Siesta Key boasts a convenient location nearly 5 minutes' walk from Jamaica Royale. Enjoying proximity to Siesta Key, which is merely 450… More

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Jamaica Royale 066

5830 Midnight Pass Rd, Unit 066, Siesta Key, United States Show map

The spacious 2-bedroom Jamaica Royale 066 Apartment Siesta Key is only 600 metres from Jamaica Royale and can accommodate up to 6 guests. Big Sarasota Pass is 4.2 km from the apartment while Siesta… More

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Harbor Towers 424

5855 Midnight Pass Road #424, Siesta Key, United States Show map

The 1-bedroom Harbor Towers 424 Apartment Siesta Key boasts a convenient setting and in nearly a 5-minute walk from Jamaica Royale. Around 7 km from the upscale Saint Armands Circle Outdoor Mall… More

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Harbor Towers 709

5855 Midnight Pass Road #709, Siesta Key, United States Show map

The 1-bedroom Harbor Towers 709 Apartment Siesta Key enjoys a prime location only a 6-minute walk from Jamaica Royale. The spacious 98 m² apartment features Wi-Fi, along with parking for guests… More

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Midnight Cove II 831F

1200 Cove II Place, Unit 831F, Siesta Key, United States Show map

Featuring a heated pool, the spacious Midnight Cove II 831F Apartment Siesta Key is a 5-minute walk from Siesta Harbour Condominium Apt Harbor. This apartment capacity is based on up to 4 guests. More

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Jamaica Royale 005

5830 Midnight Pass Rd, Unit 005, Siesta Key, United States Show map

The 2-bedroom Jamaica Royale 005 Apartment Siesta Key enjoys a prime location only a 7-minute walk from Jamaica Royale. At this spacious apartment, Wi-Fi and parking are also provided. More

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Sunset Royale - 208

711 Beach Rd, Unit 208, Siesta Key, United States Show map

The 1-bedroom Sunset Royale - 208 Apartment Siesta Key lies in a prime location in Siesta Key, around a 5-minute walk from Public Beach Access 10. Featuring a golf course and a dining table, this… More

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Midnight Cove II 923C

1100 Cove II Place, Unit 923C, Siesta Key, United States Show map

The spacious 2-bedroom Midnight Cove II 923C Apartment Siesta Key lies in a prime location in Siesta Key, nearly a 5-minute walk from Siesta Harbour Condominium Apt Harbor. Situated right around the… More

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Our House At The Beach 204W By Beachside Management

1001 Beach Rd, Siesta Key, United States Show map

Situated within 25 minutes' walk of Grand Canal, the spacious 112 m² Our House At The Beach 204W By Beachside Management Siesta Key provides guests with Wi-Fi for either business or leisure. Siesta… More

From US$ 368 Book Now

New Listing! The Village Breeze, 2 Units - 4 Bedroom 4 Baths, Pool Walk To Beach And Siesta Key Village

5136 Calle Minorga, Siesta Key, United States Show map

Situated nearly a 10-minute drive from Siesta Key Beach Access 7, spacious 4-bedroom The Village Breeze, 2 Units - 4 Bedroom 4 Baths, Pool Walk To Beach And Siesta Key Village apartment provides… More

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Gulf And Bay Club- D405

5760 Midnight Pass Rd, Unit D405, Siesta Key, United States Show map

The spacious 2-bedroom Gulf And Bay Club- D405 Apartment Siesta Key is only 6 minutes' stroll from Jamaica Royale and welcomes guests with a Jacuzzi. The apartment is situated in a prime location, in… More

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Coastal Surfside 298 By Beachsidemanagement

298 Beach Road, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 169 m² Coastal Surfside 298 By Beachsidemanagement Siesta Key apartment, which is merely 5 minutes on foot from Sarasota Beach and only 1.4… More

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Siesta Royale 14

6334 Midnight Pass Rd, #14, Siesta Key, United States Show map

The 49 m² Siesta Royale 14 Apartment Siesta Key lies in a beachfront location in Siesta Key, only a 6-minute walk from Green Turtle Shell & Gift City. Situated in close proximity to Crescent Arms… More

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Siesta Beach House #304

5950 Midnight Pass Rd, #304, Siesta Key, United States Show map

The spacious 2-bedroom Siesta Beach House #304 Siesta Key is also located merely 9 minutes' walk from Crescent Arms. This 92 m² apartment features Wi-Fi, along with private parking for guests… More

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Gulf And Bay Club- E109

5750 Midnight Pass Rd, Unit E109, Siesta Key, United States Show map

The spacious Gulf And Bay Club- E109 Apartment Siesta Key is merely an 8-minute walk from Jamaica Royale and welcomes guests with a Jacuzzi. Offering barbecue, a golf course, and a dining table, the… More

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Midnight Cove II 944C

1100 Cove II Place, Unit 944C, Siesta Key, United States Show map

The spacious 130 m² Midnight Cove II 944C Apartment Siesta Key is a good choice for accommodating up to 4 guests, offering a prime setting within 25 minutes' walk of Siesta Key Beach. The 2-bedroom… More

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Jamaica Royale 403

5830 Midnight Pass Rd, Unit 403, Siesta Key, United States Show map

The spacious 2-bedroom Jamaica Royale 403 Apartment Siesta Key is a good choice for accommodating up to 6 guests, offering a prime setting just 1.4 km from Siesta Beach Pavillion. Wi-Fi and parking… More

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Midnight Cove II 922C

1100 Cove II Place, Unit 922C, Siesta Key, United States Show map

The spacious 130 m² Midnight Cove II 922C Apartment Siesta Key is just a 5-minute stroll from Crescent Arms and can accommodate up to 6 guests. The 2-bedroom apartment is within a 2-km distance of… More

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Tivoli By The Sea

625 Beach Rd, Siesta Key, United States Show map

Tivoli By The Sea Apartment Siesta Key lies in a prime location in Siesta Key, approximately a 5-minute walk from Public Beach Access 10. At this apartment, Wi-Fi and parking are also provided. More

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Midnight Cove II 612F

1400 Cove II Place, Unit 612F, Siesta Key, United States Show map

Featuring a convenient location, the 84 m² Midnight Cove II 612F Apartment Siesta Key offers views of the pool, around a 25-minute walk from Siesta Key Drum Circle. This 2-bedroom apartment provides… More

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Harbor Towers 330

5855 Midnight Pass Road #330, Siesta Key, United States Show map

The 98 m² Harbor Towers 330 Apartment Siesta Key is located a mere 1.9 km from Siesta Key Marina and about a 25-minute walk from Siesta Key Beach Access 7. Wi-Fi and parking are provided for guests'… More

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The Village Breeze I - Heated Pool, Beaches, Daiquiris, Seafood, White-Sand!

5116 Calle Minorga, Siesta Key, United States Show map

The 2-bedroom The Village Breeze I - Heated Pool, Beaches, Daiquiris, Seafood, White-Sand! Siesta Key apartment offers proximity to such tourist attractions as Siesta Key Craft Festival Museum… More

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Off The Hook - B

328 Calle Miramar - B, Siesta Key, United States Show map

Siesta Key Beach is only 1.1 km from the spacious 85 m² Off The Hook - B Apartment Siesta Key, while Sarasota Beach is situated nearby. The 2-bedroom apartment provides access to luxurious amenities,… More

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Gulf And Bay Club- F105

5740 Midnight Pass Rd, Unit F105, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the 2-bedroom Gulf And Bay Club- F105 Apartment Siesta Key, which is just 1.6 km from Siesta Key Beach and around 15 minutes by car from the friendly… More

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Jamaica Royale 201

5830 Midnight Pass Rd, Unit 201, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Jamaica Royale 201 Apartment Siesta Key, which is nearly 20 minutes' walk from Crescent Arms and within 5 km of Bee Ridge Park. More

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Midnight Cove II 940B

1100 Cove II Place, Unit 940B, Siesta Key, United States Show map

Located about 200 metres from Crescent Arms and the shaped Crescent Beach, the spacious 2-bedroom Midnight Cove II 940B Apartment Siesta Key features views of the pool. Wi-Fi and a car park are also… More

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Gulf Villa Just 3 Min To #1 Beach - Pool

368 Canal Road, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 85 m² Gulf Villa Just 3 Min To #1 Beach - Pool Siesta Key, which is only 350 metres from Seaside Vacation Villas and approximately a 10… More

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Hibiscus Villa Just 3 Min To #1 Beach - Pool - Bbq

378 Canal Road, Siesta Key, United States Show map

Featuring a swimming pool, the spacious Hibiscus Villa Just 3 Min To #1 Beach - Pool - Bbq Siesta Key is within 200 metres of Seaside Vacation Villas. This apartment can host up to 4 guests. More

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Jamaica Royale 010

5830 Midnight Pass Rd, Unit 010, Siesta Key, United States Show map

The 2-bedroom Jamaica Royale 010 Apartment Siesta Key is located 16 minutes' walk from Siesta Key Drum Circle and offers Wi-Fi for either business or leisure. This spacious apartment capacity is… More

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Blue Dolphin Cottage Walk To Siesta Key Beach

5310 Avenida Navarra, Siesta Key, United States Show map

Blue Dolphin Cottage Walk To Siesta Key Beach boasts a convenient location just 500 metres from Siesta Key Beach Access 2. Wi-Fi is provided for both business and leisure activities. More

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Harbor Towers 216

5855 Midnight Pass Road #216, Siesta Key, United States Show map

The spacious 107 m² Harbor Towers 216 Apartment Siesta Key is around 200 metres from Jamaica Royale and can accommodate up to 6 guests. Area attractions include Nora Patterson Bay Island Park, 4.2 km… More

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Siesta Beach House Unit 201

5950 Midnight Pass Rd, #201, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 2-bedroom Siesta Beach House Unit 201 Siesta Key, which is just 1.7 km from Siesta Key Beach and within 25 minutes' walk of Siesta Key… More

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Jamaica Royale T31

5830 Midnight Pass Rd, Unit T31, Siesta Key, United States Show map

The spacious 111 m² Jamaica Royale T31 Apartment Siesta Key is just 600 metres from Jamaica Royale and can accommodate up to 4 guests. Grand Canal is 2.4 km from the 2-bedroom apartment, while the… More

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Siesta Royale 12

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

Located only 5 minutes' stroll from Crescent Arms, the spacious 67 m² Siesta Royale 12 Apartment Siesta Key accommodates up to 6 guests. Sarasota Beach is a short way from the 2-bedroom apartment… More

From US$ 381 Book Now

Jamaica Royale 077

5830 Midnight Pass Rd, Unit 077, Siesta Key, United States Show map

The spacious 2-bedroom Jamaica Royale 077 Apartment Siesta Key boasts a prime location a mere 500 metres from Jamaica Royale. Wi-Fi and parking are also available at the apartment. More

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Jamaica Royale T62

5830 Midnight Pass Rd, Unit T62, Siesta Key, United States Show map

The spacious 111 m² Jamaica Royale T62 Apartment Siesta Key is only 600 metres from Jamaica Royale and can accommodate up to 4 guests. Siesta Key Marina is 2.6 km from the 2-bedroom apartment, and… More

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Beach Way 310

5600 Beach Way Drive, Siesta Key, United States Show map

Featuring a swimming pool, the spacious Beach Way 310 Siesta Key apartment is a 6-minute walk from Siesta Key Beach Access #10. This apartment capacity is based on up to 6 guests. More

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Peppertree Penthouse #803

1125 W Peppertree Dr #803, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 112 m² Peppertree Penthouse #803 Apartment Siesta Key, which is 4.3 km from Red Bug Slough Preserve and about 25 minutes on foot from… More

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Walk To Siesta Beach, Wifi, Renovated Ground Floor Unit, Covered Parking

5625 Midnight Pass Road #609, Siesta Key, United States Show map

Located merely a 5-minute walk from Jamaica Royale and Siesta Key, Walk To Siesta Beach, Wifi, Renovated Ground Floor Unit, Covered Parking Siesta Key apartment features views of the pool. More

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The Terra Grove Villa - Sk Collection

1231 Cr-758, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 112 m² The Terra Grove Villa - Sk Collection Siesta Key, which is within 20 minutes' walk of Siesta Key Beach and within a 3-km distance of… More

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Jamaica Royale 301

5830 Midnight Pass Rd, Unit 301, Siesta Key, United States Show map

The 2-bedroom Jamaica Royale 301 Apartment Siesta Key boasts a prime setting and in merely 7 minutes' walk from Jamaica Royale. Featuring spa therapy and a golf course, this spacious apartment has an… More

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Updated And Clean, Two Heated Pool, Tennis, And Beach Access

1232 Siesta Bayside Drive, Siesta Key, United States Show map

To enjoy your vacation in Siesta Key, stay at the spacious 139 m² Updated And Clean, Two Heated Pool, Tennis, And Beach Access Siesta Key apartment, which is only 1.7 km from Crescent Arms and about… More

From US$ 214 Book Now

Harbor Towers 525

5855 Midnight Pass Road #525, Siesta Key, United States Show map

Located only a 5-minute walk from Jamaica Royale, Harbor Towers 525 Apartment Siesta Key accommodates up to 6 guests. At this spacious 121 m² apartment, Wi-Fi and a car park are also provided. More

From US$ 285 Book Now

Midnight Cove II 412F

1600 Cove II Place, Unit 412F, Siesta Key, United States Show map

The spacious Midnight Cove II 412F Apartment Siesta Key is 5 minutes' walk from Crescent Arms and can accommodate up to 6 guests. Wi-Fi and parking are also available at this apartment. More

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Midnight Cove II 611F

1400 Cove II Place, Unit 611F, Siesta Key, United States Show map

The 2-bedroom Midnight Cove II 611F Apartment Siesta Key enjoys a prime location a mere 7 minutes' walk from the shaped Crescent Beach. At the spacious 84 m² apartment, Wi-Fi and a car park are also… More

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Gulf And Bay Club- B107

5780 Midnight Pass Rd, Unit B107, Siesta Key, United States Show map

The spacious Gulf And Bay Club- B107 Apartment Siesta Key features a prime location a 14-minute walk from Siesta Beach Pavillion and hosts up to 4 guests. At this apartment, Wi-Fi and a car park are… More

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2 Bed2 Bath Condo! 14 Mile To #1 Siesta Beach Ground Floor Wwasher & Dryer

5643 Midnight Pass Road #911, Siesta Key, United States Show map

The spacious 2 Bed2 Bath Condo! 14 Mile To #1 Siesta Beach Ground Floor Wwasher & Dryer Siesta Key is located just 1 km from Siesta Key Drum Circle and about a 10-minute walk from Siesta Beach… More

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Harbor Towers 131

5855 Midnight Pass Road #131, Siesta Key, United States Show map

The spacious Harbor Towers 131 Apartment Siesta Key boasts views of the pool and is located 25 minutes' walk from Grand Canal. Wi-Fi and a car park are among the essentials at guests' disposal. More

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