Vacation Rentals in Siesta Key, Florida

50 Properties Available

Beach Chalet - Ocean Views - Condo Complex - Beach & Village Walkable! Private vacation home
Beach Chalet - Ocean Views - Condo Complex - Beach & Village Walkable!
$5127 / night
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Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly ??? Private vacation home
Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly ???
$4223 / night
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Siesta Key Oceanfront Palace with Private Beach Private vacation home
Siesta Key Oceanfront Palace with Private Beach
$4099 / night
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Entire Building, Sundeck w/ Ocean view, 20ft to Beach Access, 500ft from Village Private vacation home
Entire Building, Sundeck w/ Ocean view, 20ft to Beach Access, 500ft from Village
$3679 / night
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Beach Chalet Condo - Ocean View - Siesta Key Beach & Village Walkability! Chalet
Beach Chalet Condo - Ocean View - Siesta Key Beach & Village Walkability!
$3405 / night
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NEW! Village Vibe | 2 Private Heated Pools, Walk to Beach, In the Heart of Siesta Key Village Private vacation home
NEW! Village Vibe | 2 Private Heated Pools, Walk to Beach, In the Heart of Siesta Key Village
$3124 / night
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Unmatched Rooftop & Gulf Views-Resort Style Pool\/Waterslide\/Spa - Steps to Beach Private vacation home
Unmatched Rooftop & Gulf Views-Resort Style Pool\/Waterslide\/Spa - Steps to Beach
$2863 / night
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Beachfront Luxury, Direct Beach Access, Gulf Views, Resort Style Pool w\/ Spa Private vacation home
Beachfront Luxury, Direct Beach Access, Gulf Views, Resort Style Pool w\/ Spa
$2834 / night
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Luxurious 4 Bedroom Home on Siesta Key, Steps From Siesta Beach! Private vacation home
Luxurious 4 Bedroom Home on Siesta Key, Steps From Siesta Beach!
$2340 / night
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New Listing! Spacious, 100% Private, near the Siesta Key Beach and Village! Private vacation home
New Listing! Spacious, 100% Private, near the Siesta Key Beach and Village!
$2269 / night
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Sea Spray ~ Near Beach ~ Dock ~ Pool Slide Private vacation home
Sea Spray ~ Near Beach ~ Dock ~ Pool Slide
$2177 / night
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Siesta Key Village - Townhouse Fourplex - Private Heated Pool - Beach Walkable Private vacation home
Siesta Key Village - Townhouse Fourplex - Private Heated Pool - Beach Walkable
$2157 / night
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Azure Way Estate | Luxury Waterfront Estate on Siesta Key Private vacation home
Azure Way Estate | Luxury Waterfront Estate on Siesta Key
$1998 / night
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Summer House ~ Near Beach ~ Pool & Slide Private vacation home
Summer House ~ Near Beach ~ Pool & Slide
$1992 / night
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Miramar Villa
Miramar
$1977 / night
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Beautiful pool with waterslide, 2 min walk to the beach - High Tide Private vacation home
Beautiful pool with waterslide, 2 min walk to the beach - High Tide
$1947 / night
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Steps to Beach - Resort Pool/Slide/Spa/Gulf Views Private vacation home
Steps to Beach - Resort Pool/Slide/Spa/Gulf Views
$1889 / night
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Gulf Views/Steps to Beach/Resort Pool w/Slide/Spa Private vacation home
Gulf Views/Steps to Beach/Resort Pool w/Slide/Spa
$1872 / night
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Pool Volleyball-Gulf Views-Steps to Beach-Rooftop Private vacation home
Pool Volleyball-Gulf Views-Steps to Beach-Rooftop
$1820 / night
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Steps to Beach/Gulf Views/Pool Volleyball/Slide Private vacation home
Steps to Beach/Gulf Views/Pool Volleyball/Slide
$1774 / night
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Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village Private vacation home
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village
$1724 / night
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On the Rocks ~ Near Beach ~ Pool & Slide Private vacation home
On the Rocks ~ Near Beach ~ Pool & Slide
$1703 / night
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16 Guest Pool house walk to the beach and village Private vacation home
16 Guest Pool house walk to the beach and village
$1667 / night
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Beach Road Condo - Private Decks - Siesta Key Beach & Village Walkability! Chalet
Beach Road Condo - Private Decks - Siesta Key Beach & Village Walkability!
$1656 / night
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Private pool walk to beach and village Private vacation home
Private pool walk to beach and village
$1647 / night
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Siesta Key Beachfront Suites Compound: 6 Bdrm Beachfront Private vacation home
Siesta Key Beachfront Suites Compound: 6 Bdrm Beachfront
$1620 / night
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Exclusive complex - Private Heated Pool - 100 Steps to Beach - Village 5 minute walk Private vacation home
Exclusive complex - Private Heated Pool - 100 Steps to Beach - Village 5 minute walk
$1610 / night
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Salty Dog ~ Canal Front ~ Pool/Spa ~ Rooftop Private vacation home
Salty Dog ~ Canal Front ~ Pool/Spa ~ Rooftop
$1607 / night
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Bahama Mama ~ Near Beach ~ Pool & Spa Private vacation home
Bahama Mama ~ Near Beach ~ Pool & Spa
$1578 / night
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Dry Dock ~ Canal Front ~ Pool/Spa ~ Rooftop Private vacation home
Dry Dock ~ Canal Front ~ Pool/Spa ~ Rooftop
$1575 / night
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? Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table! Private vacation home
? Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!
$1539 / night
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New Listing! Pool and Private Patio. Leave the car behind. Steps to the best beach on Siesta Key! Apartment
New Listing! Pool and Private Patio. Leave the car behind. Steps to the best beach on Siesta Key!
$1508 / night
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Private Home with Pool and Sundeck! Private vacation home
Private Home with Pool and Sundeck!
$1466 / night
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Beach Chalet - Deck - Siesta Key Village and Beach Walkable! Chalet
Beach Chalet - Deck - Siesta Key Village and Beach Walkable!
$1382 / night
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Private Canal Home , short Walk to Siesta Key Beach Private vacation home
Private Canal Home , short Walk to Siesta Key Beach
$1336 / night
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Siesta Key Exclusive Beachside Compound: 3 Units Private vacation home
Siesta Key Exclusive Beachside Compound: 3 Units
$1317 / night
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Coastal Elegance with Breathtaking Gulf Views: Residence 601 Condo
Coastal Elegance with Breathtaking Gulf Views: Residence 601
$1271 / night
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Breezy Beachfront Charm with Direct Gulf Views: Residence 307 Condo
Breezy Beachfront Charm with Direct Gulf Views: Residence 307
$1249 / night
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Spacious Fifth Floor Luxury Rental with Oversized Terrace: Residence 502 Condo
Spacious Fifth Floor Luxury Rental with Oversized Terrace: Residence 502
$1243 / night
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Key Life Living l Private Heated Pool & 5 Minute Walk to Crescent Beach Private vacation home
Key Life Living l Private Heated Pool & 5 Minute Walk to Crescent Beach
$1243 / night
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Bimini Breeze ~ Near Beach/Village ~ Pool Private vacation home
Bimini Breeze ~ Near Beach/Village ~ Pool
$1238 / night
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Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock Private vacation home
Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock
$1237 / night
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Majestic Beachside Retreat ~ Pool ~ Hot Tubs ~ BBQ Private vacation home
Majestic Beachside Retreat ~ Pool ~ Hot Tubs ~ BBQ
$1223 / night
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Exclusive Home - Private Pool - Siesta Key Village & Beach Walkable! Private vacation home
Exclusive Home - Private Pool - Siesta Key Village & Beach Walkable!
$1222 / night
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Breathtaking Gulf Views on Siesta: Residence 501 Condo
Breathtaking Gulf Views on Siesta: Residence 501
$1219 / night
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Beathtaking Costal Luxury with Direct Beach and Gulf Views: Residence 405 Condo
Beathtaking Costal Luxury with Direct Beach and Gulf Views: Residence 405
$1184 / night
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Beachfront Luxury with Spectacular Gulf Views: Residence 303 Condo
Beachfront Luxury with Spectacular Gulf Views: Residence 303
$1167 / night
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Coastal Contemporary Residence with Spectacular Gulf Views: Residence 403 Condo
Coastal Contemporary Residence with Spectacular Gulf Views: Residence 403
$1161 / night
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Siesta Soul | Multilevel Home Located in Siesta Key Village w\/ Private Pool, Fire Pit, Walk to Beach Private vacation home
Siesta Soul | Multilevel Home Located in Siesta Key Village w\/ Private Pool, Fire Pit, Walk to Beach
$1134 / night
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Aruba ~ Near Beach & Village ~ Private Pool Private vacation home
Aruba ~ Near Beach & Village ~ Private Pool
$1123 / night
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