Siesta Key Holiday Rentals
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1010 rentals in Siesta Key.
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Newly Renovated Beach House on canal * 5 minute walk to village and beach
3 bedrooms
2 bathrooms
Sleeps 8
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WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY
2 bedrooms
1 bathroom
Sleeps 4
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WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY
2 bedrooms
2 bathrooms
Sleeps 4
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Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa
5 bedrooms
4 bathrooms
Sleeps 13
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Top Floor Oceanfront View Of The #1 Beach In The USA! - Beautiful Decor!
1 bedroom
1 bathroom
Sleeps 3
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Newly renovated condo with premium features on Siesta Key
2 bedrooms
2 bathrooms
Sleeps 6
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Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*
2 bedrooms
2 bathrooms
Sleeps 4
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BEST HOUSE ON SIESTA - Sleeps 24+ - Heated Private Pool w/ Slide, Spa, Gratto,
0 bedrooms
8 bathrooms
Sleeps 24
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Best Location - luxury villa with pool, very close to beach and restaurants!
2 bedrooms
3 bathrooms
Sleeps 4
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Fantastic Beachfront Condo, at Surf & Racquet Resort on Siesta Key Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Palm Oasis - Relax in Comfort - 1 rental per calendar month
4 bedrooms
3 bathrooms
Sleeps 10
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2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!
2 bedrooms
1 bathroom
Sleeps 5
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Siesta Key/Derby Bay
3 bedrooms
2 bathrooms
Sleeps 6
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Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
2 bedrooms
2 bathrooms
Sleeps 6
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Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
1 bedroom
1 bathroom
Sleeps 4
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Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!
2 bedrooms
1 bathroom
Sleeps 4
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Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!
2 bedrooms
1 bathroom
Sleeps 4
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A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach
3 bedrooms
2 bathrooms
Sleeps 9
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1 Bedroom/ 1 Bath Condo Steps From Siesta Key Sand with Pool Access-Gulf Holiday
1 bedroom
1 bathroom
Sleeps 4
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Super Cute, Super Clean Large One Bedroom - Fully Remodeled!
1 bedroom
1 bathroom
Sleeps 4
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Steps From Siesta Key Beach! 1BR w/ Heated Pool
1 bedroom
1 bathroom
Sleeps 4
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Tropical bungalow steps from the baby powder sand of Siesta Beach and Village
1 bedroom
1 bathroom
Sleeps 4
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2 Bed/2 Bath Condo Resort View on Siesta Key Beach
2 bedrooms
2 bathrooms
Sleeps 5
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GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key Old Florida Cottage, Great Location at a Great Price
1 bedroom
1 bathroom
Sleeps 2
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Quiet and Comfortable Condo Near Turtle Beach
2 bedrooms
2 bathrooms
Sleeps 5
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Siesta Key Vacation Townhouse directly across the street from #1 Beach in the US
2 bedrooms
2 bathrooms
Sleeps 6
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Charming Siesta Key Village Unbeatable Location
1 bedroom
1 bathroom
Sleeps 4
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4 Bedroom with Gulf View Siesta Key FL Beach Fun
4 bedrooms
4 bathrooms
Sleeps 10
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Siesta Beach House - 311 / Beach Cove
2 bedrooms
3 bathrooms
Sleeps 7
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Rent Siesta Now: A Shore Thing!
3 bedrooms
2 bathrooms
Sleeps 8
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Siesta Key - Sarasota, Super Cute One Bedroom, Steps to the Beach!
1 bedroom
1 bathroom
Sleeps 4
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Aloha Kai - 2 beautful unit and close to pool!
2 bedrooms
2 bathrooms
Sleeps 4
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Direct Gulf-Front / End Unit Fisherman's Cove A201
2 bedrooms
2 bathrooms
Sleeps 4
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Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach
1 bedroom
1 bathroom
Sleeps 4
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CONTACT US FOR GREAT APRIL AND MAY DISCOUNTS!
2 bedrooms
2 bathrooms
Sleeps 6
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Sandy Toes Town Home
3 bedrooms
3 bathrooms
Sleeps 6
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Seaside Villas Unit 3BR 5241
3 bedrooms
3 bathrooms
Sleeps 8
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Deluxe 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village
3 bedrooms
3 bathrooms
Sleeps 8
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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key
3 bedrooms
2 bathrooms
Sleeps 8
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Dolphin Bungalow - Courtyard View
1 bedroom
1 bathroom
Sleeps 4
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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated
1 bedroom
1 bathroom
Sleeps 2
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Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool
2 bedrooms
2 bathrooms
Sleeps 6
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Crystal Sands Unit 308 Siesta Key, Florida
2 bedrooms
2 bathrooms
Sleeps 6
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Private Studio Apartment - Separate, Private Entrance - Walk to Siesta Village
0 bedrooms
1 bathroom
Sleeps 2
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2 BR, 2 Bath, Siesta Key Village Condo with Pool
2 bedrooms
2 bathrooms
Sleeps 4
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SEA SHELL - Siesta Key Beach View Vacation Condo - 2 BR - on Crescent Beach
2 bedrooms
2 bathrooms
Sleeps 6
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1BR - Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta Key Village
1 bedroom
1 bathroom
Sleeps 4
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Peaceful Haven on Siesta Key with Beach Access
2 bedrooms
2 bathrooms
Sleeps 6
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