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Holiday Rentals with Pools in Siesta Key

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967 rentals in Siesta Key.
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FALL DISCOUNTS!
IT DOESN'T GET ANY BETTER THAN THIS!  FULL FRONT VIEWS- FROM ALL LIVING AREA
It Doesn't Get Any Better Than This! 
Full Gulf Front-Spectacular views from every room
Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Beautiful lanai, with spectacular floor to ceiling views of the beach, gulf, wildlife and sunset.
An amazing sunset seen within the condo, or if you prefer on the beach.
Enjoy the quiet sunset, wonderful beach and relaxing.  Life is good!
Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Tastefully decorated with a beachy look and feel!
Palm Trees and Paradise
#1 beach in the world - seconds from the condo
Newly discounted rates! Gorgeous one bedroom across from beach, near village!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, All pools
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Enjoy a Large Heated Pool and updated exercise room
King bed with full bath and Gulf View
4 Bedroom with Gulf View Siesta Key FL Beach Fun
Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, All pools
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SAVE $200 for 7 nights May 14 or May 28!!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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2 BR, 2 Bath, Siesta Key Village Condo with Pool
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Doveplum 121 at Midnight Cove Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Buttonwood 477 at Midnight Cove Siesta Key, FL.
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Save time - get the best Siesta Key rentals sent straight to your email!
Firethorn 522 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Siesta Key Gulf Side~1st Floor Villa, 3 Heated Pools, Updated, Beachy Chic #100
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Newly renovated condo with premium features on Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Walk To Siesta Village And Beach/Pool & Hot Tub
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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LAST MINUTE PRICE!! BEACH OPEN!! SIESTA KEY , PRIVAT POOL !
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Pet friendly Home- Blocks from World Famous Siesta Key Beach
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Siesta Beach-January Specials
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Couple's Fun Getaway, Quick to Village, Easy to Beach! Super Location on key!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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View World-famous Siesta Beach from Lanai! Closest Condo Complex to the Beach
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, All pools
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Siesta Key, beach front condo on America's #1 Beach! 2 BR, 2 Bath, Sleeps 6
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Private 4 Bedroom Single Family Coastal Home w/Pool 1 Block to Siesta Key Beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Super clean and Modern Townhouse, Style And Comfort, Steps From PRIVATE Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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An intercoastal delight with beach access Sept to October 2020 $89 per night
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Sit Back And Watch The Parade Of Boats From Your Luxurious Condo!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Large canal house, 5BR with Heated pool
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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LuLu's Loggerhead - Walk to Siesta Key Beach. In Village, Heated Pool, WiFi, Upd
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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☀️�️ LUX CONDO w/ PRIVATE HEATED POOL * SIESTA BEACH ☀️�️
Condo/Apartment
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
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* Special Nov 28 -Dec 12th only $150 per night * On Beach Ocean front on beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Newly Renovated Home on Canal, New Pool, Steps from Siesta Key Beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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NEARLY BEACHFRONT-PRIVATE Heated Pool and Spa with Covered Pool Bar and Patio
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps, All pools
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Perfectly Remodeled Townhome, Steps From the Private Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Siesta Key Jamaica Royale 71 Beachside
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Siesta Key Getaway!!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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CHATEAU du SOLEIL 10% DISCOUNT Dec 5-19
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps, All pools
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BEAUTIFUL & IMPECCABLY MAINTAINED BEACHFRONT CONDO ON USA’S #1 SIESTA KEY BEACH!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Top Rated Gulf Side, Steps from Beach, Great Amenities 2 pools, tennis, hot tub
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Clean and Beautiful Condo with Private Beach in Beautiful Siesta Key #1 Beaches
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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LuLu's Leatherback Walk to Beach & Village, Heated Pool, WiFi, Barbecue Station,
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Siesta Key Condo w/Private Beach Access, Wifi Included, Heated Pool, Tennis & B
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Heart of Siesta Key Village, Walk to Gulf/beach, WiFi, Heated Community Pool & T
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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Steps from World-Famous SiestaBeach*Spacious 2/2 Condo w/garage*tranquil setting
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Luxurious Beach Condo on Siesta Key 605 South
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Siesta Key private beach access
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Perfect Location! Walk to Siesta Key Village & the Beach! Amazing Pool area!!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps, All pools
More info
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Siesta Key For Me * The Palm Bay Club
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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