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Siesta Key Holiday Rentals with Pools

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972 rentals in Siesta Key.
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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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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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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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Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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#1 Beach - 'Super Clean' - 2 Level Townhouse - 1400sf 2Br/2.5 Bth- 5 Star Rating
Condo/Apartment
2 bedrooms
3 bathrooms
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 Bedroom Siesta Key Beach Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Beautiful condo directly across from Siesta Beach - beach, gulf and pool views
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
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Guaranteed Cleanliness and Hotel linens! 1 Small Dog allowed, Walk to Beach, He
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Save time - get the best Siesta Key rentals sent straight to your email!
Our Beach Cottage
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
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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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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Quiet and Comfortable Condo Near Turtle Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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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Sandy Toes Town Home
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Firethorn 330 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Direct Gulf-Front / End Unit Fisherman's Cove A201
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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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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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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Firethorn 332 at Midnight Cove Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Buttonwood 447 at Midnight Cove Siesta Key, FL.
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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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Chinaberry 453 at Midnight Cove Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Doveplum 621 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Firethorn 522 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Firethorn 632 at Midnight Cove Siesta Key
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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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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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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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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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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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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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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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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
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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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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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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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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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BEAUTIFUL & IMPECCABLY MAINTAINED BEACHFRONT CONDO ON USA’S #1 SIESTA KEY BEACH!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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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BEST HOUSE ON SIESTA - Sleeps 24+ - Heated Private Pool w/ Slide, Spa, Gratto,
Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 24
Match: Sleeps, All pools
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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
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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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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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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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New remodel. Steps to Siesta Beach! Poolside,1st flr. Near Siesta Village- Save!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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