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Siesta Key Romantic Beach Rentals

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1624 rentals in Siesta Key.
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View from Condo (Living Room & Master Bedroom)
Living Area
GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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2 BR, 2 Bath, Siesta Key Village Condo with Pool
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Your private resort
Welcome to paradise!
Living area 2 has a leather Eurolounger that folds into full size bed.
A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
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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
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180 degree panorama view of the Gulf from your lanai
Lanai seating and dining
DR table easily accommodates 6
See Rates for Discounts Through October!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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4 Bedroom with Gulf View Siesta Key FL Beach Fun
Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 10
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Firethorn 610 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Firethorn 821 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Across The Street From #1 Beach- w/ RELAXED CANCELLATION POLICY Thru 12/31/2022
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Siesta Key Gulf Side~1st Floor Villa, 3 Heated Pools, Updated, Beachy Chic #100
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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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
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Beach Front 3BR 2 BA Villa Near Siesta Key Village
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Walk To Siesta Village And Beach/Pool & Hot Tub
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Super clean and Modern Townhouse, Style And Comfort, Steps From PRIVATE Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
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Large canal house, 5BR with Heated pool
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
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Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Newly renovated condo with premium features on Siesta Key
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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LuLu's Leatherback Walk to Beach & Village, Heated Pool, WiFi, Barbecue Station,
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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LAST MINUTE PRICE!! BEACH OPEN!! SIESTA KEY , PRIVAT POOL !
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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Siesta Key Condo w/Private Beach Access, Wifi Included, Heated Pool, Tennis
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Sit Back And Watch The Parade Of Boats From Your Luxurious Condo!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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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
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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
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Pet friendly Home- Blocks from World Famous Siesta Key Beach
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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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
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Private 4 Bedroom Single Family Coastal Home w/Pool 1 Block to Siesta Key Beach
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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View World-famous Siesta Beach from Lanai*Paradise just steps from sand & surf
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Perfectly Remodeled Townhome, Steps From the Private Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
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*Steps from World-Famous Siesta Beach*Spacious, Tranquil 2/2+garage*Paradise!*
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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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
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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
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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
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Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key Getaway!!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
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Siesta Key Jamaica Royale 71 Beachside
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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LuLu’s Green in the Heart of Siesta Key Village, 4 Minute Walk to Beach, Pool, W
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Steps to Village and Beaches! Remodeled, two Private Patios! Casa Tranquilla.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
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☀️ ️ NEW HIGH END LUXURY SIESTA HOME W/PRIVATE HEATED POOL & BEACH ACCESS ️
Condo/Apartment
5 bedrooms
5 bathrooms
Sleeps 10
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Beautiful, Spectacular view on the Ocean, new furniture, oversized deck/balcony
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Top Location on Siesta Key! Private Gate into Village! No car required!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
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Perfect Location. Roof Top Deck. Gulf Views. Heated Pool/Spa w/ Rain Curtain
Rental Home
6 bedrooms
7 bathrooms
Sleeps 18
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5th Floor Siesta Key Condo Across From Pristine Sand & Blue Waters 2bd/2b Views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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BEST HOUSE ON SIESTA - Sleeps 24+ - Heated Private Pool w/ Slide, Spa, Gratto,
Rental Home
8 bedrooms
8 bathrooms
Sleeps 23
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Newly Renovated Home on Canal, New Pool, Steps from Siesta Key Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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BEAUTIFUL & IMPECCABLY MAINTAINED BEACHFRONT CONDO ON AMAZING SIESTA KEY BEACH
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Clean and Beautiful Condo with Private Beach in Beautiful Siesta Key #1 Beaches
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
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"CHATEAU du SOLEIL" *** SINGLE Family Home *** 1-1/2 Blocks to Beach
Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
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Siesta Key Vacation Rentals
Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.
More
Siesta Key Vacation Rentals
Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.
Lions, Tigers & Circuses
When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.
Gardens & Aquariums
Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.
Locomotives & Science
Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theater, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.
History & Baseball
From your money-saving Siesta Bay vacation rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.