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Siesta Key Cottages

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0+ rooms, 2+ guests
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$1,000+
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15 rentals in Siesta Key.
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Key West style beach cottage JUST STEPS from #1 SIESTA KEY BEACH!
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Cottages
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Siesta Beach Place-Starfish Cottage, Steps to the Sand, View of Pool, Access #11
1 bedroom
1 bathroom
Sleeps 4
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1 other traveler has booked this property
Beach Place Cottages - Seahorse Cottage - Peak of the Gulf - Beach Access #11
1 bedroom
1 bathroom
Sleeps 4
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2 other travelers have booked this property
Walk to Beach, Fully Renovated with Highend Finishings, Wifi/Cable, Heated Pool,
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Cottages
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Lush Siesta Key Cottage - 4 Blocks to Main St!
2 bedrooms
2 bathrooms
Sleeps 3
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2 Bedroom/ 1 One Bath Gem Just Steps from Siesta Key Beach!!-Barefoot Bungalow
2 bedrooms
1 bathroom
Sleeps 4
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Cute 2Bedroom/ 1Bath Cozy Cottage Steps from Siesta Key Beach!-Barefoot Bungalow
2 bedrooms
1 bathroom
Sleeps 4
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Cute 2Bedroom/1Bath Cottage- Across from Siesta Key Beach Access-Cottage by Sea
2 bedrooms
1 bathroom
Sleeps 6
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'Cottage by the Sea' 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032
1 bedroom
1 bathroom
Sleeps 4
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Siesta Key Old Florida Cottage, Great Location at a Great Price
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Cottages
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Prem 2Bed/2Bath Gate House Cottage with private beach access!
2 bedrooms
2 bathrooms
Sleeps 4
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Rent Siesta Now Vacation Rentals - Twin Palms 2-BEDROOM, 1 BATH, SLEEPS 6
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Cottages
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Siesta Key Beach Cottages on Crescent
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key 'Casa Serena' w/Private Pool + Lanai!
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Cottages
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Incredible Cottage in Paradise ⭐Walk to the Beach or Village - Very Convenient
1 bedroom
1 bathroom
Sleeps 2
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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.
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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.
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.