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Vacation rentals in Siesta Key, Florida

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All 358 Rentals in Siesta Key
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$330
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
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$1,620
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$190
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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Also consider
Sea Shell Condos Directly on Siesta Key Beach
2 Bedrooms, sleeps 6
$191 / night
Siesta Key Pool Home 1 block to BEACH
3 Bedrooms, sleeps 8
$107 - $198 / night
Casa Van Lopik (c)- Your lush island getaway.
3 Bedrooms, sleeps 10
$246 - $648 / night
Old Man and the Sea Inn 2BR- 1 marlin to the sand!
2 Bedrooms, sleeps 8
$156 - $492 / night
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$3,463
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
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$112
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
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$112
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$64
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
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$1,174
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$128
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
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$1,024
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$92
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$151
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$123
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
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$112
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
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$74
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 7
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$2,787
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
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$107
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1 Bedroom, 1 Bathroom, Sleeps 2
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$190
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2 Bedrooms, 1 Bathroom, Sleeps 6
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$179
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$196
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
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$145
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
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$303
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
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$112
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
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$196
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
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$327
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$363
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$307
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
$168
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$120
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$168
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
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From
$168
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$242
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 10
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$1,005
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
$1,027
Per Week
1 Bedroom, 1 Bathroom, Sleeps 4
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From
$327
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
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From
$327
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
42 photos Details
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From
$1,353
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
43 photos Details
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From
$447
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$337
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
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From
$239
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
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Suitability

  • Wheelchair access (49)
  • Elder access (131)
  • Suitable for children (226)
  • Pet friendly (48)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (299)
  • Internet (298)
  • Parking (250)
  • All pools (228)
  • Other outdoor space (225)
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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.