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Vacation rentals in Siesta Key, Florida

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Property owner typically means…
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  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 271 Rentals in Siesta Key
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$71
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 7
25 photos Details
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$160
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
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$84
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (10) Make Enquiry
Also consider
Enjoy Quiet Turtle Beach & View Sunsets From Lanai
2 Bedrooms, sleeps 6
$160 / night
Cathy's Crescent Condos-Siesta Key,  FL GULF FRONT
2 Bedrooms, sleeps 6
$213 - $335 / night
4 Bedroom with Gulf View Siesta Key FL Beach Fun
4 Bedrooms, sleeps 10
$313 - $335 / night
Fabulous Siesta Key Condo
2 Bedrooms, sleeps 4
$177 / night
From
$2,665
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
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$3,311
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
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$107
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
14 photos Details
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From
$107
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
26 photos Details
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From
$980
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 8
12 photos Details
Reviews (1) Make Enquiry
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From
$748
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (6) Make Enquiry
From
$107
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details
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From
$139
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
18 photos Details
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From
$171
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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From
$183
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
13 photos Details
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From
$134
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
14 photos Details
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From
$182
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
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From
$107
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
22 photos Details
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From
$160
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
26 photos Details
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From
$187
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
21 photos Details
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From
$1,549
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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From
$187
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
33 photos Details
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From
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
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From
$92
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
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From
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
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From
$427
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
15 photos Details
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From
$118
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
17 photos Details
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From
$182
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
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From
$459
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
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From
$85
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
17 photos Details
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From
$99
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details
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From
$256
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 10
23 photos Details
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From
$214
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
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From
$192
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
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From
$2,564
Per Month
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details
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From
$229
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
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From
$1,246
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
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From
$182
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
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From
$125
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details
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From
$214
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 4
13 photos Details
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From
$61
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
11 photos Details
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From
$128
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
32 photos Details
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Suitability

  • Wheelchair access (46)
  • Elder access (122)
  • Suitable for children (214)
  • Pet friendly (36)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (259)
  • Internet (258)
  • Parking (213)
  • All pools (198)
  • Other outdoor space (198)
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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.