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Vacation Rentals in Siesta Key, Florida

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  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 203 Rentals in Siesta Key
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From
$145
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (4) Make Inquiry
From
$144
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (5) Make Inquiry
From
$3,800
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details
Reviews (4) Make Inquiry
Also consider
Siesta Key 2/2 Near Beach
2 Bedrooms, sleeps 5
$550 - $1,050 / week
Kid friendly Luxury home on Siesta Key
4 Bedrooms, sleeps 10
$240 / night
Crystal Sands Unit 308 Siesta Key, Florida
2 Bedrooms, sleeps 6
$220 / night
Book in May and  receive 10% to enjoy the best beach
2 Bedrooms, sleeps 6
$170 - $270 / night
From
$975
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
17 photos Details
Reviews (1) Make Inquiry
From
$700
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details
Reviews (6) Make Inquiry
From
$1,050
Per Week
other traveler has booked this property
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (2) Make Inquiry
From
$132
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
52 photos Details
Reviews (8) Make Inquiry
From
$84
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (18) Make Inquiry
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From
$999
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (5) Make Inquiry
From
$155
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Inquiry
From
$135
Per Night
other travelers have booked this property
2 Bedrooms, 1 Bathroom, Sleeps 4
31 photos Details
Reviews (2) Make Inquiry
From
$2,495
Per Month
other travelers have booked this property
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
Reviews (1) Make Inquiry
From
$594
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (12) Make Inquiry
From
$121
Per Night
other traveler has booked this property
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (2) Make Inquiry
From
$166
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
38 photos Details
Reviews (1) Make Inquiry
From
$134
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
20 photos Details
Reviews (28) Make Inquiry
From
$121
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 4
16 photos Details
Reviews (3) Make Inquiry
From
$1,125
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details
Reviews (1) Make Inquiry
From
$1,040
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 5
27 photos Details
Reviews (18) Make Inquiry
From
$790
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
Reviews (3) Make Inquiry
From
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
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From
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (8) Make Inquiry
From
$1,100
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 7
19 photos Details
Reviews (4) Make Inquiry
From
$1,100
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 7
18 photos Details
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From
$1,850
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
14 photos Details
Reviews (5) Make Inquiry
From
$125
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (3) Make Inquiry
From
$150
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (7) Make Inquiry
From
$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (10) Make Inquiry
From
$113
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
18 photos Details
Reviews (7) Make Inquiry
From
$135
Per Night
other travelers have booked this property
2 Bedrooms, 1 Bathroom, Sleeps 4
27 photos Details
Reviews (3) Make Inquiry
From
$121
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
22 photos Details
Reviews (1) Make Inquiry
From
$5,200
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (1) Make Inquiry
From
$597
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (5) Make Inquiry
From
$215
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details
Reviews (28) Make Inquiry
From
$115
Per Night
other travelers have booked this property
2 Bedrooms, 1 Bathroom, Sleeps 5
12 photos Details
Reviews (17) Make Inquiry
From
$800
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
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From
$96
Per Night
other traveler has booked this property
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details
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From
$850
Per Week
other travelers have booked this property
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
Reviews (6) Make Inquiry
From
$110
Per Night
other travelers have booked this property
2 Bedrooms, 1 Bathroom, Sleeps 5
14 photos Details
Reviews (1) Make Inquiry
From
$749
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Reviews (16) Make Inquiry
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Book Online(94)

Suitability

  • Wheelchair access (42)
  • Elder access (123)
  • Suitable for children (148)
  • Pet friendly (33)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (194)
  • Other outdoor space (167)
  • Wi-Fi (164)
  • All pools (157)
  • Washer/Dryer (149)
  • View all amenities
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Book Online(94)

Suitability

  • Wheelchair access (42)
  • Elder access (123)
  • Suitable for children (148)
  • Pet friendly (33)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (194)
  • Other outdoor space (167)
  • Wi-Fi (164)
  • All pools (157)
  • Washer/Dryer (149)
  • View all amenities
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.