We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Siesta Key Villas

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Communities
Show more
141 rentals in Siesta Key.
Sort by:
Tripadvisor Sort
Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
92 other travelers have booked this property
Relaxing 2bed/2bath Pool Side, Steps from Siesta Key Beach!-Bianco Sands1126
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
Siesta Key private beach access
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
1 other traveler has booked this property
Deluxe 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
100 other travelers have booked this property
Enjoy the sunsets from the rooftop lanai!
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Top Location on Siesta Key! Private Gate into Village! - Gertrudes Village House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Sunset Point Siesta Key FL AWESOME RENTAL !!
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
16 other travelers have booked this property
Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Siesta Key rentals sent straight to your email!
Jamaica Royale #100-Peaceful Gulf Side Condo
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
12 other travelers have booked this property
Island House Beach Resort - Villa 35
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
22 other travelers have booked this property
Deluxe 4-BR Siesta Key Townhouse & Garden Apt - Heated Pool - Siesta Key Village
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
Island House Beach Resort - Villa 39
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort Villa 6
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 3
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Tropical Villa - Siesta Villa Palma
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
15 other travelers have booked this property
Island House Beach Resort - Villa 7
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 10B
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
In the Heart of Siesta Key Village and Steps to the #1 Beach
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 4
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
CASA BLANCA B17 2 Bdrm, 2 bath Villa on Crescent Beach
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
1 other traveler has booked this property
Island House Beach Resort - Villa 8
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Spacious 4bed air-con villa on Siesta Key
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
9 other travelers have booked this property
Island House Beach Resort Villa 15
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Siesta Key 3 Bedrm, 3½ bath Villa 2900 SF sleeps 8
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 37
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 33
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 24
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 11
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 26
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Newly remodeled with beach and Pool Access!! -Crescent St. Perlita.
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
2 other travelers have booked this property
Island House Beach Resort - Villa 10A
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 36
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 1
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Siesta Key Oceanfront on Gulf with western sunsets, 1250 sq ft Townhome
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
2 other travelers have booked this property
Siesta Key/Derby Bay
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
7 other travelers have booked this property
Island House Beach Resort - Villa 5
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Villa Laughing Gull - Cozy, Private Siesta Key Villa
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
5 other travelers have booked this property
Island House Beach Resort - Villa 38
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 28
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 19
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Aloha Kai - Unit 26- Awesome unit &full Gulf front!!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
Island House Beach Resort Villa 18
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 27
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 25
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Island House Beach Resort - Villa 32
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
Siesta Villa Whispering Palms
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Check in
Check out
Payment Protection
Island House Beach Resort - Villa 22
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Villas
More info
Vrbo.com logo
Check in
Check out
PreviousNext
123
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.