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1858 Villa rentals in Siesta Key, FL
8.5 4 reviews
Siesta Key, FL
08/04 – 08/05
$1254/nightfor 1 night
Vinca - 5251d
1 4
house , Siesta Key
Vinca - 5251D is a short 5-minute walk from Siesta Key Beach, known for its powdery white sand and calm waters, and within a 1.2-mile radius of Crescent Beach. This vacation rental has received very good user ratings, and good ratings for location and cleanliness. This 1-bedroom, 1-bathroom home offers 740 square feet of space and can accommodate up to 4 guests. Enjoy modern amenities like air conditioning, a swimming pool, free parking, and Wi-Fi, along with a fully equipped kitchen and a TV with satellite channels.
9.8 34 reviews
Siesta Key, FL
07/09 – 07/11
$2380/nighttotal: $4760 (2 )
186 M² House ∙ 4 Bedrooms ∙ 12 Guests
4 4
house , Siesta Key
Casa Mahalo, a Siesta Key Village duplex, is a two-minute walk from Siesta Key Beach. This 1990-square-foot vacation rental boasts four bedrooms, three bathrooms, accommodates up to twelve guests, includes a private heated pool (heated November 15th to April 15th), a private cabana with an outdoor refrigerator, and provides beach essentials.
Siesta Key, FL
06/25 – 07/01
$307/nighttotal: $1842 (6 )
Casa Mar - 63 Premium
1 4
house , Siesta Key
Casa Mar - 63 Premium, located in Sarasota, offers a one-bedroom, one-bathroom house a short walk from Crescent Beach and under a mile from Siesta Key Beach, with easy access to the Sarasota County Visitor Information Center and History Museum. This Siesta Key vacation rental sleeps three guests and features a kitchen with a fridge, microwave, and dishwasher, a private pool, a tennis court, free Wi-Fi, and on-site parking; nearby attractions include Marina Jack Restaurant and Marina (7 miles) and the John and Mable Ringling Museum of Art (11 miles).
10 29 reviews
Siesta Key, FL
08/31 – 09/02
$1337/nighttotal: $2674 (2 )
191 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 2
house , Siesta Key
Serenity Cottage, located on Siesta Key's southern end, is a two-minute walk from Crescent Beach and a short drive from Siesta Key Village and Siesta Key Beach. This 2,050-square-foot vacation rental boasts three bedrooms, three bathrooms, sleeps eight, and features a private heated pool and spa (heated November 15th–April 15th), a renovated kitchen, multiple balconies, a screened-in dining area with a gas grill, free WiFi, and a two-car garage.
Siesta Key, FL
07/14 – 08/11
$248/nighttotal: $6944 (28 )
1200-303 Bay-side Garden Views Await
2 3
house , Siesta Key
This bay-side garden view vacation home in Sarasota offers a prime location, just a 4-minute walk to Crescent Beach and conveniently situated 7.8 miles from Marina Jack Restaurant And Marina and 11 miles from the Ringling Museum. This 2-bedroom, 2-bathroom house accommodates up to 11 guests and features a fully equipped kitchen with a microwave, complimentary Wi-Fi, air conditioning, an outdoor swimming pool, and on-site parking.
Siesta Key, FL
07/17 – 07/24
$292/nighttotal: $2044 (7 )
Crescent Royale Condominiums 205
1 2
house , Siesta Key
This vacation home is located in Siesta Key, just a 4-minute walk from Siesta Key Beach and 11 miles from the John and Mable Ringling Museum of Art. This 890 sq ft, 1-bedroom, 1-bathroom condo accommodates up to 5 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, a terrace, a fitness center, tennis court, and parking.
10 1 review
Siesta Key, FL
07/12 – 07/18
$339/nighttotal: $2034 (6 )
Bayfront 2br Siesta Key Condo With Private Beach Access
2 2
house , Siesta Key
This Siesta Key condo provides direct private beach access and is a 10-minute walk from Crescent Beach, situated 11 miles from Sarasota Bradenton International Airport. This 1190 square foot vacation rental accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring a swimming pool, sauna, garden, and complimentary high-speed WiFi.
10 2 reviews
Siesta Key, FL
06/23 – 06/30
$317/nighttotal: $2219 (7 )
62 M² House ∙ 1 Bedroom ∙ 4 Guests
1 2
house , Siesta Key
This studio condo, Aloha Kai #63, offers direct access to Crescent Beach, ranked the #1 beach in the U.S., and is located within the gated Aloha Kai resort, just a short walk from dining and entertainment on Siesta Key. This 670 square foot unit accommodates up to 4 guests and features air conditioning, a full kitchen, a swimming pool, a spa, and complimentary community amenities including shuffleboard and ping pong.
Siesta Key, FL
07/18 – 07/22
$400/nighttotal: $1600 (4 )
Lulu's Key House Kemp Ridley 1/1 Downstairs
1 4
house , Siesta Key
LuLu's Key House offers a one-bedroom, one-bathroom rental home in Siesta Key, Florida, a 5-minute walk from Siesta Key Beach and 1.2 miles from Crescent Beach. This 640-square-foot Siesta Key vacation rental sleeps up to 7 guests and features a fully equipped kitchen, air conditioning, a private pool, free Wi-Fi, and parking; it's close to the John and Mable Ringling Museum of Art.
9.5 34 reviews
Siesta Key, FL
07/12 – 07/18
$508/nighttotal: $3048 (6 )
Minorga On The Gulf
1 2
house , Siesta Key
Minorga on the Gulf, a Siesta Key vacation home, is a 7-minute walk from Siesta Key Beach and within 6-10 miles of Sarasota attractions like the Ringling Museum and Sarasota Opera. This one-bathroom rental offers free private parking, a fully equipped kitchen with a dishwasher, Wi-Fi, satellite TV, in-unit laundry, and a private swimming pool, all within easy reach of Crescent Beach (1.5 miles) and Sarasota Bradenton International Airport (SRQ, less than 10 miles).
9.8 721 reviews
Siesta Key, FL
08/09 – 08/15
$307/nighttotal: $1842 (6 )
Siesta Key Island Rentals
1 4
house , Siesta Key
This beautiful home is located on Siesta Key, just a short distance from both Siesta Key Beach and Crescent Beach, offering easy access to the area's famous white sand and clear waters. It boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers. The property features a private swimming pool, a Jacuzzi, a terrace, and a garden, perfect for relaxing and enjoying the Florida sunshine. Guests can also enjoy a variety of activities, including swimming, diving, fishing, and tennis.
This Key West-style Victorian house on Siesta Key is located eight steps from Siesta Key Beach's path, a four-minute walk from restaurants, and 60 yards from Point of Rocks Reef, perfect for snorkeling. This eight-bedroom, six-bathroom vacation rental sleeps up to 16 guests (with an option for 30), boasting a private garden, fitness center, multiple fully equipped kitchens, a shared gas grill, hammocks, a deck, and complimentary snorkel gear.
Search Vacation Homes with a Pool in Siesta Key, FL
Dip in whenever you like, as these vacation homes in Siesta Key, FL come with a swimming pool on-site.
10 1 review
Siesta Key, FL
06/25 – 07/01
$319/nighttotal: $1914 (6 )
62 M² House ∙ 1 Bedroom ∙ 4 Guests
1 4
house , Siesta Key
This 670 sq ft, 1-bedroom, 1-bathroom villa offers direct access to Crescent Beach, ranked the #1 beach in the U.S., and is located within the family-friendly Aloha Kai resort on Siesta Key. This accommodation sleeps 4 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, spa, private sunroom, and complimentary beach toys and floats, with easy access to nearby restaurants and island exploration via the Siesta Key trolley.
9.5 2 reviews
Siesta Key, FL
09/04 – 09/08
$570/nighttotal: $2280 (4 )
Casita Morning Star - 6920
2 8
house , Siesta Key
Casita Morning Star is a Siesta Key vacation rental located a short walk from Crescent Beach and one mile from Turtle Beach, offering easy access to the John and Mable Ringling Museum of Art (11 miles away) and the Sarasota Opera (7.6 miles away). This 1,500-square-foot house features three bedrooms, three bathrooms, a private pool, spa, and can accommodate up to 19 guests, with a fully equipped kitchen, free Wi-Fi, and free parking.
Siesta Key, FL
07/14 – 08/11
$206/nighttotal: $5768 (28 )
1255-306 Stroll To Warm Bay Breezes
2 3
house , Siesta Key
This house is located in Sarasota, a 2-minute walk from Crescent Beach and 7.7 miles from Marina Jack Restaurant and Marina. This 2-bedroom, 2-bathroom vacation rental accommodates up to 11 guests and features an outdoor swimming pool, fitness center, tennis court, on-site parking, and complimentary Wi-Fi.
9.6 533 reviews
Siesta Key, FL
09/12 – 09/19
$216/nighttotal: $1512 (7 )
Drift Inn A, Heated Pool, Beach And Amenities, 2-3 Min Walk.
2 2
cottage , Siesta Key
This charming cottage is located just a short walk from the world-famous Siesta Key Beach, known for its soft, sugar-white sand. It consistently receives excellent ratings for location, cleanliness, and overall user experience. The cottage offers two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a private outdoor pool, a patio, a fully equipped kitchen, a peaceful garden, and free Wi-Fi, making it perfect for a relaxing and enjoyable vacation.
Best Siesta Key, FL houses with a kitchen
10 9 reviews
Siesta Key, FL
08/01 – 08/08
$223/nighttotal: $1561 (7 )
Vista Hermosa 3rd Floor - Elevator
1 5
house , Siesta Key
This Siesta Key condo rental is centrally located, less than a mile from Crescent Beach and Siesta Key Beach, and about 1.9 miles from Turtle Beach, offering easy access to shops and restaurants. The 1000-square-foot apartment sleeps six guests in three bedrooms and two bathrooms, boasting amenities such as a swimming pool, tennis court, free Wi-Fi, and barbecue grills.
Siesta Key, FL
07/06 – 07/13
$325/nighttotal: $2275 (7 )
Crescent Royale Condominiums 1b
2 3
house , Siesta Key
Crescent Royale 1B, a two-bedroom Siesta Key vacation rental, is located a three-minute walk from Siesta Key Beach and eleven miles from the John and Mable Ringling Museum of Art. This 1210-square-foot condo sleeps seven guests and boasts a private balcony with Gulf views, a private entrance, a pool, a fitness center, tennis courts, and on-site parking, plus complimentary Wi-Fi and massage services.
9.8 58 reviews
Siesta Key, FL
06/23 – 06/30
$416/nighttotal: $2912 (7 )
Siesta Villa Laughing Gull
2 2
house , Siesta Key
This Siesta Key vacation rental is just a short walk from Crescent Beach and a quick drive to Siesta Key Beach, offering easy access to the area's beautiful beaches. The property has excellent ratings for location, cleanliness, and overall guest experience. This three-bedroom house comfortably accommodates five guests and features a fully equipped kitchen, a relaxing garden and terrace, and a private pool. Enjoy amenities like air conditioning, free parking, and Wi-Fi, along with a convenient location near cultural attractions and the airport.
Siesta Key, FL
07/30 – 08/09
$343/nighttotal: $3430 (10 )
6415 Midnight Pass #608
2 5
house , Siesta Key
This Siesta Key vacation rental, 6415 Midnight Pass #608, is a 7-minute walk from Crescent Beach, 1.6 miles from Turtle Beach, and 1.8 miles from Siesta Key Beach, offering convenient access to Siesta Key's famed beaches and the John and Mable Ringling Museum of Art (11 miles away). This 1,290-square-foot condo boasts two bedrooms, two bathrooms, accommodates up to 11 guests, and features a private balcony, swimming pool, Jacuzzi, sauna, spa, fitness center, tennis court, and free Wi-Fi.
Frequently Asked Questions about villa rentals in Siesta Key, FL
What are the must-see attractions in and around Siesta Key, FL?
You absolutely have to visit Siesta Key Beach, famous for its soft, sugar-white sand. The Siesta Key Drum Circle, held every Sunday afternoon, is a vibrant local tradition. And for a taste of history, head to the Siesta Key Historical Society Museum.
What are the best villa rentals in Siesta Key, FL?
What types of wildlife can travelers expect to see in the area of Siesta Key, FL?
You might spot dolphins playing in the Gulf of Mexico, or see a variety of birds like pelicans and seagulls. Keep your eyes peeled for the occasional manatee in the waters around Siesta Key.
What are the best villa rentals with a pool in Siesta Key, FL?
The best time to visit Siesta Key is during the shoulder seasons, from April to May or September to October. The weather is still warm, but the crowds are smaller and the prices are lower.
What are the best villa rentals with a jacuzzi in Siesta Key, FL?
When is it easiest to book a villa rental in Siesta Key, FL?
You'll find the best deals on villa rentals during the off-season, from November to March. But if you're looking for a more lively atmosphere, you can still find great deals during the shoulder seasons.
What are the best villa rentals for families and kids in Siesta Key, FL?
What are the top hiking trails near Siesta Key, FL?
Siesta Key itself doesn't have many hiking trails, but you can find some great trails at nearby Myakka River State Park. The Upper Myakka Trail is a popular choice, offering stunning views of the river and surrounding wetlands.
What are the best pet friendly villa rentals in Siesta Key, FL?
What are the advantages of renting a house or a villa in Siesta Key, FL
Renting a villa offers more space and privacy compared to a hotel room. You can enjoy a home-cooked meal in the fully equipped kitchen and relax in the private pool without having to share with other guests.
What are the best villa rentals with parking in Siesta Key, FL?
Are there popular destinations near Siesta Key, FL?
You can easily take a day trip to Sarasota, which has a vibrant arts scene and a beautiful downtown area. St. Armands Circle is a popular shopping and dining destination, and the Ringling Museum is a must-see for art lovers.
Destinations nearby
Best Siesta Key, FL houses with air conditioning
Siesta Key, FL
07/14 – 08/11
$241/nighttotal: $6748 (28 )
1200-406 Embrace Spectacular Water Views
2 3
house , Siesta Key
This 2-bedroom, 2-bathroom house in Siesta Key offers spectacular water views and is a 4-minute walk from Crescent Beach, 7.8 miles from the Sarasota Opera, and 11 miles from The John and Mable Ringling Museum of Art. This accommodation for up to 11 guests features a full kitchen with microwave and oven, air conditioning, a swimming pool, fitness center, tennis court, on-site parking, and free Wi-Fi, with elevator access and a 10:00 AM check-out time.
Siesta Key, FL
07/02 – 07/05
$788/nighttotal: $2364 (3 )
New Listing - Dates Available Now! Beach & Village, Pool, Dock, Game Room!
1 2
house , Siesta Key
This Siesta Key house is located 5 minutes on foot from Siesta Key Beach and 10 miles from the John and Mable Ringling Museum of Art. This 1-bedroom, 1-bathroom home accommodates up to 4 guests and features a private dock, game room, fitness center, hot tub, and a kitchen with a fridge, microwave, and toaster, with free Wi-Fi available.
Siesta Key, FL
12/29 – 01/31
$460/nighttotal: $15180 (33 )
Walk To Siesta Key Beach, Heated Pool And Numerous Restaurants/bars/shops
2 2
house , Siesta Key
This villa is located in Siesta Key's South Village, a short walk from Siesta Key Beach and local dining and entertainment options. This 700 sq ft rental offers 2 bedrooms, 1 bathroom, sleeps 4 guests, and features a full kitchen, private backyard with a grill, and access to a heated community pool.
9.6 131 reviews
Siesta Key, FL
06/27 – 07/04
$340/nighttotal: $2380 (7 )
Crescent Arms Condominiums
2 2
house , Siesta Key
This Siesta Key vacation rental is located just a 3-minute walk from Crescent Beach and a short drive from Siesta Key Beach and Turtle Beach. It boasts excellent user, location, and cleanliness ratings. This 2-bedroom, 2-bathroom house offers 900 square feet of living space and can comfortably accommodate up to 5 guests. The home features a private beach area, a swimming pool, a terrace, a garden, and a spa, along with amenities like a fully equipped kitchen, free parking, and a 24-hour front desk.
Neighborhoods and points of interest in Siesta Key, FL
Best Siesta Key, FL villas and beach houses with jacuzzi
Siesta Key, FL
07/06 – 07/09
$2089/nighttotal: $6267 (3 )
Blue Lagoon
5 2
house , Siesta Key
This Siesta Key vacation rental, Blue Lagoon, is a six-minute walk from Crescent Beach and under a mile from Siesta Key Beach. The 3,600-square-foot house boasts one bedroom, five bathrooms, sleeps eighteen guests, and includes a private terrace, pool, and fully equipped kitchen.
Siesta Key, FL
12/25 – 01/02
$1325/nighttotal: $10600 (8 )
Walk To Siesta Key Beach And Village
1 5
house , Siesta Key
This 1-bedroom, 1-bathroom vacation home in Siesta Key is a 5-minute walk to Siesta Key Beach and Siesta Key Village, and 10 miles from The John and Mable Ringling Museum of Art. This pet-friendly rental accommodates up to 5 guests and offers a private patio, an outdoor pool, a hot tub, a fitness center, on-site dining, and a kitchen with an oven, microwave, and toaster.
Siesta Key, FL
09/12 – 09/19
$229/nighttotal: $1603 (7 )
113 M² Villa ∙ 2 Bedrooms ∙ 6 Guests
2 2
house , Siesta Key
This newly renovated villa is located in Siesta Key, a short stroll from Siesta Beach and adjacent to Horizons West Bayside Park, offering intercoastal waterway access and opportunities for dolphin and manatee viewing. This 1220 square foot villa accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with new appliances, vaulted ceilings, an open floor plan, a master suite with an oversized rain shower, a covered patio with outdoor grills, and access to two community pools.
Siesta Key, FL
12/25 – 01/02
$3608/nighttotal: $28864 (8 )
Siesta Beach 3 Min Walk To Village And Patio
4 5
house , Siesta Key
This 4-bedroom, 4-bathroom house rental in Siesta Key is located a 5-minute walk from Siesta Key Beach and a 3-minute walk to Siesta Village, with the John and Mable Ringling Museum of Art 10 miles away. This pet-friendly vacation home accommodates up to 12 guests and features a private hot tub, communal hot tub access, a children's playground, an outdoor pool, free Wi-Fi, a patio, and a full kitchen.