Compare cheap villa rentals in Siesta Key, FL from 100+ sites!

1858 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Siesta Key, FL villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

1858 Villa rentals in Siesta Key, FL

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.

62 M² House ∙ 1 Bedroom ∙ 4 Guests - Siesta Key, FL
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.
Casita Morning Star - 6920 - Siesta Key, FL
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.
1255-306 Stroll To Warm Bay Breezes - Siesta Key, FL
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.
Drift Inn A, Heated Pool, Beach And Amenities, 2-3 Min Walk. - Siesta Key, FL
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

Vista Hermosa 3rd Floor - Elevator - Siesta Key, FL
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.
Crescent Royale Condominiums 1b - Siesta Key, FL
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.
Siesta Villa Laughing Gull - Siesta Key, FL
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.
6415 Midnight Pass #608 - Siesta Key, FL
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

Destinations nearby

Best Siesta Key, FL houses with air conditioning

1200-406 Embrace Spectacular Water Views - Siesta Key, FL
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.
New Listing - Dates Available Now! Beach & Village, Pool, Dock, Game Room! - Siesta Key, FL
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.
Walk To Siesta Key Beach, Heated Pool And Numerous Restaurants/bars/shops - Siesta Key, FL
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.
Crescent Arms Condominiums - Siesta Key, FL
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

Blue Lagoon - Siesta Key, FL
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.
Walk To Siesta Key Beach And Village - Siesta Key, FL
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.
113 M² Villa ∙ 2 Bedrooms ∙ 6 Guests - Siesta Key, FL
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 Beach 3 Min Walk To Village And Patio - Siesta Key, FL
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.
©2026 cozycozy.com