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Longboat Key, FL villas
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304 Villa rentals in Longboat Key, FL

Find the Best Holiday Houses with Swimming Pool in Longboat Key, FL

Having a pool at your Longboat Key, FL vacation home lets you enjoy a dip to complement a day by the water without extra planning.

150 M² House ∙ 3 Bedrooms ∙ 8 Guests - Longboat Key, FL
10 17 reviews
Longboat Key, FL
07/01 – 07/05
$496/nighttotal: $1984 (4 )

150 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 8
house , Bradenton
This Bradenton vacation home is conveniently located near Anna Maria Island's beaches, a short drive from Lakewood Ranch, Sarasota, and Tampa.
The 1600-square-foot property boasts three bedrooms, two bathrooms, sleeps eight guests, and features a private screened-in pool with solar heating, a fully stocked kitchen, high-speed Wi-Fi, and on-site beach equipment, cornhole, and putting green.
Villa 5 Mins Walk To Img Academy. Sleeps 6. Pool\ngated And 2 Free Parking Spots - Longboat Key, FL
10 4 reviews
Longboat Key, FL
07/15 – 07/24
$394/nighttotal: $3546 (9 )

Villa 5 Mins Walk To Img Academy. Sleeps 6. Pool\ngated And 2 Free Parking Spots

3 6
house , Bayshore Gardens
This modern villa in The Bollettieri Resort Villas, Bradenton, offers a prime location adjacent to IMG Academy, with easy access to Lido Beach (2 miles away), Coquina Beach (4 miles away), St. Armands Circle, and the Mall at University Town Center.
This ground-floor residence accommodates up to 6 guests, featuring 3 bedrooms and 3 bathrooms, air conditioning, a swimming pool, a hot tub, internet, and a kitchen equipped with a microwave oven and dishwasher.
Tiny Treasures Retreat - Longboat Key, FL
Longboat Key, FL
08/20 – 08/21
$144/nightfor 1 night

Tiny Treasures Retreat

2 2
house , Bayshore Gardens
Tiny Treasures Retreat in Bradenton is 4.5 miles from Sarasota International Convention Center and 4.9 miles from the John and Mable Ringling Museum of Art, with Sarasota Bradenton International Airport 3.1 miles away.
This 200 square foot rental accommodates up to 11 guests with 2 bedrooms, 1 bathroom, a kitchen, air conditioning, WiFi, parking, and a private swimming pool.
Outrigger Resort #7 - Longboat Key, FL
Longboat Key, FL
06/27 – 07/04
$394/nighttotal: $2758 (7 )

Outrigger Resort #7

1 2
house , Longboat Key
Outrigger Resort #7 is a beachfront condo in Longboat Key, offering direct access to Longboat Key Beach, just a 2-minute walk away, and is located 14 miles from the John and Mable Ringling Museum of Art. This accommodation sleeps up to 7 guests and features a well-equipped kitchen with a dishwasher, microwave, and oven, plus a balcony with sea views, air conditioning, a swimming pool, garden, fitness center, tennis court, and free private parking.

Best Longboat Key, FL houses with a kitchen

Blue Agave Villa By Beach Boutique Rentals - Longboat Key, FL
9.8 105 reviews
Longboat Key, FL
06/27 – 07/04
$333/nighttotal: $2331 (7 )

Blue Agave Villa By Beach Boutique Rentals

2 2
cottage , Holmes Beach
Frangipani Villa is a ground-level cottage located just steps from the beach path in Holmes Beach, offering easy access to the beach, shops, and restaurants. This charming cottage has received excellent ratings for location, cleanliness, and overall experience.
The cottage features a private porch with Adirondack chairs and a bistro table, perfect for enjoying the tropical surroundings. Guests can take advantage of beach chairs, towels, and umbrellas provided, along with a fully equipped kitchen, pet-friendly accommodations, and a tranquil garden with a fountain.
Silver Sands #234 - Longboat Key, FL
Longboat Key, FL
07/11 – 07/17
$350/nighttotal: $2100 (6 )

Silver Sands #234

1 3
house , Longboat Key
This beachfront villa in Longboat Key, Silver Sands #234, offers direct access to the sand and is 15 miles from the John and Mable Ringling Museum of Art.
This accommodation features a full kitchen, WiFi, air conditioning, a swimming pool, and parking, accommodating up to 7 guests.
Resort Style Condo By The Beach With Heated Pool At Runaway Bay - Longboat Key, FL
9.0 1 review
Longboat Key, FL
06/27 – 07/04
$250/nighttotal: $1750 (7 )

Resort Style Condo By The Beach With Heated Pool At Runaway Bay

1 2
house , Bradenton Beach
This Bradenton Beach condo, a short walk from Bradenton Beach and Cortez Beach, offers easy access to Anna Maria City Pier (5.3 miles away) and the John and Mable Ringling Museum of Art (14 miles away).
The 700-square-foot, one-bedroom, one-bathroom unit sleeps seven, features a fully equipped kitchen with dishwasher, and includes a private heated pool and tennis court on-site.
Catalina Comfort By Skyrun Anna Maria - Longboat Key, FL
9.5 4 reviews
Longboat Key, FL
07/01 – 07/05
$484/nighttotal: $1936 (4 )

Catalina Comfort By Skyrun Anna Maria

3 8
house , West Bradenton
Catalina Comfort, a three-bedroom West Bradenton home, is located 1.7 miles from Palma Sola Causeway Park and 11 miles from Sarasota Bradenton International Airport.
This 1890-square-foot vacation rental boasts a private pool, outdoor play equipment, and accommodates up to 15 guests, with easy access to nearby beaches and cycling routes.

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Best Longboat Key, FL houses with air conditioning

'Colorful Cottage' W/ Lanai: 7 Mi To Cortez Beach! - Longboat Key, FL
Longboat Key, FL
07/15 – 07/24
$234/nighttotal: $2106 (9 )

'Colorful Cottage' W/ Lanai: 7 Mi To Cortez Beach!

3 6
house , Bradenton
This Bradenton vacation rental is conveniently located just 7 miles from the beautiful beaches and 10 miles from the renowned Ringling Museum of Art.
This 3-bedroom, 2-bathroom house offers a comfortable stay for up to 6 guests, with amenities including a fully equipped kitchen, a private swimming pool, and a relaxing patio.
Family Nest Bradenton - Longboat Key, FL
10 10 reviews
Longboat Key, FL
08/20 – 08/22
$189/nighttotal: $378 (2 )

Family Nest Bradenton

1 2
house , Bayshore Gardens
This apartment in Bayshore Gardens is located in a quiet, family-friendly neighborhood, 12 minutes by car from Sarasota-Bradenton Airport and 5 minutes from IMG Academy, offering easy access to Gulf Coast beaches, Sarasota, and Tampa.
This 2-bedroom, 1-bathroom condo accommodates up to 5 guests and features air conditioning, internet, a kitchen with a fridge and microwave, and on-site parking.
Art And Design In Bradenton Villa - Longboat Key, FL
9.8 43 reviews
Longboat Key, FL
07/15 – 07/24
$359/nighttotal: $3231 (9 )

Art And Design In Bradenton Villa

1 6
house , Bayshore Gardens
This villa is part of the Bollettieri Resort, just a short drive from Bradenton Beach in Bayshore Gardens. It has received excellent ratings for its location, cleanliness, and overall user experience.
The 3-bedroom, 3-bathroom villa comfortably accommodates up to 6 guests. It features a modern design, smart home features, a swimming pool, and a garden. Guests have access to all the resort amenities, including daily cleaning service upon request, and a secure environment.
Sand Dollar Beach Side Villa - Longboat Key, FL
9.5 65 reviews
Longboat Key, FL
06/27 – 07/04
$324/nighttotal: $2268 (7 )

Sand Dollar Beach Side Villa

2 2
house , Holmes Beach
This Holmes Beach vacation rental is located just steps from Anna Maria Island, an 8-minute walk from the town center and 1.2 miles from Bradenton Beach. Guests consistently rate the location, cleanliness, and overall experience as excellent.
The 870-square-foot home has two bedrooms and comfortably accommodates six guests. Enjoy a private patio, a fully equipped kitchen, a swimming pool, and a spa, all while taking advantage of the free parking and Wi-Fi.

Best Longboat Key, FL villas and beach houses with jacuzzi

Modern-boho Bradenton Bungalow W/ Private Hot Tub! - Longboat Key, FL
9.8 4 reviews
Longboat Key, FL
08/20 – 08/22
$290/nighttotal: $580 (2 )

Modern-boho Bradenton Bungalow W/ Private Hot Tub!

3 2
house , Bradenton
This Bradenton bungalow is located 6.8 miles from Sarasota Bradenton International Airport and 8.7 miles from The John and Mable Ringling Museum of Art.
This 1000-square-foot house features three bedrooms, one bathroom, and accommodates up to 11 guests, boasting a private hot tub, fully equipped kitchen, and free Wi-Fi.
Water Front Private Pool Spa Home With Boat Docking Available Home - Longboat Key, FL
9.9 86 reviews
Longboat Key, FL
10/10 – 10/17
$394/nighttotal: $2758 (7 )

Water Front Private Pool Spa Home With Boat Docking Available Home

4 4
house , Bradenton
Located just a short drive from Anna Maria Sound and Palma Sola Botanical Park, this 4-bedroom, 2280-square-foot vacation home in Bradenton offers a tranquil ambiance with a private garden and excellent ratings for location, cleanliness, and user experience.
The spacious interior boasts a fully equipped kitchen, free WiFi, and laundry facilities, while outside, guests can enjoy a swimming pool, Jacuzzi, spa, and ample parking.
Beach Castle Resort #12 - Longboat Key, FL
9.0 1 review
Longboat Key, FL
10/10 – 10/17
$325/nighttotal: $2275 (7 )

Beach Castle Resort #12

1 4
house , Longboat Key
Beach Castle Resort #12 is a house located in Longboat Key, just a 4-minute walk from Longboat Key Beach and 14 miles from the John and Mable Ringling Museum of Art.
This 910 sq ft accommodation features 2 bedrooms and 2 bathrooms, accommodates up to 11 guests, and includes a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a patio, a balcony, and complimentary WiFi and parking.
108 Tiny #2 House Bradenton - Longboat Key, FL
Longboat Key, FL
07/11 – 07/17
$275/nighttotal: $1650 (6 )

108 Tiny #2 House Bradenton

2 3
house , Bradenton
This Bradenton tiny house, located 12 miles from the Sarasota International Convention Center and Ringling Museum of Art, offers convenient access to Sarasota and Bradenton attractions.
The 360-square-foot property features two bedrooms, one bathroom, and a fully equipped kitchen, comfortably accommodating up to seven guests and including amenities such as a private hot tub and free Wi-Fi.
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