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304 Villa rentals in Longboat Key, FL
Longboat Key, FL
07/01 – 07/08
$256/nighttotal: $1792 (7 )
Cozy Seashore
2 2
house , Bradenton
Cozy Seashore, a Bradenton vacation home, is conveniently located 6.2 miles from Sarasota Bradenton International Airport and within 8 miles of the Sarasota International Convention Center and the Ringling Museum of Art. This 1,170-square-foot rental boasts two bedrooms, two bathrooms, accommodates seven guests, and features a private balcony with lake views, a swimming pool, a fitness center, a tennis court, and free Wi-Fi.
9.7 152 reviews
Longboat Key, FL
07/20 – 07/22
$288/nighttotal: $576 (2 )
Tides Inn On The Bay Vacation Homes
1 1
house , Bradenton Beach
Tides Inn on the Bay Vacation Homes is ideally located steps away from Cortez Beach and a short walk from Bradenton Beach. It boasts excellent user, location, and cleanliness ratings. The house features one bathroom, a fully equipped kitchen, air conditioning, and a terrace or balcony. Guests can also enjoy a barbecue on the sun terrace, or go fishing nearby. Free Wi-Fi and private parking are also available.
9.6 74 reviews
Longboat Key, FL
07/15 – 07/24
$345/nighttotal: $3105 (9 )
New Private 3 Bedroom Pool Home Sleeps 10 Short Drive To Local Beaches Home
3 6
house , Bradenton
This Bradenton house is conveniently located just a short drive from Palma Sola Causeway Park, approximately 11 miles from the Ringling Museum of Art, and 30 miles from Tropicana Field. The property has consistently received excellent ratings for user experience, location, and cleanliness. The vacation rental comfortably sleeps 10 guests and features 3 bedrooms within its 1650 square feet of space. Enjoy amenities such as a private pool, free Wi-Fi, air conditioning, a fully equipped kitchen, and free parking.
Longboat Key, FL
07/15 – 07/24
$311/nighttotal: $2799 (9 )
Dans Florida Condos Ocean Oasis At Runaway Bay
2 6
house , Bradenton Beach
This vacation home in Bradenton Beach offers ocean views from a private patio and is a 9-minute walk to Bradenton Beach, with Anna Maria City Pier 5.3 miles away. This 1280 sq ft residence accommodates 11 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, garden, sauna, fitness center, and free private parking.
9.3 4 reviews
Longboat Key, FL
07/11 – 07/17
$203/nighttotal: $1218 (6 )
Resort-style Living Near Img, Anna Maria Island, And Bradenton Beach
2 3
house , Bradenton
This Bradenton vacation home is conveniently located approximately 8 miles from the Sarasota International Convention Center and a short drive from Anna Maria Island and Bradenton Beach. The 910-square-foot property features two bedrooms, two bathrooms, accommodates four guests, and includes a private balcony, swimming pool, Jacuzzi, and free Wi-Fi.
9.5 2 reviews
Longboat Key, FL
07/11 – 07/17
$288/nighttotal: $1728 (6 )
Ami Condo With Pool, Walk To Beach & Bridge St
1 3
house , Bradenton Beach
This Bradenton Beach condo is a short walk from Bradenton Beach and Bridge Street, placing you within 14 miles of the Ringling Museum of Art and 12 miles of Sarasota Bradenton International Airport. This one-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen with a dishwasher, in-unit laundry, free Wi-Fi, secure parking, and access to a community pool and playground.
10 2 reviews
Longboat Key, FL
07/11 – 07/17
$203/nighttotal: $1218 (6 )
Pelican Paradise Villa
1 3
house , Bradenton
Pelican Paradise Villa in Bradenton offers a convenient location, just 3 miles from the Greens of Manatee Golf Club, 7.8 miles from the Van Wezel Performing Arts Hall, and 6.2 miles from Sarasota Bradenton International Airport. This one-bedroom, two-bathroom vacation rental sleeps seven guests and boasts a fully equipped kitchen, private parking, a swimming pool, a fitness center, and in-unit laundry; enjoy nearby golfing, cultural attractions, and easy airport access.
9.3 3 reviews
Longboat Key, FL
07/01 – 07/05
$571/nighttotal: $2284 (4 )
Bloom Lagoon! Tropical Home With Heated Pool And Grill! Pet Friendly!
3 8
house , Bradenton
This Bradenton vacation home, near Palma Sola Causeway Park (1.6 miles) and within 30 miles of The Ringling Museum, The Dali Museum, and Tropicana Field, offers convenient access to major attractions. This 1,910-square-foot property boasts three bedrooms, two bathrooms, sleeps up to 15 guests, and features a heated pool, grill, and fully equipped kitchen with a dishwasher, plus free Wi-Fi.
10 1 review
Longboat Key, FL
07/01 – 07/05
$566/nighttotal: $2264 (4 )
Swaying Palms! Coastal Home With Amazing Pool Just A Short Drive From Anna Maria Island!
4 8
house , Bradenton
This Bradenton vacation home is conveniently located near Anna Maria Island's beaches, 6.2 miles from Sarasota Bradenton International Airport, and 3.3 miles from the Greens of Manatee Golf Club. This 2,050-square-foot house features four bedrooms, two bathrooms, sleeps up to 15 guests, and includes a private pool, Jacuzzi, spa, and fully equipped kitchen with modern appliances; free Wi-Fi and parking are also provided.
Longboat Key, FL
11/01 – 04/01
$311/nighttotal: $46961 (151 )
Kayaks, Bikes & Bay Access: Bradenton Escape!
3 2
house , Longboat Key
This 3-bedroom townhome is located in a waterfront community in Bradenton, offering convenient access to Anna Maria Island and local dining, with a private lanai featuring lake views. This pet-friendly rental accommodates up to 8 guests and includes a resort-style outdoor pool, hot tub, provided kayaks, two bicycles, tennis court, volleyball court, workout room, and an outdoor kitchen with a gas grill.
10 1 review
Longboat Key, FL
11/01 – 04/01
$793/nighttotal: $119743 (151 )
Luxury Beachfront House On Exclusive Longboat Key
4 2
house , Longboat Key
This beachfront Longboat Key home offers unparalleled Gulf of Mexico views and is minutes from Longboat Key's town center. The four-bedroom, two-bathroom house sleeps eight guests and boasts a modern interior, private beach access, and all the conveniences of home including a full kitchen with dishwasher, high-speed internet, and flat-screen TVs.
9.4 66 reviews
Longboat Key, FL
08/20 – 08/21
$211/nightfor 1 night
The "Grouper"
1 2
cottage , Cortez
This Cortez Sunny Shores cottage, located within 3 miles of H2O Watersportz, Anna Maria Sound, Bradenton Beach Marina, Bradenton Beach, and Fish Hole Adventure Golf, offers easy access to Anna Maria Island's beaches and attractions. This one-bedroom, one-bathroom vacation rental sleeps two guests and features a kitchenette with a refrigerator and microwave, air conditioning, a private patio, and free internet access; pets are welcome.
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.
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.
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.
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.
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
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.
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.
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.
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.
Frequently Asked Questions about villa rentals in Longboat Key, FL
What are the best activities in Longboat Key, FL?
Longboat Key is a great place to relax and enjoy the outdoors. You can spend your days swimming, sunbathing, kayaking, or paddleboarding. There are also plenty of opportunities for fishing, biking, and hiking. In the evenings, you can enjoy a delicious meal at one of the many waterfront restaurants.
What are the best villa rentals in Longboat Key, FL?
What are the advantages of renting a house or a villa in Longboat Key, FL
Renting a house or villa provides more space and privacy compared to a hotel. It often comes with amenities like a private pool, a fully equipped kitchen, and laundry facilities. You can also enjoy a more relaxed and home-like atmosphere.
What are the best villa rentals with a pool in Longboat Key, FL?
What food festivals or culinary events take place in and around Longboat Key, FL?
Longboat Key doesn't have its own food festival, but you can visit the Sarasota Seafood & Music Festival in nearby Sarasota. It features live music, seafood vendors, and family-friendly activities.
What are the best villa rentals with a jacuzzi in Longboat Key, FL?
What exclusive experiences are available when visiting Longboat Key, FL?
You can enjoy a private charter fishing trip, go on a sunset cruise, or take a guided kayak tour through the mangroves. For a truly luxurious experience, you can book a spa treatment at one of the many resorts on the island.
What are the best villa rentals for families and kids in Longboat Key, FL?
Which part of Longboat Key, FL would be ideal for a villa rental?
The south end of Longboat Key is a popular choice for villa rentals. It offers a quieter and more secluded atmosphere compared to the north end, which is closer to the main shopping and dining areas.
What are the best pet friendly villa rentals in Longboat Key, FL?
Best Longboat Key, FL houses with air conditioning
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.
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.
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.
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
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.
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.
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.
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.