Search holiday homes in Longboat Key, FL from 100+ sites!
304 available villa offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
304 Villa rentals in Longboat Key, FL
Longboat Key, FL
07/15 – 07/24
$300/nighttotal: $2700 (9 )
Min To Img - Heated Pool - Putt Putt - Sleeps 6
1 6
house , South Bradenton
This house in South Bradenton is located a short distance from IMG Academy, offering convenient access for visitors. This 1250 sq ft vacation rental accommodates up to 10 guests with 2 bedrooms, 2 bathrooms, air conditioning, a fully equipped kitchen with a dishwasher, a heated swimming pool, and free Wi-Fi and parking.
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.
Longboat Key, FL
07/15 – 07/24
$319/nighttotal: $2871 (9 )
Min To Img - Heated Pool W Slide - Games-sleeps 5
1 6
house , South Bradenton
This vacation home in South Bradenton offers convenient access to IMG Academy, located just 0.5 miles away. This 1250 sq ft rental sleeps up to 9 guests and features 2 bathrooms, a fully equipped kitchen with a dishwasher and microwave, air conditioning, a heated swimming pool with a slide, gaming facilities, free WiFi, and on-site parking.
10 1 review
Longboat Key, FL
07/01 – 07/08
$507/nighttotal: $3549 (7 )
Beach Castle Resort #9
1 2
house , Longboat Key
Beach Castle Resort #9 in Longboat Key is a beachfront condo offering a 3-minute walk to Longboat Key Beach and is 14 miles from the John and Mable Ringling Museum of Art. This 1040 sq ft condo accommodates up to 11 guests and features 2 bathrooms, a full kitchen with a dishwasher, microwave, and fridge, air conditioning, a swimming pool, hot tub, fitness center, tennis court, and private parking.
Longboat Key, FL
07/15 – 07/24
$321/nighttotal: $2889 (9 )
Sun Stack At Runaway Bay 251 By Seabreeze Vacation
2 6
house , Bradenton Beach
This Bradenton Beach vacation rental is a 6-minute walk to Bradenton Beach and 12-13 miles from Sarasota International Convention Center and the John and Mable Ringling Museum of Art. This 1100 sq ft, 2-bedroom, 2-bathroom house accommodates up to 11 guests and offers a swimming pool, fitness center, tennis court, and private parking.
9.0 1 review
Longboat Key, FL
07/15 – 07/24
$248/nighttotal: $2232 (9 )
Shorewalk 202 - By Skyrun Anna Maria
1 6
house , Bradenton
This Anna Maria vacation home offers convenient access to cycling routes and attractions within the Bradenton region. This 1170 sq ft rental accommodates up to 11 guests with 2 bathrooms, a fully equipped kitchen, air conditioning, WiFi, a private pool, and outdoor play equipment.
10 3 reviews
Longboat Key, FL
08/22 – 09/05
$268/nighttotal: $3752 (14 )
Townhome, Tennis Resort, Pool, Tiki Bar, Beach
1 3
house , Longboat Key
This fully furnished, three-level townhouse is located in the Cedars East Resort district of Longboat Key, a short walk from the beach. This turnkey property offers resort-style living with a heated junior Olympic pool, on-site restaurant, tiki bar, and direct fishing dock access, accommodating up to 5 guests with 2 bedrooms, 2 bathrooms, and a private garage.
9.9 7 reviews
Longboat Key, FL
07/01 – 07/05
$588/nighttotal: $2352 (4 )
Grotto Pool House, 3 Bed, 2 Bath, Img 3 Miles, Ami
2 8
house , Bradenton
This Bradenton vacation home is conveniently located near IMG Academy (3 miles) and Anna Maria Island (AMI), with the Ringling Museum of Art approximately 9.4 miles away. This 1700-square-foot property boasts two bedrooms, two bathrooms, sleeps up to 15 guests, and features a private pool, outdoor fireplace, fully equipped kitchen, laundry service, and outdoor play equipment.
8.0 1 review
Longboat Key, FL
07/15 – 07/24
$251/nighttotal: $2259 (9 )
Popeyes Poole Paradise By Skyrun Anna Maria
2 6
house , Bradenton
This Anna Maria vacation home is located 1.7 miles from Palma Sola Causeway Park in Bradenton, with the Ringling Museum and Sarasota International Convention Center 11 miles away. This 1590 square foot house accommodates up to 11 guests with 2 bedrooms and 1 bathroom, featuring a private pool, spa, full kitchen with a dishwasher and microwave, air conditioning, WiFi, and free parking.
9.5 2 reviews
Longboat Key, FL
08/22 – 09/05
$281/nighttotal: $3934 (14 )
Silver Sands #244
1 3
house , Longboat Key
Silver Sands #244 is a beachfront vacation home in Longboat Key, offering direct access to Longboat Key Beach and located 15 miles from the John and Mable Ringling Museum of Art. This rental accommodates up to 7 guests and features a well-equipped kitchen, air conditioning, a swimming pool, a terrace, a balcony with sea views, and complimentary private parking.
Longboat Key, FL
07/01 – 07/05
$504/nighttotal: $2016 (4 )
Manatee Cottage
1 8
house , Bradenton
Manatee Cottage, a one-bedroom house in Bradenton, Florida, is located 4.1 miles from the Greens of Manatee Golf Club and 7.5 miles from Sarasota Bradenton International Airport. This three-bathroom vacation rental boasts a private pool, free parking, a fully equipped kitchen, free Wi-Fi, cable TV, and a washer, comfortably accommodating up to 15 guests and offering nearby cycling opportunities.
10 1 review
Longboat Key, FL
08/22 – 09/05
$175/nighttotal: $2450 (14 )
134 M² House ∙ 2 Bedrooms ∙ 7 Guests
2 3
house , Longboat Key
This 3-story townhome is located in the Cedars East district on the bay side of Longboat Key, offering convenient access to gulf beaches, shopping, and dining. This pet-friendly accommodation sleeps up to 7 guests and features 2 bedrooms, 2 bathrooms, a screened-in lanai, a full kitchen, air conditioning, a swimming pool, spa, fitness center, tennis courts, and parking within the Cedars East tennis resort.
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.
9.8 7 reviews
Longboat Key, FL
12/26 – 12/31
$397/nighttotal: $1985 (5 )
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too
1 2
cottage , Bradenton Beach
This renovated 700 sq ft cottage in Bradenton Beach offers 1 bedroom and 1 bathroom, accommodating up to 4 guests, and is located just steps from the Gulf beaches and a community pool, with Bridge Street Bistro and Anna Maria Oyster Bar within walking distance. Guests can enjoy amenities such as a full kitchen with a dishwasher, air conditioning, internet, and parking, with an option to book a second adjacent unit for larger groups.
Longboat Key, FL
08/20 – 08/21
$660/nightfor 1 night
Silver Sands #239
1 2
house , Longboat Key
Silver Sands #239 is a beachfront condo in Longboat Key, offering direct access to Longboat Key Beach, a 2-minute walk away, and situated 15 miles from the John and Mable Ringling Museum of Art. This rental property accommodates up to 11 guests across 2 bedrooms, featuring a fully equipped kitchen with a dishwasher and oven, complimentary private parking, free WiFi, and facilities for disabled guests, with opportunities for cycling nearby.
Longboat Key, FL
07/01 – 07/08
$282/nighttotal: $1974 (7 )
Gertie's Lime House
1 2
house , Holmes Beach
Gertie's Lime House is a one-bedroom vacation rental in Holmes Beach, Florida, a two-minute walk from the beach and 3.7 miles from the Anna Maria City Pier. This 680-square-foot home features a fully equipped kitchen, private pool, free Wi-Fi, and accommodates up to seven guests, offering easy access to Holmes Beach's cycling routes.
10 1 review
Longboat Key, FL
07/11 – 07/17
$278/nighttotal: $1668 (6 )
Luxury 2 Bed And 2bath Lakefront Condo Near Img And Anna Maria Island
2 3
house , Bradenton
This lakefront condo in Bradenton, Florida, is conveniently located near IMG Academy and Anna Maria Island, about 8.1 miles from the Ringling Museum of Art and 6.2 miles from Sarasota Bradenton International Airport (SRQ). This two-bedroom, two-bathroom vacation rental sleeps seven, boasting a private pool, Jacuzzi, tennis court, and fully equipped kitchen including a dishwasher and microwave; free Wi-Fi is also provided.
Best Longboat Key, FL houses with a kitchen
9.0 1 review
Longboat Key, FL
07/11 – 07/17
$448/nighttotal: $2688 (6 )
Silver Sands #242
1 3
house , Longboat Key
This beachfront condo, Silver Sands #242, offers direct access to Longboat Key Beach and is located 15 miles from the John and Mable Ringling Museum of Art and Sarasota International Convention Center, with Sarasota Bradenton International Airport also 15 miles away. This rental features a well-equipped kitchen with a dishwasher, microwave, and oven, air conditioning, a swimming pool, a terrace with sea views, a garden, fitness center, tennis court, and parking, accommodating up to 7 guests.
10 57 reviews
Longboat Key, FL
07/11 – 07/17
$211/nighttotal: $1266 (6 )
Pet-friendly Bradenton Home 1.5 Mi To Cortez Beach
2 3
house , Cortez
This pet-friendly vacation rental is located in Bradenton, Florida, just a short drive from the beach, the John and Mable Ringling Museum of Art, and the Greens of Manatee Golf Club. Guests have consistently rated this property excellent for its cleanliness, location, and overall experience. This comfortable two-bedroom home spans 1000 square feet and comfortably accommodates up to four guests. Enjoy amenities such as a fully equipped kitchen, air conditioning, private parking, a terrace, a garden, and a spa, perfect for a relaxing getaway.
9.8 10 reviews
Longboat Key, FL
07/15 – 07/24
$318/nighttotal: $2862 (9 )
108 Main Bradenton
3 6
house , Bradenton
This Bradenton house rental is conveniently located a 14-minute walk from Palma Sola Causeway Park, 11 miles from Sarasota Bradenton International Airport, and within 30 miles of attractions like Tropicana Field and The Dali Museum. This 2,000-square-foot home features three bedrooms, two bathrooms, sleeps up to 19 guests, and includes a fully equipped kitchen, in-unit laundry, and free Wi-Fi.
10 4 reviews
Longboat Key, FL
07/01 – 07/08
$218/nighttotal: $1526 (7 )
Peaceful Villa, 3.3 Mi To The Beach & Big Parking
2 2
house , Cortez
This non-smoking villa in Bradenton offers a seaside location, a 10-minute drive to Coquina Beach and a 20-minute drive to Bean Point Beach. This 740 sq ft house accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring air conditioning, Wi-Fi, a full kitchen, on-site parking, and a barbecue.
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
8.0 1 review
Longboat Key, FL
08/20 – 08/21
$547/nightfor 1 night
Silver Sands #253
1 2
house , Longboat Key
This Silver Sands #253 villa offers a direct beachfront location in Longboat Key, situated 15 miles from the John and Mable Ringling Museum of Art and 17 miles from the Sarasota International Convention Center. This residence accommodates up to 7 guests with 1 bathroom, featuring a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, fitness center, tennis court, and parking, along with complimentary private parking and free Wi-Fi.
9.0 1 review
Longboat Key, FL
08/22 – 09/05
$288/nighttotal: $4032 (14 )
Silver Sands #254
1 3
house , Longboat Key
Silver Sands #254 is a beachfront condo in Longboat Key, offering direct access to Longboat Key Beach and located 15 miles from Sarasota International Airport and the John and Mable Ringling Museum of Art. This accommodation features a private balcony, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, and parking, with facilities accessible for disabled guests and proximity to cycling activities.
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 2 reviews
Longboat Key, FL
07/11 – 07/17
$207/nighttotal: $1242 (6 )
10 Mi To Anna Maria Island: Bradenton Family Home
2 3
house , South Bradenton
This South Bradenton home, a 1,330-square-foot house, is conveniently located 1.1 miles from the Greens of Manatee Golf Club and a short drive from Anna Maria Island and Sarasota Bradenton International Airport. The two-bathroom residence sleeps nine guests and features a fully equipped kitchen with a dishwasher, in-unit laundry, free Wi-Fi, and a private entrance.
Best Longboat Key, FL villas and beach houses with jacuzzi
9.8 47 reviews
Longboat Key, FL
07/18 – 07/21
$2692/nighttotal: $8076 (3 )
260 M² House ∙ 6 Bedrooms ∙ 12 Guests
6 9
house , Bradenton Beach
This six-bedroom Bradenton Beach home on 11th Street South is steps from both the Gulf of Mexico and the bay, offering easy access to Bean Point and Bridge Street via the free trolley. This 2,800-square-foot vacation rental boasts a gourmet kitchen, private pool and jacuzzi, tennis court, and accommodates up to twelve guests with amenities including bikes, beach chairs, and smart TVs throughout.
Longboat Key, FL
07/11 – 07/17
$466/nighttotal: $2796 (6 )
The Beach Club At Anna Maria #6 And #7
1 3
house , Bradenton Beach
This beachfront vacation home in Bradenton Beach offers immediate access to the beach and is located 12-14 miles from Sarasota International Convention Center, John and Mable Ringling Museum of Art, and Sarasota Bradenton International Airport. This non-smoking rental accommodates up to 11 guests with 2 bathrooms, a fully equipped kitchen, air conditioning, complimentary Wi-Fi, and access to an on-site hot tub and fitness room, plus private parking.
Longboat Key, FL
07/01 – 07/05
$447/nighttotal: $1788 (4 )
211 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 8
house , Bradenton
This Bradenton house rental, located five minutes from downtown Bradenton and fifteen minutes from Anna Maria Island beaches, offers easy access to Bradenton's attractions and nearby Sarasota-Bradenton International Airport. The 2,260-square-foot property boasts three bedrooms, two bathrooms, sleeps eight guests, and includes a private pool, in-ground spa, fully equipped kitchen, and ample parking for cars, RVs, and boats.
Longboat Key, FL
07/01 – 07/08
$212/nighttotal: $1484 (7 )
Resort-style Condo 6 Mi To Bradenton Beach!
2 2
house , Bradenton
This resort-style condo in Bradenton is located 7.7 miles from the John and Mable Ringling Museum of Art and 5.6 miles from Sarasota Bradenton International Airport. This 1170 square foot apartment accommodates up to 11 guests with 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, hot tub, terrace, tennis court, and on-site parking.