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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.

Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Longboat Key, FL
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.
Silver Sands #239 - Longboat Key, FL
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.
Gertie's Lime House - Longboat Key, FL
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.
Luxury 2 Bed And 2bath Lakefront Condo Near Img And Anna Maria Island - Longboat Key, FL
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

Silver Sands #242 - Longboat Key, FL
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.
Pet-friendly Bradenton Home 1.5 Mi To Cortez Beach - Longboat Key, FL
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.
108 Main Bradenton - Longboat Key, FL
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.
Peaceful Villa, 3.3 Mi To The Beach & Big Parking - Longboat Key, FL
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

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Best Longboat Key, FL houses with air conditioning

Silver Sands #253 - Longboat Key, FL
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.
Silver Sands #254 - Longboat Key, FL
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.
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.
10 Mi To Anna Maria Island: Bradenton Family Home - Longboat Key, FL
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

260 M² House ∙ 6 Bedrooms ∙ 12 Guests - Longboat Key, FL
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.
The Beach Club At Anna Maria #6 And #7 - Longboat Key, FL
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.
211 M² House ∙ 3 Bedrooms ∙ 8 Guests - Longboat Key, FL
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.
Resort-style Condo 6 Mi To Bradenton Beach! - Longboat Key, FL
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.
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