Villas and Holiday homes in Longboat Key, FL

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Longboat Key, FL holiday homes
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304 Villa rentals in Longboat Key, FL

Silver Sands #245 - Longboat Key, FL
Longboat Key, FL
10/10 – 17/10
£237/nighttotal: Â£1659 (7 )

Silver Sands #245

1 4
house, Longboat Key
This beachfront property, Silver Sands #245, offers direct access to Longboat Key Beach and is located 24 kilometres from the John and Mable Ringling Museum of Art.
This holiday home accommodates up to seven guests and features a well-equipped kitchen with a dishwasher, microwave, and fridge, air conditioning, a swimming pool, a terrace with sea views, a garden, a fitness centre, a tennis court, and private parking.
Gorgeous Remodel With Large Yard - Longboat Key, FL
Longboat Key, FL
01/07 – 05/07
£315/nighttotal: Â£1260 (4 )

Gorgeous Remodel With Large Yard

3 8
house, Bradenton
This remodelled holiday home in Bradenton is situated 9 kilometres from Sarasota Bradenton International Airport and within a 12.2-kilometre radius of the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art.
This property offers accommodation for up to 15 guests with 3 bedrooms, 2 bathrooms, a fully equipped kitchen, and complimentary Wi-Fi, and welcomes pets for an additional fee.
The Collection # 4 - Longboat Key, FL
9.2 5 reviews
Longboat Key, FL
01/07 – 08/07
£116/nighttotal: Â£812 (7 )

The Collection # 4

1 2
house, Bradenton
This holiday home in Bradenton is located 13.2 kilometres from Sarasota International Convention Centre and 13.8 kilometres from the John and Mable Ringling Museum of Art, with complimentary WiFi and private parking.
This property offers a fully equipped kitchen, air conditioning, one bedroom, one bathroom, and can accommodate up to three guests within its 48 square metre floor area, featuring an outdoor dining area.
Sunny Daze - Longboat Key, FL
10 2 reviews
Longboat Key, FL
01/07 – 05/07
£339/nighttotal: Â£1356 (4 )

Sunny Daze

3 8
house, Bradenton
Sunny Daze, a three-bedroom house in Bradenton, Florida, is conveniently located 10km from the Greens of Manatee Golf Club and 15km from Sarasota Bradenton International Airport.
This 201-square-metre property sleeps up to 15 guests and boasts a private pool, garden, free Wi-Fi, and parking; nearby attractions include the Ringling Museum of Art (18km).
211 M² House ∙ 3 Bedrooms ∙ 8 Guests - Longboat Key, FL
Longboat Key, FL
01/07 – 05/07
£334/nighttotal: Â£1336 (4 )

211 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 8
house, Bradenton
This three-bedroom Bradenton property is situated 8km from Bradenton's city centre, 24km from Anna Maria Island and Bradenton Beaches, and 7.4km from IMG Academy, offering easy access to local attractions and water activities.
The 210-square-metre house boasts a private pool, in-ground spa, ample parking (including for RVs and boats), a fully equipped kitchen, and sleeps eight guests; enjoy discounted rates with the 'Extended Stay Offer' for bookings of seven or more nights.
Near Beaches & Img Academy, Mins To Downtown - Longboat Key, FL
9.4 9 reviews
Longboat Key, FL
16/07 – 21/07
£135/nighttotal: Â£675 (5 )

Near Beaches & Img Academy, Mins To Downtown

2 2
house, South Bradenton
Bradenton Retreat is situated in South Bradenton, just 13 kilometres from the Ringling Museum of Art and less than 50 kilometres from both Tropicana Field and The Dali Museum, offering a peaceful escape from the hustle and bustle of city life. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house has two bedrooms and one bathroom, comfortably accommodating up to four guests. Guests can enjoy outdoor dining and relaxation on the private terrace, and the property is within easy reach of beaches, golf courses, and cultural attractions.
Downtown Getaway Casita - Longboat Key, FL
9.6 22 reviews
Longboat Key, FL
16/07 – 21/07
£122/nighttotal: Â£610 (5 )

Downtown Getaway Casita

2 2
house, Bradenton
This Bradenton casita is conveniently located 10-13 kilometres from Sarasota Bradenton International Airport, the Sarasota Convention Center, and the Ringling Museum of Art.
This one-bedroom property offers 84 square metres of space, sleeping up to seven guests and boasting two bathrooms, a private garden with barbecue facilities, free parking, and free Wi-Fi.
Tranquil Days - Longboat Key, FL
10 2 reviews
Longboat Key, FL
01/07 – 05/07
£238/nighttotal: Â£952 (4 )

Tranquil Days

3 8
house, West Bradenton
Tranquil Days, a three-bedroom house in West Bradenton, is situated approximately 14 kilometres from Sarasota Bradenton International Airport and 18 kilometres from The John and Mable Ringling Museum of Art.
This 147-square-metre property sleeps up to 15 guests and boasts a fully equipped kitchen, garden, free Wi-Fi, and convenient parking, with cycling opportunities nearby.
Family Fun House: Pool & Mini-golf - Longboat Key, FL
10 2 reviews
Longboat Key, FL
14/07 – 16/07
£281/nighttotal: Â£562 (2 )

Family Fun House: Pool & Mini-golf

1 4
house, Bayshore Gardens
This detached house in Bradenton offers convenient access to Bayshore Gardens, being 5 kilometres from the John and Mable Ringling Museum of Art and the Sarasota International Convention Centre, and 5 kilometres from Sarasota Bradenton International Airport.
This spacious property, spanning 158 square metres and accommodating up to 16 guests in 5 bedrooms, features air conditioning, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, on-site parking, an outdoor swimming pool, a private mini-golf course, and an outdoor seating area.
Outrigger Resort #6 - Longboat Key, FL
Longboat Key, FL
27/06 – 04/07
£367/nighttotal: Â£2569 (7 )

Outrigger Resort #6

1 2
house, Longboat Key
Outrigger Resort #6, a beachfront villa in Longboat Key, offers direct access to the beach and is located 22.5 kilometres from the John and Mable Ringling Museum of Art and 25.7 kilometres from the Sarasota International Convention Centre.
This non-smoking holiday home accommodates up to seven guests with one bathroom, a well-equipped kitchen including a dishwasher and microwave, and a private balcony providing sea views, whilst on-site facilities include a swimming pool, fitness centre, tennis court, and private parking, with cycling opportunities nearby.
3 Mi To Riverwalk Pet-friendly Home With Yard! - Longboat Key, FL
10 4 reviews
Longboat Key, FL
01/07 – 05/07
£166/nighttotal: Â£664 (4 )

3 Mi To Riverwalk Pet-friendly Home With Yard!

3 8
house, Palmetto
This pet-friendly holiday home in Palmetto, Florida, is located 5 km from the Palmetto Riverwalk and 15 km from Sarasota Bradenton International Airport, offering easy access to Sarasota's attractions including the Ringling Museum of Art.
The 139 square metre property boasts three bedrooms, two bathrooms, sleeps up to 15 guests, and includes a fully equipped kitchen, spa, private parking, air conditioning, Wi-Fi, and laundry facilities.
Beach Castle Resort #22 - Longboat Key, FL
Longboat Key, FL
10/10 – 17/10
£251/nighttotal: Â£1757 (7 )

Beach Castle Resort #22

1 4
house, Longboat Key
Beach Castle Resort #22 is a detached house located in Longboat Key, a mere 4-minute walk from the beach and 22.5 kilometres from the John and Mable Ringling Museum of Art.
This 85 square metre detached house accommodates up to 11 guests, offering two bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, a fitness centre, a tennis court, and free Wi-Fi and parking.

Best Longboat Key, FL villas and holiday homes with air conditioning

Direct Beachfront Gulf With Amazing Views - Longboat Key, FL
9.8 103 reviews
Longboat Key, FL
08/10 – 12/10
£529/nighttotal: Â£2116 (4 )

Direct Beachfront Gulf With Amazing Views

2 6
house, Longboat Key
This Longboat Key villa is located just a short walk from both Longboat Key Beaches and Cannons Marina, offering easy access to the area's attractions. It has received excellent user ratings, making it a popular choice for travellers. This two-bedroom, two-bathroom property spans 92 square metres and comfortably accommodates up to six guests. Enjoy a private pool, fireplace, barbecue grills, and a balcony with stunning views, perfect for relaxing and enjoying the Florida sunshine.
Beach Castle Resort #17 - Longboat Key, FL
9.2 4 reviews
Longboat Key, FL
14/07 – 16/07
£330/nighttotal: Â£660 (2 )

Beach Castle Resort #17

1 4
house, Longboat Key
This Longboat Key holiday home is situated a 4-minute walk from the beach, 22.5 kilometres from the Ringling Museum of Art, and 25.7 kilometres from Sarasota Bradenton International Airport.
This property offers 59 square metres of living space for up to 7 guests, featuring air conditioning, a fully equipped kitchen with a dishwasher, a private patio, and access to a communal swimming pool, hot tub, and fitness centre.
Silver Sands #246 - Longboat Key, FL
9.5 2 reviews
Longboat Key, FL
10/10 – 17/10
£237/nighttotal: Â£1659 (7 )

Silver Sands #246

1 4
house, Longboat Key
Silver Sands #246 is a beachfront villa in Longboat Key, just steps from Longboat Key Beach and approximately 24 kilometres from the John and Mable Ringling Museum of Art.
This villa accommodates up to seven guests and features direct beach access, a well-equipped kitchen with a dishwasher, microwave, and oven, complimentary WiFi, air conditioning, a swimming pool, a fitness centre, tennis courts, and private parking, with facilities for disabled guests also available.
Green Sea Foam - Longboat Key, FL
Longboat Key, FL
01/07 – 05/07
£249/nighttotal: Â£996 (4 )

Green Sea Foam

3 8
house, Bradenton
This Bradenton house, Green Sea Foam, is conveniently located under 15 kilometres from both the Sarasota International Convention Center and the Ringling Museum of Art, and just over 11 kilometres from Sarasota Bradenton International Airport (SRQ).
This spacious property boasts 179 square metres of floor area, offering three bedrooms, two bathrooms, and sleeping arrangements for up to 19 guests, complete with a fully equipped kitchen, patio, and fireplace.

Top-Rated Holiday Houses with a Jacuzzi in Longboat Key, FL

Returning to a private hot tub after a day outdoors adds a touch of luxury to these holiday homes in Longboat Key, FL.

Poolside Oasis Sleeps 8 Game Room Putt Putt - Longboat Key, FL
Longboat Key, FL
01/07 – 05/07
£572/nighttotal: Â£2288 (4 )

Poolside Oasis Sleeps 8 Game Room Putt Putt

3 8
house, Bradenton
This detached house in Bradenton offers a private pool, game room, and on-site putt-putt golf, located approximately 16 kilometres from the John and Mable Ringling Museum of Art and the Sarasota International Convention Centre, with Sarasota Bradenton International Airport 13 kilometres away.
The property spans 114 square metres, features 2 bathrooms, and accommodates up to 8 guests with a fully equipped kitchen, free Wi-Fi, and on-site parking.
191 M² House ∙ 4 Bedrooms ∙ 8 Guests - Longboat Key, FL
10 6 reviews
Longboat Key, FL
01/07 – 05/07
£370/nighttotal: Â£1480 (4 )

191 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 8
house, Bradenton
This Bradenton property, centrally located within a short drive (under 32km) of Sarasota-Bradenton International Airport and Anna Maria Island, offers easy access to beaches, Sarasota, Tampa, and Lakewood Ranch.
This four-bedroom, two-bathroom house boasts 190 square metres of living space, sleeping up to eight guests and featuring a private pool, spa, and fully equipped kitchen; high-speed Wi-Fi and a self check-in smart lock are also provided.
Blessed Ashore-ance - Longboat Key, FL
Longboat Key, FL
20/07 – 22/07
£249/nighttotal: Â£498 (2 )

Blessed Ashore-ance

1 1
house, Bradenton
This Blessed Ashore-ance property is located in Bradenton, approximately 12.9 kilometres from the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art, with Sarasota Bradenton International Airport 10 kilometres away.
This air-conditioned holiday home accommodates up to seven guests, featuring two bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, on-site parking, a children's playground, a hot tub, and an outdoor dining area, with cycling opportunities nearby.
Beach View Retreat - Longboat Key, FL
Longboat Key, FL
27/06 – 04/07
£735/nighttotal: Â£5145 (7 )

Beach View Retreat

1 2
house, Holmes Beach
Beach View Retreat, a beachfront property in Holmes Beach, Florida, is situated 5.5km from Anna Maria City Pier and 27km from The John and Mable Ringling Museum of Art.
This five-bedroom, four-bathroom holiday home boasts 269 square metres of floor space, accommodating up to 19 guests and offering a private pool, free Wi-Fi, and parking; nearby attractions include Holmes Beach, Anna Maria Island, and Bradenton Beach.

Frequently asked questions about villa rentals in Longboat Key, FL

Destinations nearby

Best Longboat Key, FL villas and holiday homes with a kitchen

Peaceful Villa, 3.3 Mi To The Beach & Big Parking - Longboat Key, FL
10 4 reviews
Longboat Key, FL
16/07 – 21/07
£185/nighttotal: Â£925 (5 )

Peaceful Villa, 3.3 Mi To The Beach & Big Parking

2 2
house, Cortez
This oceanfront villa in Bradenton offers direct access to Coquina Beach, just 1.6 kilometres away, and Bean Point Beach, 3.2 kilometres distant, placing it conveniently for water activities.
This 69 square metre holiday home, accommodating up to four guests, features two bedrooms, one bathroom, air conditioning, Wi-Fi, and a fully equipped kitchen, with on-site parking provided.
Manatee Cottage - Longboat Key, FL
Longboat Key, FL
01/07 – 05/07
£376/nighttotal: Â£1504 (4 )

Manatee Cottage

1 8
house, Bradenton
Manatee Cottage, a self-catering holiday home in Bradenton, Florida, is situated 6.4km from Sarasota Bradenton International Airport and 6.6km from the Greens of Manatee Golf Club.
This one-bedroom property boasts three bathrooms, sleeps up to 15 guests, includes a private pool, free parking, and features a fully equipped kitchen with a dishwasher, microwave, and fridge; free Wi-Fi and cable TV are also provided.
The Beach On Longboat Key #101 - Longboat Key, FL
Longboat Key, FL
08/10 – 12/10
£298/nighttotal: Â£1192 (4 )

The Beach On Longboat Key #101

1 6
house, Longboat Key
This beachfront abode in Longboat Key offers direct access to the sands of Longboat Key Beach, situated 17.7 kilometres from the John and Mable Ringling Museum of Art and 20.9 kilometres from Sarasota International Convention Centre.
This residence accommodates up to eleven guests with two bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a fitness centre, a tennis court, and parking, with disabled guest facilities available.
Paradise Palms - Chic Prime Spot W Pool - Longboat Key, FL
8.5 38 reviews
Longboat Key, FL
16/07 – 21/07
£203/nighttotal: Â£1015 (5 )

Paradise Palms - Chic Prime Spot W Pool

2 2
house, Bradenton
This Bradenton holiday home, Paradise Palms, enjoys a convenient location near Palma Sola Causeway Park, an 8-minute walk away, and is within easy driving distance (approximately 10km) of Anna Maria City Pier and 22km from The John and Mable Ringling Museum of Art.
The 88 square metre property offers two bedrooms, two bathrooms, sleeps eleven guests, and includes a private pool, garden, fully equipped kitchen with dishwasher, free Wi-Fi, and air conditioning.

Check Out Holiday Homes with a Pool in Longboat Key, FL

Take a dip whenever you fancy; these holiday homes near the water in Longboat Key, FL feature excellent on-site swimming pools for your enjoyment.

Ville Villekulla! Private Pool Home Near Historic Palmetto! - Longboat Key, FL
10 1 review
Longboat Key, FL
01/07 – 05/07
£379/nighttotal: Â£1516 (4 )

Ville Villekulla! Private Pool Home Near Historic Palmetto!

4 8
house, Palmetto
This Palmetto property, Ville Villekulla, is a private pool house conveniently located 13 kilometres from Sarasota Bradenton International Airport and within a 16-45 kilometre radius of attractions including The Ringling Museum, Tropicana Field, The Dali Museum, and John's Pass.
The 182 square metre self-catering villa boasts four bedrooms, two bathrooms, sleeps fifteen guests, and offers a fully equipped kitchen, private pool, free Wi-Fi, and on-site parking.
Resort Perks! Family Condo 3 Mi To Img Academy - Longboat Key, FL
Longboat Key, FL
16/07 – 21/07
£173/nighttotal: Â£865 (5 )

Resort Perks! Family Condo 3 Mi To Img Academy

2 2
apartment, Bradenton
This family condo in Bradenton offers convenient access, situated 11.4 kilometres from the John and Mable Ringling Museum of Art and Sarasota International Convention Centre, and 8 kilometres from Sarasota Bradenton International Airport, with private parking and complimentary WiFi.
Boasting 102 square metres of floor area, this residence accommodates up to 11 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, an outdoor swimming pool, and a garden for relaxation.
The Beach Club At Anna Maria #1 - Longboat Key, FL
Longboat Key, FL
14/07 – 16/07
£318/nighttotal: Â£636 (2 )

The Beach Club At Anna Maria #1

1 4
house, Bradenton Beach
This beachfront holiday home in Bradenton Beach offers direct access to the shore and is located just a few steps from the beach itself, approximately 19 kilometres from Sarasota Bradenton International Airport and 22 kilometres from the Sarasota International Convention Centre and the John and Mable Ringling Museum of Art.
This holiday cottage, accommodating up to seven guests, features a well-equipped kitchen with a dishwasher and microwave, air conditioning, complimentary WiFi, a swimming pool, a hot tub, and a fitness centre, with cycling opportunities available nearby.
192 M² House ∙ 3 Bedrooms ∙ 8 Guests - Longboat Key, FL
Longboat Key, FL
01/07 – 05/07
£333/nighttotal: Â£1332 (4 )

192 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 8
house, Bradenton
This Bradenton holiday home is situated 5 minutes from Bradenton's city centre, a 7-minute walk from Lewis Park, and 35 minutes' drive from Sarasota-Bradenton International Airport.
This three-bedroom, three-bathroom property boasts 191 square metres of living space, a private heated pool, ample outdoor entertaining areas, and sleeps up to eight guests, making it ideal for families or groups.

Search Holiday Homes by the Shore in Longboat Key, FL

Explore scenic shoreside paths from comfortable coastal holiday homes in Longboat Key, FL situated a short drive from beaches.

Villa 5 Mins Walk To Img Academy. Sleeps 6. Pool Gated And 2 Free Parking Spots - Longboat Key, FL
10 4 reviews
Longboat Key, FL
01/11 – 01/04
£264/nighttotal: Â£39864 (151 )

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

3 2
house, South Bradenton

Top Luxury Holiday Homes in Longboat Key, FL

These upscale holiday homes in Longboat Key, FL set a high standard, offering stylish interiors and premium features for a sophisticated stay.

Resort-style Condo 6 Mi To Bradenton Beach! - Longboat Key, FL
Longboat Key, FL
16/07 – 21/07
£174/nighttotal: Â£870 (5 )

Resort-style Condo 6 Mi To Bradenton Beach!

2 2
apartment, Bradenton

Browse Holiday Homes for Families in Longboat Key, FL

Choosing the right holiday home makes all the difference for a family trip to Longboat Key, FL, offering ample room.

Cozy 2bd+2 Ba Beach Cottage; Screened Florida Rm, Sleep Porch; Vr22-00059 - Longboat Key, FL
10 80 reviews
Longboat Key, FL
27/06 – 04/07
£273/nighttotal: Â£1911 (7 )

Cozy 2bd+2 Ba Beach Cottage; Screened Florida Rm, Sleep Porch; Vr22-00059

2 2
cottage, Sarasota
House ∙ 3 Bedrooms ∙ 7 Guests - Longboat Key, FL
10 4 reviews
Longboat Key, FL
01/07 – 08/07
£250/nighttotal: Â£1750 (7 )

House ∙ 3 Bedrooms ∙ 7 Guests

3 2
house, Bradenton
Villa ∙ 2 Bedrooms ∙ 8 Guests - Longboat Key, FL
10 1 review
Longboat Key, FL
27/06 – 04/07
£428/nighttotal: Â£2996 (7 )

Villa ∙ 2 Bedrooms ∙ 8 Guests

2 2
house, Longboat Key
House ∙ 2 Bedrooms ∙ 5 Guests - Longboat Key, FL
10 5 reviews
Longboat Key, FL
16/07 – 21/07
£218/nighttotal: Â£1090 (5 )

House ∙ 2 Bedrooms ∙ 5 Guests

2 2
house, Bradenton

Discover Pet-Friendly Holiday Homes in Longboat Key, FL

Your dog-friendly holiday home in Longboat Key, FL ensures easy beach access and handy outdoor taps for cleaning.

Sleeps 6 - Heated Pool & Games - 6 Min To Img - Longboat Key, FL
Longboat Key, FL
16/07 – 21/07
£266/nighttotal: Â£1330 (5 )

Sleeps 6 - Heated Pool & Games - 6 Min To Img

2 2
house, South Bradenton
Coastal Luxury 7mi To Anna Maria Private Cottage - Longboat Key, FL
10 8 reviews
Longboat Key, FL
16/09 – 19/09
£173/nighttotal: Â£519 (3 )

Coastal Luxury 7mi To Anna Maria Private Cottage

1 2
cottage, Bradenton
Coastal Cottage - Longboat Key, FL
9.0 1 review
Longboat Key, FL
16/07 – 21/07
£244/nighttotal: Â£1220 (5 )

Coastal Cottage

3 2
house, Bradenton
Amazing 3 Br Private Pool Home Near Anna Maria Island - 7th Heaven - Longboat Key, FL
9.3 3 reviews
Longboat Key, FL
01/07 – 08/07
£238/nighttotal: Â£1666 (7 )

Amazing 3 Br Private Pool Home Near Anna Maria Island - 7th Heaven

3 2
house, West Bradenton

Search Holiday Houses with Free Parking in Longboat Key, FL

On-site parking removes one more worry from your list, as these holiday homes in Longboat Key, FL include dedicated spaces for a stress-free arrival.

Spacious Home With Heated Pool 3 Miles From Img! - Longboat Key, FL
Longboat Key, FL
01/07 – 05/07
£363/nighttotal: Â£1452 (4 )

Spacious Home With Heated Pool 3 Miles From Img!

4 8
house, Bayshore Gardens
The Beach Club At Anna Maria #8 - Longboat Key, FL
10 1 review
Longboat Key, FL
14/07 – 16/07
£278/nighttotal: Â£556 (2 )

The Beach Club At Anna Maria #8

1 4
house, Bradenton Beach
La Playa #202d - Longboat Key, FL
Longboat Key, FL
01/07 – 08/07
£669/nighttotal: Â£4683 (7 )

La Playa #202d

1 2
house, Longboat Key
Silver Sands #238 - Longboat Key, FL
10 1 review
Longboat Key, FL
08/10 – 12/10
£415/nighttotal: Â£1660 (4 )

Silver Sands #238

1 6
house, Longboat Key
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