Discover the magic of Longboat Key, a captivating location in beautiful Florida. Whether you are a family, a group, or a solo traveller, you can find your ideal Longboat Key villa within our selection.

Planning a vacation with friends or family? You definitely want to start your search with a villa. Look to elevate your experience with villas featuring expansive terraces that invite the outdoors in. Enjoy the panoramic views of Longboat Key from your private terrace, complemented by fully-equipped kitchens and high-end amenities that promise a luxurious stay tailored to families and groups seeking an extraordinary getaway.

Whether you are after a getaway for the perfect family holiday or a quite romantic retreat, our selection of Longboat Key villas should help you find what you are after. With prices starting from $68 and going up to $5,670, our selection of Longboat Key villas have something for everyone.

Top Amenities: Internet / Wifi, Kitchen or Kitchenette, Air conditioner, Pool and TV

Points of Interest: St. Pete Pier™, Mote Marine Laboratory & Aquarium, The John and Mable Ringling Museum of Art, Sunken Gardens and Imagine Museum: Contemporary glass art

Unlock the secrets of Longboat Key by booking your villa now. Experience the diverse culture and scenery of Florida.

Top villas in Longboat Key

Beachfront
Property view
4.0
Good(4 Reviews)
Sunny Gulf Coast Villa Direct Beach and Pool Access
Villa
 in Longboat Key
Pool · Kitchen or Kitchenette · Air conditioner

Experience the best of Longboat Key with this Villa available for $386. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beach towels, snorkeling
4.0
Good(2 Reviews)
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Villa
 in Longboat Key
Pool · Kitchen or Kitchenette · Air conditioner

Experience the best of Longboat Key with this Villa available for $244. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Interior
5.0
Outstanding(109 Reviews)
Major Upgrades beach Open Jan 11-18- 1 of a kind home right on the beach open
Villa
 in Longboat Key
8 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette
Top rated

This Villa in Longboat Key, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Beach towels, snorkeling
4.0
Good(2 Reviews)
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Villa
 in Longboat Key
2 guests
Pool · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at Sunny Gulf Coast Villa: Direct Beach & Pool Access, our elegant Villa in Longboat Key. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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On the beach, sun loungers, beach towels
4.9
Outstanding(87 Reviews)
Direct Beachfront Gulf with Amazing Views
Villa
 in Longboat Key
6 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Soak up the beauty of Longboat Key in our Villa, Direct Beachfront Gulf with Amazing Views . With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.

$$$$
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Beach nearby, sun loungers
4.9
Outstanding(45 Reviews)
A perfect location, lakeside home ,private heated pool, very close to beaches
Villa
 in Bradenton
6 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette

Looking for a memorable stay in Longboat Key? Our Villa might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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On the beach
4.6
Outstanding(25 Reviews)
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Villa
 in Longboat Key
6 guests · 2 bedrooms · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner

When traveling to Longboat Key, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $267 per night.

$$$$
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Beach nearby, sun loungers, beach towels
5.0
Outstanding(11 Reviews)
Spectacular 5-star Condo. Walk to beach & restaurants. Just remodeled.
Villa
 in Longboat Key
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner

Soak up the beauty of Longboat Key in our Villa, Spectacular 5-star Condo. Walk to beach & restaurants. Just remodeled.. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
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Beach nearby
4.7
Outstanding(11 Reviews)
Beach Castle Resort #27 by RVA
Villa
 in Longboat Key
8 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Longboat Key with a stay at Beach Castle Resort #27 by RVA, a top rated Villa with amenities such as Air conditioner, Dishwasher and Laundry, and more.

$$$$
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Outdoor pool, a heated pool
4.7
Outstanding(10 Reviews)
Longboat Key canal front Villa with a private dock.Great Family retreat.
Villa
 in Longboat Key
6 guests · 2 bedrooms · 3 baths
Garden · Pool · Pets allowed

Looking to create some memories in Longboat Key? Look no further than our Villa, Longboat Key canal front Villa with a private dock.Great Family retreat.. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beach nearby, sun loungers, beach towels
5.0
Outstanding(7 Reviews)
Updated Villa Condo -Steps to Beautiful White-Sand Beach
Villa
 in Longboat Key
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Longboat Key? Look no further than our Villa, Updated Villa Condo -Steps to Beautiful White-Sand Beach. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Outdoor pool
5.0
Outstanding(2 Reviews)
Villa next to IMG Academy. Sleeps 6. Pool. Gated and 2 free parking spots
Villa
 in Bradenton
6 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Longboat Key? Look no further than our Villa, Villa next to IMG Academy. Sleeps 6. Pool. Gated and 2 free parking spots. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Villas with internet & wifi in Longboat Key

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Pool
5.0
Outstanding(2 Reviews)
Villa next to IMG Academy. Pool. Sleeps 8. Gated and 2 free parking spots.
Villa
 in Bradenton
8 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner

This Villa in Longboat Key, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Sun loungers, beach towels
5.0
Outstanding(2 Reviews)
New Listing: Sun, Sea Breeze & Seagulls – The Ultimate Beach Location
Villa
 in Longboat Key
4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Longboat Key, at $257 per night for your next great vacation.

$$$$
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Private kitchen
Longboat Key 1st Floor Condo Resort Style Recreation-Beach Across the Street
Villa
 in Longboat Key
2 guests · 1 bedroom · 1 bath
Pets allowed · Air conditioner · Internet / Wifi

Discover the beauty of Longboat Key with a stay at Longboat Key 1st Floor Condo Resort Style Recreation-Beach Across the Street, a top rated Villa with amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Aerial view
Longboat Key North Shore, BEAUTIFUL PRIVATE BEACH 1.5 blocks away.
Villa
 in Longboat Key
4 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

This Villa for $248 in Longboat Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Beach
Waterfront Getaway Island Villa at Longboat Key
Villa
 in Longboat Key
4 guests · 1 bedroom · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Longboat Key, at $187 per night for your next great vacation.

$$$$
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Beach
Longboat Key home rental w/ PRIVATE Pool & 1 minute to private beach access!
Villa
 in Longboat Key
6 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Villa in Longboat Key has everything you need for a rejuvenating stay. Treat yourself to Longboat Key home rental w/ PRIVATE Pool & 1 minute to private beach access! 's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
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Marina
5.0
Outstanding(1 Review)
One-of-a-Kind Villa in Beach Castle Direct Views of the Bay, Walk to Beach
Villa
 in Longboat Key
8 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Longboat Key with a stay at One-of-a-Kind Villa in Beach Castle Direct Views of the Bay, Walk to Beach, a top rated Villa with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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