Winter Vacation Rentals & Cabin Rentals in Longboat Key, FL

Compare 14,496 available beachfront holiday vacation home properties, starts from $28

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ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in Longboat Key, FL: Top Deals

Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
4.6 (12 reviews)
Gulf and beach view apartment
Apartment
$158 /night
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Beach Castle #18
Beach Castle #18
Beach Castle #18
Beach Castle #18
Beach Castle #18
Beach Castle #18
Beach Castle #18
Beach Castle #18
4.0 (6 reviews)
Beach Castle #18
Castle
$120 /night
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1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
1/1 Bed & Bath Lux Condos
4.5 (15 reviews)
1/1 Bed & Bath Lux Condos
Hotel
$68 /night
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Sea Club I
Sea Club I
Sea Club I
Sea Club I
Sea Club I
Sea Club I
Sea Club I
4.3 (52 reviews)
Sea Club I
Hotel
$150 /night
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Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
4.1 (99 reviews)
Turtle Crawl Inn - Longboat Key
Hotel
$230 /night
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Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
5.0 (3 reviews)
Luxury Beachfront Villa with Gulf Views
Villa
$250 /night
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The Beach on Longboat Key
The Beach on Longboat Key
The Beach on Longboat Key
The Beach on Longboat Key
The Beach on Longboat Key
The Beach on Longboat Key
The Beach on Longboat Key
4.9 (12 reviews)
The Beach on Longboat Key
Hotel
$169 /night
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2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
4.5 (10 reviews)
2 BR Longboat Key Gulf Front Beach Villa
House · 6 Guests · 2 Bedrooms
$300 /night*
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Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
4.7 (10 reviews)
Amazing Panoramic Beach View and The Most Beautiful Sunset In The World
Hotel
$170 /night
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Similar Inspirational Vacation Rental Destinations

Which Price Range Is Considered As A Good Deal in Longboat Key, FL Area?
Vacation Condo & House Rental Price Information in Longboat Key, FL
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The graph shows the percentages of vacation homes in each price bucket. Longboat Key has the largest percentage (27.53%) of homes in $100 - $150 price range.
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What activities, communities and places of interest are available for snowbirds in Longboat Key, FL?
Activities, Communities and Places of Interest for Snowbirds in Longboat Key, FL
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Longboat Key is a great place for snowbirds as it has an array of activities that appeal to seniors. The city is conveniently located near numerous healthcare facilities such as Manatee Memorial Hospital and Blake Medical Center, making medical care easily accessible. In addition, the city offers plenty of outdoor activities such as fishing and kayaking. Furthermore, there are many shopping centers including St. Armands Circle which is renowned for its unique stores and restaurants.

  • Sarasota Jungle Gardens

    Sarasota Jungle Gardens is a 10-acre botanical garden with a variety of exotic plants, birds, reptiles, and animals. It features a petting zoo, aviary, and nature trails, perfect for seniors looking for a leisurely activity.

  • Mote Marine Laboratory & Aquarium

    Mote Marine Laboratory & Aquarium is a non-profit aquarium dedicated to research and education. It features more than 100 species of marine life, including sharks, sea turtles, and dolphins. Seniors can also take part in interactive programs like touch tanks and behind-the-scenes tours.

  • Selby Botanical Gardens

    Selby Botanical Gardens is a 13-acre urban oasis with gardens, ponds, and trails. It features an amphitheater, butterfly garden, and Japanese garden, perfect for snowbirds who enjoy spending time outdoors.

How Many Rental Accommodations Are Pets Friendly in Longboat Key, FL?
Percentage of Pet Friendly Rental Properties in Longboat Key, FL
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22.41% of vacation homes in Longboat Key are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Where Should We Visit in Longboat Key, FL Area?
Destinations To Visit During the Winter in Longboat Key, FL
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When you have only limited times to spend in Longboat Key, FL, we highly recommend you to visit those famous places:

Which Airports Should I Choose To Get To Longboat Key, FL?
Airports Options in Longboat Key, FL
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Here are the airports that located near Longboat Key:

Other Vacation Rentals Ideas

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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