0 Bedrooms for 1 Guest
Price $10 - $1000+

5,150 Longboat Key Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Longboat Key holiday rentals from 12 rental sites including HomeAway, Booking.com, TripAdvisor, and more, ranging from $25 to $2450 a night. 
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    Information about Longboat Key

    About Longboat Key

    Located on the Gulf side of Florida, Longboat Key offers a winter getaway for anyone trying to escape the harsh winters in the North.  The town is situated on a barrier island next to Sarasota and Manatee and is part of both counties.  Beaches line the entire western shoreline of Longboat Key, making it a perfect destination.

    Things to Do in Longboat Key

    Along the entire eleven mile western coast of Longboat Key is white sand and turquoise blue water.  It’s easy to find your own personal oasis.  Whitney Beach at the north end offers public parking.  There are eleven different access points along the western coast.  At the north end of Longboat Key, Beer Can Island can be reached in a shallow boat or walked to when the tide is low and offers a stunning location for parties, picnics, fishing, and swimming.  Besides the pristine beaches, the Longboat Key Center for the Arts is a mecca for artists and art-lovers.  It was established in 1952 and houses the Durante Gallery, Cultural Media Room and lots of classroom spaces.  Also the Longboat Key Education Center is a non-profit adult enrichment center, which offers a myriad of classes and recreational activities.  Whether you’re a shopaholic or just looking for a souvenir, there are a variety of places up and down Longboat Key for you.  Places, like St. Armands Circle or The Chart House, are sure to fulfill your shopping desires!  When you get hungry, be sure to try Lazy Lobster of Longboat and Mar Vista Dockside Restaurant.  Also the Blue Dolphin Café is exceptional.

    Longboat Key Day Trips

    If you find yourself wanting to leave Longboat Key for the day, then drive out to Sarasota or Bradenton.  Sarasota has so much to offer from amazing dining to shopping.  Be sure to see the Ringling Museum of Art and the Mote Marine Aquarium & Laboratory.  The Circus Arts Conservatory in Sarasota is home to world-class circus productions and student ones.  You can also take weekend trapeze or aerial classes.  Or take a walk through the Jungle Gardens and see what Florida was like in a forgotten era.  All car-lovers must check out the Sarasota Classic Car Museum, which is recognized as the second oldest, continuously run antique car museum in the country!  If you’re heading to Bradenton, take a walk along the Mantee River where the 1.5 miles of paved path becomes host to all kinds of festivals, art shows and concerts.

    Longboat Key Accommodations

    Staying in Longboat Key and the deals you can get will depend on the season, but regardless if it’s high or low season, this is the place to be.  There are all kinds of options to fit everyone’s needs, wants, and budget.  If you’re looking for a home, then Rolling Waves Beach Cottages or Sun ‘n’ Sea Cottages will be perfect.  Each company offers individual homes to make your stay more personal and unique.  If you want everything taken care of without the worry or fuss, then a resort is the way to go.  Longboat Key has phenomenal resorts to choose from, like Zota Beach Resort, Silver Sands Gulf Beach Resort, Longbeach Key Club Beach & Resort, and Sand Cay Beach Resort.

    Transportation in Longboat Key

    If you don’t plan on going off Longboat Key, then renting a bicycle is a perfect way to enjoy the sites and get around.  Or rent a scooter.  Otherwise, a car is the preferred mode of transportation, especially if you plan to visit Sarasota or Bradenton.

    Vacation Rentals in Longboat Key

    Find the best Longboat Key vacation rentals with Tripping.com. Choose from 5,233 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $2450 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 3,314 of homes in Longboat Key offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 2,910 rentals with pool or jacuzzi, or relax with the family in one of the 4,084 homes with cable TV.

    For all those dog lovers and cat lovers, Longboat Key offers 948 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 12 rental sites in Longboat Key where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 1,944 HomeAway rentals, 1,286 Booking.com short term rentals and 933 TripAdvisor vacation rentals.