498 Longboat Key Vacation Rentals & Short Term Rentals

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Compare Longboat Key vacation rentals from 10 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $50 to $6000 a night.

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

Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Longboat Key offers 498 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $231 a night, or a long-term rental for an average price of $4385 a month.

These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 447 of Longboat Key’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 370 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 439 cozy homes.

Traveling with pets? Choose from 85 pet-friendly rentals in Longboat Key for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

Search properties from 10 rental sites in Longboat Key where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 399 HomeAway rentals, 60 TripAdvisor short term rentals and 21 Booking.com vacation rentals.