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Longboat Key Vacation Rentals

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385 rentals in Longboat Key.
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Pet Friendly on Longboat Key
2 bedrooms
1 bathroom
Sleeps 6
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1 other traveler has booked this property
Beautiful Condo in Tropical Setting
2 bedrooms
2 bathrooms
Sleeps 4
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Las Hermanas/Starfish #3 Beach front Longboat Key
1 bedroom
1 bathroom
Sleeps 4
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23 other travelers have booked this property
Beachfront Studio #1 Longboat Key
0 bedrooms
1 bathroom
Sleeps 4
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27 other travelers have booked this property
Las Hermanas/Starfish #2 Beachfront Longboat Key
1 bedroom
1 bathroom
Sleeps 4
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19 other travelers have booked this property
Beachfront Unit 4, Cozy Getaway for two
0 bedrooms
1 bathroom
Sleeps 2
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46 other travelers have booked this property
Oceanfront 3 bedroom Condo on Longboat Key- Available in Summer ONLY
3 bedrooms
2 bathrooms
Sleeps 6
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Charming Beach House in Longboat Key/ pool/pet/dock
3 bedrooms
2 bathrooms
Sleeps 6
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6 other travelers have booked this property
~ The Beach on Longboat Key ~ * OCEAN FRONT DLX STUDIO *
0 bedrooms
1 bathroom
Sleeps 3
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20 other travelers have booked this property
~ BEACH FRONT APARTMENT ~
1 bedroom
1 bathroom
Sleeps 3
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38 other travelers have booked this property
Longboat Key Retreat
2 bedrooms
2 bathrooms
Sleeps 4
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8 other travelers have booked this property
Holiday Home Directly by Sea - Self Catering
2 bedrooms
2 bathrooms
Sleeps 6
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Lovely Tropical Staycation
2 bedrooms
3 bathrooms
Sleeps 6
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4 other travelers have booked this property
BeauTrully a Paridise for You Palm Trees
2 bedrooms
2 bathrooms
Sleeps 4
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55+ Community with pool and club house
2 bedrooms
2 bathrooms
Sleeps 6
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Beach front condo in Longboat Key
1 bedroom
1 bathroom
Sleeps 4
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2 other travelers have booked this property
Tropical Waterfront Home in Historic Village
2 bedrooms
2 bathrooms
Sleeps 5
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Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent
2 bedrooms
2 bathrooms
Sleeps 4
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1 other traveler has booked this property
2016 Renovated, Open Concept Resort Property: Pool, Tennis, Bikes, Beach Access
2 bedrooms
3 bathrooms
Sleeps 6
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Booking now for Spring 2021
2 bedrooms
2 bathrooms
Sleeps 4
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Relax In Paradise! Just Minutes From St. Armand Circle And Sarasota Attractions.
2 bedrooms
2 bathrooms
Sleeps 6
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Fun and Elegance In Longboat Key - Beautiful Townhome, Exceptional Reviews!
2 bedrooms
3 bathrooms
Sleeps 2
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Spectacular Beach View, Heated Pool, Tennis Courts
3 bedrooms
2 bathrooms
Sleeps 8
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Can't Get Closer to the Beach Without Getting Your Feet Wet!
2 bedrooms
2 bathrooms
Sleeps 4
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Direct Gulf front Condo on top floor, corner unit
1 bedroom
1 bathroom
Sleeps 6
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Pet Friendly Longboat Key Condo with View of Gulf
1 bedroom
1 bathroom
Sleeps 4
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Georgeous Condo Directly On The Beautiful Longboat Key!!!!
1 bedroom
1 bathroom
Sleeps 5
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Steps from Beach or Bay
3 bedrooms
4 bathrooms
Sleeps 6
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Hideaway Bay Exclusive Home – Platinum Waterfront Property
3 bedrooms
4 bathrooms
Sleeps 10
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Beachfront Family friendly where EVERY room has an ocean/beach view!
2 bedrooms
2 bathrooms
Sleeps 6
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A little piece of Paradise! Exceptional Reviews!
2 bedrooms
1 bathroom
Sleeps 4
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600 Feet to Beach - Pool/5 Restaurants/Conv.Store all close by
2 bedrooms
1 bathroom
Sleeps 4
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AFFORDABLE Beach Waterfront Condo Longboat Key, FL
2 bedrooms
1 bathroom
Sleeps 4
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Wonderful Bay Front Condo! See Manatees Right From Your Doorstep!
1 bedroom
1 bathroom
Sleeps 4
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Beach Escape to Longboat Key, Waterfront Sunrises/Sunsets, Gulf Beach Access
2 bedrooms
3 bathrooms
Sleeps 5
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Just refurbished luxurious two bedroom Beachplace condo with brand new kitchen!
2 bedrooms
2 bathrooms
Sleeps 4
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Rare Beach to Bay Condo
2 bedrooms
2 bathrooms
Sleeps 5
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ZILLI VILLA
2 bedrooms
2 bathrooms
Sleeps 10
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Short Term Rental Condo
2 bedrooms
2 bathrooms
Sleeps 4
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Best location on Longboat Key
1 bedroom
1 bathroom
Sleeps 5
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GULF FRONT 2 BR 2 BATHROOM CONDO
2 bedrooms
2 bathrooms
Sleeps 4
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Longboat Key Bayfront condo in Bay Isles
2 bedrooms
2 bathrooms
Sleeps 4
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3 other travelers have booked this property
GORGEOUS gated Multi-level LONGBOAT KEY HOME with DOCK ~ Near beach & private!
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful, CLEAN, turnkey 1 Bedroom Gulf coast condo. Ground floor. Beachfront.
1 bedroom
1 bathroom
Sleeps 3
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Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft
2 bedrooms
3 bathrooms
Sleeps 6
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Two Story Condo on the Gulf of Mexico
4 bedrooms
4 bathrooms
Sleeps 10
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1 other traveler has booked this property
Endless Summer: 3 BR / 3 BA House on Longboat Key by RVA, Sleeps 9
3 bedrooms
3 bathrooms
Sleeps 9
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Island Paradise: 3 BR + Den / 2 BA House on Longboat Key by RVA, Sleeps 8
3 bedrooms
2 bathrooms
Sleeps 8
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Beach Castle #12: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
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Cedars East #844: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6
2 bedrooms
3 bathrooms
Sleeps 6
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Beachfront condos and bayside villas – your vacation rental on Longboat Key
Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.
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Beachfront condos and bayside villas – your vacation rental on Longboat Key
Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.
Longboat Key - the upscale coastal vacation destination
This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.
Cultural treasures along Sarasota Bay
Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.
Waterfront dining
Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.
Visitor reviews aid vacation rental selection
You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.