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Longboat Key Family & Kid Friendly Rentals

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637 rentals in Longboat Key.
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One-of-a-kind home right on the gulf of Mexi
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Living room with two sleeper sofas
Plenty of comfortable seating
See wildlife on the beach and dolphins and manatees in the Gulf
ZILLI VILLA
Rental Home
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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cancellation below MKT price had cancellation $199 Aug 13-15
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Few days on sale 5th floor Penthouse take a peek 100 + 5 star reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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LUXURY UPGRADED BEACHFRONT CONDO WITH BREATHTAKING VIEWS
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Unit is a wow take a peek Aug & Sept sale
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Gorgeous condo on the beautiful Longboat Key beach
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps, Kid friendly
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Zilli Tower 503
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Unit #309 great rates, 2 Bed/2 Bath, view of ocean, steps to the sandy beach.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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Hidden Bay/Beach Paradise
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Save time - get the best Longboat Key rentals sent straight to your email!
client said view crazy Aug sale arrive 19- leave 21 cancellation
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Zilli Ocean Front 101
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Breathtaking Beach Front Property Ground Floor Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Upscale Beachplace Condo Gulf & Bay Views *LAST MINUTE AUGUST SPECIAL 50% OFF*
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Beautiful Beachfront Condo With Balcony, View of the Gulf
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Incredible Panoramic Gulf View and The Most Beautiful Sunset.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Beautiful Updated Beachfront Condo on the Gulf of Mexico
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Love the beach? Tennis? Swimming? This great family friendly retreat has it all!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Kid friendly
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Direct Beachfront Gulf with Amazing Views
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Unit #218 Sand Cay Beach Resort Gulf Front
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Beachcomber unit 303
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Unit #208 Sand Cay Beach Resort Pool and Garden View
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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Tranquil canal-front home with heated pool, deep water dock & walk to beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Panoramic beach View and amazing Sunset.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Ground Floor 2 Beds 1 bath beach cottage short walk to beach on North end LBK
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Updated Beach Style Condo at Sand Cay with Great Ocean Views.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Unit #120 Sand Cay Beach Resort Gulf View
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Bayfront Longboat Key House with Pool and 3 min walk to the beach
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Beach view. Year around Balcony Sunsets.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Private Beach Cottage On The North End Of LBK. 2 Bedrooms 1 Bath On 2nd Floor
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Charming LBK canal home, walk to beach, Solar heated pool, boat/kids/pet welcome
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Longboat Key Beachfront - Beautifully Updated with Prime Location
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 6
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Luxurious Longboat Vacation Home w/ gorgeous views- Walk to Beach
Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, Kid friendly
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Unit #201 Sand Cay Beach Resort Gulf View
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Pet Friendly Longboat Key Condo with View of Gulf
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, Kid friendly
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Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Beachfront Villa on Serene Gulf of Mexico
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Beach Castle #23: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Inn on the Beach 3007
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Can't Get Closer to the Beach Without Getting Your Feet Wet!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Unit #211 Sand Cay Beach Resort Pool and Garden View
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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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.