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Longboat Key Romantic Vacation Rentals

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599 rentals in Longboat Key.
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One-of-a-kind home right on the gulf of Mexi
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2 bedrooms
2 bathrooms
Sleeps 8
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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
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2 bedrooms
2 bathrooms
Sleeps 10
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Luxury unit $149 2 days next Saturday& Sunday Private Island beach open
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Welcome back rate $175 Penthouse Superior decor private island beach open
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Beautiful Beach Views that will let you see 2020 in a whole new perspective
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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This unit is a wow $175 amazing decor private island beach open
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Unit #309 Enjoy great rates, just steps to the sandy beach!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Zilli Tower 503
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Outrigger 9 Gulf Front first level walk out to the beach Oct-Nov $195 per night
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Last minute CXL $169 2 day min inquire with in private island beach open
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Hidden Bay/Beach Paradise
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4 bedrooms
4 bathrooms
Sleeps 8
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Beautiful, newly renovated Gulf Front at Sand Cay with private beach on Longboat
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Zilli Ocean Front 101
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Upscale Beachplace Condo w/ Gulf & Bay Views *DEC 2020 OPEN*
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Breathtaking Beach Front Property Ground Floor Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Beautiful Updated Beachfront Condo on the Gulf of Mexico
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Amazing Panoramic Gulf View and The Most Beautiful Sunset In The World.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Beautiful Beachfront Condo With Balcony, View of the Gulf
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Penthouse Condo with Awesome Views !
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Love the Beach? Love tennis? The pool? Great family home with many amenities!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Unit #218 Sand Cay Beach Resort Gulf Front
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Beach is Open - Direct Beachfront Gulf of Mexico, Amazing Views
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Unit #208 Sand Cay Beach Resort Pool and Garden View
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Tranquil waterfront with heated pool, dock and walk to beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Beachcomber unit 303
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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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
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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
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Beach view. Year around Balcony Sunsets.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Panoramic beach View and amazing Sunset.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Updated Beach Style Condo at Sand Cay with Great Ocean Views.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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PRIVATE BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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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
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Bayfront Longboat Key House with Pool and Beach Access
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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Charming beach house on Longboat Key, with private pool&beach access, pool, pet
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Unit #120 Sand Cay Beach Resort Gulf View
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Longboat Key Beachfront - Beautifully Updated with Prime Location
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Longboat Vacation Home w/ gorgeous views- Walk to Beach
Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
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The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Pet Friendly Longboat Key Condo with View of Gulf
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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On the beach! Luxury gulf front condo, 2B/2B, pool, tennis, WiFi. Amazing view.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
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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
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Can't Get Closer to the Beach Without Getting Your Feet Wet!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Beach is Open - Beachfront Villa on Serene Gulf of Mexico
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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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
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Beach Castle #3: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
Condo/Apartment
2 bedrooms
2 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.