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Longboat Key Vacation Rentals

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596 rentals in Longboat Key.
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Zilli Ocean Front 101

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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One-of-a-kind home right on the gulf of Mexi

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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ZILLI VILLA

Rental Home
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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Zilli Tower 503

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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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

Rental Home
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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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 12
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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 Updated Beachfront Condo on the Gulf of Mexico

Condo/Apartment
2 bedrooms
2 bathrooms
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 #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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Beach is Open - Direct Beachfront Gulf of Mexico, Amazing Views

Rental Home
2 bedrooms
2 bathrooms
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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Beach view. Year around Balcony Sunsets.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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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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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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Bayfront Longboat Key House with Pool and Beach Access

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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Panoramic beach View and amazing Sunset.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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Unit #218 Sand Cay Beach Resort Gulf Front

Condo/Apartment
2 bedrooms
2 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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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
Match: Sleeps
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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
Match: Sleeps
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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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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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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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Can't Get Closer to the Beach Without Getting Your Feet Wet!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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NO REGRETS! Bright elevated beautiful sunny home. Quick walk to beach and bay.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
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Top Lage am Kanal, Exklusive Innenausstattung, Pool, Strand nah

Rental Home
2 bedrooms
3 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
Match: Sleeps
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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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Frequently Asked Questions about Longboat Key





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.