Longboat Key Florida Vacation Rentals, Hotels & Resorts

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Rentals in Longboat Key, FL

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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Longboat Key, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Longboat Key condo

Sea Grape Inn #1-Beautiful BEACHFRONT property, steps from ocean.

Sea Grape Inn #1-Beautiful BEACHFRONT property, steps from ocean.

LOCATION, LOCATION, LOCATION! Tastefully updated condo directly on the Gulf of Mexico. Brand new tile floors, fresh paint throughout and stylish furnishings! Updated in 2018, this stunning 2 bedroom 2 bath condo boasts the prime location at the com ....

2 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat key condo

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2 Bedroom(s) 2 Bath(s) Condo
Longboat key, Fl

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Longboat Key condo

Silver Sands #258

Silver Sands #258: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beac ....

1 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Longboat Key, FL

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Longboat Key house

Longboat Key 35

Turnkey 3 bedroom 2 bath canal front home with boat lift on north end of Longboat Key!

Canal front home available on the Northern end of Longboat Key featuring an open floor plan, 3 bedrooms and 2 baths. This turnkey furnished home has access to sailboat water via Sarasota Bay. Centrally located, there's a wealth of amenities you can a ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Longboat Key, FL

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Longboat Key condo

Silver Sands #240

Silver Sands #240: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beac ....

1 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Longboat Key, FL

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Longboat key house

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6 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 16
Longboat key, FL

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Longboat Key condo

LaPlaya 201C

Breathtaking Gulf panorama from this corner unit with private stairway to the beach!

Beachfront 3 Bedroom, 2 Bath townhouse condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. LaPlaya Condominiums provides a private beach, sheltered pool with sundeck, and beachfront grills so you won’t miss ....

3 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key condo

The Shore #211

The Shore #211: 2 BR / 2 BA Condo on Longboat Key with RVA, Sleeps 4

RVA asks that you imagine the wonderful sunsets you can capture right from your own balcony at The Shore. Located directly on the shore of the Gulf of Mexico, you never have to travel far to enjoy the beach. Amenities include a heated pool, full serv ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
Longboat Key, FL

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Longboat Key condo

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1 Bedroom(s) 0 Bath(s) Condo
Longboat Key, FL

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Longboat Key condo

OCEAN FRONT SPECIAL FROM $99

*OCEAN FRONT SPECIAL FROM $99 * Sep - Dec

~ DIRECT BEACH FRONT CONDO ~ *OCEAN FRONT SPECIAL FROM $99 * Sep - Dec . The Beach on Longboat Key-Gulf Front Condo. This beautiful beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a c ....

1 Bedroom(s) 1 Bath(s) Condo - Sleeps 2
Longboat Key, FL

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Longboat Key condo

Turtle Crawl Inn Condo 401

180 Panoramic beach View and amazing Sunset.

GULF FRONT - ON THE SAND SPECTACULAR GULF VIEWS AND SUNSET VISTAS! The Turtle Crawl Inn encompass all that is hallmark to a Gulf front vacation. Many others on the island claim to be Gulf front, but actually include a view only from a certain vantag ....

1 Bedroom(s) 1 Bath(s) Condo - Sleeps 6
Longboat Key, FL

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Longboat Key condo

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2 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key house

The Beach on Longboat Key #220

The Beach on Longboat Key #220: HOTEL / 1 BA Resort on Longboat Key by RVA, Sleeps 2

RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium complex. New designs were created using South Beach flair, resulting in comfortably modern furnishings and decorations. Located dire ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 2
Longboat Key, FL

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Longboat Key condo

Club Longboat Key Condo #415

Spacious Club Longboat Key steps to the sand, private beach paradise! Pools, Gym, Tennis, Sunsets!

Looking for beachfront paradise ? It doesn't get better than Club Longboat . This spacious condo comfortably sleeps 6 within 2 separate bedrooms and a queen pullout sofa. This newly remodeled condo is beautifully updated with coastal feel , includi ....

3 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key condo

Beachplace 5-301

Beachplace 5-301: 2 BR/ 2 BA Condo on Longboat Key by RVA, Sleeps 4

RVA offers two-bedroom, two-bath unit located in building 5 features some of the most beautiful Gulf front and bay front views in all of Beachplace. Located directly between the Gulf of Mexico and Sarasota Bay, you can enjoy views of both from Unit 5 ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
Longboat Key, FL

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Longboat Key condo

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3 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key condo

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2 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key condo

Outrigger #7

Outrigger Resort #7: 1 BR / 1 BA Condo on Longboat Key by RVA, Sleeps 4

RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger Resort. The Outrigger grounds offer coin-operated laundry facilities, BBQ areas, and direct beach access. This unit is perfect ge ....

1 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Longboat Key, FL

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Longboat Key condo

Sand Cay Beach Resort #319

Beautiful, newly renovated Gulf Front #319 at Sand Cay Beach Resort on Longboat

Enjoy this beautiful, newly renovated Gulf-front sunny unit with vaulted ceilings and spectacular views with accommodation for up to 6. The open floor plan of living room, dining room, kitchen and den offer full views of the sparkling turquoise water ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 6
Longboat Key, FL

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Longboat Key condo

Villas of Avignon #104

Villas of Avignon #104: 3 BR / 3 BA Condo on Longboat Key by RVA, Sleeps 7

Resort Vacation Accommodations welcomes you to Villas of Avignon - where you can enjoy a secluded beach, heated community pool, private balconies, community hot tub and secure access. This eight unit complex is a deluxe vacation getaway located on ex ....

3 Bedroom(s) 3 Bath(s) Condo - Sleeps 7
Longboat Key, FL

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Longboat Key house

Cedars East #850

Cedars East #850: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 4

RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent beaches and tropical sunsets that are picture-perfect are daily occurrences. Guests enjoy an unforgettable Florida vacation in our s ....

2 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 4
Longboat Key, FL

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Longboat Key house

Longboat Key 33

Luxury 4 bedroom beach front home with breathtaking views on Longboat Key!

Fabulous New Construction on Longboat Key, sleek, modern luxury at its finest. This seasonal rental is located directly on the Gulf of Mexico. A luxurious four bedroom, five and a half bath beach front home with breathtaking views of the Gulf and upg ....

4 Bedroom(s) 6 Bath(s) Vacation Rental
Longboat Key, FL

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Longboat Key condo

Covet II Condominium

Beach Front, Covert II Condominium

Beach front - Full view of the Gulf of Mexico. Fully furnished and equiped. Includes Long Distance phone service within the US, 2 TV's with cable service, WiFi high speed internet, Screened Gulf front Lanai with table and chairs for a great dining ....

1 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Longboat Key, FL

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Longboat Key condo

LaPlaya 109A

Enjoy the balmy Gulf breezes in this corner end unit right on the beach!

Beachfront 2 Bedroom, 2Bath condo in the center of beautiful Longboat Key, an island just a few miles north of Sarasota. LaPlaya Condominiums provides a private beach, sheltered pool with sundeck, and beachfront grills so you won’t miss a minute ....

2 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key house

Island Paradise

Island Paradise: 3 BR + Den / 2 BA House on Longboat Key by RVA, Sleeps 8

RVA features a relaxing, serene home beautifully furnished and ready for you to enjoy Longboat Key's sunshine. This home offers privacy un-matched with a tropical caged pool area offering a heated hot tub and pool. This large home seems to never end, ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Longboat Key, FL

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Longboat Key condo

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2 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key condo

Beach Castle Resort #2

Beach Castle #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Between the azure blue of the Southwest Florida skies, and the turquoise Gulf of Mexico waters sits Beach Castle Resort on Longboat Key. A true beach-to-bay community, Beach Castle rests on one of the narrowest points of this prestigious island, allo ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 6
Longboat Key, FL

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Longboat Key condo

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2 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Longboat Key, FL

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Longboat Key condo

Longboat Key 45

Lovely updated condo at SeaPlace! Just steps from the beach!

Tropical Oasis at Seaplace on Longboat Key. This two bedroom, two bath condo is located on the Gulf of Mexico and is your perfect home away from home. Master bedroom features a King sized bed, hurricane shutters and a large walk-in closet. The guest ....

2 Bedroom(s) 2 Bath(s) Condo
Longboat Key, FL

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Longboat Key townhome

Longboat Key 68

Luxury beach front town home with amazing views of the Gulf from every level!

Modern Beachfront townhome available on Longboat Key! This 3 story home has been beautifully updated and comes turnkey furnished for your convenience. This 3 bedroom, 3 bath vacation home comfortably sleeps 6. The spacious master suite is on its own ....

3 Bedroom(s) 3 Bath(s) Townhome
Longboat Key, FL

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Find Affordable Longboat Key Hotels & Vacation Rentals

Plan your Longboat Key Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Longboat Key, Florida. Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Tampa Bay Area.


Vacation Rentals Nearby Tampa Bay Destinations

Find nearby vacation rentals and some of the Best Hotels with cheap rates in Longboat Key, FL for you visit to the area, all a short drive to Longboat Key, Florida. Spend quality time with your family and friends with cheap hotel rates you can afford, visit the nearby beaches for nightlife, entertainment and a wide variety of beach activities. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.

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