Longboat Key Florida Vacation Rentals, Hotels & Resorts

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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

La Playa 202D

Picture this from your lanai or sundeck: Palm trees, beach, turqoise Gulf of Mexico...

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

Longboat Key 25

Enjoy breathtaking direct Gulf views from this 2nd floor condo at Longboat Terrace!

Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. En ....

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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Longboat Key house

Longboat Key 39

Charming and pet friendly 2 bedroom 2 bath vacation home in Longboat Key!

Charming and Pet Friendly vacation home. Located in the Long Beach Village, the Historic Community on Longboat Key, just 5 minutes to beach access or bay. This 2 bedroom, 2 bath single family vacation home is non-smoking, turnkey furnished and equipp ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
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 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 house

Endless Summer

Endless Summer: 3 BR / 3 BA House on Longboat Key by RVA, Sleeps 9

RVA presents Endless Summer on the exclusive island known for its tasteful luxury and secluded vacations. This three-bedroom, three-bathroom vacation home sits in the popular community of Country Club Shores and is directly on a canal that leads to t ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 9
Longboat Key, FL

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Longboat Key condo

Banyan Bay Club, LBK

Newly Renovated Open floor plan Ground Floor Condo

Feb and April available Walk to private Gulf Beach, Bay Dock and Shops 6 guests, King, two twins and a full size sleeper , 2 baths Beautiful newly renovated 2 bedroom ground floor condo with a view of the bay and walking distance to private gulf beac ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 6
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

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

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

Silver Sands #241

Silver Sands #241: 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 29

Luxury Rental home with private pool in Longboat Key available weekly!

Luxury Rental Home on Longboat Key. Newly built 4 bedroom, 4.5 bath single family home with a private attached guest suite. This home has many luxury details including the gourmet kitchen which is equipped with a wet bar and all WOLF appliances, SUBZ ....

4 Bedroom(s) 5 Bath(s) Vacation Rental
Longboat Key, FL

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Longboat Key apartment

Islander Club - On the beach

Islander Club - Waterfront- Amazing vacation 2bdr/2bathroom apartment

Wonderful 2 bedroom 2 bath apartment directly on the beach. This 3rd floor Islander Club condo is in perfect condition and has everything needed for an extended or winter stay. Master bedroom suite with king size bed has access to both balcony and o ....

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

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Longboat Key condo

Vacation Home

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1 Bedroom(s) 0 Bath(s) Condo - Sleeps 4
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

Silver Sands #254

Silver Sands #254: 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 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 condo

LaPlaya 101A

Step out to the beach from your screened lanai. Light and bright end unit.

Beachfront 2 Bedroom, 2 Bath 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 condo

Vacation Home

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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

Outrigger #8

Outrigger Resort #8: 1 BR / 1 BA Condo on Longboat Key by RVA, Sleeps 2

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. Relax by the heated com ....

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

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Longboat Key condo

Vacation Home

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

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Longboat Key house

Cedars East #862

Cedars East #862: 2 BR / 2.5 BA Townhome on Longboat Key by RVA, Sleeps 6

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 6
Longboat Key, FL

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Longboat Key condo

Vacation Home

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2 Bedroom(s) 2 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 house

Seaside Paradise

Seaside Paradise: 3 BR / 2.5 BA House on Longboat Key by RVA, Sleeps 6

RVA offers island living at Seaside Paradise. This charming 3-bedroom, 2.5-bathroom vacation home sits directly on the Gulf of Mexico waters and encompasses all that you would picture in a cozy beach cottage. Located directly on the white sandy beach ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Longboat Key, FL

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Longboat Key condo

LaPlaya 205D

Spectacular sunsets and sunbathing from your private Gulf-front lanai or sundeck.

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

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

Silver Sands #245S

Silver Sands #245S: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

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 ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 6
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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