Longboat Key Florida Vacation Rentals, Hotels & Resorts

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We have partnered with a major provider of vacation rentals, 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 house

Waterside Home

Waterside Home: 3 BR + Den / 2 BA House on Longboat Key by RVA, Sleeps 6

Welcome to Waterside Home - a blue, stilted home on residential Norton Street. This quiet neighborhood on the northern-end of the island of Longboat Key is known for it's peaceful views and serenity. One visit and you will quickly discover why area r ....

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

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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 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

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

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 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

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

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 house

Cedars East #660

Cedars East #660: 2 BR / 2 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) 2 Bath(s) Vacation Rental - Sleeps 6
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 villa

Longboat Key 51

Spacious 3 bedroom 2.5 bath villa with private pool in Bay Isles of Longboat Key!

Nestled behind the gates of the prestigious Bay Isles of Longboat Key, this spacious 3 bedroom, 2.5 bath villa is a perfect seasonal getaway. Gorgeous views of the Habourside Course of the Longboat Key Club from the private swimming pool. This home o ....

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

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Longboat Key condo

Beach Castle Resort #4

Beach Castle #4: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to launch your kayak and cast a line, a chance to spot exotic birds that stop here for our mild temperatures and to view a picture-perf ....

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 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

Vacation Home

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

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Longboat Key townhome

539 Forest Way, Cedars Resort

Fun and Elegance In Longboat Key - Beautiful Townhome, Exceptional Reviews!

Dreaming of a vacation on the world-renowned powder white sands of beautiful Longboat Key? This is the perfect location at Cedars Tennis Resort - just steps away from the beach. An included benefit for our guests is that we provide full membership p ....

2 Bedroom(s) 3 Bath(s) Townhome - 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 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

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

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 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

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

Vacation Home

Relax. Unwind. Enjoy! Spectacular Beachfront Condo

Literally touching the sand, this spectacular condo is right on the beach! The views take your breath away the minute you walk through the front door. Feel the sun on your face, wind in your hair as you walk out onto the sand from the first-floor p ....

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

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 house

Longboat Key 24

Large Pet Friendly Canal Front Pool Home in Country Club Shores on Longboat Key!

Welcome to the popular Country Club Shores community on South Longboat Key. This 3 bedroom, 2 bath European-style, canal front home features streamlined furnishings, granite bathrooms with rain showers, updated kitchen with sleek stainless-steel appl ....

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

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Longboat Key house

Longboat Key 65

Tranquil paradise in Country Club Shores with walking distance to beach!

3 bedroom/2 bath Tranquil Paradise in Country Club Shores, Walk to Private Gulf Beach ​​​​​​​ Wake up each morning to water views of Sarasota Bay in this newly refurnished tropical romantic paradise situated on a deep water canal in sou ....

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