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

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

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

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 house

Cedars East #509

Cedars East #509: 2 BR / 2.5 BA Townhouse 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 condo

Silver Sands #255

Silver Sands #255: 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 #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

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

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

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 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

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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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

The Beach on Longboat Key #101

The Beach on Longboat Key #101: 1 BR + Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6

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

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Longboat Key condo

Players Club Condo

Beautiful Beachfront Condo Longboat Key

Spacious, sunny, recently updated 2 bedroom/ 2 bathroom apartment, in the exclusive Players Club Condominium, located directly on the private, powdery-white Longboat Key Beach. The 4th floor unit has a spectacular view stretching from the condo’s ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
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 cottage

Spanish Main Yacht Club

55+ Community With Pool, clubhouse and deeded beach

Our villa has 2 bedrooms, 2 bathrooms, living/ dining room, full kitchen and two bonus rooms. Spanish Main Yacht Club is on the bay which comes into the center of the community via a beautiful marina - manatees and dolphins often stop by! .Our unit i ....

2 Bedroom(s) 2 Bath(s) Cottage - 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

Vacation Home

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2 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 condo

Beach Castle Resort #11

Beach Castle #11: 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

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 townhome

CEDARS EAST 840

Pet Friendly Townhome in Popular Cedars Resort

$1,000/WEEK SUMMER / FALL RENTAL RATE (plus tax and fees) - BAYSIDE TOWNHOUSE in Cedars East Tennis Resort. Spacious 2-bedroom, 2-1/2 bath turnkey furnished townhouse with gorgeous Bay views. Ground level parking garage with storage, 2nd level is ....

2 Bedroom(s) 7 Bath(s) Townhome
Longboat Key, FL

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Longboat Key condo

Longboat arms

Wonderful End Condo With Full Awesome Bayview 1 Minute Walk To The Great Beach

This is a wonderful 2 bedroom+ 2 bathroom condo on Longboat key, on the third -End Level with awesome bay view. Watch Manatees, Dolphins and wildlife from almost any place in that condo. The perfect condo for your vacation or snowbirds. Rental min ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 3
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

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

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

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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3 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 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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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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