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

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 condo

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3 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 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

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

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 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

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 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

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

Vacation Home

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2 Bedroom(s) 2 Bath(s) Condo
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 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 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 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

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

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 #238

Silver Sands #238: 3 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 8

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 ....

3 Bedroom(s) 2 Bath(s) Condo - Sleeps 8
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 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

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

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

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 condo

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2 Bedroom(s) 2 Bath(s) Condo
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 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 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

Vacation Home

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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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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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