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 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 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

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

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

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

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

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 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

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 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 condo

Vacation Home

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1 Bedroom(s) 0 Bath(s) Condo
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

Vacation Home

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2 Bedroom(s) 2 Bath(s) Condo
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

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 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

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

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 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 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

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 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

Vacation Home

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6 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 16
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 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

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

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

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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