Longboat Key Florida Vacation Rentals, Hotels & Resorts

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Rentals in Longboat Key, FL

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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

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

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 #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

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

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

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2 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 104E

Perfectly located near the path th the beach, just steps from the pool.

2 Bedroom & 1 bathroom, ground-floor condo just steps to the beach or sheltered pool. Fully furnished with everything you need for a relaxing island getaway on beautiful Longboat Key. Open floor plan, updated kitchen and bath with relaxing beach-sty ....

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

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Longboat Key condo

Longboat Key 20

A rare, 2 bedroom 2 bath, short-term, rental opportunity at Bayport Beach!

A rare, short-term, rental opportunity at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes turnkey furnished and equipped with flat screen TV's, cable and WiFi. This beautifully appointed residence features a large out ....

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 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

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

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 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 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 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

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1 Bedroom(s) 0 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

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 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

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

Cedars East #850

Cedars East #850: 2 BR / 2.5 BA Townhome 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 #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

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

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 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

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 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

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 condo

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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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