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

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

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

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

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 condo

Silver Sands #242

Silver Sands #242: 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

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 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

Longboat Key 45

Lovely updated condo at SeaPlace! Just steps from the beach!

Tropical Oasis at Seaplace on Longboat Key. This two bedroom, two bath condo is located on the Gulf of Mexico and is your perfect home away from home. Master bedroom features a King sized bed, hurricane shutters and a large walk-in closet. The guest ....

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 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

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 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

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

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

Vacation Home

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1 Bedroom(s) 0 Bath(s) Condo - Sleeps 4
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

Longboat Key 54

Longboat Key 54 in Longboat Key. Furnished, 2 bedrooms, 2 bath condo

Furnished, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. This ground floor unit is centrally located and minutes away from urban activities with in-unit washer and dryer. The master bedroom features a queen bed, walk-in clo ....

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

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 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 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

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 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 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

Vacation Home

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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 condo

Vacation Home

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1 Bedroom(s) 0 Bath(s) Condo
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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