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 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

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

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

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

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 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 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

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

Vacation Home

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2 Bedroom(s) 2 Bath(s) Condo
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 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

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

Vacation Home

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1 Bedroom(s) 0 Bath(s) Condo
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

Silver Sands #241S

Silver Sands #241S: 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

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

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 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

Vacation Home

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2 Bedroom(s) 2 Bath(s) Condo
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

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

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) 1 Bath(s) Condo - 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

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

Vacation Home

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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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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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