Longboat Key

Longboat Key on the FL Gulf coast has a long history as a vacation retreat and has been the destination of choice for many generations of visitors to Florida. The natural beauty of the area is the highlight with a mix of high rise vacation rental options

Beautiful Gulf Views from the Living Room and the Master Bedroom - Unit 208

Condo

2 Bed 2 Bath Sleeps 4

Beautiful Gulf Views from the Living Room and the Master Bedroom - Unit 208 Longboat Key

2 bedroom; 2 bath (showers only) second floor condo overlooking the Gulf of MexicoSleeping accommoda

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Veranda Beach Club, Beach Side in Longboat Key, Florida

Condo

2 Bed 2 Bath Sleeps 6

Veranda Beach Club, Beach Side in Longboat Key, Florida Longboat Key

This is a lovely two (2) Bedroom, two (2) Bath, beach side unit with a partial view @ the Veranda B

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Beautiful Ground Floor Gulf View Condo

Condo

2 Bed 2 Bath Sleeps 6

Beautiful Ground Floor Gulf View Condo Longboat Key

You will love our 2 bedroom, 2 bath condo with a spacious 1,100 square feet of room to call your own

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Rent this historic and famous Longboat Key Beach House by the week. Sleeps 6

Guest_house

3 Bed 2 Bath Sleeps 6

Rent this historic and famous Longboat Key Beach House by the week. Sleeps 6 Longboat Key

Vacation in a piece of Longboat Key history!! This is the home depicted in the famous poster by John

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Paradise on beautiful Sarasota Bays with pool

Condo

2 Bed 2 Bath Sleeps 4

Paradise on beautiful Sarasota Bays with pool Longboat Key

Bay and pool views from lanai, living room and master bedroom. Master bedroom has a king bed and new

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SEA CLUB III BEACHSIDE CONDO ON LONGBOAT KEY

Condo

2 Bed 2 Bath Sleeps 6

SEA CLUB III BEACHSIDE CONDO ON LONGBOAT KEY Longboat Key

SEA CLUB III - WEEKLY VACATION RENTAL - BEACHSIDE CONDO ON LONGBOAT KEY. Perfect Location on the bea

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Walk to the beach and restaurants - Tropical location

House

2 Bed 2 Bath Sleeps 4

Walk to the beach and restaurants - Tropical location Longboat Key

Welcome to your Longboat Key Village island home, a private beach to bay getaway! Located on the bea

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Beach Place   6 floor penthouse with ocean and bay views.

Condo

2 Bed 2 Bath Sleeps 6

Beach Place 6 floor penthouse with ocean and bay views. Longboat Key

Spectacular 2 bedroom and 2 bathroom 1400 ft.² 6 floor Penthouse condo in" Beach Place" community.

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Amazing condo, our building is right on the Beach. Unit 401

Condo

1 Bed 1 Bath Sleeps 4

Amazing condo, our building is right on the Beach. Unit 401 Longboat Key

THIS UNIT DOES NOT FACE THE BEACH or HAVE A BEACH VIEW.Welcome to the Longboat Key Sarasota’s most

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Silver Sands #242: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Condo

1 Bed 1 Bath Sleeps 4

Silver Sands #242: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4 Longboat Key

If your requested dates appear to be unavailable, please contact our local team at (877) 230-9838

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SIMPLY PERFECT! Gorgeous 2/2-Low Rate! Beach Villa-Quiet South Longboat Key, FL

Villa

2 Bed 2 Bath Sleeps 4

SIMPLY PERFECT! Gorgeous 2/2-Low Rate! Beach Villa-Quiet South Longboat Key, FL Longboat Key

HERE IT IS...THIS IS THE LONG-TERM RENTAL YOU HAVE BEEN WAITING FOR! 21 DAY MINIMUM... ...P

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Steps from Beach or Bay

House

3 Bed 2 Bath Sleeps 6

Steps from Beach or Bay Longboat Key

Enjoy the privacy of our fenced Key West style pool home. The house is surrounded by Joan Durante na

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Windward Bay Longboat Key Villa steps to Beach, Bay, Marina, 2 heated pools!

Villa

1 Bed 1 Bath Sleeps 4

Windward Bay Longboat Key Villa steps to Beach, Bay, Marina, 2 heated pools! Longboat Key

Make this charming Beach Villa your seasonal escape!! This spacious 1 bedroom 1 bath bright and sunn

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Elegant 1of-a-kind home on gulf of Mexico  a few weeks open till Mid September

Villa

2 Bed 2 Bath Sleeps 8

Elegant 1of-a-kind home on gulf of Mexico a few weeks open till Mid September Longboat Key

It is part of the Zilli Collection each with the Zilli touch of amazing view , decor ,( not typical

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Silver Sands #241: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Condo

1 Bed 1 Bath Sleeps 4

Silver Sands #241: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4 Longboat Key

If your requested dates appear to be unavailable, please contact our local team at (877) 230-9838

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Direct Beachfront - Beautiful Sunsets - Mid Longboat Key Unit 406

Condo

2 Bed 2 Bath Sleeps 4

Direct Beachfront - Beautiful Sunsets - Mid Longboat Key Unit 406 Longboat Key

Unit 406 Wake up every morning listening to the gulf and sea birds. This totally remodeled fourth fl

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Silver Sands #244: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Condo

1 Bed 1 Bath Sleeps 4

Silver Sands #244: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4 Longboat Key

If your requested dates appear to be unavailable, please contact our local team at (877) 230-9838

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Newly Renovated 2/2 W/ Private Beach Access!

Condo

2 Bed 2 Bath Sleeps 5

Newly Renovated 2/2 W/ Private Beach Access! Longboat Key

Beautiful, spacious 2/2 condo on Longboat Key available for immediate rental! Newly remodeled with d

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Beautiful Gulf Front Apt. at Sand Cay Beach Resort on Longboat Key, FL

Condo

2 Bed 2 Bath Sleeps 4

Beautiful Gulf Front Apt. at Sand Cay Beach Resort on Longboat Key, FL Longboat Key

Enjoy this beautiful Gulf-front sunny unit with vaulted ceilings and spectacular views. The open flo

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Relaxing Updated Cottage with Private Hot Tub ~ Pet Friendly!

Cottage

1 Bed 1 Bath Sleeps 3

Relaxing Updated Cottage with Private Hot Tub ~ Pet Friendly! Longboat Key

Beautiful beach cottage in wonderful Longboat Key, Florida! A wonderful getaway for a peaceful beach

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More Florida Vacation Rentals at HomeAway

Longboat Key is one of many popular Florida Gulf Coast Vacation Rental areas for travelers the world over. Longboat key and adjacent Sarasota offer a variety of activities for the sports minded ( fishing, jogging, etc) and for those looking to relax and enjoy some culture (symphony, arts and more).