101 Rentals: Longboat Key

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Get help finding your rental: 941.900.4552

Longboat Key Luxury Vacation Rental Home / Estate for Rent

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Luxury Longboat Key Vacation Rental Private Home with Pool

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

One of the Very Few Beach Houses for Rent on Longboat Key

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Four Bedroom Longboat Key On Beach with Views

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  • Platinum
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 5 Bathrooms

The Ultimate Longboat Key Luxury Rental

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Luxurious 4 Bedroom Island Escape in Longboat Key

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Longboat Key Luxury Three Bedrooms Vacation Rental Home

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat key Vacation Home on the Gulf Side

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 5 Bathrooms

Longboat Key Beach Home Full Gulf View Available Now

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 4 Bathrooms

Longboat Key Beachfront Private Beach Estate with Cottage

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 5 Bathrooms

Longboat Key 4 Bedroom Home with Private Pool and Boat Dock

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Home Rental with Private Pool

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Three Bedroom Fabulous Vacation Rental Property

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 9
  • 3 Bedrooms
  • 3 Bathrooms

Four Bedroom Vacation Rental Home on Longboat Key FL

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 7
  • 4 Bedrooms
  • 3 Bathrooms

Beachside North Longboat Vacation Home Sleeps 10 Guests.

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Beach House - Three Bedrooms Sleeps 6 Guests

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Beautiful 2 Bedroom Home + Den On a Canal!

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

A Rare Beachfront Longboat Key Vacation Home Great Views

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Beautiful 3 Bedroom Home Walking Distance to the Beach

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 7
  • 3 Bedrooms
  • 2 Bathrooms

Walk to Beach House on Longboat Key-

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Longboat Key 4 bed one minute walk to private beach access!

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

Lovely 3 Bed 3 Bath Longboat Key Home

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Luxury Vacation Rental Homes on South Longboat Key

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Spacious Luxury Gulf Front Vacation Home - Sleeps 10 Guests

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 4 Bedrooms
  • 4 Bathrooms

Luxury Longboat Key Vacation Home Available New Rental!

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

A Great Two Bedroom Vacation Rental Home on Longboat Key

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Longboat key True Luxury on The South End of Longboat Key

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Rental Home on South End of Island

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  • Gold
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Luxury Four Bedroom Vacation Rental on Longboat Key Sleeps 8

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Longboat Key Luxury Beachfront Rental Home Five Bedrooms

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 6 Bathrooms

Longboat Key 4 Bedroom Vacation Rental Sleeps 8

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Luxury 3 Bed Longboat Key Canal View Vacation Home Sleeps 6

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Luxury Longboat Key 3 Bedroom Vacation Home with Pool

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Three Bedroom on Lovely Longboat Key Rare Find!

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Florida Beach Rental Three Bedroom Villa 2 Bath

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

New Longboat Key Rental - South End

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Two Bedroom Two Bathroom Single Family Home Sleeps 6 Guests

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Private Pool and Canal View from this Four Bedroom Rental

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Walk to Beach Two Bedroom Home in Longboat Key

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Longboat Key Luxury 5 Bedroom Vacation Home Sleeps 10

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 6 Bathrooms

Lovely Four Bedroom Rental on South End of Longboat Key

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Longboat Key Canal Front Three Bedrooms Home

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Canal Front Vacation Home in Longboat Key

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Luxury Vacation Rental Home Three Bedrooms

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Pool Home Sleeps Eight Guests.

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Longboat Key Luxury Vacation Rental Home Four Bedrooms

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 4 Bedrooms
  • 3 Bathrooms

Longboat Key Golf Course View Rental Home

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Home Sleeps Eight Guests

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Bay View 5 Bedroom Walk to Beach Home

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

Charming Vacation Rental on Longboat Key. Call Today.

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Three Bedroom Villa One Block to Beach

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 7
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key 2 Bedroom Vacation Condo Bay Views Sleeps 4

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Canalside Three-Bedroom Vacation Home in Longboat Key

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Home Sleeps 8 Guests withPrivate Pool

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Canal Front 5 Bedroom Family Vacation Pool Home Sleeps 10

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 4 Bathrooms

Great Value Longboat Key Vacation Cottage Sleeps Six Guests.

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  • Silver
  • Home/Villa
  • Hot Tub / No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Homes with Pools to Rent in Country Club Shores

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Rental Home Two Bedrooms

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

North End Longboat Key Three Bedroom Vacation Rental Home

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Gulfside Longboat Key 2 Bedroom Villa Short Walk to Beach

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Country Club Shores Longboat Key Vacation Rentals

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Country Club Shores Longboat Key Vacation Rental

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Three Bedroom Value Rental Property- Longboat Key

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Three Bedroom Canal Front Home

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Weekly Beach Vacation Home on Longboat Key 4 Bedrooms

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Luxury Longboat Key Vacation Home on Beach Pool

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Longboat Key Bayside Townhome Close to the Beaches Sleeps 4

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Rental Property Home on Canal

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Rental Home One Bedroom

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom

Luxury Longboat Key Vacation Rental Home 3 Bedroom

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

A Longboat Key Dreamy Three Bedroom For Rent Available Today

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Longboat key Upscale Luxury Accommodation

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Beach House with Pool On Longboat Key

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Three Bedroom Pool Home for Rent on Longboat Key

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Home 878750

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 8
  • 2 Bedrooms
  • 1 Bathroom

Longboat Key Home 878751

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 7
  • 2 Bedrooms
  • 1 Bathroom

Longboat key Vacation Cottage with Full Gulf Views

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

Longboat Key Home 878753

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 1 Bedroom
  • 1 Bathroom

Longboat Key Rental 13 Steps from Beach 2 Bedrooms Sleeps 10

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 2 Bedrooms
  • 2 Bathrooms

Exclusive Longboat Key Rental in Queens Harbour - Bay Views

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 10
  • 5 Bedrooms
  • 5 Bathrooms

Longboat Key 2 Bedroom Vacation Rental Home on Longboat Key

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Longboat Key 2 Bedroom Vacation Rental on the Beach

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

Spacious 3 Bedroom Family Home with Private Pool

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Rentals Home with Private Pool

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Home 893634

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom

Longboat Key Home 893633

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom

Longboat Key Vacation Pool Home 3 Bedrooms Sleeps 6 Guests

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  • Silver
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Contemporary Luxury Vacation Home Exceptional Location

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom

Longboat Key Charming Rental Home with Three Bedrooms

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Bayside Rental Short Walk To Beach Three Bedrooms Sleeps 6

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Three Bedroom Rental with Two Bathrooms in Longboat key Fl

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Great Value Longboat Key Bayside Vacation Home Sleeps Six

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat KeyVacation home 5 minute walk to beach

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 9
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Bay View Two Bedroom Condo

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Home Sleeps Six Guests.

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Rental Home One Bedroom

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom

Longboat Key Vacation Rental Home Two Bedrooms

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 1 Bathroom

Longboat Key Vacation Rental Home Two Bedrooms

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 6
  • 2 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Home Sleeps Four

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Longboat Key Three Bedroom Walk to Beach Home

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Longboat Key Vacation Home Sleeps Four Short Walk to Beach

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 1 Bathroom