Houses Longboat Key

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915 houses

Charming Beach House in Longboat Key/ pool/pet/dock

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$253

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$148

761 Penfield

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$424

Private Bungalow on Canal a block from Beach

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$201

GORGEOUS gated Multi-level LONGBOAT KEY HOME with DOCK ~ Near beach & private!

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 49 minutes

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$153

BBB on Marbury lane-Beach, boating, BBQ!

Longboat Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 52 minutes

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$286

Tropical Waterfront Home in Historic Village

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 5

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$737

Beautiful Island Sanctuary Best Location in South Longboat Key!

Longboat Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 1 minutes

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$487

Fabulous Longboat Key - A Mermaids' Oasis 4 minute walk to beach!

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 8

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$172

637 Norton

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 8

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$622

EXTREME POLYNESIAN BEACH HOUSE with BOAT/ KAYAKS

Longboat Key house

6 bedrooms / 6 bathrooms / sleeps 20

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$802

Castle in the Sky Near Beach and Tennis

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 10

“Great Family Holiday Vacation” Our two families of 8 people total enjoyed our stay at Castle in the sky very much. The house is large but very comfortable. The weather in January can be fickle so one day the air conditioner is on, the next day the heater was on but the house is overall bright and cheerful and the décor is very pleasant. We ate in about half the time and walked to some nearby restaurants which were convenient. The kitchen has plenty of room and is well stocked with silverware and cookware. The resort pool is heated and there is a nature park nearby which we used for a jogging trail which was great. The water was too cold for the beach but there is a lot of beach chairs and items to use in the garage if you need them This was the largest home we found on Flipkey that could accommodate our group and wouldn't break the bank. We weren't directly on the water but there's so much to do nearby that it didn't really matter to us. We would stay again and likely will next winter. The owner was forthright with everything and pleasant to work with.

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$228

Great rentals within 20 miles that match your search

Barb's BaySide Retreat

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 6

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$145

NW Bradenton Exectitive Home

Bradenton house

4 bedrooms / 3 bathrooms / sleeps 10

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$457

Mangrove Bay Cottage Siesta Drive vacation rental

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$150

STUNNING GULF VIEWS+STEPS TO MOST SOUGHT AFTER BEACH+PEACEFUL NORTH END

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

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$273

Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach

Siesta Key house

4 bedrooms / 5 bathrooms / sleeps 12

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$689

3 Bedroom House

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 11 minutes

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$145

5 bedroom luxury home with pool and lake view

Bradenton house

5 bedrooms / 3 bathrooms / sleeps 10

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$216

Old Island Charm - Newly Renovated

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$386

Palms (ANN776)

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 54 minutes

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Price per night from

$310

Tropical Pool Home Near Siesta Key, Pet Friendly! Private POOL

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$87

The Seascape -Relax Enjoy Private Pool, Hot Tub, Game Room

Palma Sola house

4 bedrooms / 3 bathrooms / sleeps 8

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$159

Our Beach House

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 2 minutes

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$328

The Shells Villa - Next to Beach & Village

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 10

“Great Experience and Location!” We could not have been happier with our Experience at Shell Villa. Location to the Village was super close as described. Access to the beach was great both through the private walkway or the public access about two block away. The house was well stocked and the floor plan was perfect for our two families. Best place I have rented on SK in 5 years.

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$247

Beach, Please A ~ Less than 100 steps to the beach!

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 5

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$125

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Famous Holiday” Everything was so perfekt ... WE CAME back next Year THE HOUSE BEAUTIFUL AND CLEAN.. THE Area perfekt

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$206

TROPICCAL, 4 min from the beaches!

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 3 hours 51 minutes

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$87

BEACH NEAR, EXCLUSIVE VILLA, PRIVATE POOL, QUIET SEA VIEW

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

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$173

Directly on the beach New construction with beautiful views and beach front

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$461

636ontheKey - The "Belle of the Beach"

Siesta Key house

4 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$1,152

Cozy RENOVATED 3/2 Fenced Beach Home near Siesta Key Beach and downtown SRQ!

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 6

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$173

Tropical retreat with pool and gardens in the heart of Sarasota

Sarasota house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$211

Sarasota Historic Home close to everything

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$150

Luxury house in the heart of Tara Golf & Country Club,Bradenton Florida

Braden River house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$173

Spectacular Beach House With GulfView Only Steps to a Pristine Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$346

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

2 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$357

⭐Near Siesta Key Beach, Shopping and More! Pet Friendly

Gulf Gate Estates house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 40 minutes

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Price per night from

$144

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houses in Longboat Key

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