Houses Longboat Key

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74 houses

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$148

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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$287

Beautiful Island Sanctuary Best Location in South Longboat Key!

Longboat Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 55 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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$173

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Longboat Key Bayfront condo in Bay Isles

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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$211

Zilli Tower 503

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 53 minutes

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$206

Steps to the Sand! Longboat Key 2 Bed 2 & 1/2 Bath Gulf Front Condo with Den.

Longboat Key apartment

2 bedrooms / 3 bathrooms / sleeps 6

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$411

Bayside Bliss

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

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$115

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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$332

Beautiful Longboat Key Penthouse Unit for Rent - partial Gulf view

Longboat Key penthouse

3 bedrooms / 4 bathrooms / sleeps 10

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$347

GULF FRONT 2 BR 2 BATHROOM CONDO

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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$192

Two Story Condo on the Gulf of Mexico

Longboat Key condo

4 bedrooms / 4 bathrooms / sleeps 10

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$542

Beach front condo in Longboat Key

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 35 minutes

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$357

225* BEACH FRONT APARTMENT *

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

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$160

Beautiful Gulf Front, Newly Renovated #319 Sand Cay on Longboat Key, Sarasota

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$296

Florida Ocean Front Condo April 11 -21, 2020

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 31 minutes

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$413

EXTREME POLYNESIAN BEACH HOUSE with BOAT/ KAYAKS

Longboat Key house

6 bedrooms / 6 bathrooms / sleeps 20

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$805

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

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$253

Private Bungalow on Canal a block from Beach

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

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$201

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

Tropical Waterfront Home in Historic Village

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 5

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$737

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

761 Penfield

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$424

637 Norton

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 8

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$622

Great rentals within 20 miles that match your search

Sea Haze Cottage - Gorgeous waterfront pool beachhouse

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

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$346

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

Pvt Pool Home Mins to Anna Maria Is & IMG Academy

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 6

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$329

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$357

Charming 2 Bedroom/2 Bath Cottage on a Canal

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 8 minutes

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$263

Secluded Cottage on 6 Acres IN TOWN 10min to Beach

Sarasota house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 18 minutes

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$144

Sandy Toes Siesta Key Florida (6798)

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“Very good” It's was great stay ,close to the beach (3-5)min walk,private,quite for vacation location. Car was parked in the garage and we loved it !!! Also you have everything you possibly need in a kitchen !! And condo has everything you need to go to the beach too !!(beach chairs,umbrellas,towels ....Will stay again Thank you Kathey and Joe

Responds fast! avg. 1 hour 2 minutes

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$345

Downtown Bungalow

Bradenton house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 1 minutes

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$173

3 bedroom/2 bath - Close to Nathan Benderson Park and Seista Key Beach

Fruitville house

3 bedrooms / 2 bathrooms / sleeps 6

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$173

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

5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 22 minutes

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$401

The Key Of Siesta

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 6

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$133

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 10 minutes

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Price per night from

$378

Minutes to Siesta Key Beach and downtown Sarasota!

Sarasota house

2 bedrooms / 1 bathroom / sleeps 4

“lovely neighborhood , close to it all” the neighborhood was quaint, clean and quiet with a great walking park near-by and a community swimming pool. It was close to the downtown and shopping and the Keys. The house was cutely decorated but the bathroom was very small, old and no electrical outlets, so you need to take all your hair appliances into the bedroom. It reminded me of college dorm living, taking all your things into and out of the bathroom. The lanai was big but there was construction going on next door in Jan. and it was noisy at times. The museums, botanical gardens and beaches are nearby. Great restaurants too.

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$165

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rentals in Longboat Key

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