Houses Longboat Key

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828 houses

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 10

“Rain” The house was adorable. It was well stocked considering we couldn't go out due to the rain. It is close to the beach,just a short walk.

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Price per night from

$303

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SHOREWALK VACATION VILLA

Bradenton apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$144

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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$231

Brand new dog-friendly home w/ private pool in prime location

Holmes Beach house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 50 minutes

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$249

Beautiful Braden River Waterfront Retreat!

Bradenton house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 0 minutes

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$151

Sea Haze Cottage - Gorgeous waterfront pool beachhouse

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

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$345

Westbay Point Moorings 274

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$161

The Majaec Inn Getaway with many Amenities Preview listing

Sarasota house

1 bedroom / 1 bathroom / sleeps 2

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$144

Cozy villa with large pool area in walking distance to the beach and village

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$264

2 bedroom/1 bath Contemporary Beach Cottage

Siesta Key house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$196

Casa Antigua - Sparkling 4 BR, Heated Pool, Minutes From Siesta Key [sleeps 8]

Sarasota house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$266

Palms (ANN776)

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 56 minutes

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Price per night from

$305

Private Bungalow on Canal a block from Beach

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$202

Stunning 2,550 Sq.ft House, FL

Bradenton house

4 bedrooms / 2 bathrooms / sleeps 8

“Awesome stay” We had a great stay at this property. We were there for my wife graduation our family and us loved it and will rent this property again.

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$178

Casita Blanca- 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]

Sarasota house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$301

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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Price per night from

$246

Siesta Key Luxury Condo Across the Street

Siesta Key house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$155

Unique Siesta Key Pool Home

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$195

Bay Winds112

Cortez house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$137

Barb's BaySide Retreat

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$144

Ebb Tide

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$270

Aloha Kai Unit 10

Siesta Key house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$199

Vacation Sarasota in great location to all venues....

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$144

Pool home, mins to Anna Maria Is & IMG Academy

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$287

Casa Coconut AMI #1 Two BR steps away from Manatee Beach

Bradenton Beach house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$185

March 2019 Avail! Inquire- Siesta Key home with dock and private pool

Siesta Key house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$492

Stunning & Bright Sarasota Home

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$161

Home for vacation rental in sunshine Sarasota, FL

Gulf Gate Estates house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$115

Siesta Key Canal + Pool Home- 3 Bedroom

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$516

Three bedroom house directly on beach with gulf vi

Siesta Key house

3 bedrooms / 4 bathrooms / sleeps 7

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Price per night from

$344

3 Bedroom Oasis w/Pool,hot tub, pool table, wetbar, boat parking and more!

Palma Sola house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$287

Siesta Key Beachfront 3 Bedroom Home, Sarasota

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 9

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Price per night from

$516

ANNA MARIA'S BEST LOCATION! PANORAMIC VIEW of Pool Dock & Bayou to Gulf

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$401

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$148

Westbay Point Moorings 214

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$196

White Sands Beach House

Holmes Beach house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$381

Water View, 100 Fishing Dock! Teton 40 Ft. Trailer W/3 Slide Outs

Palmetto house

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$91

Coquina Sands, view beach from balcony, priv pool

Holmes Beach house

2 bedrooms / 3 bathrooms / sleeps 6

“Great place, great location, great vacation” We stay at Anna Maria for 12 days and if we could we would be there for 12 years. Awesome place and great host. Everything was ready for us. Only high marks. Thanks

Responds fast! avg. 3 hours 18 minutes

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Price per night from

$227

Viewing 38 of 828
rentals in Longboat Key

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