Houses Longboat Key

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42 houses

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

EXTREME POLYNESIAN BEACH HOUSE with BOAT/ KAYAKS

Longboat Key house

6 bedrooms / 6 bathrooms / sleeps 20

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$803

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Beautiful Longboat Key Penthouse Unit for Rent - partial Gulf view

Longboat Key penthouse

3 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$349

Short Term Rental Condo

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$149

Bayside Bliss

Longboat Key condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$115

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$332

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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Price per night from

$409

Beautiful Condo in Tropical Setting

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

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$107

Two Story Condo on the Gulf of Mexico

Longboat Key condo

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$540

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

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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Price per night from

$230

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

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$254

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

$201

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

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$172

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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Price per night from

$287

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$148

Tropical Waterfront Home in Historic Village

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$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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Price per night from

$153

761 Penfield

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$424

637 Norton

Longboat Key house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$622

Great rentals within 20 miles that match your search

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 50 minutes

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$296

PALM'S HOUSE

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

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Price per night from

$181

Oct To Dec 2020 SPECIAL -$1,899 Per Week - WRITE OR CALL

Anna Maria Island house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 59 minutes

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Price per night from

$230

A Pearl of a Beach Home - with luxury private heated pool and hot tub

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do anything to make things go smoothly.

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$230

Stunning Beach Front Pool Home (Sand Castle Unit)

Sarasota house

4 bedrooms / 2 bathrooms / sleeps 11

“Wonderful Stay!” We had such a great time in Siesta Key and the house was great. The shaded sitting area in front of the beach was an added bonus, as well as walking distance to the downtown area. The deck and pool could use a little updating, but overall the house was very clean and comfortable. This was by far our favorite beach trip and beach house to date! The owners were prompt to answer any questions and Sheila was there to greet us when we arrived and show us around. Also - the house was stocked with the essentials (paper towels, toilet paper, detergent, etc.) which was really convenient. We absolutely loved it!

Responds fast! avg. 3 hours 2 minutes

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Price per night from

$630

The House Of Peace

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 8

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$182

Flamingo Cottage Retreat ❤️ 3.4 miles to Siesta Keys

Gulf Gate Estates house

2 bedrooms / 2 bathrooms / sleeps 5

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$98

1-Story Bradenton Home w/Pool - 10 Mins to Beach!

Bradenton house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 5 minutes

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$207

Anna Maria Island "High End" Vacation Rental

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

“Excellent” Beautiful place, secluded and private. Very clean and Pet friendly. Could not ask for anything more.

Responds fast! avg. 3 hours 10 minutes

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$344

Escape, Fun, Paradise, Nature, Privacy , Weddings, Retreats, Reunions, Getaways

Bradenton house

8 bedrooms / 5 bathrooms / sleeps 20

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Price per night from

$1,145

636ontheKey - The "Belle of the Beach"

Siesta Key house

4 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$1,145

Luxury 3 Bedrooms/3 Full Baths, Private Heated Pool with Waterfall, Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 8

“Christmas at the Beach” It was a wonderful family vacation for two families going away for Christmas! There were 4 adults and 6 children! The pool was amazing and the house was perfect! Anna Maria Island is gorgeous and the house is in a perfect location for the beach, food and shopping! The owners were available for any needs that needed to be met! Awesome Owners!

Responds fast! avg. 2 hours 11 minutes

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$287

Spacious home moments away from the beach, gorgeous views & near plenty to do!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 50 minutes

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Price per night from

$664

Vibrant Beach House – Private Pool and Steps to the Beach

Anna Maria house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 50 minutes

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$292

Incredible, dog-friendly house with private heated pool, close to the beach!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 50 minutes

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$257

Sea Mist

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

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$280

Blue Bungalow

Bradenton house

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$115

Bay side family-home w/pool, 2 blocks from Bean Point beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 28 minutes

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Price per night from

$148

Viewing 38 of 42
rentals in Longboat Key

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