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Longboat Key Rentals with Pools

1,739 apartments in Longboat Key with pools

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

Longboat Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 0.02 mi
  • •  Swimming pool
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$254

Longboat Key Condo w/ Pool Access- Walk to Bay!

Longboat Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$229

Outrigger Resort unit #3

Longboat Key apartment

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$246

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

Longboat Key apartment

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$409

Two Story Condo on the Gulf of Mexico

Longboat Key condo

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$541

225* BEACH FRONT APARTMENT *

Longboat Key apartment

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$160

Renovated Beachfront Condo with Spectacular Ocean View unit 403

Longboat Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$216

Newly renovated 2/2 w/ private beach access!

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$122

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

Longboat Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$296

1/1 $165 DIRECTLY ON THE BEACH(OCT, NOV,DEC, OPENINGS 3 OR MORE NIGHTS)

Longboat Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“beautiful condo & wonderful stay” My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at home immediately. Everything we needed was furnished in the condo. You are steps away from the beach, walking right out of the unit on the 2nd floor to the balcony and down a flight of stairs. The condo faces east/west , so you can see the sun rising through the bedroom in the front, and the sun setting through the open living room/kitchen area or out on the balcony where there are chairs. Spectacular water views all day long. This is a very spacious 1 bdr unit with a nice open floor plan. The office staff was also very helpful and gracious and the grounds are kept in great shape. The property does not have the amenities of a hotel; there is no bar or restaurant, and that suited us just fine. This is a very quiet and relaxing property. Overall, a great stay and we plan on returning for getaways hopefully once or twice a year.

Price per night from

$176

ZILLI VILLA

Longboat Key villa

  • Beach / lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$263

~ STUDIO - DIRECT BEACH FRONT CONDO ~

Longboat Key apartment

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$114

Amazing views of the Gulf and beach from your own balcony unit 301

Longboat Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$201

~ The Beach on Longboat Key ~ * OCEAN FRONT DLX STUDIO *

Longboat Key studio

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • Studio
  • 1 bathroom
  • sleeps 3

“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.

Price per night from

$114

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

Longboat Key house

  • Beach / lakeside relaxation
  • •  Nearest beach 0.4 mi
  • •  Swimming pool
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$153

Florida Ocean Front Condo April 11 -21, 2020

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$413

Zilli Ocean Front 101

Longboat Key condo

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$206

Beach Front 1 Bedroom Condo on Gulf of Mexico #10

Longboat Key apartment

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Ask about children
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$181

Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent

Longboat Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$161

Beach front condo in Longboat Key

Longboat Key condo

  • Beach / lakeside relaxation
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$355

Lovely Tropical Longboat Town house

Longboat Key townhouse

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$147

2 bedroom poolside condo steps from ocean beach and dock on bay 4-13 to 4-20

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$300

Holiday Home Directly by Sea - Self Catering

Longboat Key apartment

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$213

1 bedroom single story family friendly resort March 21 - March 28, 2020

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$213

Beautiful Island Sanctuary Best Location in South Longboat Key!

Longboat Key house

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$487

Unit #201 Gulf View

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$284

Unit #102 Gulf Front Sand Cay Beach Resort

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$307

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • Nearest beach 0 mi
  • •  Swimming pool
  • •  Child Friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$160

Unit #312 Pool and Garden View

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$244

Unit #307 Pool and Garden

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$215

Unit #205 Gulf View

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$284

Unit #116 Gulf Front 5 night minimum

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$303

Unit #114 Pool and Garden View

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$244

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • Nearest beach 0.01 mi
  • •  Swimming pool
  • •  Child Friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$115

Unit #305 Gulf View 5 night minimum

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$265

Unit #104 Gulf Front

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$307

Unit #115 Gulf View

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$268

Unit #120 Gulf View

Longboat Key condo

  • Swimming pool
  • •  Child Friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$255

Viewing 38 of 1,739
rentals in Longboat Key

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