Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Cottages
Homes
Apartments
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Condos
Estates
Farmhouses
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Longboat Key Cottages or Houses(195)

195 Results
$286 - $400
per night
3 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 4 night minimum stay
(14)
$195 - $225
per night
4 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 5 night minimum stay
(11)
$1,500 - $2,300
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(8)
$1,800 - $2,500
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(4)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(28)
$2,950 - $4,950
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
7 night minimum stay
(15)
$3,150 - $4,200
per week
7 night minimum stay
  • 3 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(5)
  • 4 BR,
  • Sleeps 12
7 night minimum stay
(11)
$3,250
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(5)
$186 - $214
per night
13 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
13 night minimum stay
(3)
$1,750 - $2,765
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
1 Review
$3,000 - $4,000
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(19)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(18)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
$130 - $175
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
1 - 7 night minimum stay
$175 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$155 - $210
per night
2 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
$230 - $405
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
$230 - $405
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
$175 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$230 - $405
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
$175 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$190 - $325
per night
2 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 5
2 - 7 night minimum stay
$175 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$230 - $405
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
$175 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$230 - $405
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
$175 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$1,375 - $1,725
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
Advertisement
 

Recent Longboat Key Reviews

Most beautiful, wonderful place!

5 of 5
My new husband and I spent a week's honeymoon at this beautiful house, and it was plain perfect. It is the most comfortable, stylish, immaculate rental we've ever stayed in, and the private-island location and gardens are spectacular. Deciding where to watch the amazing sunset each night was the most trouble we encountered on the whole trip (which of the decks? which hammock? from the dock? the adirondacks...?). It is the most magical place -- we couldn't recommend it more highly, and we can't wait to go back with friends and family. Thank you Stephen and Catherine!
  • Submitted: Sep 26, 2014
  • Stayed: Sep 2014

Fantastic Vacation

5 of 5
We had an awesome vacation. My wife and I along with our two teenagers and a friend for each had an incredible vacation. The house was fantastic, clean, well furnished and a close walk to the beach. The pool was a great way to end the afternoon. There are many restaurants in close proximity. We enjoyed an inshore fishing trip as well as kayaking in close by Sarasota. I would definitely recommend this. We hope to return soon.
  • Submitted: Aug 19, 2014
  • Stayed: Jul 2014

Breath Taking

5 of 5
We just returned home to Colorado after a week in this beautiful home. The home is clean, decorated beautiful and comfortable for all. My husband, son and grandson along with myself had the most peaceful and relaxing week. Our 7 year old grandson loved that he could swim in the Gulf then move to the pool. We did get to see some dolphins in the distance. Look forward to going back.
  • Submitted: Jul 20, 2014
  • Stayed: Jul 2014