Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

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

Book Faster

Location Type

Even More Filters

Features

Managed By

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

Longboat Key Rentals(204)

204 Results
$300 - $400
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
(15)
$1,550 - $2,300
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(8)
$1,867 - $2,217
per week
7 - 30 night minimum stay
  • 3 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 30 night minimum stay
(5)

Why HomeAway?

We're the leader in vacation rentals
More than one million listings worldwide
Experienced property owners or managers
Average five years in the business
$1,800 - $2,200
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(4)
$195 - $225
per night
4 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 5 night minimum stay
(12)
$2,950 - $4,950
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
7 night minimum stay
(16)
$1,750 - $2,765
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(3)
  • 4 BR,
  • Sleeps 12
7 night minimum stay
(14)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(28)
$2,500
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
(5)

Why HomeAway?

We help you travel with confidence
Every listing guaranteed against fraud
We offer a best price guarantee
No booking fees and low online prices
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(19)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(18)
$3,500 - $4,000
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
(9)
$155 - $235
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$135 - $175
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
1 - 7 night minimum stay
$155 - $235
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$180 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$180 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$155 - $235
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$180 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$180 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$1,425 - $1,725
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$295 - $425
per night
2 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night minimum stay
$180 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$180 - $295
per night
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
$180 - $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
$230 - $405
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
Advertisement
 

Recent Longboat Key Reviews

Unique and inviting

5 of 5
We had stayed in Sarasota before and would always admire the prominent house as we crossed the bridge adjacent. On this trip, we made sure to stay here. With a toddler, teenagers and adults, nothing could really be more perfect. Having your own boat adds to the thrill. The house encompasses everything from boat adventure to a nap between the trees. It truly covers all you'd want from a holiday, whatever it may be. The owner is very hospitable and approachable and makes the stay even more comfortable. We will certainly be back.
  • Submitted: Dec 21, 2014
  • Stayed: Nov 2014

It is a fantastic property and a wonderful stay

5 of 5
My stay was very comfortable them home is in wonderful condition and the bed was very comfortable to sleep in which is always a concern. It is also a very short walk to the beach! Great stay! I highly recommend it.
  • Submitted: Dec 9, 2014
  • Stayed: Dec 2013

Location, location, location

5 of 5
Words can not be found to express our total enjoyment of this beach front rental. We could have chosen any place else in the Sarasota area but we elected to stay at the Zilli Villa on Longboat key while we attended a destination wedding at the Ritz siesta club on lido key. The location of this villa on the island really makes it perfect to get anywhere in a reasonable amount of time either by bike or by car, the sunsets are spectacular and the home is immaculate. The owners appear to actually love and use this home themselves and have made tasteful updates to this home without ruining the essence of the old Florida feel of this home. The owners were easy to deal with and responsive with our booking transaction. We were traveling with my son who spent some of the time working from his computer with a front row view of the Gulf of Mexico. Our 4 year old grandson found plenty to do with the pails, shovels, games and pool floats! The 2000 sq. feet of space kept us all out of each others way when we wanted "alone" time. This was our first trip to the west coast of Florida and we were so pleasantly surprised that we will be sure to return for a longer length of stay. Barbara
  • Submitted: Dec 5, 2014
  • Stayed: Nov 2014