624 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Siesta Key Vacation Rentals(624)

624 Results
$1,045 - $2,200
per week
7 - 28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 28 night minimum stay
(25)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 - 28 night minimum stay
(6)
$150 - $264
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(21)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 30 night minimum stay
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night minimum stay
(14)
$185 - $293
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(38)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(32)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(16)
$875 - $1,330
per week
7 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night minimum stay
(7)
$182 - $207
per night
4 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
4 - 7 night minimum stay
(19)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
6 - 7 night minimum stay
(25)
$3,745 - $4,970
per week
7 - 30 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 - 30 night minimum stay
(13)
$1,071 - $1,725
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(21)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(7)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night minimum stay
(25)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
6 - 7 night minimum stay
(6)
$1,595 - $1,895
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(53)
$180 - $300
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 - 7 night minimum stay
(20)
$900 - $1,100
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
7 night minimum stay
(48)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
(20)
$1,395 - $1,995
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(17)
$5,000
per week
7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
7 night minimum stay
(14)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
28 - 30 night minimum stay
(9)
$2,250 - $3,950
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(22)
$185 - $271
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(18)
$795 - $1,295
per week
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(25)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 3 night minimum stay
2 Reviews
$750 - $1,495
per week
2 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(8)
Advertisement
 

Recent Siesta Key Reviews

Home away from home!

5 of 5
Our stay at Siesta Jewel was amazing! The rental is in a great location-- we didn't move our car unless we went golfing. I couldn't imagine staying anywhere else on Siesta Key. The beach access point isn't crowded and the Village is just around the corner. I definitely hope to stay here again. ?
  • Submitted: Mar 25, 2015
  • Stayed: Mar 2015

Adorable Cottage with an Awesome Location

5 of 5
No Complaints at all!! Extremely clean and comfortable cottage literally across the street from the beach. My Husband and I were impressed from the moment we arrived at the designer decor and high-end furnishing and finishes. Much nicer than even pictured! Walking distance to Siesta Key Village and all it's great bars and restaurants, we especially loved The Cottage, Senor Siesta, and our daily nightcap at The Hub. Owner thought of everything -- bath & beach towels, Tommy Bahama chairs & umbrella, games, books, and even bikes!! Dave, was very easy to communicate with and returned our security deposit within a only couple days of our departure. We can't wait to rebook!!
  • Submitted: Mar 18, 2015
  • Stayed: Feb 2015

Awesome

5 of 5
Amazing. Beautifully furnished and equipped. View of the beach was awesome and so was Sandy. Would highly recommend.
  • Submitted: Mar 5, 2015
  • Stayed: Feb 2015