Vacation Rentals by Siesta Key Luxury Rental Properties - Stay In Style on Siesta Key Florida!

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Amenities
  Air Conditioning
  Dishwasher
  Fireplace
  Grill
  Hot Tub (Private)
  Luxury
  Pets Allowed
  Pool (Private)
  Ski-in/Ski-out
  Washer/Dryer
  Wheelchair Accessible

Activities and Interests
  Beach
  Biking
  Boating
  Canoeing
  Casino
  Corporate and Executive
  Fishing
  Deep Sea Fishing
  For Sale
  Golfing
  Group and Reunion
  Honeymoon
  Horseback Riding
  Hunting
  Lake
  Mountain Biking
  State National Parks
  Nightclub and Disco
  Over 55 Community
  Sailing
  Scuba Diving
  Skiing
  Cross Country Skiing
  Snowmobiling
  Spa
  Surfing
  Theatre
  Wedding
  White Water Rafting
  Wineries and Vineyards
  Fly Fishing
  Wind Surfing
  Hang Gliding
  Disney
  LegoLand
  Hiking
  Rental Exchange
  Specials
  Ultra Luxury
  Family Vacations
  Kayaking

All Vacation Rentals from Siesta Key Luxury Rental Properties

Sun Deck in pool perfect for tanning or kids
$1,005/night
Home in Siesta Key Florida
9 Beds • 7 Full Baths • Sleeps 23
Siesta Key Luxury Rental Properties

Pool & Back Elevation
$840/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties

Sunset View - Siesta Key Luxury Rental Properties
$640/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties

Pool, Spa, Sun shelf, Swim Up Bar, Lounge Chairs, Patio
$840/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties

Sunset View
$495/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties

Tropical Pool Setting for Spacious 8 Bedroom Home
$790/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties

Serenity
$790/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties

Amazing Backyard with Private Heated Pool
$735/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties

Aloft on Canal - Siesta Key Luxury Rental Properties
$1,005/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties

Enjoy dinner on the Balcony with Gulf and Sunset Views
$1,015/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties

Image Coming Soon
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties

Seashell Esta - By Siesta Luxury Rental Properties
$1,115/night
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 20
Siesta Key Luxury Rental Properties

Island House by Siesta Key Luxury Rental
$790/night
Home in Siesta Key Florida
7 Beds • 6 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties

Talk to the Sand - Siesta Key Luxury Rental Properties
$715/night
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties

Village Time - Siesta Luxury Rental Properties
$640/night
Townhouse in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 28
Siesta Key Luxury Rental Properties

Heated pool with spa!
$750/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties

Dry Dock by Siesta Key Luxury Rental Properties
$640/night
Townhouse in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties

Blue Paradise by Siesta Key Luxury Rental Properties
$840/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties

High Tide-Siesta Key Luxury Rental Properties
$1,065/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties

Plenty of space for 4 or more vehicles, Access to Left side
$735/night
Home in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 17
Siesta Key Luxury Rental Properties

Shell-Abrate Good Times - By Siesta Key Luxury Rental Properties
$1,015/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties

Sugar Sand Cottage - By Siesta Key Luxury Rental Properties
$840/night
Home in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties

Stunning 4 Bed with Large Loft. Huge Back Yard Pool Area
$735/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties

On The Rocks - Siesta Key Luxury Rental Properties
$725/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties

Paradise Cove
$735/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties

Casa Azul
$530/night
Townhouse in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties

Bahama Mama- Siesta Key Luxury Rental Properties
$685/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties

Southern Exposure - Siesta Key Luxury Rental Properties
$590/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Casa Playa - Siesta Key Luxury Rental Properties
$330/night
Home in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Private Pool
$475/night
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties

Balconies Overlooking the Pool Area
$335/night
Townhouse in Siesta Key Florida
4 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties

Heated Lap Pool
$505/night
Home in Siesta Key Florida
4 Beds • 5 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Changing Channels - Siesta Key Luxury Rental Properties
$450/night
Townhouse in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

John Ringling House - Lido Key Vacations
$235/night
Home in Lido Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Mainsail - Siesta Key Luxury Rental Properties
$590/night
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Brisas Del Mar - Siesta Key Luxury Rental Properties
$215/night
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Beach House Residence #301
$450/night
Condo in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Sunset Cove - Siesta Key Luxury Rental Properties
$170/night
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties

Island Time West - Siesta Key Luxury Vacations Rental Properties
$350/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties

Island Time East - Siesta Key Luxury Rental Properties
$350/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties

Exterior and Main Entrance
$300/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties

Island Sun by Siesta Key Luxury Rental Properties
$285/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 11
Siesta Key Luxury Rental Properties

Siesta Sun by Siesta Key Luxury Rental Properties
$350/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Living Area
$255/night
Duplex in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties

Private Pool Sunset
$590/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties

Image Coming Soon
Condo in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties

Image Coming Soon
Home in Sarasota Florida
3 Beds • 2 Full Baths • Sleeps 6
Siesta Key Luxury Rental Properties

Living space
$165/night
Townhouse in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties