FR Beach Rentals
Vacation Rental Managers Testimonials Manager Login
Book Direct & Save with a Vacation Rental Manager
Vacation Rental Managers Testimonials

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

  1. « Siesta Key Rentals
Siesta Key Luxury Rental Properties - Stay In Style on Siesta Key Florida!
Book Direct
Number of Guests
Bedrooms
Bathrooms
more filters
Price Range
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

Sorted by
Pool & Back Elevation
$915/night
Siesta Palooza
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset View - Siesta Key Luxury Rental Properties
$100/night
Sunset View
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
$915/night
Sunset Gulf
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset View
$495/night
Sunset View
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
$795/night
Point Break
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties
Sun Deck in pool perfect for tanning or kids
$1,080/night
Sunset Splash
Home in Siesta Key Florida
8 Beds • 7 Full Baths • Sleeps 23
Siesta Key Luxury Rental Properties
Serenity
$795/night
Surf View (SKLRP)
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Amazing Backyard with Private Heated Pool
$855/night
Sea Spray
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
$915/night
Aloft on Canal
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
$1,125/night
Ocean Overlook
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Image Coming Soon
Between the Waves
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Seashell Esta - By Siesta Luxury Rental Properties
$1,225/night
Seashell Esta
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 20
Siesta Key Luxury Rental Properties
Island House by Siesta Key Luxury Rental
$855/night
Island House
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
$795/night
Talk To The Sand
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Village Time - Siesta Luxury Rental Properties
$690/night
Village Time
Townhouse in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 28
Siesta Key Luxury Rental Properties
Heated pool with spa!
$855/night
Summer House
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
$690/night
Dry Dock
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
$915/night
Blue Paradise
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
High Tide-Siesta Key Luxury Rental Properties
$1,210/night
High Tide (SKLRP)
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
$795/night
Salty Dog (SKLRP)
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
$1,270/night
Shell-Abrate Good Times
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
$915/night
Sugar Sand Cottage
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
$795/night
The Pool House
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
$915/night
On The Rocks (SKLRP)
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties
Paradise Cove
$855/night
Paradise Cove
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Casa Azul
$530/night
Casa Azul
Townhouse in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Bahama Mama- Siesta Key Luxury Rental Properties
$745/night
Bahama Mama
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
Southern Exposure (SKLRP)
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Casa Playa - Siesta Key Luxury Rental Properties
$325/night
Casa Playa
Home in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Private Pool
$500/night
Siesta Tropical Villa
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Balconies Overlooking the Pool Area
$375/night
Tarpon Villa
Townhouse in Siesta Key Florida
4 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Heated Lap Pool
$590/night
The Hideaway (SKLRP)
Home in Siesta Key Florida
4 Beds • 5 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Changing Channels - Siesta Key Luxury Rental Properties
$410/night
Changing Channels
Townhouse in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
John Ringling House - Lido Key Vacations
$240/night
John Ringling House
Home in Lido Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Mainsail - Siesta Key Luxury Rental Properties
$650/night
Mainsail
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
Brisas Del Mar
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Beach House Residence #301
$450/night
Beach House Residence #301
Condo in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Sunset Cove - Siesta Key Luxury Rental Properties
$165/night
Sunset Cove
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
$285/night
Island Time West
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
$285/night
Island Time East
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Exterior and Main Entrance
$350/night
Aruba
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
Island Sun
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
Siesta Sun
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Living Area
$260/night
Fins Up
Duplex in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Private Pool Sunset
$590/night
Casa Siesta
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
IMG_7844
$120/night
Fire-Sky Penthouse
Condo in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Always Siesta Time by Tropical Sands Accommodations (4)
$120/night
Always Siesta Time
Home in Sarasota Florida
3 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Living space
$170/night
Private Beach House
Townhouse in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties