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

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

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Pool & Back Elevation
$1,025/night
Siesta Palooza
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
View from the Balcony
$925/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
$930/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
$1,105/night
Sunset Splash
Home in Siesta Key Florida
8 Beds • 7 Full Baths • Sleeps 23
Siesta Key Luxury Rental Properties
Recently Remodeled and Absolutely Stunning
$1,040/night
Surf View (SKLRP)
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Roof Top Deck - Awesome Sunset, Gulf, and Beach Views
$880/night
Sea Spray
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Roof Top Deck - Amazing Sunset, Beach, and Gulf Views
$1,045/night
Aloft on Canal
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Open Concept Living with Tremendous Views of Siesta Key
$1,400/night
Ocean Overlook
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Seashell Esta - By Siesta Luxury Rental Properties
$1,290/night
Seashell Esta
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 20
Siesta Key Luxury Rental Properties
Beautiful Pool Area
$925/night
Island House
Home in Siesta Key Florida
7 Beds • 6 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties
Talk To The Sand
$825/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
$650/night
Village Time
Townhouse in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 28
Siesta Key Luxury Rental Properties
Heated pool with spa !
$875/night
Summer House
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Amazing Pool and Back Yard Area - Waterfront Dock
$765/night
Dry Dock
Townhouse in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
This 6 Bedroom Home is Absolutely Stunning
$995/night
Blue Paradise
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Pool w/ Waterfall at Twilight
$1,230/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
$880/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
$1,230/night
Shell-Abrate Good Times
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Image Coming Soon
Ready Sunset Glow
Home in Sarasota Florida
6 Beds • 6 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Old Image-Relax in the heated pool
$995/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
What a Backyard!
$925/night
On The Rocks (SKLRP)
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties
Paradise Cove
$880/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
Pool and Back Yard Area
$805/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
$650/night
Southern Exposure (SKLRP)
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Casa Playa
$390/night
Casa Playa
Home in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Backyard at Sunset
$945/night
Modern Marvel
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
601 Avenida De Mayo
$475/night
Siesta Tropical Villa
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Plenty of seating for all in the living room
$410/night
Tarpon Villa
Townhouse in Siesta Key Florida
4 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
The Hideaway - Gated Private Residence with Heated Pool
$545/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
$375/night
Changing Channels
Townhouse in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Stunning Waterfront Home with Oversized Pool and Spa
$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
$245/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 (1)
$150/night
Sunset Cove
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Gorgeous Private Pool with Hot Tub/Waterfall Feature
$345/night
Island Time West
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Cute and Cozy 3 Bedroom Townhome (Right Side)
$345/night
Island Time East
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Amazing 3/2.5 Home w/ Private Heated Pool
$435/night
Aruba
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Expansive Living Room w/ Great Built In Entertainment Center
$345/night
Siesta Sun
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Great Room - Living, Dining, Kitchen
$310/night
Island Sun
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Games, Bikes, Paddleboards, Kayaks, Jet Ski and Boat Rentals
$285/night
Fins Up
Duplex in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Cute little house minutes from the beach
$410/night
yyBeach Retreat (SKLRP)
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Catch some rays on the Rooftop Deck!
$550/night
Casa Siesta
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Image Coming Soon
Off Tropic
Home in Sarasota Florida
3 Beds • 3 Full Baths • Sleeps 6
Siesta Key Luxury Rental Properties
Treasure on the Canal - By Siesta Luxury Rental Properties
$150/night
Treasure on the Canal
Home in Sarasota Florida
3 Beds • 2 Full Baths • Sleeps 6
Siesta Key Luxury Rental Properties
Image Coming Soon
Fan Palms
Home in Siesta Key Florida
3 Beds • 3 Full Baths
Siesta Key Luxury Rental Properties