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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  Air Conditioning
  Dishwasher
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  Grill
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All Vacation Rentals from Siesta Key Luxury Rental Properties

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Pool & Back Elevation
$700/night
Siesta Palooza
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
View from the Balcony
$639/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
$764/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
$827/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
$605/night
Surf View
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
$807/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
$782/night
Aloft on Canal
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Ocean Overlook - Amazing Home, Pool, and Views
$929/night
Ocean Overlook
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Image Coming Soon
Lucky In Lido
Home in Sarasota Florida
8 Beds • 9 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Image Coming Soon
Mac Daddy
Sarasota Florida
8 Beds • 8 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Beautiful Pool Area
$555/night
Island House
Home in Siesta Key Florida
7 Beds • 6 Full Baths • Sleeps 21
Siesta Key Luxury Rental Properties
Seashell Esta
$717/night
Seashell Esta
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 20
Siesta Key Luxury Rental Properties
Talk To The Sand
$699/night
Talk To The Sand
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Heated pool with spa !
$729/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
$641/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
$855/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
$960/night
High Tide
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
$625/night
Salty Dog
Home in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 17
Siesta Key Luxury Rental Properties
Shell-Abrate Good Times
$775/night
Shell-Abrate Good Times
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Courtyard Castle
$576/night
Courtyard Castle
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 1
Siesta Key Luxury Rental Properties
Old Image-Relax in the heated pool
$866/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
$555/night
The Pool House
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
What a Backyard!
$761/night
On The Rocks
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties
Pool and Back Yard Area
$605/night
Bahama Mama
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Paradise Cove
$648/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
Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Southern Exposure - Siesta Key Luxury Rental Properties
$496/night
Southern Exposure
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Backyard at Sunset
$700/night
Modern Marvel
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Lost Shaker of Salt
$263/night
Lost Shaker of Salt
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 13
Siesta Key Luxury Rental Properties
Plenty of seating for all in the living room
$298/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
$492/night
The Hideaway
Home in Siesta Key Florida
4 Beds • 5 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Changing Channels - Siesta Key Luxury Rental Properties
$339/night
Changing Channels
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Stunning Waterfront Home with Oversized Pool and Spa
$595/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
$276/night
Brisas Del Mar
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Casa Playa
$350/night
Casa Playa
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
Gorgeous Private Pool with Hot Tub/Waterfall Feature
$295/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)
$295/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
$384/night
Aruba
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Salt Break - Siesta Key Luxury Rental Properties
$185/night
yySalt Break (Under Constru...
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
$430/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
$275/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
$230/night
Fins Up
Duplex in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
3 Bed. 3 Bath. Sleeps 9 in Beds. 1 Block to Village & Beach
$305/night
Blue Lagoon
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties
Sea La Vie- Siesta Key Luxury Rental Properties
$230/night
Sea La Vie
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties
Cute little house minutes from the beach
$315/night
Beach Retreat
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Catch some rays on the Rooftop Deck!
$500/night
Casa Siesta
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties