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  4. Florida Gulf Coast
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  6. Siesta Key
  7. Siesta Key Luxury Rental Properties
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Vacation Rentals by Siesta Key Luxury Rental Properties - Stay In Style on Siesta Key Florida!

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  Air Conditioning
  Dishwasher
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  Grill
  Hot Tub (Private)
  Luxury
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Sorted by
Siesta Palooza
Pool & Back Elevation
$1,275/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset View
Sunset from the Master Suite Balcony
$1,150/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset Gulf
View from the Balcony
$1,150/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Point Break
Tropical Pool Setting for Spacious 8 Bedroom Home
$1,275/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties
Sunset Splash
Sun Deck in pool perfect for tanning or kids
$1,300/night
Home in Siesta Key Florida
8 Beds • 7 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties
Surf View
Recently Remodeled and Absolutely Stunning
$1,150/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Sea Spray
Roof Top Deck - Awesome Sunset, Gulf, and Beach Views
$1,300/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Aloft on Canal
Roof Top Deck - Amazing Sunset, Beach, and Gulf Views
$1,300/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Ocean Overlook
Ocean Overlook - Amazing Home, Pool, and Views
$1,400/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Island House
Beautiful Pool Area
$1,000/night
Home in Siesta Key Florida
7 Beds • 6 Full Baths • Sleeps 23
Siesta Key Luxury Rental Properties
Summer House
Heated pool with spa !
$1,100/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Dry Dock
Amazing Pool and Back Yard Area - Waterfront Dock
$1,100/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Blue Paradise
This 6 Bedroom Home is Absolutely Stunning
$1,250/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
High Tide
Pool w/ Waterfall at Twilight
$1,250/night
Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Salty Dog
Plenty of space for 4 or more vehicles, Access to Left side
$1,100/night
Home in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 17
Siesta Key Luxury Rental Properties
Sugar Sand Cottage
Old Image-Relax in the heated pool
$1,300/night
Cottage in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties
The Pool House
Stunning 4 Bed with Large Loft. Huge Back Yard Pool Area
$1,000/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
On The Rocks
What a Backyard!
$1,050/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties
Bahama Mama
Pool and Back Yard Area
$925/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Modern Marvel
Backyard at Sunset
$1,150/night
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Tarpon Villa
Plenty of seating for all in the living room
$375/night
Townhouse in Siesta Key Florida
4 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
The Hideaway
The Hideaway - Gated Private Residence with Heated Pool
$650/night
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Mainsail
Stunning Waterfront Home with Oversized Pool and Spa
$900/night
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Island Time West
Gorgeous Private Pool with Hot Tub/Waterfall Feature
$375/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Island Time East
Cute and Cozy 3 Bedroom Townhome (Right Side)
$375/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Aruba
Amazing 3/2.5 Home w/ Private Heated Pool
$425/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Siesta Sun
Expansive Living Room w/ Great Built In Entertainment Center
$425/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Island Sun
Great Room - Living, Dining, Kitchen
$300/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Fins Up
Games, Bikes, Paddleboards, Kayaks, Jet Ski and Boat Rentals
$275/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Blue Lagoon
3 Bed. 3 Bath. Sleeps 9 in Beds. 1 Block to Village & Beach
$400/night
Bungalow in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties
Beach Retreat
Cute little house minutes from the beach
$425/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Casa Siesta
Catch some rays on the Rooftop Deck!
$700/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Private Beach House
Living space
$225/night
Townhouse in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties
Bimini Breeze
Gorgeous Pergula Awning form an Amazing Patio Area
$350/night
Home in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
The Mahi
Adorable Living Room
$225/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Salty Summer
Enjoy your morning coffee listening to birds in the trees
$225/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Summer Salt
Large shared pool area
$225/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Southern Comfort
Full view of dining room and living room
$225/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Villa Marina
Full view of downstairs
$225/night
Villa in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Siesta Key Luxury Rental Properties