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  7. Siesta Key Luxury Rental Properties
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Vacation Rentals by Siesta Key Luxury Rental Properties - Stay In Style on Lido Key and Siesta Key Florida!

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Amenities
  Air Conditioning
  Dishwasher
  Fireplace
  Grill
  Hot Tub (Private)
  Luxury
  Pets Allowed
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  Lake
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  State National Parks
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  Over 55 Community
  Sailing
  Scuba Diving
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  Cross Country Skiing
  Snowmobiling
  Spa
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  Wineries and Vineyards
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  Hang Gliding
  Disney
  LegoLand
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  Rental Exchange
  Specials
  Ultra Luxury
  Family Vacations
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Sorted by
Siesta Palooza
Pool & Back Elevation
$1,000/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
$850/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset Gulf
View from the Balcony
$850/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
$1,000/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
$1,000/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
$850/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
$1,000/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
$1,000/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
The Plaza
Front of House close view
$1,050/night
Home in Siesta Key Florida
8 Beds • 7 Full Baths • Sleeps 21
Siesta Key Luxury Rental Properties
Ocean Overlook
Ocean Overlook - Amazing Home, Pool, and Views
$1,050/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Island House
Beautiful Pool Area
$750/night
Home in Siesta Key Florida
7 Beds • 6 Full Baths • Sleeps 23
Siesta Key Luxury Rental Properties
The Oasis
The Oasis-7 Beds 7.5 Baths - Sleeps 22 - Steps to Beach
$1,200/night
Home in Siesta Key Florida
7 Beds • 7 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Summer House
Heated pool with spa !
$1,000/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
The Upper Deck
Sunset Views from The Lookout
$850/night
Townhouse in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 20
Siesta Key Luxury Rental Properties
Dry Dock
Amazing Pool and Back Yard Area - Waterfront Dock
$750/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
$1,000/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
The Rooftop
Pool Area and Waterfall at Sunset
$850/night
Townhouse in 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
$750/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
$1,100/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
$900/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
On The Rocks
What a Backyard!
$800/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties
Crescent Beach House
Pool Area
$700/night
Townhouse in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties
Bahama Mama
Pool and Back Yard Area
$600/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Point of Rocks
Always Time for the Pool!
$650/night
Townhouse in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Modern Marvel
Backyard at Sunset
$700/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
$300/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
$500/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
$750/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
$300/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)
$300/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
$350/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
$325/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
$225/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
$179/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
$300/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
$325/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!
$500/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Private Beach House
Living space
$159/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
$300/night
Home in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
The Mahi
Adorable Living Room
$159/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
$169/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Summer Salt
Large shared pool area
$169/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
$169/night
Condo in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Villa Marina
Full view of downstairs
$169/night
Villa in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Siesta Key Luxury Rental Properties