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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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  Air Conditioning
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Sorted by
Siesta Palooza
Siesta Key family vacation home with 8 bedrooms a elevator and heated pool
$550/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset View
Ocean View Vacation Home in Siesta Key Florida with 8 bedrooms and private pool and hot tub
$500/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset Gulf
Gulf View vacation Home Sleeps 25 in Siesta Key steps to the beach with pool and 8 bedrooms
$500/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Point Break
Pet Friendly Siesta Key large family reunion home rental with 8 bedrooms sleeps 24
$550/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties
Dream Island
Welcome to Dream Island!
$625/night
Home in Lido Key Florida
8 Beds • 8 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties
Sunset Splash
Siesta Key family vacation home with 8 bedrooms sleeps 25 with large pool and patio area pet friendly
$600/night
Home in Siesta Key Florida
8 Beds • 7 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties
Surf View
Large home rental close Beach and Siesta Village with pool and 8 bedrooms sleeps 22 pet friendly
$500/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Sea Spray
Unique 8 bedroom luxury vacation home rental in Siesta Key Close to the beach with pool and hot tub
$550/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Aloft on Canal
Group vacation home in Siesta Key with pool, jacuzzi and 8 bedrooms sleeps 22
$550/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Island House
Siesta Key group vacation home with pool close to beach and village 7 bedrooms sleeps 23
$500/night
Home in Siesta Key Florida
7 Beds • 6 Full Baths • Sleeps 23
Siesta Key Luxury Rental Properties
Beach Views
EXAMPLE - Aerial View of Home
$525/night
Home in Lido Key Florida
7 Beds • 7 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties
All Decked Out
Relax by the Pool!
$525/night
Lido Key Florida
7 Beds • 7 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties
The Shore House
Example Photo - Private Heated Pool and Spa
$475/night
Home in Lido Key Florida
7 Beds • 4 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties
Summer House
Example Pool
$600/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Dry Dock
Siesta Key 6 bedroom vacation home rental with large pool and patio area pet friendly sleeps 18
$500/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Blue Paradise
Luxury Siesta Key Home Rental with heated pool next to village and beach 6 bedrooms
$550/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Salty Dog
Siesta Key 6 bedroom luxury vacation home on canal with boat dock and large pool and patio area
$500/night
Home in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 17
Siesta Key Luxury Rental Properties
The Big Top
Luxurious Lido Key 6 bedroom home rental close to everything
$475/night
Home in Lido Key Florida
6 Beds • 5 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
Sugar Sand Cottage
You can't beat this view!
$425/night
Cottage in Siesta Key Florida
5 Beds • 3 Full Baths • Sleeps 19
Siesta Key Luxury Rental Properties
Captain's Quarters
Welcome to Paradise!
$450/night
Home in Lido Key Florida
5 Beds • 5 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
The Pool House
Siesta Key vacation home with large pool and patio 5 bedrooms and is pet friendly walk to the beach
$450/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
On The Rocks
Siesta Key luxury vacation home walk to village and beach 5 bedrooms with pool sleeps 15 pet friendly
$500/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 15
Siesta Key Luxury Rental Properties
Bahama Mama
Siesta Key pet friendly family vacation home with 5 bedrooms walk to village and beach sleeps 14
$450/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Modern Marvel
Siesta Key Village 4 bedroom gulf front vacation home with pool/spa and putting green
$500/night
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Tarpon Villa
4 Bedroom 2.5 Bathroom Townhome for Rent in Siesta Key Walk to Beach
$229/night
Townhouse in Siesta Key Florida
4 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Siesta Penthouse
Penthouse rental in Siesta Key Florida 4 bedrooms with pool and 1 block to beach and village
$300/night
Penthouse in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Mainsail
Mainsail Siesta Key Florida Siesta Key Luxury Rental Properties
$400/night
Home in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Island Time West
Pool Area and Balcony Area
$199/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Island Time East
Siesta Key Pet Friendly 3 bedroom vacation rental with pool sleeps 14 close to beach
$199/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Aruba
Siesta Key 3 bedroom pool home for rent perfect for families sleeps 12
$249/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
The Canopy
Private Patio
$129/night
Lido Key Florida
3 Beds • 2 Full Baths • Sleeps 11
Siesta Key Luxury Rental Properties
Beach Club Breeze
Siesta Key 3 Bedroom 3 Bath Home w/ 12 Person Hot Tub or Heated Pool Sleeps 10
$159/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
The Daiquiri Deck
Pet Friendly house rental steps to Siesta Key Village with 3 bedrooms short walk to the beach
$189/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Siesta Sun
Beautiful Furnishings and Large Open Floorplan
$229/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Waikiki House
Large Open Living Space
$329/night
Condo in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Island Sun
Siesta Key vacation home with pool and pet friendly 3 bedrooms sleeps 10 Steps to the Beach
$179/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Fins Up
Siesta Key Vacation home with 3 bedrooms close to the village and beach
$159/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Maui House
Beautifully Decorated Living Space
$329/night
Condo 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
$199/night
Bungalow in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties
Beach Retreat
Quaint Cottage. Sleeps 6. Private Heated Pool
$209/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Private Beach House
Siesta Key 2 bedroom vacation rental sleeps 9 close to the beach and village
$129/night
Townhouse in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties
Crab Shack
Tropical Breeze Resort - The Crab Shack - Sleeps 8
$299/night
Condo in Siesta Key Florida
2 Beds • 1 Full Bath • Sleeps 9
Siesta Key Luxury Rental Properties
Bimini Breeze
Siesta Key cottage rental with large pool and patio area 2 bedrooms sleeps 8
$189/night
Home in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
The Mahi
Pet Friendly house rental Siesta Key Florida 2 bedrooms short walk to the beach
$129/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Salty Summer
Pet Friendly Siesta Key family vacation rental steps to the beach and village
$139/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Summer Salt
Siesta Key Family vacation rental with 2 bedrooms close to beach and village
$139/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Reel Lucky
Siesta Key pet friendly accommodations close to the beach and village
$129/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Key Lime Cabana
Large Living Room and Dining Space
$219/night
Condo in Siesta Key Florida
2 Beds • 1 Full Bath • Sleeps 8
Siesta Key Luxury Rental Properties