1. Vacation Rental Managers
  2. United States
  3. Florida
  4. Florida Gulf Coast
  5. Sarasota Area
  6. Siesta Key
  7. Siesta Key Luxury Rental Properties
  8. Vacation Rentals

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

Book Direct Manager Profile
Number of Guests
Bedrooms
Bathrooms
more filters
Price Range
Amenities
  Air Conditioning
  Dishwasher
  Fireplace
  Grill
  Hot Tub (Private)
  Luxury
  Pets Allowed
  Pool (Private)
  Ski-in/Ski-out
  Washer/Dryer
  Wheelchair Accessible
Activities and Interests
  Beach
  Biking
  Boating
  Canoeing
  Casino
  Corporate and Executive
  Fishing
  Deep Sea Fishing
  For Sale
  Golfing
  Group and Reunion
  Honeymoon
  Horseback Riding
  Hunting
  Lake
  Mountain Biking
  State National Parks
  Nightclub and Disco
  Over 55 Community
  Sailing
  Scuba Diving
  Skiing
  Cross Country Skiing
  Snowmobiling
  Spa
  Surfing
  Theatre
  Wedding
  White Water Rafting
  Wineries and Vineyards
  Fly Fishing
  Wind Surfing
  Hang Gliding
  Disney
  LegoLand
  Hiking
  Rental Exchange
  Specials
  Ultra Luxury
  Family Vacations
  Kayaking
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
$900/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
$1,100/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
$950/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
$975/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
$975/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
$1,100/night
Siesta Key Florida
8 Beds • 7 Full Baths • Sleeps 21
Siesta Key Luxury Rental Properties
Ocean Overlook
Ocean Overlook - Amazing Home, Pool, and Views
$1,100/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
$1,250/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
$900/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
$900/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
$900/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
$800/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
$1,000/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
$850/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
On The Rocks
What a Backyard!
$900/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
$750/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Tarpon Villa
Plenty of seating for all in the living room
$250/night
Townhouse in Siesta Key Florida
4 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Modern Marvel
Backyard at Sunset
$900/night
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 11
Siesta Key Luxury Rental Properties
The Hideaway
The Hideaway - Gated Private Residence with Heated Pool
$650/night
Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Siesta Penthouse
Relax by a divine heated pool
$450/night
Penthouse in Siesta Key Florida
4 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Mainsail
Stunning Waterfront Home with Oversized Pool and Spa
$700/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
$275/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
Beach Club Breeze
3 Bedroom 3 Bath Home w/ 12 Person Hot Tub or Heated Pool
$189/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
The Daiquiri Deck
Pool Area
$219/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Siesta Sun
Expansive Living Room w/ Great Built In Entertainment Center
$300/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
$200/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
$350/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Private Beach House
Living space
$149/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
$325/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
Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Villa Marina
Full view of downstairs
$169/night
Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 6
Siesta Key Luxury Rental Properties