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!

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Number of Guests
Bedrooms
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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
  Disney
  Family Vacations
  Fishing
  Deep Sea Fishing
  Fly Fishing
  For Sale
  Golfing
  Group and Reunion
  Hang Gliding
  Hiking
  Honeymoon
  Horseback Riding
  Hunting
  Kayaking
  Lake
  LegoLand
  Mountain Biking
  Nightclub and Disco
  Over 55 Community
  Rental Exchange
  Sailing
  Scuba Diving
  Skiing
  State National Parks
  Cross Country Skiing
  Snowmobiling
  Spa
  Specials
  Surfing
  Theatre
  Ultra Luxury
  Wedding
  White Water Rafting
  Wind Surfing
  Wineries and Vineyards
Sorted by
Siesta Palooza
EXAMPLE - Pool and Patio Area with Balconies
$500/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
$500/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Sunset Gulf
Sunset from Master Suite Balcony
$500/night
Home in Siesta Key Florida
8 Beds • 5 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Point Break
EXAMPLE - Pool Area
$450/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 24
Siesta Key Luxury Rental Properties
Sunset Splash
Pool area - awesome
$500/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
$500/night
Home in Siesta Key Florida
8 Beds • 8 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Sea Spray
Heated Pool and Spa, Slide, Gratto, and more
$600/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Aloft on Canal
Heated Resort Pool - Slide, Grotto, Swim Up Bar, Jacuzzi
$600/night
Home in Siesta Key Florida
8 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Beach Views
EXAMPLE - Aerial View of Home
$425/night
Home in Lido Key Florida
7 Beds • 7 Full Baths • Sleeps 25
Siesta Key Luxury Rental Properties
Island House
Pool and Seating Area
$450/night
Home in Siesta Key Florida
7 Beds • 6 Full Baths • Sleeps 23
Siesta Key Luxury Rental Properties
The Shore House
Example Photo - Private Heated Pool and Spa
$425/night
Home in Lido Key Florida
7 Beds • 4 Full Baths • Sleeps 21
Siesta Key Luxury Rental Properties
Summer House
Example Pool
$400/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 22
Siesta Key Luxury Rental Properties
Dry Dock
Covered seating by the pool
$400/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Blue Paradise
EXAMPLE - Distance to the Beach and Rooftop View
$400/night
Home in Siesta Key Florida
6 Beds • 6 Full Baths • Sleeps 18
Siesta Key Luxury Rental Properties
Salty Dog
Pull up your boat and dock right at the house
$400/night
Home in Siesta Key Florida
6 Beds • 5 Full Baths • Sleeps 17
Siesta Key Luxury Rental Properties
Captain's Quarters
Welcome to Paradise!
$375/night
Lido Key Florida
5 Beds • 5 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
The Pool House
Stunning 4 Bed with Large Loft. Huge Back Yard Pool Area
$400/night
Home in Siesta Key Florida
5 Beds • 4 Full Baths • Sleeps 16
Siesta Key Luxury Rental Properties
Bahama Mama
EXAMPLE - Kitchen, Dining, Living Area
$400/night
Home in Siesta Key Florida
5 Beds • 5 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Modern Marvel
Exterior of Home
$400/night
Home in Siesta Key Florida
4 Beds • 4 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Island Time West
Pool Area and Balcony Area
$179/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Island Time East
Example Private Game Room
$169/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 14
Siesta Key Luxury Rental Properties
Aruba
Exterior of the home from the Street
$219/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 12
Siesta Key Luxury Rental Properties
Beach Club Breeze
Front of Home. Fence to Pool Area
$169/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
The Daiquiri Deck
Pool Area
$179/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
$219/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Island Sun
Living Room and Sliding Door to Balcony overlooking the Pool
$169/night
Home in Siesta Key Florida
3 Beds • 2 Full Baths • Sleeps 10
Siesta Key Luxury Rental Properties
Fins Up
1/2 Block to the Beach, 1/2 - 1 Block to Siesta Village
$169/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
$159/night
Bungalow in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 9
Siesta Key Luxury Rental Properties
Summer Sun
Exterior - Corner Unit Townhome - Steps to Village
$159/night
Townhouse in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Beach Retreat
Quaint Cottage. Sleeps 6. Private Heated Pool
$199/night
Home in Siesta Key Florida
3 Beds • 3 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Private Beach House
Front entrance
$139/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
$159/night
Home in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
The Mahi
Huge Private Back Yard
$139/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Salty Summer
Open floor plan with seating for everyone
$139/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties
Summer Salt
Large shared pool area
$139/night
Duplex in Siesta Key Florida
2 Beds • 2 Full Baths • Sleeps 8
Siesta Key Luxury Rental Properties