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Vacation Rentals by Siesta Key Luxury Rental Properties

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Showing 1-28 of 28 Rentals

Sunset View
Home in Siesta Key Florida
Sunset from the Master Suite Balcony
$600/night
8 Beds • 5 Full Baths
Sleeps 25
Siesta Key Luxury
Sunset Gulf
Home in Siesta Key Florida
Sunset from Master Suite Balcony
$600/night
8 Beds • 5 Full Baths
Sleeps 25
Siesta Key Luxury
Sunset Splash
Home in Siesta Key Florida
Pool area - awesome
$625/night
8 Beds • 7 Full Baths
Sleeps 24
Siesta Key Luxury
Surf View
Home in Siesta Key Florida
Recently Remodeled and Absolutely Stunning
$500/night
8 Beds • 8 Full Baths
Sleeps 22
Siesta Key Luxury
Sea Spray
Home in Siesta Key Florida
Heated Pool and Spa, Slide, Gratto, and more
$975/week
8 Beds • 6 Full Baths
Sleeps 22
Siesta Key Luxury
Aloft on Canal
Home in Siesta Key Florida
Heated Resort Pool - Slide, Grotto, Swim Up Bar, Jacuzzi
$550/night
8 Beds • 6 Full Baths
Sleeps 22
Siesta Key Luxury
Island House
Home in Siesta Key Florida
Pool and Seating Area
$350/night
7 Beds • 6 Full Baths
Sleeps 23
Siesta Key Luxury
Lido Key Retreat
Home in Lido Key Florida
Pool View
$400/night
7 Beds • 5 Full Baths
Sleeps 17
Siesta Key Luxury
Summer House
Home in Siesta Key Florida
Example Pool
$450/night
6 Beds • 6 Full Baths
Sleeps 22
Siesta Key Luxury
Dry Dock
Home in Siesta Key Florida
Covered seating by the pool
$400/night
6 Beds • 6 Full Baths
Sleeps 18
Siesta Key Luxury
Salty Dog
Home in Siesta Key Florida
Pull up your boat and dock right at the house
$375/night
6 Beds • 5 Full Baths
Sleeps 17
Siesta Key Luxury
The Pool House
Home in Siesta Key Florida
Stunning 4 Bed with Large Loft. Huge Back Yard Pool Area
$450/night
5 Beds • 4 Full Baths
Sleeps 16
Siesta Key Luxury
Ringling Manor
Home in Lido Key Florida
Gated Entryway
$299/night
4 Beds • 3 Full Baths
Sleeps 8
Siesta Key Luxury
John Ringling House
Home in Lido Key Florida
Sprawling John Ringing Estate Home. National Historic Site
$199/night
3 Beds • 3 Full Baths
Sleeps 14
Siesta Key Luxury
Island Time West
Siesta Key Florida
Pool Area and Balcony Area
$169/night
3 Beds • 2 Full Baths
Sleeps 13
Siesta Key Luxury
Island Time East
Siesta Key Florida
Example Private Game Room
$169/night
3 Beds • 2 Full Baths
Sleeps 13
Siesta Key Luxury
Aruba
Home in Siesta Key Florida
Exterior of the home from the Street
$259/night
3 Beds • 2 Full Baths
Sleeps 12
Siesta Key Luxury
Beach Club Breeze
Home in Siesta Key Florida
Front of Home. Fence to Pool Area
$219/night
3 Beds • 3 Full Baths
Sleeps 10
Siesta Key Luxury
The Daiquiri Deck
Home in Siesta Key Florida
Pool Area
$179/night
3 Beds • 3 Full Baths
Sleeps 10
Siesta Key Luxury
Siesta Sun
Home in Siesta Key Florida
Beautiful Furnishings and Large Open Floorplan
$259/night
3 Beds • 3 Full Baths
Sleeps 10
Siesta Key Luxury
Summer Sun
Townhouse in Siesta Key Florida
Exterior - Corner Unit Townhome - Steps to Village
$259/night
3 Beds • 3 Full Baths
Sleeps 10
Siesta Key Luxury
Blue Lagoon
Bungalow in Siesta Key Florida
3 Bed. 3 Bath. Sleeps 9 in Beds. 1 Block to Village & Beach
$199/night
3 Beds • 3 Full Baths
Sleeps 10
Siesta Key Luxury
Island Sun
Home in Siesta Key Florida
Living Room and Sliding Door to Balcony overlooking the Pool
$179/night
3 Beds • 2 Full Baths
Sleeps 10
Siesta Key Luxury
Fins Up
Home in Siesta Key Florida
1/2 Block to the Beach, 1/2 - 1 Block to Siesta Village
$149/night
3 Beds • 2 Full Baths
Sleeps 10
Siesta Key Luxury
Beach Retreat
Home in Siesta Key Florida
Quaint Cottage. Sleeps 6. Private Heated Pool
$179/night
3 Beds • 3 Full Baths
Sleeps 8
Siesta Key Luxury
Private Beach House
Siesta Key Florida
Front entrance
2 Beds • 2 Full Baths
Sleeps 9
Siesta Key Luxury
Bimini Breeze
Home in Siesta Key Florida
Gorgeous Pergula Awning form an Amazing Patio Area
$240/night
2 Beds • 2 Full Baths
Sleeps 8
Siesta Key Luxury
The Mahi
Duplex in Siesta Key Florida
Huge Private Back Yard
$149/night
2 Beds • 2 Full Baths
Sleeps 8
Siesta Key Luxury



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