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Vacation Rentals by Siesta Key Luxury Rental Properties

Showing 1-28 of 28 Rentals

Sunset View
Home in Siesta Key Florida
Sunset from the Master Suite Balcony
$600/night

Sunset Gulf
Home in Siesta Key Florida
Sunset from Master Suite Balcony
$600/night

Sunset Splash
Home in Siesta Key Florida
Pool area - awesome
$625/night

Surf View
Home in Siesta Key Florida
Recently Remodeled and Absolutely Stunning
$500/night

Sea Spray
Home in Siesta Key Florida
Heated Pool and Spa, Slide, Gratto, and more
$975/week

Aloft on Canal
Home in Siesta Key Florida
Heated Resort Pool - Slide, Grotto, Swim Up Bar, Jacuzzi
$550/night

Island House
Home in Siesta Key Florida
Pool and Seating Area
$350/night

Lido Key Retreat
Home in Lido Key Florida
Pool View
$400/night

Summer House
Home in Siesta Key Florida
Example Pool
$450/night

Dry Dock
Home in Siesta Key Florida
Covered seating by the pool
$400/night

Salty Dog
Home in Siesta Key Florida
Pull up your boat and dock right at the house
$375/night

The Pool House
Home in Siesta Key Florida
Stunning 4 Bed with Large Loft. Huge Back Yard Pool Area
$450/night

Ringling Manor
Home in Lido Key Florida
Gated Entryway
$299/night

John Ringling House
Home in Lido Key Florida
Sprawling John Ringing Estate Home. National Historic Site
$199/night

Island Time West
Siesta Key Florida
Pool Area and Balcony Area
$169/night

Island Time East
Siesta Key Florida
Example Private Game Room
$169/night

Aruba
Home in Siesta Key Florida
Exterior of the home from the Street
$259/night

Beach Club Breeze
Home in Siesta Key Florida
Front of Home. Fence to Pool Area
$219/night

The Daiquiri Deck
Home in Siesta Key Florida
Pool Area
$179/night

Siesta Sun
Home in Siesta Key Florida
Beautiful Furnishings and Large Open Floorplan
$259/night

Summer Sun
Townhouse in Siesta Key Florida
Exterior - Corner Unit Townhome - Steps to Village
$259/night

Blue Lagoon
Bungalow in Siesta Key Florida
3 Bed. 3 Bath. Sleeps 9 in Beds. 1 Block to Village & Beach
$199/night

Island Sun
Home in Siesta Key Florida
Living Room and Sliding Door to Balcony overlooking the Pool
$179/night

Fins Up
Home in Siesta Key Florida
1/2 Block to the Beach, 1/2 - 1 Block to Siesta Village
$149/night

Beach Retreat
Home in Siesta Key Florida
Quaint Cottage. Sleeps 6. Private Heated Pool
$179/night

Private Beach House
Siesta Key Florida
Front entrance

Bimini Breeze
Home in Siesta Key Florida
Gorgeous Pergula Awning form an Amazing Patio Area
$240/night

The Mahi
Duplex in Siesta Key Florida
Huge Private Back Yard
$149/night