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Vacation Rentals by Siesta Key Luxury Rental Properties

Showing 1-29 of 29 Rentals

Sunset View
Home in Siesta Key Florida

Sunset from the Master Suite Balcony

8 Beds • 5 Full Baths
Sleeps 25

Sunset Gulf
Home in Siesta Key Florida

Sunset from Master Suite Balcony

8 Beds • 5 Full Baths
Sleeps 25

Sunset Splash
Home in Siesta Key Florida

Pool area - awesome

8 Beds • 7 Full Baths
Sleeps 24

Surf View
Home in Siesta Key Florida

Recently Remodeled and Absolutely Stunning

8 Beds • 8 Full Baths
Sleeps 22

Sea Spray
Home in Siesta Key Florida

Heated Pool and Spa, Slide, Gratto, and more

8 Beds • 6 Full Baths
Sleeps 22

Aloft on Canal
Home in Siesta Key Florida

Heated Resort Pool - Slide, Grotto, Swim Up Bar, Jacuzzi

8 Beds • 6 Full Baths
Sleeps 22

Island House
Home in Siesta Key Florida

Pool and Seating Area

7 Beds • 6 Full Baths
Sleeps 23

The Shore House
Home in Lido Key Florida

Example Photo - Private Heated Pool and Spa

7 Beds • 4 Full Baths
Sleeps 21

Lido Key Retreat
Home in Lido Key Florida

Pool View

7 Beds • 5 Full Baths
Sleeps 17

Summer House
Home in Siesta Key Florida

Example Pool

6 Beds • 6 Full Baths
Sleeps 22

Dry Dock
Home in Siesta Key Florida

Covered seating by the pool

6 Beds • 6 Full Baths
Sleeps 18

Salty Dog
Home in Siesta Key Florida

Pull up your boat and dock right at the house

6 Beds • 5 Full Baths
Sleeps 17

The Pool House
Home in Siesta Key Florida

Stunning 4 Bed with Large Loft. Huge Back Yard Pool Area

5 Beds • 4 Full Baths
Sleeps 16

Ringling Manor
Home in Lido Key Florida

Gated Entryway

4 Beds • 3 Full Baths
Sleeps 8

John Ringling House
Home in Lido Key Florida

Sprawling John Ringing Estate Home. National Historic Site

3 Beds • 3 Full Baths
Sleeps 14

Island Time West
Townhouse in Siesta Key Florida

Pool Area and Balcony Area

3 Beds • 2 Full Baths
Sleeps 13

Island Time East
Townhouse in Siesta Key Florida

Example Private Game Room

3 Beds • 2 Full Baths
Sleeps 13

Aruba
Home in Siesta Key Florida

Exterior of the home from the Street

3 Beds • 2 Full Baths
Sleeps 12

Beach Club Breeze
Home in Siesta Key Florida

Front of Home. Fence to Pool Area

3 Beds • 3 Full Baths
Sleeps 10

The Daiquiri Deck
Home in Siesta Key Florida

Pool Area

3 Beds • 3 Full Baths
Sleeps 10

Siesta Sun
Home in Siesta Key Florida

Beautiful Furnishings and Large Open Floorplan

3 Beds • 3 Full Baths
Sleeps 10

Summer Sun
Townhouse in Siesta Key Florida

Exterior - Corner Unit Townhome - Steps to Village

3 Beds • 3 Full Baths
Sleeps 10

Blue Lagoon
Bungalow in Siesta Key Florida

3 Bed. 3 Bath. Sleeps 9 in Beds. 1 Block to Village & Beach

3 Beds • 3 Full Baths
Sleeps 10

Island Sun
Home in Siesta Key Florida

Living Room and Sliding Door to Balcony overlooking the Pool

3 Beds • 2 Full Baths
Sleeps 10

Fins Up
Home in Siesta Key Florida

1/2 Block to the Beach, 1/2 - 1 Block to Siesta Village

3 Beds • 2 Full Baths
Sleeps 10

Beach Retreat
Home in Siesta Key Florida

Quaint Cottage. Sleeps 6. Private Heated Pool

3 Beds • 3 Full Baths
Sleeps 8

Private Beach House
Townhouse in Siesta Key Florida

Front entrance

2 Beds • 2 Full Baths
Sleeps 9

Bimini Breeze
Home in Siesta Key Florida

Gorgeous Pergula Awning form an Amazing Patio Area

2 Beds • 2 Full Baths
Sleeps 8

The Mahi
Duplex in Siesta Key Florida

Huge Private Back Yard

2 Beds • 2 Full Baths
Sleeps 8

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Siesta Key Luxury Rental Properties

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