Luxury Vacation Rentals in Siesta Key
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 10 vacation rentals – enter your dates for availability.
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 2 - Dec 4
312
Siesta Key, Florida
Wander Siesta Key Sands
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Dec 2 - Dec 4
716
Siesta Key, Florida
Wander Siesta Key Retreat
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Dec 7 - Dec 9
824
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 8 - Dec 10
722
Sarasota, FL, US
Wander Sarasota Keyview
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Nov 29 - Dec 1
48
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Dec 8 - Dec 10
310
Siesta Key, Florida
Wander Siesta Key Dunes
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Dec 8 - Dec 10
622
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Dec 19 - Dec 21
412
Welcome to Siesta Key
Discover Wander’s collection of luxury vacation rentals in Siesta Key, where the polish of a five-star stay meets the privacy of a modern coastal home. Each residence is professionally managed, beautifully designed, and exactly as photographed, so arrival feels effortless.
Every home features hotel-grade touches like pristine cleaning, premium linens, ultra fast WiFi, fully equipped kitchens, and dedicated workspaces. Many also include private pools or spa areas and inspiring views. With 24/7 concierge support, work and relaxation fit naturally into your time away.
Destinations near Siesta Key
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 2 - Dec 4
716
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 2 - Dec 4
312
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Dec 8 - Dec 10
310
Siesta Key, Florida
Wander Siesta Key Haze
Next avail.
Dec 3 - Dec 9
511
Siesta Key, FL, US
Wander Siesta Key Bayfront
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Nov 17 - Nov 23
47
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Dec 7 - Dec 9
824
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 8 - Dec 10
722
Sarasota, FL, US
Wander Sarasota Keyview
Next avail.
Nov 29 - Dec 1
48
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 5 - Dec 7
312
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 5 - Dec 7
716
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Dec 12 - Dec 14
824
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 12 - Dec 14
722
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Dec 12 - Dec 14
310
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Dec 12 - Dec 14
622
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Dec 19 - Dec 21
412
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Siesta Key
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 2 - Dec 4
312
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 2 - Dec 4
716
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Dec 7 - Dec 9
824
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 8 - Dec 10
722
Sarasota, FL, US
Wander Sarasota Keyview
Next avail.
Nov 29 - Dec 1
48
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Dec 8 - Dec 10
310
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Dec 8 - Dec 10
622
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Dec 19 - Dec 21
412
Discover more of Siesta Key
Powder-soft quartz sand and turquoise Gulf waters set the scene on Siesta Key. Siesta Beach glows with cool-to-the-touch quartz, while Crescent Beach and Turtle Beach offer quieter stretches and striking sunsets.
Days move at an unhurried pace, from morning beach walks to golden-hour rituals along the shore. Siesta Village brings small-island energy with boutiques and live music, and Sarasota sits just over the bridge for galleries and performance. This is why Wander's luxury vacation rentals in Siesta Key are the perfect choice, whether you're traveling for work or leisure.