Luxury Vacation Rentals with a Private Pool 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 private pool 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
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
Welcome to private poolside luxury in Siesta Key
Claim your own slice of island luxury with Wander’s portfolio of luxury private pool vacation rentals in Siesta Key. Each home is architecturally striking, impeccably clean, and professionally operated, so what you see is exactly what you get.
Spend unhurried mornings by your private heated pool, then step inside to hotel-grade touches like plush linens, ultra fast WiFi, and inspiring views, all backed by 24/7 concierge support.
Designed for work and play, our residences pair serene outdoor lounges with thoughtful interiors that make every stay effortless.
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
Next avail.
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 beyond the pool in Siesta Key
Sugar-soft quartz sand, turquoise Gulf water, and sunsets that feel cinematic define Siesta Key. The beaches stay cool underfoot and the surf is gentle, making long shoreline walks and easy swims a daily ritual.
Paddle mangrove tunnels on calm bays, snorkel the limestone at Point of Rocks, or drift between laid-back cafés and live music in the Village. Sarasota’s galleries and theaters sit just over the bridge, yet the Key keeps its breezy rhythm.
All of this is why Wander's luxury private pool vacation rentals in Siesta Key are the perfect choice, whether you're traveling for work or leisure.