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 Dunes
Next avail.
Feb 9 - Feb 11
622
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Jan 20 - Jan 22
722
Siesta Key, FL
Wander Siesta Key Bayfront
Next avail.
Jan 16 - Jan 22
47
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Jan 31 - Feb 2
310
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Jan 24 - Jan 26
312
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Jan 19 - Jan 21
412
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Jan 19 - Jan 21
716
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Jan 29 - Jan 31
824
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 Palms
Next avail.
Jan 20 - Jan 22
722
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Jan 31 - Feb 2
310
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Jan 29 - Jan 31
824
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Jan 19 - Jan 21
716
Siesta Key, Florida
Wander Siesta Key Haze
Next avail.
May 16 - May 22
511
Siesta Key, FL
Wander Siesta Key Bayfront
Next avail.
Jan 16 - Jan 22
47
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Feb 9 - Feb 11
622
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Jan 24 - Jan 26
312
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Feb 14 - Feb 16
622
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Feb 21 - Feb 23
722
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Feb 14 - Feb 16
310
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Feb 14 - Feb 16
312
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Feb 21 - Feb 23
412
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Feb 7 - Feb 9
824
Highlights in Siesta Key
Discover the award-winning white-sand beaches, vibrant village life, and stunning Gulf sunsets that make this barrier island a paradise.
Siesta Beach
Siesta Key Village
Crescent Beach
Point of Rocks
Turtle Beach
Siesta Key Drum Circle
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 Dunes
Next avail.
Feb 9 - Feb 11
622
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Jan 20 - Jan 22
722
Siesta Key, FL
Wander Siesta Key Bayfront
Next avail.
Jan 16 - Jan 22
47
Siesta Key, Florida
Wander Siesta Key Sunset
Next avail.
Jan 31 - Feb 2
310
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Jan 24 - Jan 26
312
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Jan 19 - Jan 21
412
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Jan 19 - Jan 21
716
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Jan 29 - Jan 31
824
Most popular amenities for private pool vacation rentals in Siesta Key
More popular private pool destinations near Siesta Key
Other popular amenities & vacation types in Siesta Key
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.
FAQs: Vacation Rentals in Siesta Key
Why should I book a Wander in Siesta Key over other private pool vacation rentals?
Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.
Every home in Siesta Key delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?
Which are Wander’s most popular private pool vacation rentals in Siesta Key?
Some of our most popular private pool vacation rentals in Siesta Key include Wander Siesta Key Palms, Wander Siesta Key Sunset, and Wander Siesta Key Retreat. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.
How many different private pool vacation rentals does Wander have available in Siesta Key?
Wander offers 10 private pool vacation rentals in Siesta Key, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.
What time is check-in and check-out at Wander’s private pool vacation rentals in Siesta Key?
You can check-in to Wander private pool vacation rentals in Siesta Key after 4.00pm and check-out before 10.00am.
Do Wander’s private pool vacation rentals in Siesta Key have WiFi access?
Yes. Every Wander home in Siesta Key has ultra fast, reliable WiFi so you can stay connected throughout your stay.
What is Wander’s cancellation policy?
You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.