Luxury Vacation Rentals for Large Groups 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 6 large group vacation rentals – enter your dates for availability.
Siesta Key, Florida
Wander Siesta Key Haze
Next avail.
Dec 3 - Dec 9
511
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Dec 19 - Dec 21
412
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 2 - Dec 4
716
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 8 - Dec 10
722
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Dec 8 - Dec 10
622
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Dec 7 - Dec 9
824
Welcome to your large group retreat in Siesta Key
Bring everyone together on Siesta Key with stays designed for a crowd. Our luxury vacation rentals in Siesta Key feature expansive living areas, multiple ensuite bedrooms, and flexible sleeping arrangements so groups can spread out with ease. Expect chef-ready kitchens for shared meals, long dining tables, and smooth indoor to outdoor flow to pool terraces and lounges.
Every Wander is operated to hotel standards for stress-free group travel. Count on ultra fast WiFi for many devices, pristine cleaning, and 24/7 concierge support that keeps plans on track. With private pools, fitness spaces, and thoughtful touches throughout, it is effortless to host reunions, retreats, or milestone celebrations without compromise.
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 2 - Dec 4
716
Siesta Key, Florida
Wander Siesta Key Haze
Next avail.
Dec 3 - Dec 9
511
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Dec 19 - Dec 21
412
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 8 - Dec 10
722
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Dec 8 - Dec 10
622
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Dec 7 - Dec 9
824
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Dec 19 - Dec 21
412
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 5 - Dec 7
716
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 12 - Dec 14
722
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Dec 12 - Dec 14
622
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Dec 12 - Dec 14
824
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 Haze
Next avail.
Dec 3 - Dec 9
511
Siesta Key, Florida
Wander Siesta Key Breeze
Next avail.
Dec 19 - Dec 21
412
Siesta Key, Florida
Wander Siesta Key Sands
Next avail.
Dec 2 - Dec 4
716
Siesta Key, Florida
Wander Siesta Key Palms
Next avail.
Dec 8 - Dec 10
722
Siesta Key, Florida
Wander Siesta Key Dunes
Next avail.
Dec 8 - Dec 10
622
Siesta Key, Florida
Wander Siesta Key Retreat
Next avail.
Dec 7 - Dec 9
824
Discover more large groups activities in Siesta Key
Sugar-soft quartz sand that stays cool underfoot and water tinted a vivid turquoise make Siesta Key unforgettable. From the wide expanse of Siesta Beach to the quieter stretches of Crescent and Turtle Beach, there is a shoreline for sunrise walks, lazy afternoons, and spectacular, flame-colored sunsets. Point of Rocks rewards low-tide explorers with tide pools and clear shallows.
Calm Gulf conditions invite paddleboarding and kayaking, while the Intracoastal side brings dolphins and seabirds into view. The relaxed island pace pairs with easy access to Sarasota’s cultural scene across the bridges, creating a rare blend of beach ease and city polish. This is why Wander’s luxury vacation rentals in Siesta Key are the perfect choice, whether you are traveling for work or leisure.