Luxury Vacation Rentals for Families 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 family vacation rentals – enter your dates for availability.
Siesta Key, FL, US
Wander Siesta Key Bayfront
Next avail.
Nov 17 - Nov 23
47
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 Haze
Next avail.
Dec 3 - Dec 9
511
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 2 - Dec 4
312
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
Welcome to family adventures in Siesta Key
Upgrade your family getaway with Wander’s luxury family vacation rentals in Siesta Key. Our collection features bright, contemporary homes with multiple bedrooms and flexible sleeping arrangements, so everyone from toddlers to teens has room to relax.
Expect hotel-grade comforts like pristine cleaning, premium linens, ultra fast WiFi, and 24/7 concierge service, paired with family-minded details such as spacious kitchens, generous living areas, and inviting outdoor spaces for alfresco meals. Every home looks just like the photos, making it easy to plan a seamless stay where quality time comes naturally.
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
Sarasota, FL, US
Wander Sarasota Keyview
Next avail.
Nov 29 - Dec 1
48
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 Sunset
Next avail.
Dec 12 - Dec 14
310
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 5 - Dec 7
312
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, FL, US
Wander Siesta Key Bayfront
Next avail.
Nov 17 - Nov 23
47
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 Haze
Next avail.
Dec 3 - Dec 9
511
Siesta Key, Florida
Wander Siesta Key Tides
Next avail.
Dec 2 - Dec 4
312
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
Discover more family fun in Siesta Key
Soft, cool-to-the-touch quartz sand and gentle Gulf waters make Siesta Key an effortless choice for families. The wide shoreline at Siesta Beach is ideal for sandcastles and strolls, while calm surf invites kids to splash with confidence amid sweeping Gulf views.
Variety is part of the charm. Explore the clear shallows around Point of Rocks near Crescent Beach, or find extra elbow room at Turtle Beach for shelling and laid-back afternoons. Bike-friendly roads, spectacular sunsets, and year-round warmth keep the pace easy from sunrise to starry evenings.
All of this is why Wander’s luxury family vacation rentals in Siesta Key are the perfect choice for reunions, school breaks, and long weekends.