Luxury Vacation Rentals with a Private Pool in Kissimmee
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 41 private pool vacation rentals – enter your dates for availability.
Kissimmee, Florida
Wander Orlando Grand
Next avail.
Dec 14 - Dec 16
512
Kissimmee, Florida
Wander Orlando Golden
Next avail.
Dec 2 - Dec 5
1028
Kissimmee, Florida
Wander Orlando Horizon
Next avail.
Dec 2 - Dec 5
719
Kissimmee, Florida
Wander Orlando Bliss
Next avail.
Dec 2 - Dec 5
1024
Kissimmee, Florida
Wander Orlando Springs
Next avail.
Dec 2 - Dec 6
822
Kissimmee, Florida
Wander Orlando Sol
Next avail.
Dec 8 - Dec 11
1023
Kissimmee, Florida
Wander Orlando Haven
Next avail.
Dec 2 - Dec 5
410
Kissimmee, Florida
Wander Orlando Manor
Next avail.
Dec 2 - Dec 5
828
Welcome to private poolside luxury in Kissimmee
Slip into resort mode with luxury private-pool vacation rentals in Kissimmee, Florida. Each Wander home pairs the polish of a five-star stay with the privacy of your own poolside retreat. Expect hotel-grade amenities, ultra fast WiFi, dedicated workspaces, and flawless operations backed by 24/7 concierge.
Think sunlit great rooms that open to screened lanais, heated pools with spillover spas, and outdoor lounges built for all-day relaxation. Chef-ready kitchens, premium linens, and thoughtful smart-home touches come standard. Every property looks exactly like the photos and is maintained to the highest standard, so all you have to do is arrive.
Kissimmee, Florida
Wander Orlando Oasis
Next avail.
Dec 2 - Dec 4
1140
Kissimmee, Florida
Wander Orlando Paradise
Next avail.
Dec 2 - Dec 5
1036
Kissimmee, Florida
Wander Orlando Estate
Next avail.
Dec 13 - Dec 19
1246
Kissimmee, Florida
Wander Orlando Palace
Next avail.
Dec 5 - Dec 9
924
Kissimmee, Florida
Wander Orlando Cove
Next avail.
Dec 14 - Dec 16
1436
Kissimmee, Florida
Wander Orlando Palmer
Next avail.
Dec 6 - Dec 8
510
Kissimmee, Florida
Wander Orlando Sanctuary
Next avail.
Dec 2 - Dec 5
1228
Kissimmee, Florida
Wander Orlando Tropic
Next avail.
Dec 2 - Dec 5
1031
Kissimmee, Florida
Wander Orlando Dream
Next avail.
Dec 7 - Dec 10
716
Kissimmee, Florida
Wander Orlando Starlight
Next avail.
Dec 4 - Dec 7
924
Kissimmee, Florida
Wander Orlando Treasure
Next avail.
Dec 7 - Dec 10
822
Kissimmee, Florida
Wander Orlando Enchanted
Next avail.
Jan 28 - Feb 2
816
Kissimmee, Florida
Wander Orlando Manor
Next avail.
Dec 2 - Dec 5
828
Kissimmee, Florida
Wander Orlando Bliss
Next avail.
Dec 2 - Dec 5
1024
Kissimmee, Florida
Wander Orlando Blaze
Next avail.
Jan 28 - Feb 6
820
Kissimmee, Florida
Wander Orlando Horizon
Next avail.
Dec 2 - Dec 5
719
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 Kissimmee
Kissimmee, Florida
Wander Orlando Grand
Next avail.
Dec 14 - Dec 16
512
Kissimmee, Florida
Wander Orlando Golden
Next avail.
Dec 2 - Dec 5
1028
Kissimmee, Florida
Wander Orlando Horizon
Next avail.
Dec 2 - Dec 5
719
Kissimmee, Florida
Wander Orlando Bliss
Next avail.
Dec 2 - Dec 5
1024
Kissimmee, Florida
Wander Orlando Springs
Next avail.
Dec 2 - Dec 6
822
Kissimmee, Florida
Wander Orlando Sol
Next avail.
Dec 8 - Dec 11
1023
Kissimmee, Florida
Wander Orlando Haven
Next avail.
Dec 2 - Dec 5
410
Kissimmee, Florida
Wander Orlando Manor
Next avail.
Dec 2 - Dec 5
828
Discover more beyond the pool in Kissimmee
Central Florida energy meets lakeside tranquility in Kissimmee. Here, blue-sky days stretch long and warm, setting the scene for boating on Lake Tohopekaliga, kayaking Shingle Creek, and airboat rides through the headwaters of the Everglades. Championship golf, family attractions, and year-round events keep the pace lively.
When you want a change of scenery, explore brick-lined streets in Celebration, classic car nights at Old Town, and open-air shopping and dining from Promenade at Sunset Walk to Disney Springs. With easy access to Orlando’s marquee parks and a calmer, residential feel at home base, Kissimmee makes vacation time feel effortless. This is why Wander’s luxury private-pool vacation rentals in Kissimmee, Florida are the perfect choice, whether you’re traveling for work or leisure.