Kissimmee’s Most Enticing Vacation Home Pools

At the Bear’s Den, you're not just getting a pool – you’re getting a backyard oasis. This eight-bedroom stunner boasts a private heated pool with a spa and not one, but two firepits to keep the evening chill at bay. Perfect for big families or groups, the summer kitchen makes outdoor cooking a breeze. And when you want a change of scenery, the resort's amazing pools and cabanas are just a hop, skip, and a cannonball away.

This Reunion Resort gem is literally built for vacation, featuring a custom-built pool with a spillover spa, waterfall splash pad, and even two water cannons. Who needs a water park when your backyard looks like this? The summer kitchen is ideal for grilling up a feast, and the outdoor dining area ensures you can enjoy meals al fresco. Plus, access to the resort water park means the fun doesn’t stop at your doorstep.

If you think bigger is better, the Reunion Resort’s 18000 property is your dream come true. Imagine a night swim in a pool with a sunken firepit – it’s the ultimate in vacation luxury. Accommodating up to 47 guests, this property ensures no one gets left out (though you might have to arm wrestle over the themed rooms). This colossal space combines two rental properties that can also be booked separately, perfect for any size group.

For families looking to maximize fun without blowing the budget, Elite Homes offers the perfect solution. This more affordable option features a private screened-in pool with a spillover jetted spa, ensuring both fun and relaxation. Guests also have access to the amenities at Bella Vida Resort, combining the best of private and resort-style living at hotel prices.

Eagle Bay at Reunion Resort offers a pool experience like no other, featuring a massive private pool with a connected lazy river. Float your worries away right in your backyard! And when you crave more adventure, the resort's 5-acre water park, complete with an even larger lazy river, awaits. This is where family fun meets ultimate relaxation.

Blast off into vacation mode at the Morlando Space Mansion, where the outdoor oasis includes a zero-entry pool with two slides, a cascading waterfall, and a grotto with a jetted spa on top. This space-themed paradise features a firepit, outdoor kitchen, covered lanai, and plenty of seating for all your intergalactic gatherings. It’s not just a stay – it’s an out-of-this-world experience.

Isolé Villas by Magical Vacation Homes brings a touch of elegance with its multi-level saltwater pools and a 60-foot swim lane perfect for morning laps or a fun race. The multi-level sundecks and covered outdoor dining and lounging spaces make this villa ideal for large reunions, team retreats, or any big gathering. Add in a pool table and yard games, and you’ve got the recipe for the perfect vacation.