Holiday Homes in Kissimmee

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Kissimmee

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1617)
"Loved the location and friendly staff!"
The Berkley, Orlando

Orlando Renters

3.5 star property
6.2 out of 10, (86)
"Very beautiful. Everything was nice and clean. I would recommend future guest to bring the own towels and extra toiletries. "
Orlando Renters

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (132)
"The place is beautiful, clean and Romy for a big family"
Formosa Valley Resort by UNE Homes

Encore Resort

4.0 star property
6.4 out of 10, (114)
"It was a very nice home. My family had a great time"
Encore Resort

Kissimmee Maingate Area Pool Homes by SVV

3.5 star property
8.6 out of 10, Excellent, (338)
"We had a wonderful stay. Property was very clean and located in a nice, quiet neighborhood. We appreciated that the property owners left a few essentials to hold us over until we could shop (TP/PT, hand soap, dish soap and sponges, trash bags, etc.) Property owners were very responsive to any questions or requests that we had. If I had one complaint, it would be with the pack and play that was provided. This thing has seen a LOT of miles and should be replaced, but it looks like I wasn’t...
Kissimmee Maingate Area Pool Homes by SVV

Marvelous Villa with Galactic Themed Bedroom at Encore

9.0 out of 10, Wonderful, (38)
"Property was just as advertised, spacious and comfortable in a new resort neighborhood. The kids, ages 4-10 had a blast in the Star Wars themed bedroom and garage game room. Pool was lovely even though we didn’t use much. Only a 20 minute ride to Disney parks and plenty of stores and restaurants nearby. Can’t say enough good things about resort staff from guards to management company. "
Marvelous Villa with Galactic Themed Bedroom at Encore

MO800 Champions Gate 5 Bedroom bathroom 5 Private Pool & Jaccuzi, Free Waterpark

9.0 out of 10, Wonderful, (65)
"Greatcstay"
MO800 Champions Gate 5 Bedroom bathroom 5 Private Pool & Jaccuzi, Free Waterpark

Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground

10.0 out of 10, Exceptional, (138)
"This house was wonderful - plenty of space & activities for the whole family "
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground

Sophisticated 4 En Suites w/ Private Hot Tub

9.8 out of 10, Exceptional, (10)
"We had a spectacular time in this home. It’s beautiful and it looks exactly like the pictures. We had everything that we needed and it’s in a great location. "
Sophisticated 4 En Suites w/ Private Hot Tub

Private Pool Home w/Lake View! 10min Disney! *FREE WaterPark*

9.0 out of 10, Wonderful, (27)
"Great location, nicely appointed "
Private Pool Home w/Lake View! 10min Disney! *FREE WaterPark*

Family-Friendly Home - 6 Mi to Disney!

9.2 out of 10, Wonderful, (24)
"Great stay with friends"
Family-Friendly Home - 6 Mi to Disney!

Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze

9.6 out of 10, Exceptional, (20)
"Great value and property. As advertised, thanks!"
Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze

The Bear's Den Resort Orlando

5.0 star property
7.6 out of 10, Good, (20)
"Check-in and check-out were easy. The staff was very accommodating. The home is stunningly beautiful and clean. We loved every moment of our stay and will return!"
The Bear's Den Resort Orlando

☼ Luxury Home * Private Pool ☼ 3 Miles from Disney - 200 5-Star Reviews ★ ★★ ★★

9.6 out of 10, Exceptional, (239)
"House was good. A few towels seemed stained when we arrived. Front door there was a gap inbetween the door and the wall, kind of made me feel a little uneasy. Besides that overall good stay for 4 people. "
☼ Luxury Home * Private Pool ☼ 3 Miles from Disney - 200 5-Star Reviews ★ ★★ ★★

Maple Leaf Inn & Suites

2.5 star property
7.0 out of 10, Good, (59)
"Not nearly as nice as advertised. Appeared to have long term tenants. Owner was nice. All of the cats outside were cute."
The price is AU$127
includes taxes & fees
2 Jan - 3 Jan 2025
Maple Leaf Inn & Suites

3 Bedrooms/ 3 Bathrooms/ The Hub (3205 TT)

10.0 out of 10, Exceptional, (13)
"It was a clean rental and well maintained. We had problems with some light fixtures in the kitchen being broken (not by us) when we got to the rental. I always like to check the whole property for any damages and we found that light broken hanging and shower doors weren’t installed properly etc but it is in a good neighborhood and close to most of the Disney world parks. The host would have good communication with us , as we explained what we had found when we got to the property. I would...
The price is AU$675
includes taxes & fees
14 Jan - 15 Jan 2025
3 Bedrooms/ 3 Bathrooms/ The Hub (3205 TT)

Spacious Vacation Home 20 min from Theme Parks!

9.4 out of 10, Exceptional, (33)
"The house was very nice and clean. Lots of space and the outside was well kept. The location is in a good area but it is right on a busy road so be careful parking or try to back in to the driveway. The only complaint I have is that the sprinklers system made a whistling noise at 6am in two of the rooms and with me and two others being light sleepers we couldn’t go back to bed. The beds were comfortable and the bathrooms were clean. If you have any girls with makeup on ensure to bring your own...
The price is AU$618
includes taxes & fees
8 Jan - 9 Jan 2025
Spacious Vacation Home 20 min from Theme Parks!

Perfect Home Near Disney, Amazing Amenities 2+2

9.0 out of 10, Wonderful, (16)
"Absolutely recommend everything about this place/area. Internet was a little troublesome on the main floor…but who’s really there for that. The entire process was effortless, thanks to the hosts. The condo was exactly as described. Super quaint, lovely color schemes, accents, and an all around comforting vibe. Can’t beat it. "
Perfect Home Near Disney, Amazing Amenities 2+2

Reunion Modern Sanctuary - Stunning Four Seasons Inspired Pool Oasis Home

9.8 out of 10, Exceptional, (20)
"Had 12 friends get together for a golf trip. Plenty of space in the house for all of us. And great proximity to several nice golf courses"
Reunion Modern Sanctuary - Stunning Four Seasons Inspired Pool Oasis Home

10min To Disney, Private Pool, Security Gated, Luxury stay in Kissimmee Orlando

9.4 out of 10, Exceptional, (77)
"Great place to stay. Close to Disney and a beautiful gated community. We had 10 in our party my kids and grandkids and it worked out perfect. Plenty of space and the 4 bathrooms was a big plus getting ready with teens. I give it a 5 star for location and size. "
10min To Disney, Private Pool, Security Gated, Luxury stay in Kissimmee Orlando
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Kissimmee
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Kissimmee

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1120)
"Very nice property that felt like a home. Close to all the parks and lots of shopping and dining option’s."
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1401)
"El hotel está en un lugar muy bueno bien cerca de los parques , el hotel está muy limpio con muchas condiciones muy limpio y un muy buen precio "
Vacation Village at Parkway

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1617)
"Loved the location and friendly staff!"
The Berkley, Orlando
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.