Kissimmee Vacation Rentals

    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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Kissimmee Vacation Homes

The Berkley, Orlando
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1599)
"The pool area was a great spot to relax! Lots of chairs, tables and loungers! We would definitely recommend this resort! "
The Berkley, Orlando
"Enchanted Escape" - 4 Massage Chairs & Peloton
Outdoor pool, a heated pool
"Enchanted Escape" - 4 Massage Chairs & Peloton
10.0 out of 10, Exceptional, (15)
"Everything was exactly as advertised. I was a total bridezilla prior to check in and Russ was exceptionally communicative, helpful, and patient. Will definitely book again next time!"
"Enchanted Escape" - 4 Massage Chairs & Peloton
Orlando Home w/ Lake View, Pool & Game Room!
Highchair
Orlando Home w/ Lake View, Pool & Game Room!
9.2 out of 10, Wonderful, (45)
"Wonderful stay , clean house, however there was no hot water in the master bathroom shower. There was hot water in the sink but not the shower."
Orlando Home w/ Lake View, Pool & Game Room!
Cozy Single Home with BBQ, Private Pool & Hot Tub
A heated pool
Cozy Single Home with BBQ, Private Pool & Hot Tub
9.2 out of 10, Wonderful, (13)
"The communication from Vitor is excellent. The payment process was uncomfortable for me. The payment process insisted you share a photo holding your the credit card - both a front view and a back view of the card - This was non negotiable. This was our 9th visit to Orlando, so I have a lot of places to compare this to. First the great bits: The master bed was the most comfortable bed I have ever slept in and the quality of the bedding was lovely. The two queen rooms had very comfortable beds...
Cozy Single Home with BBQ, Private Pool & Hot Tub
Hidden Gem in the heart of Kissimmee! Pet and child friendly!
Exterior
Hidden Gem in the heart of Kissimmee! Pet and child friendly!
8.4 out of 10, Very good, (15)
"We were evacuating from the West Coast for the latest Hurricane...comfortable place and responsive host. Thank you."
Hidden Gem in the heart of Kissimmee! Pet and child friendly!
Kissimmee Maingate Area Pool Homes by SVV
Outdoor pool
Kissimmee Maingate Area Pool Homes by SVV
3.5 star property
8.6 out of 10, Excellent, (336)
"Our stay at this vacation home was overall enjoyable. The house itself was excellent—well-maintained, comfortable, and equipped with everything we needed for a relaxing getaway. Communication with the owners was outstanding; they were responsive and helpful throughout our stay, which we greatly appreciated. However, the pool area was a significant disappointment. The pool had large holes—one in the shallow end and another in the deep end—which made it unsafe and less enjoyable, especially for...
Kissimmee Maingate Area Pool Homes by SVV
Sophisticated 4 En Suites w/ Private Hot Tub
Pool
Sophisticated 4 En Suites w/ Private Hot Tub
9.8 out of 10, Exceptional, (9)
"Everything was as advertised. Place was very clean and modern. Very nice accommodations. Would definitely stay there again."
Sophisticated 4 En Suites w/ Private Hot Tub
Brand New 6BD, Gameroom / Movie Theater And Pool
A heated pool
Brand New 6BD, Gameroom / Movie Theater And Pool
9.4 out of 10, Exceptional, (8)
"Wr are locals we had a cruise book as of 1year ago and it was cancelled last minute due to maintenance issues. Our daughter found this home and it did not disappoint. We stayed 5days. The house was spectacular from the themed rooms to the movie theater and game room there was somwthing to do for everyone. The pool was good also. The location was close to all attractions. The amenities that are included was awesome too. Thank you for allowing us to still have our family vacation. The house was...
Brand New 6BD, Gameroom / Movie Theater And Pool
9008 Paradise Palms Blissful Haven: 5-Bed Oasis of Luxury and Tranquility
A heated pool
9008 Paradise Palms Blissful Haven: 5-Bed Oasis of Luxury and Tranquility
8.0 out of 10, Very good, (7)
"Beautiful home, close to the parks"
9008 Paradise Palms Blissful Haven: 5-Bed Oasis of Luxury and Tranquility
Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen
Outdoor pool, a heated pool
Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen
10.0 out of 10, Exceptional, (18)
"We all enjoyed our stay here"
The price is CA $278
CA $657 total
includes taxes & fees
Dec 13 - Dec 14
Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen
Superb Townhouse Newly Renovated 1.5 miles to Disney
Pool
Superb Townhouse Newly Renovated 1.5 miles to Disney
9.8 out of 10, Exceptional, (91)
"Great place "
The price is CA $96
CA $299 total
includes taxes & fees
Dec 8 - Dec 9
Superb Townhouse Newly Renovated 1.5 miles to Disney
Resort 4 Bed Pool/Spa Villa
Exterior
Resort 4 Bed Pool/Spa Villa
9.0 out of 10, Wonderful, (19)
"Good stay"
Resort 4 Bed Pool/Spa Villa
Spacious Home with Fun Decore and Game Room-4544TB
A heated pool
Spacious Home with Fun Decore and Game Room-4544TB
9.0 out of 10, Wonderful, (14)
"The house was great and had tons of room for our family. We were just a little disappointed in the fact that where weren't many supplies or appliances to accommodate our stay. We had to go buy more towels and some cookware so we could cook at the house. The air-hockey table did not work and was very wobbly so the kids didn't get to play that and the pool table was also wobbly but manageable. We did also have to go buy batteries for all the remotes due to them being dead which is minor. Over all...
Spacious Home with Fun Decore and Game Room-4544TB
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
Outdoor pool, a heated pool
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
9.8 out of 10, Exceptional, (170)
"Had a great stay , would definitely stay here again . Great location for the parks and lots of restaurants close by . Very comfy beds and had everything in the property that we needed . The resort is very nice as well with a lovely pool . In all a great place to stay . "
Stunning 5 Bedroom townhome in prime location- Paradise Palms resort community!
Private Pool in Amazing Resort Near Disney Sleeps 8
Pool
Private Pool in Amazing Resort Near Disney Sleeps 8
9.6 out of 10, Exceptional, (7)
"My daughter's wedding took place at Cocoa Beach, Florida. This property was a gem! Only 30 minutes from the MCO Orlando Airport. We had quick access to major routes into Orlando. There are also many outlet shops, grocery, and restaurants within 5-10 minutes from the condo. I highly recommend you stay here!"
Private Pool in Amazing Resort Near Disney Sleeps 8
Newly Renovated-Star Wars Theme Theater & Bedrooms
8 bedrooms, iron/ironing board, travel crib, free WiFi
Newly Renovated-Star Wars Theme Theater & Bedrooms
10.0 out of 10, Exceptional, (6)
"The Star Wars theme was excellent. The game room was terrific. The pool was perfect. The hurricane was not, but who can control the weather! If we're ever back in Orlando area looking for a place for a large group, we would definitely return to this property."
Newly Renovated-Star Wars Theme Theater & Bedrooms
Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560
Water park
Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560
2.5 star property
Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560
Formosa Valley Resort by UNE Homes
Private pool
Formosa Valley Resort by UNE Homes
4.0 star property
9.4 out of 10, Exceptional, (128)
"My family and I really enjoyed our stay. Would definitely stay!"
Formosa Valley Resort by UNE Homes
14 Bedroom mansion that sleeps 40 people. Host your wedding reception here
Outdoor pool, a heated pool
14 Bedroom mansion that sleeps 40 people. Host your wedding reception here
10.0 out of 10, Exceptional, (18)
"We had an amazing stay! From the moment we walked in, we were greeted with a cozy, clean, and beautifully decorated space that made us feel right at home. We hosted our pre-wedding events here, and the house had everything we needed for a memorable celebration with family and friends. Communication with the host was seamless; they were always quick to respond and ensured we had all the essentials. The location was perfect too – close to everything but still peaceful and private. We can’t wait...
The price is CA $559
CA $1,963 total
includes taxes & fees
Dec 2 - Dec 3
14 Bedroom mansion that sleeps 40 people. Host your wedding reception here
Stunning Home with Private Pool/Pool Spa, Golf Course View, & Home Theater
A heated pool
Stunning Home with Private Pool/Pool Spa, Golf Course View, & Home Theater
9.0 out of 10, Wonderful, (92)
"We've stayed here for the last 2 years now. Great location and big house that suits our needs well. There are several areas that are in need of what I'd consider general and routine maintenance that have not been done. Curtain rods falling out of walls, dishwasher not leaking (a lot), toilet paper holders broken, bathroom floors not clean, an advertised video room with circa 1995 video and NO sound system. In general, proper maintenance on a periodic basis is all that's needed. Our team of...
Stunning Home with Private Pool/Pool Spa, Golf Course View, & Home Theater
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
Sign in
Sign up, it's free

Other property types in Kissimmee

Seralago Hotel & Suites Main Gate East
2 outdoor pools, a heated pool, sun loungers
Seralago Hotel & Suites Main Gate East
3.0 star property
5.2 out of 10, (5565)
"I had to wait 20 minutes for the front counter lady to come in from smoking. The security guard was sitting in the lobby playing on his phone and he just kept saying she will be back soon.. Then she told me I had booked a double bed room and I said no I booked a family suite.. So I had to show her my email and she said well I don't know why they put you in another room, let me make sure I have a clean one.. After standing in the lobby for a total of 40 minutes (including her smoke break time), I...
The price is CA $55
CA $91 total
includes taxes & fees
Nov 24 - Nov 25
Seralago Hotel & Suites Main Gate East
Ramada by Wyndham Hotel & Water Park
Water park
Ramada by Wyndham Hotel & Water Park
3.0 star property
6.8 out of 10, (1298)
"The perfect size waterpark for families with kids. Good value. "
The price is CA $99
CA $165 total
includes taxes & fees
Dec 7 - Dec 8
Ramada by Wyndham Hotel & Water Park
Margaritaville Resort Orlando Cottages by Rentyl
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (1084)
"This is our third time staying at Margaritaville (cottage the first time, villas the second and third time); I must say this villa was the least taken care of. It wasn’t super clean and the slider had some damage regarding opening/closing the blinds and locking/unlocking the sliding glass door. The front door didn’t have a safety lock at all (it looked to have been removed) so that made us a little uneasy. Our bed (queen) was very bouncy and it seemed to cave a little in the middle. Overall, it...
Margaritaville Resort Orlando Cottages by Rentyl
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
Unlock Black Friday deals