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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 2655 Condo Rentals in Kissimmee with updated reviews, rates, and availability.

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (2013)
"Very family vibe, highly recommend "
The price is $97
includes taxes & fees
$86 per night
May 4 - May 5
Vacation Village at Parkway
Caribe Cove Resort
Outdoor pool, a heated pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2249)
"our stay was amazing minus the condensation pipe leaking in the laundry room "
Caribe Cove Resort
Lifetime of Vacations Resort
Lake

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (129)
"We needed to stay for two days til our flight. I was really impressed with the grounds worker, he was constantly working and keeping the property spotless. The pool area was nice and I loved the screened in porch in the back of our unit."
Lifetime of Vacations Resort
High Point World Resort
Outdoor spa tub

High Point World Resort

3.5 star property
8.8 out of 10, Excellent, (170)
"great place to stay!"
High Point World Resort
Spacious Luxury Condo in Windsor Hills Resort! 2 Miles to Disney! 3bed/2bath
A heated pool

Spacious Luxury Condo in Windsor Hills Resort! 2 Miles to Disney! 3bed/2bath

10.0 out of 10, Exceptional, (106)
"This property was perfect for what we were looking for. Nice, close to Disney and excellent facilities. "
Spacious Luxury Condo in Windsor Hills Resort! 2 Miles to Disney! 3bed/2bath
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
Outdoor pool

Windsor Poolside Escape with Stunning Pool View-Perfect for Families!

2.0 star property
10.0 out of 10, Exceptional, (285)
"Condo"
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
Berkley Lake Townhomes
2 outdoor pools, a heated pool, open 8:00 AM to 7:00 PM, sun loungers

Berkley Lake Townhomes

3.0 star property
8.4 out of 10, Very Good, (429)
"The property was excellent and condo was very nice however I wish there was more soap to wash hands and dishes. Also , there was no soap for dish washer and laundry. There were no gargage bags to replace. In order to cook, you need to buy everything yourself like solt, pepper and oil. Even the toilet paper was limited. We asked for cutting board and frying pen and were promised tomorrow which never happed. Other than that the condo was nice. I think the kitchen needs upgrade like dishwasher."
Berkley Lake Townhomes
Ground floor 3 bed condo close to pool and WATER PARK in Windsor Hills Resort
Sport court

Ground floor 3 bed condo close to pool and WATER PARK in Windsor Hills Resort

9.6 out of 10, Exceptional, (106)
"Very nice resort that is convenient to all the parks. Only a 10 to 15 minute drive to Disney and 20 minutes to Sea World. The onsite water park is great with heated pool, hot tub, and water slides. The condo was very nice, clean, and well maintained."
Ground floor 3 bed condo close to pool and WATER PARK in Windsor Hills Resort
Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park
Outdoor pool, a heated pool

Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park

9.4 out of 10, Exceptional, (109)
"We loved our stay at this condo. Kid friendly. Close to shopping and the Magic Kingdom"
Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park
Ground floor 3 bed condo close to POOL and WATER PARK in Windsor Hills Resort
Pool

Ground floor 3 bed condo close to POOL and WATER PARK in Windsor Hills Resort

9.0 out of 10, Wonderful, (29)
"Overall, everything was excellent. The bedding, especially in the master suite could use an upgrade."
Ground floor 3 bed condo close to POOL and WATER PARK in Windsor Hills Resort
Finding Nemo Themed Room | 5 Miles to Disney
A heated pool

Finding Nemo Themed Room | 5 Miles to Disney

9.4 out of 10, Exceptional, (3)
"Pro: Easy check in process. Listing described as presented. Con: floors needed a good cleaning. 3 yo’s feet were dirty from walking on floor. Blankets used for spread on bed need to be cleared. "
Finding Nemo Themed Room | 5 Miles to Disney
Modern & comfortable, 5 mins to Disney. WiFi, water slides, pool, sports.
A heated pool

Modern & comfortable, 5 mins to Disney. WiFi, water slides, pool, sports.

9.4 out of 10, Exceptional, (66)
"The property is at a perfect location for Disney's Magic Kingdom, 10 - 15 min. drive.Nice quiet gated community with great pool and water slides for the kids at the club house.Walmart near by for grocery shopping."
Modern & comfortable, 5 mins to Disney. WiFi, water slides, pool, sports.
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
Exterior

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

9.2 out of 10, Wonderful, (131)
"Place was everything we were hoping for!! Very close to all the Disney places. Pool and area was clean and easy too acces. Furniture was a bit outdated, but we spent most of the time out side anyway. The little store and restaurant were stocked well, and the food was delicious!!"
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
EPIC 12 Bedroom Home with Private Pool!
Pool

EPIC 12 Bedroom Home with Private Pool!

10.0 out of 10, Exceptional, (5)
"Host was very easy to get in touch with. Great property! Plenty of Room for out large group of 22. Great for Adults, kids, and infants. Great Experience. Would definitely rent again!"
EPIC 12 Bedroom Home with Private Pool!
CHRIS & SUE'S CONDO AT WINDSOR PALMS 3 MILES FROM DISNEY AND ALL IT'S MAGIC
A heated pool

CHRIS & SUE'S CONDO AT WINDSOR PALMS 3 MILES FROM DISNEY AND ALL IT'S MAGIC

9.6 out of 10, Exceptional, (151)
"Overall we didn’t spend a lot of time at the condo but the condo it self was great the only problem we encountered was parking. After 6pm you won’t be able to find parking anywhere near the condo which was little upsetting since we were 3rd floor. We had to park a nice ways away but I do understand there was a lot of other family’s staying there too. It was a very nice neighborhood and it was quite at night very nice for the price. "
CHRIS & SUE'S CONDO AT WINDSOR PALMS 3 MILES FROM DISNEY AND ALL IT'S MAGIC
STAR WARS first floor 3 bedroom condo in a Galaxy just 2 miles from Disney World
Exterior

STAR WARS first floor 3 bedroom condo in a Galaxy just 2 miles from Disney World

9.2 out of 10, Wonderful, (92)
"We had a fabulous time. The condo was a perfect homebase for daytrips to the Gulf beaches and to Bok Tower Gardens. Windsor Hills ameneties are top notch. We loved starting our days lounging poolside. "
STAR WARS first floor 3 bedroom condo in a Galaxy just 2 miles from Disney World
Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal
Pool

Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal

9.8 out of 10, Exceptional, (71)
"Enjoyed our stay."
Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal
Beautiful 3 bed condo over the lake in Oakwater Resort - just 2 miles from WDW.
Pool

Beautiful 3 bed condo over the lake in Oakwater Resort - just 2 miles from WDW.

9.4 out of 10, Exceptional, (112)
"Stayed 5 nights mid March 2025. Party was 4 adults and 3 children. Property was conveniently located to Parks and other amenities. Clean and as shown in the pictures. The entire living area is on 2nd floor as they pointed out, so if you can’t do stairs, it would not be the best. Parking in the driveway in front is very convenient. The unit is very nice, we had good communication with the managers, and enjoyed our stay! Thank you!!"
Beautiful 3 bed condo over the lake in Oakwater Resort - just 2 miles from WDW.
🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝
Outdoor pool, a heated pool

🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝

9.8 out of 10, Exceptional, (247)
"Everything was very clean and well maintained. Check in process very smooth. Loved the pool area. Owners great with communication. Excellent location. Highly recommend! "
🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝
3121 308 - 3 Bedroom Corner Condo Overlooking Pond in Storey Lake Resort
A heated pool

3121 308 - 3 Bedroom Corner Condo Overlooking Pond in Storey Lake Resort

9.8 out of 10, Exceptional, (39)
"We loved our stay here! The condo is just as pictured, but even larger than expected. The lazy river waterpark/club is wonderful. They hosted a memorable spray bubble foam Easter egg hunt that was such fun for the kids! Our 8 year old liked her time there more than Disney. Short, pleasant drive to Disney. betteDisneyDiDisneyDisneyhadrive."
3121 308 - 3 Bedroom Corner Condo Overlooking Pond in Storey Lake Resort
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.
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Other property types in Kissimmee

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (2013)
"Very family vibe, highly recommend "
The price is $97
includes taxes & fees
$86 per night
May 4 - May 5
Vacation Village at Parkway
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.2 out of 10, Wonderful, (68)
"This was my second time staying here and each time was a great stay.. "
The price is $130
includes taxes & fees
$114 per night
May 1 - May 2
Barefoot'n Resort Kissimmee Orlando
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1357)
"It was a great place, great outdoor private pool for the area surrounding our villa and close to all Disney parks "
The price is $863
includes taxes & fees
$760 per night
May 2 - May 3
Margaritaville Cottages Orlando with H2O Waterpark 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.

Frequently asked questions

How much do condos in Kissimmee cost?
You can expect to pay from $97 to $97 per night for condos in Kissimmee. Whatever your budget, an epic stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best condos in Kissimmee?
Pick from multiple condos in Kissimmee with a total average guest review rating of 9.3. Berkley Lake Townhomes comes highly recommended if you’ve brought the entire family or you simply like to spread out. This 3-star stay also has pool sun loungers and an espresso maker. Lovely Vacation Townhouse With Private Pool Sl3103 is another top option. It has a 3.5-star rating and amenities such as a swimming pool and a terrace.
How many condos are there in Kissimmee?
Use up your vacation days and pick from 2655 condos in Kissimmee. For an official business trip, a family getaway or anything in between, Expedia can help you find an ideal stay in just a few clicks.