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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Featured Condo Rentals in Kissimmee and around

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1994)
"always a nice vacation when we stay here"
The price is €89
includes taxes & fees
28 Apr - 29 Apr
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)
"place is awesome "
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)
"The condo was amazing, clean and spacious. The location was great with lots of great restaurants around and the clubhouse had lots of amenities. The pool area was great, neighborhood was clean and quiet. Loved all the extras the condo had. Lots of games and movies. Linen and the bedding were very comfortable. We would certainly stay again. "
The price is €334
includes taxes & fees
13 May - 14 May
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)
"Great place! Lots of small details made it perfect!"
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, pool loungers

Berkley Lake Townhomes

3.0 star property
8.4 out of 10, Very good, (429)
"My kids love it "
Berkley Lake Townhomes
Ground floor 3 bed condo close to pool and WATER PARK in Windsor Hills Resort
Sports court

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

9.6 out of 10, Exceptional, (106)
"It's a well maintained beautiful property at a great location.Location is prefect, 15 minutes drive from Magic Kingdom, near Walmart and other aminities. "
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)
"This place was accurately advertised. Being from out of town & not knowing the area, it was GREAT that this place was in a gated & secure area. This condo was accurately advertised, honestly, it was better! "
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)
"Condo was beautiful and clean. Close to everything and very convenient to all the Disney parks. "
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)
"This property exceeded our expectations and a short trip to Orlando. The furnishings were comfortable. The condo was clean. The communication with the host was excellent. They went above and beyond to provide us with everything we needed for a wonderful vacation."
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, (65)
"This place was really nice and welcoming"
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)
"We have stayed in this resort before for the proximity to Disney. The condo is clean and has enough bed space. "
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)
The price is €1,021
includes taxes & fees
28 Apr - 29 Apr
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, (150)
"Great clean close to parks"
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)
"As always, Windsor Hills is a wonderful community to stay in! Location to WDW is great. Loved being on the first floor - no steps after long day in the park. Communication from owners was great. Would definitely stay here again. "
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)
"The property was as shown and pleasant to stay in."
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)
"This place was clean and very nice. Hosts were very good at communicating. Very close and easy to get to Disney. Walmart is next door which was helpful for forgotten items. We would very much stay here again. "
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)
"Great location to Disney parks. Close to Walmart for easy grocery orders. Beds were super comfortable. Owner was very responsive to any questions prior to arrival and during our stay. Very comfortable size for my family of 4. Would stay again."
🏝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)
"Will stay again!"
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, (1994)
"always a nice vacation when we stay here"
The price is €89
includes taxes & fees
28 Apr - 29 Apr
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, (66)
"Resort like feel. "
The price is €114
includes taxes & fees
14 May - 15 May
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, (1353)
"Very nice and relaxing place for family vacation. "
The price is €879
includes taxes & fees
2 May - 3 May
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 €89 to €1,021 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 Holiday 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 holiday days and pick from 2657 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.