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Our top choices for Winter Park condo rentals

Elegant Themed Hideaway/ Waterpark & Clubhouse

Elegant Themed Hideaway/ Waterpark & Clubhouse
Kissimmee
8.8 out of 10, Excellent, (6 reviews)
"This was an amazing stay at a very nice property! The property was very clean and the management was very welcoming and kind. Will definitely be staying here again. Thank you!"
United States
Steph G.
$534 nightly
The price is $570
Apr 20 - Apr 21
Total with taxes and fees
Elegant Themed Hideaway/ Waterpark & Clubhouse

Family Fun: Condo near Theme Parks & Pools!

Family Fun: Condo near Theme Parks & Pools!
Kissimmee
9.8 out of 10, Exceptional, (11 reviews)
"Very nice, clean, modern unit but very loud. Outside noise and neighboring units were distracting and everything in the unit echoed due to the tile floors and hard surfaces. Also, there unit only supplied 2 towels per bathroom for our 8 day stay."
United States
Karen B.
$268 nightly
The price is $300
Apr 10 - Apr 11
Total with taxes and fees
Family Fun: Condo near Theme Parks & Pools!

Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool

Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool
Lake Frederica
9.0 out of 10, Wonderful, (2 reviews)
"The property is in a good location. Easily accessible to places we wanted to visit. The condo was clean and ready for our arrival."
United States
Myra W.
$266 nightly
The price is $297
Apr 6 - Apr 7
Total with taxes and fees
Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool

Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park
South Eola
10.0 out of 10, Exceptional, (12 reviews)
"good area"
United States
Carlos F.
$156 nightly
The price is $173
Apr 5 - Apr 6
Total with taxes and fees
Lake Eola view 1 bedroom Thornton Park

Magical Moment Vacation Condos

Magical Moment Vacation Condos
4.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"Very Clean room staff were great !! Definitely would stay again !"
United States
stephanie
$331 nightly
The price is $374
Apr 28 - Apr 29
Total with taxes and fees
Magical Moment Vacation Condos

VISTA CAY RESORT 2BR/2BA UNIVERSAL

VISTA CAY RESORT 2BR/2BA UNIVERSAL
Orlando
9.2 out of 10, Wonderful, (92 reviews)
"Great location for going to Universal!"
United States
Jenna H.
$291 nightly
The price is $324
Apr 19 - Apr 20
Total with taxes and fees
VISTA CAY RESORT 2BR/2BA UNIVERSAL

Vintage 2 Bedroom 1.5 Bathroom Condo Lake View

Vintage 2 Bedroom 1.5 Bathroom Condo Lake View
South Eola
10.0 out of 10, Exceptional, (10 reviews)
"The condo was exceptionally clean and well-maintained, and the view was stunning. I would not hesitate to recommend this property to others and would gladly consider staying here again in the future."
United States
Laurie
$184 nightly
The price is $205
Apr 5 - Apr 6
Total with taxes and fees
Vintage 2 Bedroom 1.5 Bathroom Condo Lake View

Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay! Quiet and in a great neighborhood! "
United States
Nick L.
$166 nightly
The price is $184
Apr 5 - Apr 6
Total with taxes and fees
Renovated Condo Lake Eola View Great Location

LakeFront: BlueHeron Beach Resort, Orlando Florida

LakeFront: BlueHeron Beach Resort, Orlando Florida
Orlando
10.0 out of 10, Exceptional, (1 review)
"As advertised "
United States
Philip L.
$199 nightly
The price is $221
Apr 18 - Apr 19
Total with taxes and fees
LakeFront: BlueHeron Beach Resort, Orlando Florida

Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning

Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
orlando
9.8 out of 10, Exceptional, (194 reviews)
"Great place, Irina was very accommodating. Couldn’t be happier with my stay!"
United States
Darby S.
$828 nightly
The price is $920
Apr 3 - Apr 4
Total with taxes and fees
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning

PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!

PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!
Orlando
9.4 out of 10, Exceptional, (65 reviews)
"Room was great! Will stay again "
United States
gina
$272 nightly
The price is $302
Apr 4 - Apr 5
Total with taxes and fees
PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!

Family-friendly Stunning condo with pool & Lake views near Disney Park

Family-friendly Stunning condo with pool & Lake views near Disney Park
Orlando
10.0 out of 10, Exceptional, (2 reviews)
"Close to everything. Easy to access. Beautiful views. "
United States
Tommy M.
$252 nightly
The price is $281
Apr 5 - Apr 6
Total with taxes and fees
Family-friendly Stunning condo with pool & Lake views near Disney Park

Condo is just 2 miles away from Disney, wonderful Lake view family-sized

Condo is just 2 miles away from Disney, wonderful Lake view family-sized
Orlando
10.0 out of 10, Exceptional, (7 reviews)
"Loved this property. Location was great, pool was great! Clean and beautiful condo. Would most definately stay again!"
United States
jackie b.
$258 nightly
The price is $287
Apr 10 - Apr 11
Total with taxes and fees
Condo is just 2 miles away from Disney, wonderful Lake view family-sized

Cozy 1-bedroom Condo in Luxury Gated Community

Cozy 1-bedroom Condo in Luxury Gated Community
Ventura
9.8 out of 10, Exceptional, (9 reviews)
"Everything was amazing highly recommended "
United States
Jeremy P.
$197 nightly
The price is $220
Apr 13 - Apr 14
Total with taxes and fees
Cozy 1-bedroom Condo in Luxury Gated Community

Spacious Home in FantasyWorld

Spacious Home in FantasyWorld
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Thanks you so much for everything for sure this place is AMAZING, everything went perfect and resort staff was very nice and helpful all the time and yes is same as the pictures and eve more better in person. "
United States
Harley Gustavo
$304 nightly
The price is $322
Apr 13 - Apr 14
Total with taxes and fees
Spacious Home in FantasyWorld

2bd/2ba Brand new lake-view condo close to Disney

2bd/2ba Brand new lake-view condo close to Disney
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Check in process is easy, apartment is clean and roomy. "
United States
D J.
$363 nightly
The price is $406
Apr 12 - Apr 13
Total with taxes and fees
2bd/2ba Brand new lake-view condo close to Disney

Buena Vista Resort Condo w/ Pool & Private Patio

Buena Vista Resort Condo w/ Pool & Private Patio
Orlando
8.4 out of 10, Very Good, (16 reviews)
"Great resort with plenty of amenities in close walking range, including 2 pools, a convenience store, Irish pub, and Pizza Hut express. Within minutes of just about anything in Kissimee/Orlando. We highly recommend this place!"
United States
Lindsey
$261 nightly
The price is $294
Apr 8 - Apr 9
Total with taxes and fees
Buena Vista Resort Condo w/ Pool & Private Patio

Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld

Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
Orlando
10.0 out of 10, Exceptional, (1 review)
"We were very happy with our stay. It was so nice and clean and perfect! We didn't even need the shuttle because it was walking distance to Seaworld! Would definitely stay here again. No question."
United States
Eljae
$159 nightly
The price is $175
Apr 12 - Apr 13
Total with taxes and fees
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld

Modern Vista Cay nr pool•Walk to OCCC close iDrive

Modern Vista Cay nr pool•Walk to OCCC close iDrive
Orlando
10.0 out of 10, Exceptional, (55 reviews)
"We had a great experience. Super clean, easy check in, great location. "
United States
Kyle R.
Modern Vista Cay nr pool•Walk to OCCC close iDrive

Spring Special, Stylish, Relaxing, Stunning Lakeview Resort near Disney

Spring Special, Stylish, Relaxing, Stunning Lakeview Resort near Disney
Orlando
9.4 out of 10, Exceptional, (46 reviews)
"This is a wonderful place to stay. I'm very satisfied with this accommodation for giving me such a great view in Orlando."
United States
Young Gyu
$259 nightly
The price is $289
Apr 6 - Apr 7
Total with taxes and fees
Spring Special, Stylish, Relaxing, Stunning Lakeview Resort near Disney
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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Top Winter Park Hotel Reviews

Find out more about Winter Park

Winter Park Condo Rentals information

Number of reviews
479
Accommodation
2185 Condo Rentals
Lowest Price
$173
Highest Price
$920

Frequently asked questions

How much do condos in Winter Park cost?
You'll pay from $173 to $920 per night for condos in Winter Park. No matter your budget, an ideal 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 Winter Park?
A favorite is 55 W #2901. Get comfortable at this 3.5-star stay which offers a swimming pool and fitness facilities. 55 W #3006 is another highly rated condo worth considering. Spend your break at this popular 3.5-star option and make the most of amenities like a swimming pool and a lake view. You'll have your pick of multiple condos in Winter Park with a total average guest review rating of 9.7.
How many condos are there in Winter Park?
Winter Park has 2185 condos. To help you find the perfect stay, use our filters to search for the must-have hotel conveniences.
Are there any family-friendly condos in Winter Park?
Many travelers seeking family-friendly condos in Winter Park book 55 W #2901. With a 3.5-star rating and amenities such as a swimming pool and fitness facilities, you'll feel right at home here. Alternatively, have a look at 3.5-star 55 W #3006. A lake view and a deck help make it a comfy base for your Winter Park trip. Winter Park has tons of family-friendly attractions to visit when the kids are getting restless. Orlando Science Center and Orlando Museum of Art promise a fun day out for both young and old.
Why book your condo in Winter Park with Expedia?
Reserving a condo in Winter Park is as easy as clicking on your travel dates and selecting an option that has what you need. On the search for something affordable or upmarket, or a stay that also comes with a pool and free WiFi? Use Expedia's search filters to narrow your results even further and find your dream fit.
How can I find cheap condos in Winter Park?
The easiest way to compare cheap condos in Winter Park is with Expedia's easy-to-use filter tool. Refine your search results by amenities, budget and star rating to nab unbeatable bargains in just a few clicks.
What is there to do in Winter Park near my condo?
You'll find loads of terrific things that'll fill up your itinerary in Winter Park. Head for big attractions like Winter Park Country Club, Crealde School of Art and Winter Park Village. Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens are other highlights.

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