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Check prices for these dates

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

Our top choices for Winter Park condo rentals

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

Condo in Lake Frederica

Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool
10.0 out of 10, Exceptional, (1)
"We came to the area for a family Memorial Service. Our host allowed us to check in early, which was very much appreciated! The home was clean and comfortable, and there were many restaurants nearby. If we had chosen to cook, it seemed that there would have been plenty of supplies. The pool was closed for maintenance, so could not rate that area."
United States
Kelly S.
The price is HK$980
HK$2,385 total
includes taxes & fees
5 Jan - 6 Jan 2026
Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool
Smart TV
Vintage 2 Bedroom 1.5 Bathroom Condo Lake View

Condo in South Eola

Vintage 2 Bedroom 1.5 Bathroom Condo Lake View
10.0 out of 10, Exceptional, (3)
"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
The price is HK$693
HK$1,504 total
includes taxes & fees
5 Jan - 6 Jan 2026
Vintage 2 Bedroom 1.5 Bathroom Condo Lake View
Fridge, microwave, oven, stovetop
Renovated Condo Lake Eola View Great Location

Condo in South Eola

Renovated Condo Lake Eola View Great Location
10.0 out of 10, Exceptional, (10)
"It was a great stay in a great area with an amazing view! "
United States
Valerie
The price is HK$630
HK$1,302 total
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated Condo Lake Eola View Great Location
Fridge, microwave, oven, stovetop
Lake Eola view 1 bedroom Thornton Park

Condo in South Eola

Lake Eola view 1 bedroom Thornton Park
9.8 out of 10, Exceptional, (10)
"The location is exactly what I wanted without breaking the bank. The host was very informative and quick to respond. I will stay here again. "
United States
Judy G.
The price is HK$560
HK$1,223 total
includes taxes & fees
1 Jan - 2 Jan 2026
Lake Eola view 1 bedroom Thornton Park
Exterior
Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA

Condo in Orlando

Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA
2.0 star property
10.0 out of 10, Exceptional, (1)
"Truly an incredible space"
United States
Sean Parker S.
The price is HK$802
HK$2,479 total
includes taxes & fees
4 Jan - 5 Jan 2026
Disney & Universal Condo Grand Opening Specials! Amazing Views, Spacious 2B 2BA
Pool
2BD/2BA condo close to Disney at Storey Lake #96

Condo in Kissimmee

2BD/2BA condo close to Disney at Storey Lake #96
10.0 out of 10, Exceptional, (12)
"We really enjoyed our stay and the condo was perfect for our family of four. It was clean, had all the supplies we needed and my kids enjoyed the pools. It was a quick drive to Disney, the convention area and also had restaurants and shopping nearby. We would stay here again!"
United States
Jessica G.
The price is HK$701
HK$2,327 total
includes taxes & fees
5 Jan - 6 Jan 2026
2BD/2BA condo close to Disney at Storey Lake #96
TV
London House | Orlando Airport Private Condo

Condo in South Semoran

London House | Orlando Airport Private Condo
The price is HK$858
HK$2,357 total
includes taxes & fees
15 Jan - 16 Jan 2026
London House | Orlando Airport Private Condo
Pool
SL 4741 Clock Tower #204 GVPM

Condo in Kissimmee

SL 4741 Clock Tower #204 GVPM
9.0 out of 10, Wonderful, (11)
"Great location to all attractions. Perfect condo for my family."
United States
John Z.
The price is HK$701
HK$2,273 total
includes taxes & fees
4 Jan - 5 Jan 2026
SL 4741 Clock Tower #204 GVPM
Living area
Newly Remodeled! Condo in Center of all the Action!

Condo in Florida Center

Newly Remodeled! Condo in Center of all the Action!
8.8 out of 10, Excellent, (13)
"It wS straight to the ponit introduction were very clear the stay was easy and unbelievable wonderful very homie we organized put together i would definitely go back again "
United States
Von W.
The price is HK$739
HK$1,789 total
includes taxes & fees
29 Dec - 30 Dec
Newly Remodeled! Condo in Center of all the Action!
Pool
Upstay: Family-Friendly Getaway with Spa & Pool

Condo in Orlando

Upstay: Family-Friendly Getaway with Spa & Pool
9.2 out of 10, Wonderful, (5)
"Great place to stay. Close to all the major theme parks"
United States
marci m.
The price is HK$669
HK$2,131 total
includes taxes & fees
13 Jan - 14 Jan 2026
Upstay: Family-Friendly Getaway with Spa & Pool
Exterior
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER

Condo in Orlando

Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
9.6 out of 10, Exceptional, (145)
"Great place. "
United States
Jeff D.
The price is HK$1,236
HK$3,916 total
includes taxes & fees
10 Jan - 11 Jan 2026
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
Property grounds
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location

Condo in Orlando

Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
9.8 out of 10, Exceptional, (198)
"The location was great. We were only there 2 nights, and everything we needed and wanted was within a 10 minutee drive. Would highly recommend. "
United States
Lisa R.
The price is HK$770
HK$1,994 total
includes taxes & fees
29 Dec - 30 Dec
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
Pool
2BD/2BA condo close to Disney at Storey Lake #80

Condo in Kissimmee

2BD/2BA condo close to Disney at Storey Lake #80
9.6 out of 10, Exceptional, (11)
"Great place to stay and only 15 min drive to Disney on a great road!"
United States
Kyle H.
The price is HK$701
HK$2,296 total
includes taxes & fees
11 Jan - 12 Jan 2026
2BD/2BA condo close to Disney at Storey Lake #80
Pool
3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)

Condo in Orlando

3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)
10.0 out of 10, Exceptional, (3)
"Very nice and same price as Hotels in the area. Has 3 bedrooms and access to a nice outdoor pool."
United States
Ryan H.
The price is HK$1,398
HK$3,757 total
includes taxes & fees
9 Jan - 10 Jan 2026
3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)
Pool
4816 Cayview Ave #102 Xu · Luxury Lake View Near Convention Center, Universal

Condo in Orlando

4816 Cayview Ave #102 Xu · Luxury Lake View Near Convention Center, Universal
9.6 out of 10, Exceptional, (4)
"Had a great time, everything was as listed. Great location."
United States
Jackie T.
The price is HK$1,151
HK$3,057 total
includes taxes & fees
12 Jan - 13 Jan 2026
4816 Cayview Ave #102 Xu · Luxury Lake View Near Convention Center, Universal
Pool
2bd/2ba ground floor condo close to Disney, Storey Lake

Condo in Kissimmee

2bd/2ba ground floor condo close to Disney, Storey Lake
9.2 out of 10, Wonderful, (5)
"This was perfect for our stay and purpose. We were at the convention center for AAU Nationals and were happy to have a spacious area to enjoy our down time between events. The kitchen was well equipped and was perfect for making our breakfast and snacks for the day. We were very happy that we all had our own space, the bathrooms are a great size, the AC was cool and the washer / dryer was a great thing as we needed to wash uniforms every day! Getting in and out was easy as management was very...
United States
John D.
The price is HK$701
HK$2,320 total
includes taxes & fees
25 Jan - 26 Jan 2026
2bd/2ba ground floor condo close to Disney, Storey Lake
Interior
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld

Condo in Orlando

Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
10.0 out of 10, Exceptional, (1)
"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
The price is HK$1,025
HK$1,308 total
includes taxes & fees
4 Jan - 5 Jan 2026
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
Pool
VCR2-310 Reserve Deluxe Condo - Modern Decor

Condo in Orlando

VCR2-310 Reserve Deluxe Condo - Modern Decor
9.4 out of 10, Exceptional, (20)
"Great property, great location. We will hopefully back."
United Kingdom
Ian F.
The price is HK$1,244
HK$3,147 total
includes taxes & fees
4 Jan - 5 Jan 2026
VCR2-310 Reserve Deluxe Condo - Modern Decor
Pool
Luxury Waterfront Disney Area Resort

Condo in Orlando

Luxury Waterfront Disney Area Resort
10.0 out of 10, Exceptional, (3)
"Nice well planned our floor plan, 2nd bathroom helps. With all the items you may need for your stay. We will be coming back!"
United States
Carlos R.
The price is HK$1,081
HK$2,550 total
includes taxes & fees
6 Jan - 7 Jan 2026
Luxury Waterfront Disney Area Resort
Pool
Crisp &Modern with Balcony next to the Orange County Convention Center-Sea World

Condo in Orlando

Crisp &Modern with Balcony next to the Orange County Convention Center-Sea World
9.8 out of 10, Exceptional, (32)
"Everything was as described and very clean and comfortable."
United States
Bernice P.
The price is HK$1,244
HK$3,066 total
includes taxes & fees
11 Jan - 12 Jan 2026
Crisp &Modern with Balcony next to the Orange County Convention Center-Sea World
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

Caribe Royale Orlando

Caribe Royale Orlando

10/10 Excellent
"This place was a great surprise. Convenient to all the parks. Pool was great. Plenty of food options on property. Would stay again. "
jeremy 3-night trip
Posted 19 hours ago
Caribe Royale Orlando

Find out more about Winter Park

Winter Park Condo Rentals information

Number of reviews
432
Accommodation
2290 Condo Rentals
Lowest Price
HK$1,223
Highest Price
HK$3,916

Frequently asked questions

How much do condos in Winter Park cost?
You'll pay from HK$1,223 to HK$3,916 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 favourite 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 9.6.
How many condos are there in Winter Park?
Winter Park has 2290 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 travellers 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 Centre 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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