Search and Rent Winter Park Condos

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In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Winter Park condo rentals

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

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

Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool
Lake Frederica
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.
$280 nightly
The price is $311
Jan 5 - Jan 6, 2026
Total with taxes and fees
Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy 1-bedroom Condo in Luxury Gated Community

Cozy 1-bedroom Condo in Luxury Gated Community

Cozy 1-bedroom Condo in Luxury Gated Community
Ventura
10.0 out of 10, Exceptional, (1)
"Everything was amazing highly recommended "
United States
Jeremy P.
$185 nightly
The price is $205
Jan 11 - Jan 12, 2026
Total with taxes and fees
Cozy 1-bedroom Condo in Luxury Gated Community
Smart TV
Vintage 2 Bedroom 1.5 Bathroom Condo Lake View

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, (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
$174 nightly
The price is $193
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vintage 2 Bedroom 1.5 Bathroom Condo Lake View
Fridge, microwave, oven, stovetop
Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (10)
"It was a great stay in a great area with an amazing view! "
United States
Valerie
$151 nightly
The price is $167
Jan 4 - Jan 5, 2026
Total with taxes and fees
Renovated Condo Lake Eola View Great Location
Fridge, microwave, oven, stovetop
Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park
South Eola
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.
$134 nightly
The price is $148
Jan 1 - Jan 2, 2026
Total with taxes and fees
Lake Eola view 1 bedroom Thornton Park
Pool
2BD/2BA condo close to Disney at Storey Lake #96

2BD/2BA condo close to Disney at Storey Lake #96

2BD/2BA condo close to Disney at Storey Lake #96
Kissimmee
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.
$270 nightly
The price is $301
Jan 8 - Jan 9, 2026
Total with taxes and fees
2BD/2BA condo close to Disney at Storey Lake #96
TV
London House | Orlando Airport Private Condo

London House | Orlando Airport Private Condo

London House | Orlando Airport Private Condo
South Semoran
$253 nightly
The price is $276
Jan 4 - Jan 5, 2026
Total with taxes and fees
London House | Orlando Airport Private Condo
Pool
SL 4741 Clock Tower #204 GVPM

SL 4741 Clock Tower #204 GVPM

SL 4741 Clock Tower #204 GVPM
Kissimmee
9.0 out of 10, Wonderful, (11)
"Great location to all attractions. Perfect condo for my family."
United States
John Z.
$270 nightly
The price is $301
Jan 5 - Jan 6, 2026
Total with taxes and fees
SL 4741 Clock Tower #204 GVPM
Pool
2BD/2BA condo close to Disney at Storey Lake #80

2BD/2BA condo close to Disney at Storey Lake #80

2BD/2BA condo close to Disney at Storey Lake #80
Kissimmee
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.
$264 nightly
The price is $295
Jan 11 - Jan 12, 2026
Total with taxes and fees
2BD/2BA condo close to Disney at Storey Lake #80
Dining
Enchanting 4-Bed Home in Kissimmee

Enchanting 4-Bed Home in Kissimmee

Enchanting 4-Bed Home in Kissimmee
Buena Ventura Lakes
10.0 out of 10, Exceptional, (1)
"Harry potter themed house was awesome. The host was great!"
United States
Beverly P.
$436 nightly
The price is $488
Jan 21 - Jan 22, 2026
Total with taxes and fees
Enchanting 4-Bed Home in Kissimmee
Living area
Newly Remodeled! Condo in Center of all the Action!

Newly Remodeled! Condo in Center of all the Action!

Newly Remodeled! Condo in Center of all the Action!
Florida Center
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.
$207 nightly
The price is $230
Jan 17 - Jan 18, 2026
Total with taxes and fees
Newly Remodeled! Condo in Center of all the Action!
Pool
Upstay: Family-Friendly Getaway with Spa & Pool

Upstay: Family-Friendly Getaway with Spa & Pool

Upstay: Family-Friendly Getaway with Spa & Pool
Orlando
9.2 out of 10, Wonderful, (5)
"Great place to stay. Close to all the major theme parks"
United States
marci m.
$236 nightly
The price is $264
Jan 27 - Jan 28, 2026
Total with taxes and fees
Upstay: Family-Friendly Getaway with Spa & Pool
Aerial view
Condo in Best Location. Heated Pool, near Convention Ctr, across Epic Universal.

Condo in Best Location. Heated Pool, near Convention Ctr, across Epic Universal.

Condo in Best Location. Heated Pool, near Convention Ctr, across Epic Universal.
Orlando
10.0 out of 10, Exceptional, (8)
"Great location for convention."
United States
Tim O.
$384 nightly
The price is $426
Jan 3 - Jan 4, 2026
Total with taxes and fees
Condo in Best Location. Heated Pool, near Convention Ctr, across Epic Universal.
Condo, 2 Bedrooms | Pool
Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts

Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts

Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
"The pictures are exactly what the condo looks like. Very bright, spacious and clean. Would definitely book again"
Canada
Michael
$478 nightly
The price is $542
Jan 4 - Jan 5, 2026
Total with taxes and fees
Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts
Pool
3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)

3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)

3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)
Orlando
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.
$403 nightly
The price is $442
Jan 5 - Jan 6, 2026
Total with taxes and fees
3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)
Interior
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld

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)
"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
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
Exterior
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER

Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER

Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
Orlando
9.6 out of 10, Exceptional, (145)
"Great place. "
United States
Jeff D.
$436 nightly
The price is $484
Jan 10 - Jan 11, 2026
Total with taxes and fees
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
Exterior
Vista Cay 3 Bedroom, In front of new Epic Universe and Convention Center, Island

Vista Cay 3 Bedroom, In front of new Epic Universe and Convention Center, Island

Vista Cay 3 Bedroom, In front of new Epic Universe and Convention Center, Island
Orlando
9.6 out of 10, Exceptional, (256)
"Great location to Universal, very clean, spacious, and the beds are extremely comfortable. "
United States
Kimberly L.
Vista Cay 3 Bedroom, In front of new Epic Universe and Convention Center, Island
Pool
4816 Cayview Ave #102 Xu · Luxury Lake View Near Convention Center, Universal

4816 Cayview Ave #102 Xu · Luxury Lake View Near Convention Center, Universal

4816 Cayview Ave #102 Xu · Luxury Lake View Near Convention Center, Universal
Orlando
9.6 out of 10, Exceptional, (4)
"Had a great time, everything was as listed. Great location."
United States
Jackie T.
$348 nightly
The price is $385
Jan 12 - Jan 13, 2026
Total with taxes and fees
4816 Cayview Ave #102 Xu · Luxury Lake View Near Convention Center, Universal
Pool
VCR2-310 Reserve Deluxe Condo - Modern Decor

VCR2-310 Reserve Deluxe Condo - Modern Decor

VCR2-310 Reserve Deluxe Condo - Modern Decor
Orlando
9.4 out of 10, Exceptional, (20)
"Great property, great location. We will hopefully back."
United Kingdom
Ian F.
$348 nightly
The price is $388
Jan 4 - Jan 5, 2026
Total with taxes and fees
VCR2-310 Reserve Deluxe Condo - Modern Decor
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

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

10/10 Excellent
"Great "
Mohamed 3-night trip
Posted 14 hours ago
Wyndham I-Drive Avanti Resort & Conference Center

Find out more about Winter Park

Winter Park Condo Rentals information

Number of reviews
468
Accommodation
2290 Condo Rentals
Lowest Price
$148
Highest Price
$542

Frequently asked questions

How much do condos in Winter Park cost?
You'll pay from $148 to $542 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 9.6.
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 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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