A two-story house with a balcony, surrounded by lush greenery and trees.

Search and Rent Winter Park Condos

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winter Park condo rentals

A modern kitchen with grey cabinets, a wooden countertop, and a built-in stove.

1. Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park
South Eola
10.0 out of 10, Exceptional, (15 reviews)
"Clean and quiet spot with an easy check-in process. Super close to the lake with lots of restaurants within walking distance. Parking was easy to access and made getting in and out quite easy."
United States
Caroline V.
$152 nightly
The price is $168
Oct 4 - Oct 5
Total with taxes and fees
Lake Eola view 1 bedroom Thornton Park
A living room with a sofa, ottoman, coffee table, and a floor lamp.

2. Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park
South Eola
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location and stay. Communications were great, check in easy and everything was comfortable. Will stay again!"
United States
Genevieve N.
$152 nightly
The price is $168
Oct 4 - Oct 5
Total with taxes and fees
Retro lake Eola 1 Bedroom Condo Thornton park
A modern kitchen with white cabinets, a stainless steel microwave, an oven, and a dishwasher.

3. Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (18 reviews)
"Great location and home! "
United States
Emma D.
$182 nightly
The price is $202
Oct 19 - Oct 20
Total with taxes and fees
Renovated Condo Lake Eola View Great Location
A living room with a sectional sofa, two side tables with lamps, a glass coffee table, and a patterned rug.

4. Vintage 2 Bedroom Condo Lake Eola View

Vintage 2 Bedroom Condo Lake Eola View
South Eola
10.0 out of 10, Exceptional, (13 reviews)
"Amazing place to stay "
United States
Sana P.
$182 nightly
The price is $202
Oct 4 - Oct 5
Total with taxes and fees
Vintage 2 Bedroom Condo Lake Eola View
A modern kitchen with white appliances, a dining area with a round table and chairs, and a view of the outdoors through a sliding door.

5. Cozy 1-bedroom Condo in Luxury Gated Community

Cozy 1-bedroom Condo in Luxury Gated Community
Ventura
10.0 out of 10, Exceptional, (12 reviews)
"Great stay, we enjoyed it "
Canada
Kevin L.
$232 nightly
The price is $258
Oct 3 - Oct 4
Total with taxes and fees
Cozy 1-bedroom Condo in Luxury Gated Community
An aerial view of a resort with a central swimming pool, multiple lounge areas, and a variety of buildings with distinct architectural styles.

6. Crisp &Modern with Balcony next to the Orange County Convention Center-Sea World

Crisp &Modern with Balcony next to the Orange County Convention Center-Sea World
Orlando
9.6 out of 10, Exceptional, (42 reviews)
"Great spot, perfectly located, clean, quiet and very easy to check-in and out."
United States
Krystle S.
$309 nightly
The price is $343
Oct 4 - Oct 5
Total with taxes and fees
Crisp &Modern with Balcony next to the Orange County Convention Center-Sea World
A water play area with slides and water jets, surrounded by a paved walkway and palm trees, with buildings in the background.

7. 5000-408 - 3 BED, 2 BATH, POOL AND LAKEVIEW

5000-408 - 3 BED, 2 BATH, POOL AND LAKEVIEW
Orlando
9.6 out of 10, Exceptional, (274 reviews)
"My family and I really enjoyed staying at this property. It was very clean and the owner was very responsive and accommodating. Also, the check in and check out processes were very easy. We really liked how close the property was to the Disney Parks. I would definitely stay at this property again."
United States
Danielle A.
$378 nightly
The price is $421
Oct 25 - Oct 26
Total with taxes and fees
5000-408 - 3 BED, 2 BATH, POOL AND LAKEVIEW
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building with a tiled roof.

8. Lakeview Condo minutes to Convention Center, Disney & Universal Studio

Lakeview Condo minutes to Convention Center, Disney & Universal Studio
Orlando
8.8 out of 10, Excellent, (46 reviews)
"Great location from the convention center!"
United States
Jasmine M.
Lakeview Condo minutes to Convention Center, Disney & Universal Studio
A resort with a central building featuring a swimming pool, surrounded by lush greenery and a large lake.

9. Minutes to Disney, Universal, SeaWorld in a resort setting 1823 sqft 3bdrm HT

Minutes to Disney, Universal, SeaWorld in a resort setting 1823 sqft 3bdrm HT
Orlando
9.4 out of 10, Exceptional, (115 reviews)
"Great resort! Great condo! All around great experience! "
United States
Emalie C.
$357 nightly
The price is $396
Oct 12 - Oct 13
Total with taxes and fees
Minutes to Disney, Universal, SeaWorld in a resort setting 1823 sqft 3bdrm HT
A pathway leading to a building with a central archway, flanked by palm trees.

10. 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.
$777 nightly
The price is $863
Oct 2 - Oct 3
Total with taxes and fees
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
A pool area with a pergola, lounge chairs, and umbrellas.

11. IS3-205 - 3BR condo with lake view

IS3-205 - 3BR condo with lake view
Orlando
9.8 out of 10, Exceptional, (23 reviews)
"Enjoyed out stay at this condo. Everything was as advertised and would stay here again."
United States
Tammy P.
$376 nightly
The price is $416
Oct 2 - Oct 3
Total with taxes and fees
IS3-205 - 3BR condo with lake view
A dining area with a marble table, a potted plant, and a sofa in the background.

12. Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!

Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Orlando
9.8 out of 10, Exceptional, (273 reviews)
"Everything was great. This is the first place we will look for when we come back!"
United States
jeremy e.
$365 nightly
The price is $405
Oct 5 - Oct 6
Total with taxes and fees
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
A swimming pool with a unique shape surrounded by a white deck, palm trees, and a cityscape in the background.

13. 2 BD/2 BA minutes from Universal Studios & Epic Universe

2 BD/2 BA minutes from Universal Studios & Epic Universe
International Drive District
9.6 out of 10, Exceptional, (19 reviews)
"This is a great place to stay if you are planning a trip to Universal Studios. Super close, walkable to I drive, nice pool. The patio was a great perk, could see Disney fireworks, Islands of Adventure and Volcano Bay. "
United States
Jacoba A.
$236 nightly
The price is $262
Oct 4 - Oct 5
Total with taxes and fees
2 BD/2 BA minutes from Universal Studios & Epic Universe
A pathway leading to a building with a central tower, surrounded by palm trees and well-maintained gardens.

14. Universal,Disney World,Convention Center,Executive Luxury 5*Vista Cay Villa/Pool

Universal,Disney World,Convention Center,Executive Luxury 5*Vista Cay Villa/Pool
Orlando
9.4 out of 10, Exceptional, (26 reviews)
"Great place and location for our trip."
United States
Julie P.
$777 nightly
The price is $863
Oct 2 - Oct 3
Total with taxes and fees
Universal,Disney World,Convention Center,Executive Luxury 5*Vista Cay Villa/Pool
A modern building with a curved roof and a large body of water in front.

15. 3-bedroom condo just 6 minutes to Universal Orlando Resort

3-bedroom condo just 6 minutes to Universal Orlando Resort
Orlando
9.8 out of 10, Exceptional, (8 reviews)
"Great location and stay for our family."
United States
Nicole K.
$425 nightly
The price is $472
Oct 4 - Oct 5
Total with taxes and fees
3-bedroom condo just 6 minutes to Universal Orlando Resort
A dining area with a round table, chairs, and a glass-top table. There is a kitchen area with cabinets and appliances in the background.

16. Penthouse/Epic Universe Fireworks view/Private billiards table

Penthouse/Epic Universe Fireworks view/Private billiards table
ORLANDO
9.6 out of 10, Exceptional, (132 reviews)
"Condo was nice and roomy!! Everything was really clean, the beds were comfortable. We would stay here again."
United States
Virginia H.
$262 nightly
The price is $291
Oct 6 - Oct 7
Total with taxes and fees
Penthouse/Epic Universe Fireworks view/Private billiards table
A pool area with lounge chairs, palm trees, and a clear blue sky.

17. New Vista Cay 3 Bedroom 2 bath - Next to Epic Universal / Conv. Center - Ocean

New Vista Cay 3 Bedroom 2 bath - Next to Epic Universal / Conv. Center - Ocean
Orlando
9.6 out of 10, Exceptional, (168 reviews)
"For an adult only stay, this property is perfect. Close to the pool and shopping."
United States
Christine D.
$388 nightly
The price is $432
Oct 9 - Oct 10
Total with taxes and fees
New Vista Cay 3 Bedroom 2 bath - Next to Epic Universal / Conv. Center - Ocean
A bedroom with two beds, a dresser, and a television.

18. Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8

Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
Orlando
9.8 out of 10, Exceptional, (178 reviews)
"Fantastic place and host!"
United States
Brandon D.
$333 nightly
The price is $370
Oct 5 - Oct 6
Total with taxes and fees
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
A pool area with a pergola, lounge chairs, and umbrellas.

19. VCR2-409 - 3BR condo w/ Resort Access near Disney

VCR2-409 - 3BR condo w/ Resort Access near Disney
Orlando
10.0 out of 10, Exceptional, (64 reviews)
"Everything was clean. The kids enjoyed the pool. The host was great with communication. We had a great stay!"
United States
William W.
VCR2-409 - 3BR condo w/ Resort Access near Disney
A modern indoor swimming pool with clear glass walls, a hot tub, and lounge chairs.

20. 2 BR RESORT IN PERFECT LOCATION NEAR UNIVERSAL

2 BR RESORT IN PERFECT LOCATION NEAR UNIVERSAL
Florida Center
8.2 out of 10, Very good, (85 reviews)
"The property was clean and the host was helpful. Cons: the location link was inaccurate, needs more hand towels in the kitchen and bathroom, needs rugs in both bathrooms, needs new pots and pans in kitchen (all the them were damaged nonstick pots/pans)."
United States
Angela
$278 nightly
The price is $310
Oct 17 - Oct 18
Total with taxes and fees
2 BR RESORT IN PERFECT LOCATION NEAR UNIVERSAL
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

8/10 Good
"Pool was closed when we arrived. It was closed for 2 days of our visit."
Jasen 4-night trip
Posted less than an hour ago
Drury Plaza Hotel Orlando - Disney Springs Area

Find out more about Winter Park

Winter Park Condo Rentals information

Number of reviews
1,713
Accommodation
2055 Condo Rentals
Lowest Price
$168
Highest Price
$863

Frequently asked questions

How much do condos in Winter Park cost?
You'll pay from $168 to $863 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 2055 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.

Explore a world of travel with Expedia