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

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Winter Park condo rentals

Dining

Cozy 1-bedroom Condo in Luxury Gated Community

Cozy 1-bedroom Condo in Luxury Gated Community
Ventura
9.8 out of 10, Exceptional, (10 reviews)
"Great stay, we enjoyed it "
Canada
Kevin L.
$233 nightly
The price is $259
Jul 5 - Jul 6
Total with taxes and fees
Cozy 1-bedroom Condo in Luxury Gated Community
Outdoor pool, a heated pool

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, (69 reviews)
"Room was great! Will stay again "
United States
gina
$269 nightly
The price is $299
Jul 13 - Jul 14
Total with taxes and fees
PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!
2 outdoor pools, open 7:00 AM to 11:00 PM, free cabanas, pool umbrellas

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
$327 nightly
The price is $369
Jul 13 - Jul 14
Total with taxes and fees
Magical Moment Vacation Condos
Fridge, microwave, oven, stovetop

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.
$166 nightly
The price is $184
Jul 5 - Jul 6
Total with taxes and fees
Lake Eola view 1 bedroom Thornton Park
Pool

Disney 8mi~Heated Resort Pool~Hot Tub~Oasis

Disney 8mi~Heated Resort Pool~Hot Tub~Oasis
Kissimmee
9.4 out of 10, Exceptional, (3 reviews)
"The host was great and responsive. They handled every issue quickly and efficiently and communicated great and in a timely fashion. The location was quiet and felt safe. "
United States
Caleb C.
$441 nightly
The price is $464
Aug 3 - Aug 4
Total with taxes and fees
Disney 8mi~Heated Resort Pool~Hot Tub~Oasis
Condo, 2 Bedrooms | Exterior

Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo

Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"we had a great time and enjoyed the condo for the short time we were there."
United States
Sherri Ann
$497 nightly
The price is $564
Jul 8 - Jul 9
Total with taxes and fees
Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo
Property grounds

DISNEY area CONDO 2 KING BEDS 2 BUNKS 2 BATHS Large 1350 sq ft Lake View 10th fl

DISNEY area CONDO 2 KING BEDS 2 BUNKS 2 BATHS Large 1350 sq ft Lake View 10th fl
Orlando
10.0 out of 10, Exceptional, (90 reviews)
"Had a great stay "
United States
Kelvin
$275 nightly
The price is $305
Jul 16 - Jul 17
Total with taxes and fees
DISNEY area CONDO 2 KING BEDS 2 BUNKS 2 BATHS Large 1350 sq ft Lake View 10th fl
Property grounds

Sensational Water View 1 Mile to Disney Newly Renovated Superb Location

Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
Orlando
9.8 out of 10, Exceptional, (220 reviews)
"Condo is in a perfect location, close to everything. Loved that a Starbucks was right there. Place was clean and had everything we needed. Really nice view! Would def stay here again. Great hosts. Thank you!"
United States
Elizabeth
$222 nightly
The price is $246
Jul 7 - Jul 8
Total with taxes and fees
Sensational Water View 1 Mile to Disney Newly Renovated Superb Location
Smart TV

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park
South Eola
9.6 out of 10, Exceptional, (7 reviews)
"Perfect location and stay. Communications were great, check in easy and everything was comfortable. Will stay again!"
United States
Genevieve N.
$166 nightly
The price is $184
Jul 5 - Jul 6
Total with taxes and fees
Retro lake Eola 1 Bedroom Condo Thornton park
Fridge, microwave, oven, stovetop

Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (18 reviews)
"Clean, comfortable apartment close to restaurants. "
United States
Robin K.
$194 nightly
The price is $216
Jul 5 - Jul 6
Total with taxes and fees
Renovated Condo Lake Eola View Great Location
Outdoor dining

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, (3 reviews)
"Very clean and the beds were so comfortable."
United States
Dawn N.
$174 nightly
The price is $193
Aug 1 - Aug 2
Total with taxes and fees
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
Property grounds

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.
$805 nightly
The price is $893
Aug 1 - Aug 2
Total with taxes and fees
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
Exterior

Renovated Retreat | Minutes from Theme Parks!

Renovated Retreat | Minutes from Theme Parks!
International Drive District
8.0 out of 10, Very Good, (2 reviews)
"Many amenities "
United States
Kevin
$230 nightly
The price is $252
Jul 7 - Jul 8
Total with taxes and fees
Renovated Retreat | Minutes from Theme Parks!
Fridge, microwave, oven, stovetop

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, (272 reviews)
"Jim was just amazing to work with! The condo was perfect and in an ideal location to shops, restaurants and of course Universal and Disney. We just loved it!"
United States
Michelle A.
$393 nightly
The price is $436
Aug 1 - Aug 2
Total with taxes and fees
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
A heated pool

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, (49 reviews)
"Great stay!"
United States
Petra K.
$273 nightly
The price is $303
Jul 6 - Jul 7
Total with taxes and fees
Spring Special, Stylish, Relaxing, Stunning Lakeview Resort near Disney
Condo, 2 Bedrooms | Exterior

Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts

Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Great communication and close to Disney and Universal. Very roomy unit "
United States
Gilbert
$459 nightly
The price is $521
Jul 6 - Jul 7
Total with taxes and fees
Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts
WiFi, bed sheets

Inside Out Adventure Studio

Inside Out Adventure Studio
Kissimmee
$209 nightly
The price is $221
Jul 8 - Jul 9
Total with taxes and fees
Inside Out Adventure Studio
Outdoor pool

Amazing Water View, 1 Mile to Disney,Newly Renovated

Amazing Water View, 1 Mile to Disney,Newly Renovated
Orlando
9.6 out of 10, Exceptional, (134 reviews)
"We had a wonderful stay in this condo! The location was perfect for Disney activities and local shops and restaurants. The view was fantastic! We will come again!"
United States
Mary M.
Amazing Water View, 1 Mile to Disney,Newly Renovated
Property grounds

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.
$794 nightly
The price is $882
Aug 1 - Aug 2
Total with taxes and fees
Universal,Disney World,Convention Center,Executive Luxury 5*Vista Cay Villa/Pool
Pool

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, (13 reviews)
"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.
$293 nightly
The price is $327
Jul 19 - Jul 20
Total with taxes and fees
2BD/2BA condo close to Disney at Storey Lake #96
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"The kids loved the pool. They were in the water all day. Universal was across the street. The grandkids didn’t stop and I need an extra day to catch myself."
Rafael 1-night trip
Posted 5 hours ago
Universal's Cabana Bay Beach Resort

Find out more about Winter Park

Winter Park Condo Rentals information

Number of reviews
1,121
Accommodation
2236 Condo Rentals
Lowest Price
$184
Highest Price
$893

Frequently asked questions

How much do condos in Winter Park cost?
You'll pay from $184 to $893 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 2236 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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