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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Winter Park condo rentals

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
The price is AED 337
AED 1,237 total
includes taxes & fees
13 May - 14 May
Magical Moment Vacation Condos
Smart TV

Vintage 2 Bedroom Condo Lake Eola View

Vintage 2 Bedroom Condo Lake Eola View
South Eola
10.0 out of 10, Exceptional, (11 reviews)
"The place was clean and spacious. The living room was our relaxing spot. The location was great as we can see the lake.The location was safe and had a great parking spot. The host was quick to respond for any inquiries and would definitely stay here again. "
United States
Nagendra A.
The price is AED 418
AED 906 total
includes taxes & fees
11 May - 12 May
Vintage 2 Bedroom Condo Lake Eola View
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, (13 reviews)
"good area"
United States
Carlos F.
The price is AED 338
AED 715 total
includes taxes & fees
7 Jun - 8 Jun
Lake Eola view 1 bedroom Thornton Park
Dining

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)
"Great stay, we enjoyed it "
Canada
Kevin L.
The price is AED 390
AED 962 total
includes taxes & fees
11 May - 12 May
Cozy 1-bedroom Condo in Luxury Gated Community
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, (17 reviews)
"Great place to stay! Quiet and in a great neighborhood! "
United States
Nick L.
The price is AED 418
AED 813 total
includes taxes & fees
7 Jun - 8 Jun
Renovated Condo Lake Eola View Great Location
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
The price is AED 414
AED 1,913 total
includes taxes & fees
12 May - 13 May
Storey Lake Resort 2bd Condo Overlooking Water #840 2 Bedroom Condo
Property grounds

Vista Cay Jewel Luxury By Universal Orlando Rental

Vista Cay Jewel Luxury By Universal Orlando Rental
Orlando
9.6 out of 10, Exceptional, (18 reviews)
"The condo was in great condition. All the codes were correct to get into the gate and door. "
United States
Jessica H.
The price is AED 422
AED 1,297 total
includes taxes & fees
11 May - 12 May
Vista Cay Jewel Luxury By Universal Orlando Rental
Outdoor pool, a heated pool

New Vista Cay Reserve 3 Bedroom 2 bath - Next Universal / Conv. Center - Ocean

New Vista Cay Reserve 3 Bedroom 2 bath - Next Universal / Conv. Center - Ocean
Orlando
9.6 out of 10, Exceptional, (156 reviews)
"Great location for getting to the convention center and to the attractions on International Drive. "
United States
Jeff H.
The price is AED 584
AED 1,832 total
includes taxes & fees
5 Jun - 6 Jun
New Vista Cay Reserve 3 Bedroom 2 bath - Next Universal / Conv. Center - Ocean
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, (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
The price is AED 437
AED 563 total
includes taxes & fees
20 May - 21 May
Free Theme Park Shuttle Transfer, Free Breakfast, Outdoor Pool | Staybridge Near Seaworld
Pool

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
The price is AED 272
AED 1,197 total
includes taxes & fees
14 May - 15 May
Spacious Home in FantasyWorld
Smart TV

Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park
South Eola
9.2 out of 10, Wonderful, (5 reviews)
"Clean, easy stay. Great experience for what we needed."
United States
Neil L.
The price is AED 338
AED 715 total
includes taxes & fees
8 Jun - 9 Jun
Retro lake Eola 1 Bedroom Condo Thornton park
Pool

The Minions Studio

The Minions Studio
Kissimmee
The price is AED 250
AED 824 total
includes taxes & fees
19 May - 20 May
The Minions Studio
Pool

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
The price is AED 320
AED 1,011 total
includes taxes & fees
3 Jun - 4 Jun
Buena Vista Resort Condo w/ Pool & Private Patio
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)
"Excellent location. Great host. "
United States
Edward F.
The price is AED 724
AED 1,618 total
includes taxes & fees
13 May - 14 May
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
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.
The price is AED 757
AED 3,379 total
includes taxes & fees
9 May - 10 May
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
Pool

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.
The price is AED 331
AED 1,201 total
includes taxes & fees
27 May - 28 May
2bd/2ba Brand new lake-view condo close to Disney
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.
Orlando
10.0 out of 10, Exceptional, (12 reviews)
"Great location for convention."
United States
Tim O.
The price is AED 757
AED 1,659 total
includes taxes & fees
11 May - 12 May
Condo in Best Location. Heated Pool, near Convention Ctr, across Epic Universal.
Pool

2bd/2ba condo close to Disney, Storey Lake

2bd/2ba condo close to Disney, Storey Lake
Kissimmee
10.0 out of 10, Exceptional, (5 reviews)
"It was an nice smooth experience renting out the property the pictures the were posted up on vrbo about the condo is exactly how the room is 10/10 experience"
United States
Luis C.
The price is AED 265
AED 1,110 total
includes taxes & fees
25 May - 26 May
2bd/2ba condo close to Disney, Storey Lake
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, (67 reviews)
"Room was great! Will stay again "
United States
gina
The price is AED 364
AED 1,113 total
includes taxes & fees
11 May - 12 May
PAY LATER!! SALE!! Beautiful lake view, newly decorated, next to Disney & FUN!!
Outdoor pool, a heated pool

Vibrant, Modern Condo, Storey Lake Resort, within minutes of Orlando Attractions

Vibrant, Modern Condo, Storey Lake Resort, within minutes of Orlando Attractions
Kissimmee
9.8 out of 10, Exceptional, (30 reviews)
"Easy check in and communication. Condo was clean and would stay there again with my family. "
United States
Jeraka I.
The price is AED 430
AED 1,147 total
includes taxes & fees
11 May - 12 May
Vibrant, Modern Condo, Storey Lake Resort, within minutes of Orlando Attractions
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Best bang for buck. Clean rooms, amazing staff and 100 percent family oriented. "
Hazar 2-night trip
Posted 2 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Frequently asked questions

How much do condos in Winter Park cost?
You'll pay from AED 563 to AED 3,379 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 2332 condos. To help you find the perfect stay, use our filters to search for the must-have hotel conveniences.
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.