Search Condo Rentals in Winter Park

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Winter Park condo rentals

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

Ventura
10.0 out of 10, Exceptional, (1)
"Everything was amazing highly recommended "
United States
Jeremy P.
The price is AED 301
AED 743 total
includes taxes & fees
7 Jan - 8 January 2026
Cozy 1-bedroom Condo in Luxury Gated Community
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.
The price is AED 463
AED 1,134 total
includes taxes & fees
11 Dec - 12 Dec
Welcoming Cozy 2BR/2BA Condo Near Downtown Orlando & Attractions with Pool
Property grounds
Pond View~Club Cortile Resort~Pool~Hot Tub~Themed

Pond View~Club Cortile Resort~Pool~Hot Tub~Themed

2.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1)
"Thanks to Derek and Lauren being such great Hosts our stay was amazing. Great communication from start to finish, the price is beautiful and amazing very comfortable and a great atmosphere. My family and I will definitely be revisiting next visit to Orlando."
United States
Eriq B.
Pond View~Club Cortile Resort~Pool~Hot Tub~Themed
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, (9)
"It was a great stay in a great area with an amazing view! "
United States
Valerie
The price is AED 298
AED 615 total
includes taxes & fees
24 Dec - 25 Dec
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

South Eola
9.8 out of 10, Exceptional, (9)
"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 AED 264
AED 578 total
includes taxes & fees
16 Dec - 17 Dec
Lake Eola view 1 bedroom Thornton Park
Terrace/patio
DOUBLE FLAT STUDIO - UNIVERSAL STUDIOS & INTERNATIONAL DRIVE

DOUBLE FLAT STUDIO - UNIVERSAL STUDIOS & INTERNATIONAL DRIVE

International Drive District
9.2 out of 10, Wonderful, (9)
"Enjoyed our stay, very close to everything, in a safe neighborhood."
United States
Marie A.
The price is AED 367
AED 1,106 total
includes taxes & fees
17 Dec - 18 Dec
DOUBLE FLAT STUDIO - UNIVERSAL STUDIOS & INTERNATIONAL DRIVE
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

Orlando
9.6 out of 10, Exceptional, (144)
"Great place. "
United States
Jeff D.
Brand New - Vista Cay Reserve 3 Bed 2 Bath - close Universal/Conv Center- SUMMER
Pool
Buena Vista Resort Condo w/ Pool & Private Patio

Buena Vista Resort Condo w/ Pool & Private Patio

Orlando
9.2 out of 10, Wonderful, (13)
"Condo was as advertised clean and close to everything. Would highly recommend this property for any Disney vacation."
Canada
Derek M.
The price is AED 231
AED 881 total
includes taxes & fees
11 Dec - 12 Dec
Buena Vista Resort Condo w/ Pool & Private Patio
Pool
2bd/2ba ground floor condo close to Disney, Storey Lake

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

Kissimmee
9.6 out of 10, Exceptional, (7)
"Loved the place."
United States
Peter S.
2bd/2ba ground floor condo close to Disney, Storey Lake
Indoor pool
Sunny Family Escape/ Private Pool & Themed Rooms

Sunny Family Escape/ Private Pool & Themed Rooms

Kissimmee
10.0 out of 10, Exceptional, (3)
"Great property to stay at for a large group of friends or family. Good location, clean place, and plenty of amenities."
United States
Stephen B.
The price is AED 488
AED 1,532 total
includes taxes & fees
17 Dec - 18 Dec
Sunny Family Escape/ Private Pool & Themed Rooms
Pool
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
9.8 out of 10, Exceptional, (32)
"Everything was as described and very clean and comfortable."
United States
Bernice P.
Crisp &Modern with Balcony next to the Orange County Convention Center-Sea World
Living area
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.
The price is AED 349
AED 838 total
includes taxes & fees
12 Dec - 13 Dec
Newly Remodeled! Condo in Center of all the Action!
Condo, 2 Bedrooms | Pool | A heated pool
Sunset Retreat At Storey Lake Resort By Shine Villas 2 Bedroom Condo

Sunset Retreat At Storey Lake Resort By Shine Villas 2 Bedroom Condo

3.0 star property
Kissimmee
Sunset Retreat At Storey Lake Resort By Shine Villas 2 Bedroom Condo
3 outdoor pools
3648 Orlando Vacational Apartment 2nd floor, Lake view

3648 Orlando Vacational Apartment 2nd floor, Lake view

3.5 star property
Ventura
7.4 out of 10, Good, (8)
"I loved it everything about this property and wouldn't mind going again in the future"
United States
Rose M
The price is AED 450
AED 1,057 total
includes taxes & fees
21 Dec - 22 Dec
3648 Orlando Vacational Apartment 2nd floor, Lake view
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.
The price is AED 235
AED 885 total
includes taxes & fees
11 Dec - 12 Dec
Upstay: Family-Friendly Getaway with Spa & Pool
Pool
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.
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

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.
2BD/2BA condo close to Disney at Storey Lake #80
Pool
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.
The price is AED 439
AED 1,483 total
includes taxes & fees
15 Dec - 16 Dec
3 Bedrooms/ 2 Bathrooms/ Vista Cay (4024-203 BD)
Exterior
Close to Disney and Universal! Family-sized condo with pool, balcony & game room

Close to Disney and Universal! Family-sized condo with pool, balcony & game room

Orlando
9.2 out of 10, Wonderful, (7)
"We loved staying here and the amenities plus location was just a no brainer! Thank you for hosting us! "
United States
Teah S.
The price is AED 368
AED 1,479 total
includes taxes & fees
11 Dec - 12 Dec
Close to Disney and Universal! Family-sized condo with pool, balcony & game room
Outdoor pool, a heated pool
WEEKEND DEC 13-20 95+N 2.5 BDR 2 BTH 25FT AMAZING LAKEFRONT CONDO + 25FT BALCONY

WEEKEND DEC 13-20 95+N 2.5 BDR 2 BTH 25FT AMAZING LAKEFRONT CONDO + 25FT BALCONY

Orlando
9.6 out of 10, Exceptional, (176)
"The location is very close to the Disney parks and in walking distance to food and COFFEE!"
United States
janice b.
The price is AED 410
AED 1,128 total
includes taxes & fees
17 Dec - 18 Dec
WEEKEND DEC 13-20 95+N 2.5 BDR 2 BTH 25FT AMAZING LAKEFRONT CONDO + 25FT BALCONY
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Beautiful resort"
Antonese 3-night trip
Posted 4 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 578 to AED 1,532 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 9.2.
How many condos are there in Winter Park?
Winter Park has 2394 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.

Explore a world of travel with Expedia