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Check prices for these dates

Tonight
24 Nov - 25 Nov
Tomorrow
25 Nov - 26 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Holiday Rentals in Winter Park

2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas
Lake Buena Vista Resort Village & Spa

Condo resort in Orlando

4.0 star property
8.4 out of 10, Very good, (9298)
"Great stay"
United States
Jessica
Lake Buena Vista Resort Village & Spa
Lobby sitting area
The View Studio Suites and Event Venue

Aparthotel in Orlando

3.0 star property
8.4 out of 10, Very good, (1406)
"Nice breakfast, friendly staff, great location "
United States
Yessica
The price is ฿2,185
฿2,458 total
includes taxes & fees
1 Dec - 2 Dec
The View Studio Suites and Event Venue
Reception
Florida Hotel & Conference Center in the Florida Mall

Aparthotel in Orlando

3.5 star property
9.2 out of 10, Wonderful, (2264)
"Clean fresh smelling room, real friendly staff, great atmosphere. Always love staying here"
United States
Alexander
Florida Hotel & Conference Center in the Florida Mall
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas
Floridays Resort Orlando

Condo resort in International Drive District

3.5 star property
8.6 out of 10, Excellent, (11587)
"Staff was wonderful "
United States
Dana
Floridays Resort Orlando
Terrace/patio
The Point by Edge

Aparthotel in Florida Center

4.0 star property
8.4 out of 10, Very good, (812)
"Great accommodations!"
United States
Champayne
The price is ฿2,039
฿2,695 total
includes taxes & fees
30 Nov - 1 Dec
The Point by Edge
Outdoor pool
The Point Hotel & Suites

Aparthotel in Florida Center

3.5 star property
8.0 out of 10, Very good, (3291)
"Great place to stay "
United States
Kevaughn
The price is ฿4,321
฿5,234 total
includes taxes & fees
4 Dec - 5 Dec
The Point Hotel & Suites
Outdoor spa tub
Blue Tree Resort at Lake Buena Vista

Aparthotel in Orlando

3.0 star property
8.6 out of 10, Excellent, (1829)
"Very friendly and sweet staff"
United States
Autrice
Blue Tree Resort at Lake Buena Vista
Exterior
Parc Corniche Condominium Suite Hotel

Aparthotel in International Drive District

3.0 star property
8.0 out of 10, Very good, (2184)
"Room was nice and clean and the staff was professional and friendly."
United States
Kiki
The price is ฿3,032
฿5,052 total
includes taxes & fees
3 Dec - 4 Dec
Parc Corniche Condominium Suite Hotel
2 outdoor pools, pool umbrellas, pool loungers
Vista Cay Resort by Millenium at Universal Blvd

Aparthotel in Orlando

3.5 star property
8.6 out of 10, Excellent, (1571)
"We enjoyed our stay. From the villa to the pools, everything was amazing. "
United States
Serena
Vista Cay Resort by Millenium at Universal Blvd
Outdoor pool, pool umbrellas, pool loungers
WorldQuest Orlando Resort

Aparthotel in Orlando

4.0 star property
8.4 out of 10, Very good, (4018)
"Very attentive staff and clean rooms. "
United States
Diana-Patricia
WorldQuest Orlando Resort
Apartment, 2 Bedrooms | Private kitchen | Toaster
Century Millenia

Apartment in Florida Center

3.0 star property
9.0 out of 10, Wonderful, (101)
" Kitchen was fully equipped, staff was available and informative, clean, and parking was available. "
United States
Elizabeth
Century Millenia
Exterior
Blue Heron Beach Resort

Aparthotel in Orlando

3.5 star property
8.4 out of 10, Very good, (2969)
"Everything is as it shows in the photos, maintenance personnel were nice and helpful "
Mexico
Victor
Blue Heron Beach Resort
BBQ/picnic Area
Orlando's Sunshine Resort

Aparthotel in International Drive District

3.5 star property
9.2 out of 10, Wonderful, (238)
"Awesome would stay again "
United States
Gabrielle
Orlando's Sunshine Resort
2 outdoor pools, open 7:00 AM to midnight, pool umbrellas, pool loungers
Villas at Fortune Place

Aparthotel in Kissimmee

3.0 star property
8.8 out of 10, Excellent, (137)
"Stayed there for nine days and it was absolutely beautiful perfect place for a young family"
United States
Christie
Villas at Fortune Place
Outdoor pool, pool loungers
staySky Suites - I Drive Orlando

Aparthotel in International Drive District

3.0 star property
7.8 out of 10, Good, (1240)
"Everything was great!"
United States
Antonio
staySky Suites - I Drive Orlando
Full-sized fridge, microwave, oven, stovetop
Enchanted Dreams

Aparthotel in Kissimmee

3.5 star property
6.8 out of 10, (5)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
United States
Gregory
The price is ฿2,266
฿4,776 total
includes taxes & fees
30 Nov - 1 Dec
Enchanted Dreams
Terrace/patio
Enchanted Fantasy

Aparthotel in Kissimmee

3.5 star property
2.0 out of 10, (1)
"I left briefly after I arrived because there was people there & she did not try to work with me it was very frustrating while trying to get in contact with her she kept picking up & hanging up on my face even multiple attempts of Expedia contacting her I didn’t want a full refund because I understand her policy but she didn’t try to work with me for a solution. "
United States
george
The price is ฿1,942
฿4,409 total
includes taxes & fees
30 Nov - 1 Dec
Enchanted Fantasy
Indoor pool, 2 outdoor pools, open 8:00 AM to 8:00 PM, pool umbrellas
Premium Condos near Universal Studios

Condo resort in International Drive District

3.5 star property
9.2 out of 10, Wonderful, (24)
"Easy parking, building and room access. Clean, quiet, and comfortable, with basic kitchen necessities and a coffee pot/filters. My room had a beautiful view of the water with good birdwatching. Within a short walking distance to the Warped Tour shuttle, this place was perfect. "
United States
Brittany
Premium Condos near Universal Studios
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, pool loungers
Marriott's Sabal Palms

Holiday Home in Orlando

4.0 star property
9.6 out of 10, Exceptional, (202)
"Easy check in, pool was awesome "
United States
Lisa
The price is ฿8,226
฿9,255 total
includes taxes & fees
30 Nov - 1 Dec
Marriott's Sabal Palms
Exterior
WorldQuest Resort

Condo in Orlando

3.5 star property
WorldQuest Resort
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

Hilton Orlando Lake Buena Vista - Disney Springs® Area

Hilton Orlando Lake Buena Vista - Disney Springs® Area

10/10 Excellent
"I gave it a nine because I did not even see the bkfst reasturant until da going home. We are bkfst out if mkt place. It was good. "
patricia 2-night trip
Posted 6 hours ago
Hilton Orlando Lake Buena Vista - Disney Springs® Area

Find out more about Winter Park

Search for holiday rentals in Winter Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Park using one of the methods below:

  • View our selection of featured holiday rentals in Winter Park
  • Use the map to find apartments and other holiday homes in the Winter Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Park while they last

Look no further and take a look at our great range of rental properties in Winter Park!

Frequently asked questions

Can I find holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Kraft Azalea Gardens, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Winter Park. Make sure you have time to check out the university setting and gardens during your trip.

What are some of the best holiday rentals that Winter Park has to offer?

Marriott's Sabal Palms: This holiday home rental outside of Winter Park is located near the airport, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with an outdoor tennis court and 1 hot tub.

How many holiday rentals are there in Winter Park?

Expedia has 65 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Morse Museum of American Art, whereas Kraft Azalea Gardens and Lake Virginia are a couple of picturesque spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are holiday rentals like in Winter Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Park. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.