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

Winter Park Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winter Park holiday rentals

Exterior

1. Winter Park Spacious Unit - 118

Winter Park Spacious Unit - 118
Winter Park
The price is HK$784
HK$2,530 total
includes taxes & fees
6 Sept - 7 Sept
Winter Park Spacious Unit - 118
Outdoor pool

2. 1-bedroom vacation room just 12 minutes from University of Central Florida

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
9.6 out of 10, Exceptional, (4 reviews)
"Great location close to lots of things to do. Very clean and cozy. Quiet neighborhood, very friendly owners. Will definitely go back."
United States
jamie l.
1-bedroom vacation room just 12 minutes from University of Central Florida
Interior

3. Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is HK$1,317
HK$2,410 total
includes taxes & fees
9 Sept - 10 Sept
Cozy home 5min to Park Ave and Downtown Orlando
Interior

4. Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Easy booking/check-in process, great location"
United States
Julia K.
The price is HK$1,173
HK$2,225 total
includes taxes & fees
9 Sept - 10 Sept
Funky Remodeled Otown Bungalow Sleeps 8
Interior

5. Charming home @wp. Patio +Gazebo. close to highwys

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
5.4 out of 10, (3 reviews)
"Very clean and location was great"
United States
Vicki V.
The price is HK$855
HK$1,858 total
includes taxes & fees
9 Sept - 10 Sept
Charming home @wp. Patio +Gazebo. close to highwys
Coffee/tea maker, fridge, microwave, oven

6. Quiet and safe neighborhood come to this great place with lots of room for relax

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
9.6 out of 10, Exceptional, (4 reviews)
"It felt safe and secure as a community as well as the accommodations. The host was nice and unintrusive. This was actually my second time staying there. I would do it again."
United States
Olubankole S.
The price is HK$1,045
HK$2,325 total
includes taxes & fees
11 Aug - 12 Aug
Quiet and safe neighborhood come to this great place with lots of room for relax
Interior

7. Comfy Tiny Home @WP. Large Private Deck+Queen bed

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Coffee/tea maker, fridge, microwave, oven

8. Mills House @WP. Sleeps 11 Renovated. Queen beds

Mills House @WP. Sleeps 11 Renovated. Queen beds
Fairview Shores
8.0 out of 10, Very good, (2 reviews)
"Comfortable beds and plentiful TV screens. Nice central location to shopping and dining. Lights are bright without dimming options, and some fixtures not working. "
United States
Larry S.
The price is HK$1,371
HK$2,653 total
includes taxes & fees
11 Aug - 12 Aug
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

9. Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"This property is perfect for a family get together. Very clean and close to so many restaurants and entertainment. The communication the host was great. I would definely stay there again."
United States
Mary Ellen R.
The price is HK$1,961
HK$2,479 total
includes taxes & fees
11 Aug - 12 Aug
Cute 5-bedroom house in peaceful Winter Park
Smart TV, fireplace, stereo

10. The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
10.0 out of 10, Exceptional, (3 reviews)
"The home is beautiful!! The place was clean, comfortable, and exactly as described. The host was friendly, responsive, and made everything easy. I would definitely stay here again and recommend it to others."
United States
Breasia J.
The price is HK$1,899
HK$3,691 total
includes taxes & fees
9 Sept - 10 Sept
The Canopy on Periwinkle- A Home Away From Home
Private kitchen

11. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (3 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
United States
Hannah F.
The price is HK$2,181
HK$2,701 total
includes taxes & fees
10 Sept - 11 Sept
Spacious 5-bedroom house in gorgeous Winter Park
Smart TV

12. Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
8.2 out of 10, Very good, (19 reviews)
"Fabulous place with incredible value "
United States
Kyle C.
The price is HK$1,346
HK$3,290 total
includes taxes & fees
15 Aug - 16 Aug
Winter Park Charmer - Heated Pool Home - Close to everything
Smart TV

13. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
The price is HK$1,977
HK$4,995 total
includes taxes & fees
9 Sept - 10 Sept
Luxury Designer Home • Disney, Universal & Downtown
Smart TV, books, stereo

14. OASIS UNDER THE OAK TREE.

OASIS UNDER THE OAK TREE.
Goldenrod
The price is HK$565
HK$790 total
includes taxes & fees
21 Aug - 22 Aug
OASIS UNDER THE OAK TREE.
Private kitchen

15. Cute 5-bedroom,6bed house in superb Winter Park.

Cute 5-bedroom,6bed house in superb Winter Park.
Winter Park
4.0 out of 10, (1 review)
"We checked in late and were surprised to find half eaten food in the fridge and freezer. Both were very dirty with a noticeable odor. The dishwasher was full of dirty dishes. The oven was full of dirty pans. Most of the dishes in the cupboards had little bits in them as well. There was a fire alarm battery beeping in one of the bedrooms. There was no coffee maker or wine opener or wine glasses or hand soap. There were very few dishes in general, it would have been challenging to cook and serve...
United States
Nyssa S.
The price is HK$2,353
HK$2,934 total
includes taxes & fees
9 Sept - 10 Sept
Cute 5-bedroom,6bed house in superb Winter Park.
Exterior

16. ⛲️Walk to Lake Eola & restaurants

⛲️Walk to Lake Eola & restaurants
Thornton Park
9.2 out of 10, Wonderful, (48 reviews)
"Walking to distance to everything ! Host was great"
United States
Taylor
The price is HK$635
HK$1,409 total
includes taxes & fees
18 Aug - 19 Aug
⛲️Walk to Lake Eola & restaurants
1 bedroom, desk, iron/ironing board, free WiFi

17. Private guest studio in the heart of orlando.

Private guest studio in the heart of orlando.
Orlando
9.8 out of 10, Exceptional, (62 reviews)
"Super clean and updated, loved the location, and quiet neighborhood. Definitely will stay here again!"
United States
Gianna N.
The price is HK$487
HK$1,032 total
includes taxes & fees
11 Aug - 12 Aug
Private guest studio in the heart of orlando.
Iron/ironing board, free WiFi, bed sheets

18. Downtown Private Efficiency Lake Eola Central Business District

Downtown Private Efficiency Lake Eola Central Business District
Downtown Orlando
9.6 out of 10, Exceptional, (64 reviews)
"Great place to stay"
United States
James P.
The price is HK$514
HK$1,279 total
includes taxes & fees
11 Aug - 12 Aug
Downtown Private Efficiency Lake Eola Central Business District
3 bedrooms, desk, iron/ironing board, free WiFi

19. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is HK$988
HK$1,934 total
includes taxes & fees
11 Aug - 12 Aug
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Property grounds

20. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is HK$1,177
HK$2,958 total
includes taxes & fees
23 Aug - 24 Aug
Incredible Private Lakefront Cottage Retreat
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Thank you"
Omar 3-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando

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?

NEW Private Pool Resort Home 10 Min Disney: This holiday home rental outside of Winter Park offers an outdoor pool, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Winter Park?

Expedia has 51 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Morse Museum of American Art and Casa Feliz Historic Home Museum, whereas Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens 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.