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

Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winter Park vacation rentals

Exterior

1. Winter Park Spacious Unit - 118

Winter Park Spacious Unit - 118
Winter Park
10.0 out of 10, Exceptional, (1 review)
"Good property and location!"
United States
Jorge C.
The price is AED 294
AED 1,256 total
includes taxes & fees
30 Sep - 1 Oct
Winter Park Spacious Unit - 118
Coffee/tea maker, fridge, microwave, oven

2. Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (109 reviews)
"We enjoyed a great stay! "
United States
Amanda B.
The price is AED 551
AED 1,210 total
includes taxes & fees
28 Sep - 29 Sep
Stylish Boutique Guest house in Winter Park
Smart TV, fireplace, stereo

3. 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, (4 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 AED 474
AED 1,264 total
includes taxes & fees
28 Sep - 29 Sep
The Canopy on Periwinkle- A Home Away From Home
Coffee/tea maker, fridge, microwave, oven

4. 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 AED 511
AED 1,061 total
includes taxes & fees
27 Oct - 28 Oct
Quiet and safe neighborhood come to this great place with lots of room for relax
Interior

5. 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 AED 536
AED 987 total
includes taxes & fees
6 Oct - 7 Oct
Funky Remodeled Otown Bungalow Sleeps 8
Exterior

6. OASIS UNDER THE OAK TREE.

OASIS UNDER THE OAK TREE.
Goldenrod
10.0 out of 10, Exceptional, (1 review)
"This is a unique and affordable family opportunity in a residential area close to everything. Military friendly host makes you feel like you are safe with family. Plenty of space for spreading out inside the camper that still provides a private closed off space for quiet time. Less than 10 minutes from Full Sail University for visiting students. I enjoyed the quiet neighborhood and the comfortable living in this very cool urban camping setting. Lots of extras available to hang out in the...
United States
Peg W.
The price is AED 335
AED 449 total
includes taxes & fees
2 Oct - 3 Oct
OASIS UNDER THE OAK TREE.
Interior

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is AED 422
AED 755 total
includes taxes & fees
28 Sep - 29 Sep
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Smart TV

8. Apartment. Downtown Orlando 10 min & Disney 25 min

Apartment. Downtown Orlando 10 min & Disney 25 min
Fairview Shores
The price is AED 300
AED 618 total
includes taxes & fees
29 Sep - 30 Sep
Apartment. Downtown Orlando 10 min & Disney 25 min
Outdoor pool

9. 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.
The price is AED 172
AED 577 total
includes taxes & fees
5 Oct - 6 Oct
1-bedroom vacation room just 12 minutes from University of Central Florida
Interior

10. 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 AED 474
AED 945 total
includes taxes & fees
28 Sep - 29 Sep
Charming home @wp. Patio +Gazebo. close to highwys
Interior

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

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is AED 566
AED 1,020 total
includes taxes & fees
28 Sep - 29 Sep
Cozy home 5min to Park Ave and Downtown Orlando
Coffee/tea maker, fridge, microwave, oven

12. 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 AED 642
AED 1,176 total
includes taxes & fees
28 Sep - 29 Sep
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

13. Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (3 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 AED 918
AED 1,102 total
includes taxes & fees
28 Sep - 29 Sep
Cute 5-bedroom house in peaceful Winter Park
Private kitchen

14. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (4 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 AED 1,021
AED 1,217 total
includes taxes & fees
28 Sep - 29 Sep
Spacious 5-bedroom house in gorgeous Winter Park
Terrace/patio

15. 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 AED 562
AED 1,364 total
includes taxes & fees
6 Oct - 7 Oct
Winter Park Charmer - Heated Pool Home - Close to everything
Private kitchen

16. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
The price is AED 977
AED 2,209 total
includes taxes & fees
28 Sep - 29 Sep
Luxury Designer Home • Disney, Universal & Downtown
Private kitchen

17. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is AED 1,135
AED 1,345 total
includes taxes & fees
28 Sep - 29 Sep
Spacious 5-bedroom house in welcoming Winter Park
Private kitchen

18. 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 AED 1,102
AED 1,308 total
includes taxes & fees
28 Sep - 29 Sep
Cute 5-bedroom,6bed house in superb Winter Park.
Superior Suite, 1 King Bed with Sofa bed, Kitchenette | Iron/ironing board, travel crib, WiFi, individually furnished

19. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (334 reviews)
"Establishment with meticulously designed in, which made it very comfortable. I enjoyed my stay tremendously. The communication of the staff was amazing, our room is immaculate, a bar had a very in fighting comforting environment very clean get place to socialize with friends and family.I will see you next year the same time."
United States
Sondria
The price is AED 281
AED 316 total
includes taxes & fees
4 Oct - 5 Oct
Suites by The Wellborn
Coffee/tea maker, fridge, microwave, oven

20. Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (18 reviews)
"Great location and home! "
United States
Emma D.
The price is AED 393
AED 738 total
includes taxes & fees
27 Oct - 28 Oct
Renovated Condo Lake Eola View Great Location
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 Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Great place to stay! Definitely loved the bus transportation to HHN! The hotel was great with food available until 3am and Starbucks and universal gift shop right in the lobby! Stayed on the 10th floor with pool view and my 14 year old daughter was impressed!"
Elizabeth 2-night trip
Posted less than an hour ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we offer vacation rentals in Winter Park close to Kraft Azalea Gardens, or you can choose 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's the top vacation rental that Winter Park has to offer?

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !: Visitors like this Winter Park vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Winter Park?

Expedia has 55 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Albin Polasek Museum and Sculpture Gardens 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 vacation rentals like in Winter Park?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winter Park. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.