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

Winter Park Vacation Rentals

  • 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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winter Park vacation rentals

An aerial view of a residential area with modern buildings, a marina, and a large body of water.

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 SAR 300
SAR 1,284 total
includes taxes & fees
30 Sep - 1 Oct
Winter Park Spacious Unit - 118
A modern kitchen with a central island, built-in appliances, and a skylight.

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 SAR 563
SAR 1,237 total
includes taxes & fees
27 Oct - 28 Oct
Stylish Boutique Guest house in Winter Park
A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

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, (5 reviews)
"Our stay here was excellent! We were able to have a birthday party for our one-year-old grandson, turning 2 and it was an awesome day. Everything was perfect, and the host was very generous about giving us a late check out on the day we left. Would LOVE to stay here again in the future! Thank you, Glen!"
United States
t z.
The price is SAR 484
SAR 1,292 total
includes taxes & fees
29 Sep - 30 Sep
The Canopy on Periwinkle- A Home Away From Home
A modern kitchen with white cabinets, stainless steel appliances, and a black dining chair.

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 SAR 470
SAR 1,026 total
includes taxes & fees
29 Sep - 30 Sep
Quiet and safe neighborhood come to this great place with lots of room for relax
A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

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 SAR 548
SAR 1,009 total
includes taxes & fees
6 Oct - 7 Oct
Funky Remodeled Otown Bungalow Sleeps 8
A recreational vehicle (RV) parked in a backyard with a patio area, outdoor furniture, and a wooden fence.

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 SAR 297
SAR 408 total
includes taxes & fees
29 Sep - 30 Sep
OASIS UNDER THE OAK TREE.
A modern bathroom with a wooden door, a white sink, and a mirror.

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is SAR 453
SAR 796 total
includes taxes & fees
11 Oct - 12 Oct
Comfy Tiny Home @WP. Large Private Deck+Queen bed
A living room with a grey sofa, a small side table with a plant, a framed picture, and a window with curtains.

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

Apartment. Downtown Orlando 10 min & Disney 25 min
Fairview Shores
The price is SAR 339
SAR 668 total
includes taxes & fees
6 Oct - 7 Oct
Apartment. Downtown Orlando 10 min & Disney 25 min
A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.

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 SAR 179
SAR 593 total
includes taxes & fees
5 Oct - 6 Oct
1-bedroom vacation room just 12 minutes from University of Central Florida
A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

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 SAR 518
SAR 1,004 total
includes taxes & fees
29 Oct - 30 Oct
Charming home @wp. Patio +Gazebo. close to highwys
A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

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

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is SAR 648
SAR 1,120 total
includes taxes & fees
7 Oct - 8 Oct
Cozy home 5min to Park Ave and Downtown Orlando
A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an 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 SAR 652
SAR 1,197 total
includes taxes & fees
11 Oct - 12 Oct
Mills House @WP. Sleeps 11 Renovated. Queen beds
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

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 SAR 939
SAR 1,126 total
includes taxes & fees
29 Sep - 30 Sep
Cute 5-bedroom house in peaceful Winter Park
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

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 SAR 1,044
SAR 1,244 total
includes taxes & fees
29 Sep - 30 Sep
Spacious 5-bedroom house in gorgeous Winter Park
A bedroom with a wooden bed, a window with blinds, a nightstand with a lamp, and a decorative wall piece.

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, (20 reviews)
"Fabulous place with incredible value "
United States
Kyle C.
The price is SAR 551
SAR 1,365 total
includes taxes & fees
6 Oct - 7 Oct
Winter Park Charmer - Heated Pool Home - Close to everything
A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

16. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
10.0 out of 10, Exceptional, (1 review)
"Maximum upgrades in all aspects of the property. Clean, beautiful, and the host was great. Would recommend for anyone looking in Winter Park area"
United States
Cuthbert H.
The price is SAR 999
SAR 2,258 total
includes taxes & fees
29 Sep - 30 Sep
Luxury Designer Home • Disney, Universal & Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

17. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is SAR 1,160
SAR 1,374 total
includes taxes & fees
29 Sep - 30 Sep
Spacious 5-bedroom house in welcoming Winter Park
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

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 SAR 1,126
SAR 1,337 total
includes taxes & fees
29 Oct - 30 Oct
Cute 5-bedroom,6bed house in superb Winter Park.
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

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 SAR 287
SAR 323 total
includes taxes & fees
4 Oct - 5 Oct
Suites by The Wellborn
A modern kitchen with white cabinets, a stainless steel microwave, an oven, and a dishwasher.

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 SAR 401
SAR 755 total
includes taxes & fees
19 Oct - 20 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.
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

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Buenos"
Gerardo 5-night trip
Posted less than an hour ago
Rosen Inn Lake Buena Vista

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.