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

Winter Park Holiday 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 holiday 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 AU$490
includes taxes & fees
1 Oct - 2 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 AU$486
includes taxes & fees
13 Oct - 14 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 AU$567
includes taxes & fees
5 Oct - 6 Oct
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 AU$405
includes taxes & fees
1 Oct - 2 Oct
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 AU$397
includes taxes & fees
1 Oct - 2 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 AU$178
includes taxes & fees
1 Oct - 2 Oct
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 AU$296
includes taxes & fees
13 Oct - 14 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 AU$256
includes taxes & fees
13 Oct - 14 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 AU$231
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 AU$376
includes taxes & fees
12 Oct - 13 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 AU$448
includes taxes & fees
1 Oct - 2 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 AU$470
includes taxes & fees
13 Oct - 14 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 AU$441
includes taxes & fees
13 Oct - 14 Oct
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 AU$489
includes taxes & fees
13 Oct - 14 Oct
Spacious 5-bedroom house in gorgeous Winter Park
A bedroom with a wooden bed, a nightstand, a lamp, and a chair.

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 AU$562
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 AU$881
includes taxes & fees
13 Oct - 14 Oct
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 AU$545
includes taxes & fees
13 Oct - 14 Oct
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 AU$529
includes taxes & fees
13 Oct - 14 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 AU$123
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)
The price is AU$292
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

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"Everything was good. Close to Disney and everything we needed."
Justin 2-night trip
Posted 1 hour ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Find out more about Winter Park

Everything you need to know about Winter Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winter Park holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Park holiday rentals we have selected for you start as low as AU$123 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

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

How many holiday rentals are there in Winter Park?

Expedia has 55 holiday 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 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.