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
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Winter Park holiday rentals

Fridge, microwave, oven, stovetop

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
10.0 out of 10, Exceptional, (2 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
The price is HK$1,064
HK$2,344 total
includes taxes & fees
15 May - 16 May
Quiet and safe neighborhood come to this great place with lots of room for relax
Outdoor pool

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
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic Host"
United States
Marek K.
The price is HK$458
HK$1,332 total
includes taxes & fees
13 May - 14 May
1-bedroom vacation room just 12 minutes from University of Central Florida
Exterior

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is HK$810
HK$1,509 total
includes taxes & fees
17 May - 18 May
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is HK$1,116
HK$2,159 total
includes taxes & fees
27 May - 28 May
Cozy home 5min to Park Ave and Downtown Orlando
Property grounds

Virbo Host Website is not working for me. Do not book this property. Thank you

Virbo Host Website is not working for me. Do not book this property. Thank you
Fairview Shores
The price is HK$423
HK$852 total
includes taxes & fees
11 May - 12 May
Virbo Host Website is not working for me. Do not book this property. Thank you
Exterior

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$1,080
HK$2,095 total
includes taxes & fees
9 Jun - 10 Jun
Funky Remodeled Otown Bungalow Sleeps 8
Private kitchen

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
The price is HK$1,957
HK$2,443 total
includes taxes & fees
1 Jun - 2 Jun
Cute 5-bedroom house in peaceful Winter Park
Fridge, microwave, oven, stovetop

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$1,522
HK$2,843 total
includes taxes & fees
12 May - 13 May
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (1 review)
"The house was clean, in a quiet neighborhood. Everything you could need was close and traffic was not bad at all. The host answers any and all questions quick and made the experience hassle free."
United States
Stephanie S.
The price is HK$2,349
HK$2,967 total
includes taxes & fees
11 May - 12 May
Spacious 5-bedroom house in gorgeous Winter Park
Property grounds

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$767
HK$1,789 total
includes taxes & fees
12 May - 13 May
Charming home @wp. Patio +Gazebo. close to highwys
Private kitchen

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$2,505
HK$3,127 total
includes taxes & fees
1 Jun - 2 Jun
Cute 5-bedroom,6bed house in superb Winter Park.
Exterior

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
Orlando
9.4 out of 10, Exceptional, (1,514 reviews)
"Spacious rooms and clean. Great resort!!!"
United States
Javier
The price is HK$808
HK$1,129 total
includes taxes & fees
17 May - 18 May
Hilton Vacation Club Grand Beach Orlando
2 outdoor pools, open 7:00 AM to 11:00 PM, free pool cabanas

Magical Moment Vacation Condos

Magical Moment Vacation Condos
4.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"Very Clean room staff were great !! Definitely would stay again !"
United States
stephanie
The price is HK$719
HK$2,637 total
includes taxes & fees
13 May - 14 May
Magical Moment Vacation Condos
Interior

Suite Near Universal Studios w Pool & Hot Tub

Suite Near Universal Studios w Pool & Hot Tub
3.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"The room was clean and service was great!"
United States
Daija
The price is HK$509
HK$1,268 total
includes taxes & fees
12 May - 13 May
Suite Near Universal Studios w Pool & Hot Tub
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is HK$875
HK$1,637 total
includes taxes & fees
10 May - 11 May
The Front Porch
Living area

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is HK$599
HK$1,784 total
includes taxes & fees
17 May - 18 May
The Blue Aztec
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (67 reviews)
"Great place, found the heater, thank you!Would stay again, just pull the bed away from the wall for us old folk "
United States
Susan J.
The price is HK$585
HK$1,162 total
includes taxes & fees
11 May - 12 May
Tiny Hidden Cottage
Outdoor pool

“Best Stay Ever” – Recent Guest

“Best Stay Ever” – Recent Guest
Lake Mary
9.8 out of 10, Exceptional, (52 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is HK$783
HK$1,958 total
includes taxes & fees
27 May - 28 May
“Best Stay Ever” – Recent Guest
Room

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is HK$652
HK$3,229 total
includes taxes & fees
11 May - 12 May
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Interior

Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
9.8 out of 10, Exceptional, (19 reviews)
"The host is wonderful and the place was exactly what I needed. The bed was extremely comfortable and the neighborhood really quiet. I will definitely be back and stay here again."
United States
Robin L.
The price is HK$783
HK$1,302 total
includes taxes & fees
11 May - 12 May
Cozy studio in fabulous Orlando close to everything
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
"Ok"
Sylvain 2-night trip
Posted less than an hour ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

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?

Grand Luxury Lakes 3BR Townhouse near Disney: This holiday home rental outside of Winter Park is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms and a kitchen with a dishwasher.

How many holiday rentals are there in Winter Park?

Expedia has 58 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Rollins Museum of Art and Morse Museum of American Art, whereas Lake Virginia and Mead Garden 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.