Winter Park Holiday Rentals

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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 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$1,057
HK$2,227 total
includes taxes & fees
20 Apr - 21 Apr
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$486
HK$1,365 total
includes taxes & fees
20 Apr - 21 Apr
1-bedroom vacation room just 12 minutes from University of Central Florida
Private kitchen

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
The price is HK$1,713
HK$3,108 total
includes taxes & fees
13 Apr - 14 Apr
Cute 5-bedroom house in peaceful Winter Park
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$892
HK$1,600 total
includes taxes & fees
20 Apr - 21 Apr
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$1,135
HK$2,094 total
includes taxes & fees
23 Apr - 24 Apr
Cozy home 5min to Park Ave and Downtown Orlando
Fridge, microwave, oven, stovetop

Sleek, Spacious & Central – Your Ideal Getaway

Sleek, Spacious & Central – Your Ideal Getaway
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Great location in Winter Park! So many quality restaurants and things to do close by. The home is easily accessible with plenty of space. The host, Wendy was very hospitable. We left a toiletry bag and she was kind enough to let us know so we could come back. We enjoyed our one night stay!"
United States
Adam A.
The price is HK$948
HK$1,707 total
includes taxes & fees
13 Apr - 14 Apr
Sleek, Spacious & Central – Your Ideal Getaway
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$853 total
includes taxes & fees
13 Apr - 14 Apr
Virbo Host Website is not working for me. Do not book this property. Thank you
Smart TV, video games

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Goldenrod
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed our stay! Everything was clean, comfortable, and quiet. Very easy access to local restaurants and shopping, and a short drive to theme parks. We would definitely stay here again! Thank you! "
United States
Megan J.
The price is HK$1,410
HK$3,285 total
includes taxes & fees
20 Apr - 21 Apr
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Property grounds

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

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
7.0 out of 10, Good, (2 reviews)
"Very clean and location was great"
United States
Vicki V.
The price is HK$885
HK$1,875 total
includes taxes & fees
13 Apr - 14 Apr
Charming home @wp. Patio +Gazebo. close to highwys
Interior

Spacious Modern Japandi Retreat - Winter Park

Spacious Modern Japandi Retreat - Winter Park
Winter Park
10.0 out of 10, Exceptional, (6 reviews)
"Clean house, good location to where we wanted to be!"
United States
Jennifer M.
The price is HK$1,848
HK$3,960 total
includes taxes & fees
14 Apr - 15 Apr
Spacious Modern Japandi Retreat - Winter Park
Exterior

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
The price is HK$1,153
HK$2,114 total
includes taxes & fees
13 Apr - 14 Apr
Funky Remodeled Otown Bungalow Sleeps 8
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$1,252
HK$2,375 total
includes taxes & fees
13 Apr - 14 Apr
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$1,997
HK$2,980 total
includes taxes & fees
11 May - 12 May
Spacious 5-bedroom house in gorgeous Winter Park
Living area

WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS

WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS
College Park
9.0 out of 10, Wonderful, (2 reviews)
"We had a great time! Home was clean, roomy and all we had hoped for. The hosts were very communicative and quick to answer all our questions prior to our stay! Would definitely recommend!"
United States
Rita C.
The price is HK$2,161
HK$4,860 total
includes taxes & fees
20 Apr - 21 Apr
WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS
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$1,911
HK$4,228 total
includes taxes & fees
13 May - 14 May
Cute 5-bedroom,6bed house in superb Winter Park.
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$916
HK$1,684 total
includes taxes & fees
13 Apr - 14 Apr
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$585
HK$1,769 total
includes taxes & fees
4 May - 5 May
The Blue Aztec
2 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Great host, and stayed connected with us."
United States
Christopher
The price is HK$822
HK$1,963 total
includes taxes & fees
13 Apr - 14 Apr
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Living area

Boho Nights

Boho Nights
3.0 star property
Sanford
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
The price is HK$564
HK$1,158 total
includes taxes & fees
15 Apr - 16 Apr
Boho Nights
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (66 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
The price is HK$557
HK$1,131 total
includes taxes & fees
16 Apr - 17 Apr
Tiny Hidden Cottage
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

8/10 Good
"Yes. didn't eat breakfast."
Nancy 1-night trip
Posted 2 hours 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?

Magical Stay Near Universal Studios Florida: This holiday home rental outside of Winter Park is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

How many holiday rentals are there in Winter Park?

Expedia has 49 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 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.