Winter Park Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Winter Park holiday rentals

Outdoor pool

Apartment in Orlando

1-bedroom vacation room just 12 minutes from University of Central Florida
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic Host"
United States
Marek K.
1-bedroom vacation room just 12 minutes from University of Central Florida
Fridge, microwave, oven, stovetop

Apartment in Orlando

Quiet and safe neighborhood come to this great place with lots of room for relax
10.0 out of 10, Exceptional, (2 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
Quiet and safe neighborhood come to this great place with lots of room for relax
Fridge, microwave, oven, stovetop

Holiday Home in Fairview Shores

Sleek, Spacious & Central – Your Ideal Getaway
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$946
HK$1,705 total
includes taxes & fees
29 Mar - 30 Mar
Sleek, Spacious & Central – Your Ideal Getaway
TV, offices

Holiday Home in College Park

Cozy home w/full kitchen & workspace
8.0 out of 10, Very good, (2 reviews)
"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."
United States
Danielle H.
The price is HK$614
HK$2,044 total
includes taxes & fees
4 Mar - 5 Mar
Cozy home w/full kitchen & workspace
Property grounds

Apartment in Fairview Shores

Virbo Host Website is not working for me. Do not book this property. Thank you
The price is HK$422
HK$852 total
includes taxes & fees
27 Feb - 28 Feb
Virbo Host Website is not working for me. Do not book this property. Thank you
Interior

Holiday Home in Fairview Shores

Cozy home 5min to Park Ave and Downtown Orlando
The price is HK$1,080
HK$2,031 total
includes taxes & fees
4 Mar - 5 Mar
Cozy home 5min to Park Ave and Downtown Orlando
Smart TV, video games

Holiday Home in Goldenrod

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
The price is HK$1,525
HK$3,406 total
includes taxes & fees
4 Mar - 5 Mar
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Exterior

Holiday Home in Fairview Shores

Funky Remodeled Otown Bungalow Sleeps 8
The price is HK$1,178
HK$2,142 total
includes taxes & fees
9 Mar - 10 Mar
Funky Remodeled Otown Bungalow Sleeps 8
Property grounds

Holiday Home in Fairview Shores

Charming home @wp. Patio +Gazebo. close to highwys
10.0 out of 10, Exceptional, (1 review)
"Very clean and location was great"
United States
Vicki V.
The price is HK$907
HK$1,915 total
includes taxes & fees
8 Mar - 9 Mar
Charming home @wp. Patio +Gazebo. close to highwys
Exterior

Mobile Home in Fairview Shores

Comfy Tiny Home @WP. Large Private Deck+Queen bed
The price is HK$891
HK$1,598 total
includes taxes & fees
1 Mar - 2 Mar
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Private kitchen

Holiday Home in Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
The price is HK$2,135
HK$3,173 total
includes taxes & fees
2 Mar - 3 Mar
Spacious 5-bedroom house in gorgeous Winter Park
Fridge, microwave, oven, stovetop

Holiday Home in Fairview Shores

Mills House @WP. Sleeps 11 Renovated. Queen beds
6.0 out of 10, (1 review)
"The air fresheners plug ins were too powerful, we had to put them outside while we stayed in the house. Not enough power outlets. Hanging lamps on master bedroom are not practical, didn’t find the switch to turn them off. Spot light outside kept me up. The motion triggered the light to go on and off constantly. "
United States
Monica E.
The price is HK$1,277
HK$2,521 total
includes taxes & fees
2 Mar - 3 Mar
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

Holiday Home in Winter Park

Cute 5-bedroom,6bed house in superb 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$2,613
HK$5,106 total
includes taxes & fees
1 Mar - 2 Mar
Cute 5-bedroom,6bed house in superb Winter Park.
Living area

Apartment in Sanford

The Blue Aztec
3.0 star property
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec
2 bedrooms, desk, free WiFi

Apartment in Sanford

The Front Porch
3.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The Front Porch
Living area

Apartment in Sanford

Boho Nights
3.0 star property
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
Pool

Holiday Home in Union Park

Spacious & Private Guest Pool House Oasis
9.8 out of 10, Exceptional, (22 reviews)
"Great location , Very enjoy , private space, would book in the future for sure "
United States
Matt B.
The price is HK$860
HK$2,092 total
includes taxes & fees
11 Mar - 12 Mar
Spacious & Private Guest Pool House Oasis
Interior

Apartment in Sanford

Totally 80's
3.0 star property
7.6 out of 10, Good, (4 reviews)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
The price is HK$502
HK$1,088 total
includes taxes & fees
9 Mar - 10 Mar
Totally 80's
1 bedroom, iron/ironing board, WiFi, bed sheets

Apartment in Southchase

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
9.8 out of 10, Exceptional, (22 reviews)
"Quiet peaceful location"
United States
joseph B.
The price is HK$563
HK$1,010 total
includes taxes & fees
28 Feb - 1 Mar
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Exterior detail

Apartment in Orlando

Cozy Private Apartment - Stylish & Spotless — No sharing areas
10.0 out of 10, Exceptional, (29 reviews)
"Mercedes is an amazing host and has thought of - and provided EVERYTHING you need for a fantastic stay. Would ABSOLUTELY stay here again and HIGHLY recommend!!"
United States
Rick K.
The price is HK$665
HK$1,433 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Private Apartment - Stylish & Spotless — No sharing areas
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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Wonderful stay"
Tammy 1-night trip
Posted 1 day ago
Sheraton Vistana Villages Resort Villas, I-Drive/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 43 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.