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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winter Park holiday rentals

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 NZ$466
includes taxes & fees
16 Mar - 17 Mar
Cozy home w/full kitchen & workspace
The price is NZ$456
includes taxes & fees
17 Mar - 18 Mar
Cozy home 5min to Park Ave and Downtown Orlando
Comfy Tiny Home @WP. Large Private Deck+Queen bed
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic Host"
United States
Marek K.
The price is NZ$335
includes taxes & fees
1 Apr - 2 Apr
1-bedroom vacation room just 12 minutes from University of Central Florida
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
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 NZ$371
includes taxes & fees
10 Mar - 11 Mar
Sleek, Spacious & Central – Your Ideal Getaway
The price is NZ$185
includes taxes & fees
10 Mar - 11 Mar
Virbo Host Website is not working for me. Do not book this property. Thank you
10.0 out of 10, Exceptional, (1 review)
"Very clean and location was great"
United States
Vicki V.
The price is NZ$411
includes taxes & fees
29 Mar - 30 Mar
Charming home @wp. Patio +Gazebo. close to highwys
The price is NZ$654
includes taxes & fees
10 Mar - 11 Mar
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Holiday Home in Fairview Shores

Funky Remodeled Otown Bungalow Sleeps 8
The price is NZ$438
includes taxes & fees
10 Mar - 11 Mar
Funky Remodeled Otown Bungalow Sleeps 8
8.0 out of 10, Very good, (2 reviews)
"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 NZ$557
includes taxes & fees
17 Mar - 18 Mar
Mills House @WP. Sleeps 11 Renovated. Queen beds
The price is NZ$593
includes taxes & fees
30 Mar - 31 Mar
Spacious 5-bedroom house in gorgeous 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 NZ$1,023
includes taxes & fees
31 Mar - 1 Apr
Cute 5-bedroom,6bed house in superb Winter Park.
9.2 out of 10, Wonderful, (13 reviews)
"I stayed at the property from Oct 31st to Nov 2nd for the weekend. This is a very cozy and clean studio apartment which was perfect fo myself and my 2 dogs. There is a fenced in yard at lights at night so my dogs really enjoyed it also. "
United States
michael
The price is NZ$285
includes taxes & fees
30 Mar - 31 Mar
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry

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
9.8 out of 10, Exceptional, (22 reviews)
"Everything was amazing described how it was owners were super sweet and loving we were happy to find this place to stay "
United States
Pamela Y.
The price is NZ$219
includes taxes & fees
14 Mar - 15 Mar
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.

Apartment in Sanford

Boho Nights
3.0 star property
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights

Apartment in Sanford

The Blue Aztec
10.0 out of 10, Exceptional, (12 reviews)
"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"
United States
Min O.
The price is NZ$293
includes taxes & fees
10 Mar - 11 Mar
The Blue Aztec
10.0 out of 10, Exceptional, (10 reviews)
"Great host, and stayed connected with us."
United States
Christopher
The price is NZ$439
includes taxes & fees
10 Mar - 11 Mar
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
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 NZ$471
includes taxes & fees
10 Mar - 11 Mar
Spacious & Private Guest Pool House Oasis
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Park Hotel Reviews

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 favorite 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 depends 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 NZ$158 per night. Entering your travel dates in the search wizard you might find 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?

Amazing house with Pool4b(4b just 9 minutes from Ventura country club golf: This holiday home rental outside of Winter Park offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Winter Park?

Expedia has 42 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.