Winter Park Holiday Rentals

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Our top choices for Winter Park holiday rentals

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 AU$259
includes taxes & fees
13 Apr - 14 Apr
1-bedroom vacation room just 12 minutes from University of Central Florida

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 AU$160
includes taxes & fees
5 Apr - 6 Apr
Virbo Host Website is not working for me. Do not book this property. Thank you

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is AU$304
includes taxes & fees
14 Apr - 15 Apr
Comfy Tiny Home @WP. Large Private Deck+Queen bed

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 AU$324
includes taxes & fees
16 Apr - 17 Apr
Sleek, Spacious & Central – Your Ideal Getaway

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 AU$422
includes taxes & fees
14 Apr - 15 Apr
Quiet and safe neighborhood come to this great place with lots of room for relax

Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (106 reviews)
"Excellent location, peaceful setting "
United States
Christy M.
Stylish Boutique Guest house in Winter Park

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
Cozy home 5min to Park Ave and Downtown Orlando

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
The price is AU$566
includes taxes & fees
3 Apr - 4 Apr
Cute 5-bedroom house in peaceful Winter Park

Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
8.0 out of 10, Very good, (14 reviews)
"Not as advertised, very disappointed. Got in from a red eye flight and thought we could relax around the pool. But it was unkept and full of algae. Stained black mold all around the pool. And mold on the furniture and pool floats. Not a pleasant start to our family vacation."
United States
Jon F.
The price is AU$609
includes taxes & fees
3 Apr - 4 Apr
Winter Park Charmer - Heated Pool Home - Close to everything

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 AU$374
includes taxes & fees
14 Apr - 15 Apr
Charming home @wp. Patio +Gazebo. close to highwys

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 AU$597
includes taxes & fees
6 Apr - 7 Apr
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

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.
Spacious Modern Japandi Retreat - Winter Park

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 AU$908
includes taxes & fees
16 Apr - 17 Apr
WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
The price is AU$424
includes taxes & fees
14 Apr - 15 Apr
Funky Remodeled Otown Bungalow Sleeps 8

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 AU$580
includes taxes & fees
15 Apr - 16 Apr
Spacious 5-bedroom house in gorgeous Winter Park

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$483
includes taxes & fees
14 Apr - 15 Apr
Mills House @WP. Sleeps 11 Renovated. Queen beds

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.
Cute 5-bedroom,6bed house in superb Winter Park.

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (64 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 AU$211
includes taxes & fees
7 Apr - 8 Apr
Tiny Hidden Cottage

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 AU$326
includes taxes & fees
6 Apr - 7 Apr
The Blue Aztec

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 AU$374
includes taxes & fees
4 Apr - 5 Apr
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
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

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$124 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?

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

How many holiday rentals are there in Winter Park?

Expedia has 44 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.