Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Winter Park vacation rentals

Private kitchen

Vacation Home in Winter Park

Spacious 5-bedroom house in gorgeous 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.
$332 nightly
The price is $368
Apr 13 - Apr 14
Total with taxes and fees
Spacious 5-bedroom house in gorgeous Winter Park
Property grounds

Apartment in Fairview Shores

Virbo Host Website is not working for me. Do not book this property. Thank you
$99 nightly
The price is $109
Mar 16 - Mar 17
Total with taxes and fees
Virbo Host Website is not working for me. Do not book this property. Thank you
Interior

Vacation Home in Fairview Shores

Cozy home 5min to Park Ave and Downtown Orlando
$235 nightly
The price is $262
Mar 17 - Mar 18
Total with taxes and fees
Cozy home 5min to Park Ave and Downtown Orlando
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.
$250 nightly
The price is $278
Apr 13 - Apr 14
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
Fridge, microwave, oven, stovetop

Vacation 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.
$201 nightly
The price is $223
Mar 19 - Mar 20
Total with taxes and fees
Sleek, Spacious & Central – Your Ideal Getaway
Property grounds

Vacation 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.
$202 nightly
The price is $225
Mar 17 - Mar 18
Total with taxes and fees
Charming home @wp. Patio +Gazebo. close to highwys
Exterior

Mobile Home in Fairview Shores

Comfy Tiny Home @WP. Large Private Deck+Queen bed
$184 nightly
The price is $204
Mar 29 - Mar 30
Total with taxes and fees
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Exterior

Vacation Home in Fairview Shores

Funky Remodeled Otown Bungalow Sleeps 8
$246 nightly
The price is $274
Mar 18 - Mar 19
Total with taxes and fees
Funky Remodeled Otown Bungalow Sleeps 8
Fridge, microwave, oven, stovetop

Vacation Home in Fairview Shores

Mills House @WP. Sleeps 11 Renovated. Queen beds
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.
$285 nightly
The price is $318
Apr 6 - Apr 7
Total with taxes and fees
Mills House @WP. Sleeps 11 Renovated. Queen beds
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.
$159 nightly
The price is $176
Apr 13 - Apr 14
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
TV, offices

Vacation Home in College Park

Cozy home w/kitchen & work space
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.
$248 nightly
The price is $277
Mar 24 - Mar 25
Total with taxes and fees
Cozy home w/kitchen & work space
Smart TV, video games

Vacation Home in Goldenrod

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
$370 nightly
The price is $411
Mar 16 - Mar 17
Total with taxes and fees
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Private kitchen

Vacation 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.
$558 nightly
The price is $617
Mar 31 - Apr 1
Total with taxes and fees
Cute 5-bedroom,6bed house in superb Winter Park.
6 outdoor pools, free cabanas, pool umbrellas

Condo resort in Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
9.2 out of 10, Wonderful, (4,877 reviews)
"Clean, convenient amenities and beautiful grounds."
United States
Mary
$147 nightly
The price is $166
Apr 10 - Apr 11
Total with taxes and fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Lobby

Condo resort in Bay Lake

Boulder Ridge Villas at Disney's Wilderness Lodge
4.0 star property
8.8 out of 10, Excellent, (54 reviews)
"Looking for perfect compliment to your ultimate Disney World experience? Look no further than the Wilderness Lodge Villas. Not only are the rooms cozy and comfortable but the rustic atmosphere is spot on. After a long day at the Magic Kingdom, there is no better experience than taking the boat back to the lodge, especially at night. You can either recharge your batteries and go back, or you can enjoy all the amenities and atmosphere of the lodge. The only negative was that the food selection at...
United States
David O.
$496 nightly
The price is $558
Apr 14 - Apr 15
Total with taxes and fees
Boulder Ridge Villas at Disney's Wilderness Lodge
3 outdoor pools

Condo resort in Bay Lake

Disney's Beach Club Villas
5.0 star property
9.2 out of 10, Wonderful, (39 reviews)
"Clean and great location"
United States
Anonymous traveler
$733 nightly
The price is $824
Apr 12 - Apr 13
Total with taxes and fees
Disney's Beach Club Villas
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
$205 nightly
The price is $230
Apr 6 - Apr 7
Total with taxes and fees
The Front Porch
Lobby lounge

Condo resort in Orlando

Marriott's Imperial Palm Villas
4.0 star property
9.2 out of 10, Wonderful, (61 reviews)
"Amazing property definitely worth it "
United States
Yves
$319 nightly
The price is $359
Apr 12 - Apr 13
Total with taxes and fees
Marriott's Imperial Palm Villas
Exterior

Condo in Kissimmee

Stunning Seaside Theme Water View Condo - no resort fees!
9.6 out of 10, Exceptional, (35 reviews)
"Everything was clean and host was available to answer any lingering questions."
United States
Monica O.
$381 nightly
The price is $426
Mar 18 - Mar 19
Total with taxes and fees
Stunning Seaside Theme Water View Condo - no resort fees!
2 bedrooms, iron/ironing board, WiFi, bed sheets

Apartment in Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
9.8 out of 10, Exceptional, (11 reviews)
"Great host, and stayed connected with us."
United States
Christopher
$233 nightly
The price is $259
Mar 16 - Mar 17
Total with taxes and fees
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Room was clean. staff was great. "
Melissa 3-night trip
Posted 1 hour ago
Rosen Inn at Pointe Orlando

Find out more about Winter Park

Everything you need to know about Winter Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Park vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we offer vacation rentals in Winter Park close to Kraft Azalea Gardens, or you can choose 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's the top vacation rental that Winter Park has to offer?

Magical Stay Near Universal Studios Florida: Visitors like this Winter Park vacation home rental. It is equipped with a garden, air-conditioning, and free WiFi to help you feel comfortable during your stay.

How many vacation rentals are there in Winter Park?

Expedia has 44 vacation 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 vacation rentals like in Winter Park?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Winter Park. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.