Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Winter Park vacation rentals

Fridge, microwave, oven, stovetop

Stylish Boutique Guest house in Winter Park

Stylish Boutique Guest house in Winter Park
Winter Park
10.0 out of 10, Exceptional, (109 reviews)
"Excellent location, peaceful setting "
United States
Christy M.
The price is ￥23,811
￥55,143 total
includes taxes & fees
May 27 - May 28
Stylish Boutique Guest house in Winter Park
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 ￥21,144
￥46,249 total
includes taxes & fees
May 20 - May 21
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
9.6 out of 10, Exceptional, (4 reviews)
The price is ￥9,435
￥27,191 total
includes taxes & fees
May 26 - May 27
1-bedroom vacation room just 12 minutes from University of Central Florida
Smart TV

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is ￥20,081
￥39,636 total
includes taxes & fees
Jun 2 - Jun 3
Cozy home 5min to Park Ave and Downtown Orlando
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 ￥23,811
￥62,186 total
includes taxes & fees
May 27 - May 28
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Exterior

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is ￥17,707
￥32,024 total
includes taxes & fees
May 27 - May 28
Comfy Tiny Home @WP. Large Private Deck+Queen bed
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 ￥8,572
￥17,284 total
includes taxes & fees
May 20 - May 21
Virbo Host Website is not working for me. Do not book this property. Thank you
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 ￥45,584
￥57,407 total
includes taxes & fees
Jun 18 - Jun 19
Spacious 5-bedroom house in gorgeous Winter Park
Private kitchen

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (1 review)
"This property is perfect for a family get together. Very clean and close to so many restaurants and entertainment. The communication the host was great. I would definely stay there again."
United States
Mary Ellen R.
The price is ￥39,685
￥48,733 total
includes taxes & fees
Jun 14 - Jun 15
Cute 5-bedroom house in peaceful Winter Park
Exterior

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Easy booking/check-in process, great location"
United States
Julia K.
The price is ￥22,089
￥42,212 total
includes taxes & fees
May 27 - May 28
Funky Remodeled Otown Bungalow Sleeps 8
Dining

The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
The Canopy on Periwinkle- A Home Away From Home
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 ￥31,034
￥56,899 total
includes taxes & fees
May 27 - May 28
Mills House @WP. Sleeps 11 Renovated. Queen beds
2 bedrooms, desk, iron/ironing board, travel crib

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

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
5.4 out of 10, (3 reviews)
"Very clean and location was great"
United States
Vicki V.
The price is ￥15,557
￥35,796 total
includes taxes & fees
May 20 - May 21
Charming home @wp. Patio +Gazebo. close to highwys
Dining

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️
College Park
10.0 out of 10, Exceptional, (1 review)
"had a great time. beautiful house"
United States
katie L.
The price is ￥707,295
￥888,233 total
includes taxes & fees
Jun 16 - Jun 17
5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️
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 ￥50,797
￥63,083 total
includes taxes & fees
Jun 1 - Jun 2
Cute 5-bedroom,6bed house in superb Winter Park.
Exterior

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
Orlando
9.4 out of 10, Exceptional, (1,514 reviews)
"Great resort!!"
United States
Nathaniel
The price is ￥15,874
￥22,323 total
includes taxes & fees
May 27 - May 28
Hilton Vacation Club Grand Beach Orlando
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 ￥18,572
￥34,134 total
includes taxes & fees
May 20 - May 21
The Front Porch
Apartment (1 Bedroom) | Interior

Suite Near Universal Studios w Pool & Hot Tub

Suite Near Universal Studios w Pool & Hot Tub
3.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"The room was clean and service was great!"
United States
Daija
The price is ￥9,398
￥24,688 total
includes taxes & fees
Jun 2 - Jun 3
Suite Near Universal Studios w Pool & Hot Tub
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

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 ￥10,715
￥34,573 total
includes taxes & fees
May 24 - May 25
The Blue Aztec
Property grounds

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is ￥20,489
￥55,031 total
includes taxes & fees
May 20 - May 21
Incredible Private Lakefront Cottage Retreat
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

Marriott's Grande Vista

Marriott's Grande Vista

6/10 Okay
"Pool was nice atleast"
Nicole 4-night trip
Posted 5 hours ago
Marriott's Grande Vista

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
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  • 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 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?

Grand Luxury Lakes 3BR Townhouse near Disney: Visitors like this Winter Park vacation home rental. It is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms and a kitchen with a dishwasher.

How many vacation rentals are there in Winter Park?

Expedia has 60 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 Lake Virginia and Mead Garden 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.