Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Winter Park vacation rentals

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
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic Host"
United States
Marek K.
The price is ￥10,326
￥27,802 total
includes taxes & fees
Feb 23 - Feb 24
1-bedroom vacation room just 12 minutes from University of Central Florida
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 ￥18,141
￥41,729 total
includes taxes & fees
Feb 24 - Feb 25
Quiet and safe neighborhood come to this great place with lots of room for relax
Fridge, microwave, oven, stovetop

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 ￥18,761
￥34,266 total
includes taxes & fees
Feb 23 - Feb 24
Sleek, Spacious & Central – Your Ideal Getaway
TV, offices

Cozy home w/working space & kitchen

Cozy home w/working space & kitchen
College Park
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 ￥12,162
￥39,418 total
includes taxes & fees
Feb 25 - Feb 26
Cozy home w/working space & kitchen
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 ￥8,373
￥16,882 total
includes taxes & fees
Feb 26 - Feb 27
Virbo Host Website is not working for me. Do not book this property. Thank you
Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is ￥23,002
￥43,766 total
includes taxes & fees
Mar 4 - Mar 5
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
The price is ￥26,359
￥62,524 total
includes taxes & fees
Feb 24 - Feb 25
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Exterior

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
The price is ￥23,358
￥44,167 total
includes taxes & fees
Mar 9 - Mar 10
Funky Remodeled Otown Bungalow Sleeps 8
Property grounds

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

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Very clean and location was great"
United States
Vicki V.
The price is ￥17,986
￥37,949 total
includes taxes & fees
Mar 8 - Mar 9
Charming home @wp. Patio +Gazebo. close to highwys
Exterior

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is ￥17,652
￥31,681 total
includes taxes & fees
Mar 8 - Mar 9
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Private kitchen

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
The price is ￥42,949
￥63,298 total
includes taxes & fees
Mar 3 - Mar 4
Spacious 5-bedroom house in gorgeous Winter Park
Fridge, microwave, oven, stovetop

Mills House @WP. Sleeps 11 Renovated. Queen beds

Mills House @WP. Sleeps 11 Renovated. Queen beds
Fairview Shores
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 ￥38,336
￥64,758 total
includes taxes & fees
Mar 25 - Mar 26
Mills House @WP. Sleeps 11 Renovated. Queen beds
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 ￥51,787
￥102,451 total
includes taxes & fees
Mar 1 - Mar 2
Cute 5-bedroom,6bed house in superb Winter Park.
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 Blue Aztec
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
Sanford
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
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

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

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
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 ￥17,056
￥42,097 total
includes taxes & fees
Feb 23 - Feb 24
Spacious & Private Guest Pool House Oasis
Interior

Totally 80's

Totally 80's
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3 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 ￥9,949
￥21,561 total
includes taxes & fees
Feb 23 - Feb 24
Totally 80's
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.

Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Southchase
9.8 out of 10, Exceptional, (22 reviews)
"Quiet peaceful location"
United States
joseph B.
The price is ￥11,164
￥20,022 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Apartment in S Orlando, approx. 20 minutes away from Disney and Universal.
Exterior detail

Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
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 ￥13,179
￥28,394 total
includes taxes & fees
Mar 4 - Mar 5
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 Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Room was very spacious and clean staff was friendly and accommodating."
cassie 2-night trip
Posted 5 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/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
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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?

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

How many vacation rentals are there in Winter Park?

Expedia has 43 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.