A two-story house with a balcony, surrounded by lush greenery and trees.

Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Winter Park vacation rentals

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 AED 918
AED 1,153 total
includes taxes & fees
29 Jun - 30 Jun
Cute 5-bedroom house in peaceful Winter Park
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, (4 reviews)
"Nice and roomy!"
United States
Ashley C.
The price is AED 588
AED 1,480 total
includes taxes & fees
1 Jul - 2 Jul
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
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
9.4 out of 10, Exceptional, (3 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
The price is AED 489
AED 1,077 total
includes taxes & fees
29 Jun - 30 Jun
Quiet and safe neighborhood come to this great place with lots of room for relax
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, (2 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
United States
Hannah F.
The price is AED 911
AED 1,145 total
includes taxes & fees
7 Jul - 8 Jul
Spacious 5-bedroom house in gorgeous Winter Park
Interior

The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
10.0 out of 10, Exceptional, (2 reviews)
"Our stay here was excellent! We were able to have a birthday party for our one-year-old grandson, turning 2 and it was an awesome day. Everything was perfect, and the host was very generous about giving us a late check out on the day we left. Would LOVE to stay here again in the future! Thank you, Glen!"
United States
t z.
The price is AED 732
AED 1,518 total
includes taxes & fees
29 Jun - 30 Jun
The Canopy on Periwinkle- A Home Away From Home
Interior

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 AED 503
AED 982 total
includes taxes & fees
21 Jul - 22 Jul
Funky Remodeled Otown Bungalow Sleeps 8
Interior

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is AED 380
AED 708 total
includes taxes & fees
27 Jul - 28 Jul
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is AED 422
AED 862 total
includes taxes & fees
1 Jul - 2 Jul
Cozy home 5min to Park Ave and Downtown Orlando
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 AED 638
AED 1,230 total
includes taxes & fees
1 Jul - 2 Jul
Mills House @WP. Sleeps 11 Renovated. Queen beds
Interior

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.
Charming home @wp. Patio +Gazebo. close to highwys
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)
"Great location close to lots of things to do. Very clean and cozy. Quiet neighborhood, very friendly owners. Will definitely go back."
United States
jamie l.
The price is AED 215
AED 625 total
includes taxes & fees
7 Jul - 8 Jul
1-bedroom vacation room just 12 minutes from University of Central Florida
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 AED 7,810
AED 10,035 total
includes taxes & fees
29 Jun - 30 Jun
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 AED 1,102
AED 1,388 total
includes taxes & fees
29 Jul - 30 Jul
Cute 5-bedroom,6bed house in superb Winter Park.
6 outdoor pools, free cabanas, pool umbrellas

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
4.0 star property
Orlando
9.2 out of 10, Wonderful, (5,929 reviews)
"I can’t wait to come back again, Best place for family Vacation!!!"
United States
Ivelisse
The price is AED 497
AED 559 total
includes taxes & fees
28 Jul - 29 Jul
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Lobby

Marriott's Imperial Palm Villas

Marriott's Imperial Palm Villas
4.0 star property
Orlando
9.2 out of 10, Wonderful, (63 reviews)
"Brilliant place would highly recommend and close to Disney parks"
United Kingdom
Matthew
The price is AED 1,054
AED 1,186 total
includes taxes & fees
20 Jul - 21 Jul
Marriott's Imperial Palm Villas
Apartment, Patio | Living area

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is AED 485
AED 1,165 total
includes taxes & fees
19 Jul - 20 Jul
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Apartment (2 Bedrooms) | Interior

Upstay: Family-friendly Getaway With Spa & Pool

Upstay: Family-friendly Getaway With Spa & Pool
3.5 star property
Orlando
10.0 out of 10, Exceptional, (1 review)
"Clean room"
United States
Yves marie
The price is AED 322
AED 895 total
includes taxes & fees
1 Jul - 2 Jul
Upstay: Family-friendly Getaway With Spa & Pool
Waterslide

The Cabins at Disney's Fort Wilderness Resort

The Cabins at Disney's Fort Wilderness Resort
4.5 star property
Bay Lake
9.2 out of 10, Wonderful, (566 reviews)
"This is one of my favorite Disney properties. The cabins are amazing!!"
United States
Mike
The Cabins at Disney's Fort Wilderness Resort
2 bedrooms, iron/ironing board, WiFi, bed sheets

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)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is AED 386
AED 957 total
includes taxes & fees
3 Jul - 4 Jul
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Smart TV, table tennis

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (25 reviews)
"Quiet neighborhood, good location."
United States
River
The price is AED 579
AED 1,037 total
includes taxes & fees
29 Jun - 30 Jun
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
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 Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Great customer service and security was phenomenal. I forgot a sweater and they were able to locate it and secure it for me."
Yotuel 3-night trip
Posted less than an hour ago
Rosen Inn Lake Buena Vista

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 52 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Rollins Museum of Art and Morse Museum of American Art, whereas Kraft Azalea Gardens and Lake Virginia are a couple of picturesque spots to enjoy the outdoors. Kia Center and Universal Studios Florida 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.