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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winter Park vacation rentals

An aerial view of a residential area with modern buildings, a marina, and a large body of water.

1. Winter Park Spacious Unit - 118

Winter Park Spacious Unit - 118
Winter Park
10.0 out of 10, Exceptional, (1 review)
"Good property and location!"
United States
Jorge C.
The price is ￥7,916
￥51,214 total
includes taxes & fees
Oct 12 - Oct 13
Winter Park Spacious Unit - 118
A living room with a grey sofa, a small side table with a plant, a framed picture, and a window with curtains.

2. Apartment. Downtown Orlando 10 min & Disney 25 min

Apartment. Downtown Orlando 10 min & Disney 25 min
Fairview Shores
The price is ￥14,287
￥28,145 total
includes taxes & fees
Oct 12 - Oct 13
Apartment. Downtown Orlando 10 min & Disney 25 min
A modern bathroom with a wooden door, a white sink, and a mirror.

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is ￥18,206
￥32,712 total
includes taxes & fees
Oct 12 - Oct 13
Comfy Tiny Home @WP. Large Private Deck+Queen bed
A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.

4. 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 ￥9,340
￥27,031 total
includes taxes & fees
Nov 2 - Nov 3
1-bedroom vacation room just 12 minutes from University of Central Florida
A recreational vehicle (RV) parked in a backyard with a patio area, outdoor furniture, and a wooden fence.

5. OASIS UNDER THE OAK TREE.

OASIS UNDER THE OAK TREE.
Goldenrod
10.0 out of 10, Exceptional, (1 review)
"This is a unique and affordable family opportunity in a residential area close to everything. Military friendly host makes you feel like you are safe with family. Plenty of space for spreading out inside the camper that still provides a private closed off space for quiet time. Less than 10 minutes from Full Sail University for visiting students. I enjoyed the quiet neighborhood and the comfortable living in this very cool urban camping setting. Lots of extras available to hang out in the...
United States
Peg W.
The price is ￥16,243
￥21,360 total
includes taxes & fees
Oct 30 - Oct 31
OASIS UNDER THE OAK TREE.
A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

6. 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 ￥23,121
￥43,959 total
includes taxes & fees
Oct 21 - Oct 22
Funky Remodeled Otown Bungalow Sleeps 8
A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

7. Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Very cute place. Nice outdoor patio."
United States
tyson s.
The price is ￥27,491
￥49,352 total
includes taxes & fees
Oct 14 - Oct 15
Cozy home 5min to Park Ave and Downtown Orlando
A modern kitchen with white cabinets, stainless steel appliances, and a black dining chair.

8. 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
9.6 out of 10, Exceptional, (4 reviews)
"It felt safe and secure as a community as well as the accommodations. The host was nice and unintrusive. This was actually my second time staying there. I would do it again."
United States
Olubankole S.
The price is ￥22,005
￥47,791 total
includes taxes & fees
Nov 1 - Nov 2
Quiet and safe neighborhood come to this great place with lots of room for relax
A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

9. 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 ￥20,422
￥41,854 total
includes taxes & fees
Oct 12 - Oct 13
Charming home @wp. Patio +Gazebo. close to highwys
A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

10. 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 ￥27,491
￥52,537 total
includes taxes & fees
Oct 12 - Oct 13
Mills House @WP. Sleeps 11 Renovated. Queen beds
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

11. Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (3 reviews)
"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 ￥39,578
￥49,868 total
includes taxes & fees
Oct 12 - Oct 13
Cute 5-bedroom house in peaceful Winter Park
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

12. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (4 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 ￥42,427
￥51,159 total
includes taxes & fees
Nov 1 - Nov 2
Spacious 5-bedroom house in gorgeous Winter Park
A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

13. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
10.0 out of 10, Exceptional, (1 review)
"Maximum upgrades in all aspects of the property. Clean, beautiful, and the host was great. Would recommend for anyone looking in Winter Park area"
United States
Cuthbert H.
The price is ￥42,110
￥95,698 total
includes taxes & fees
Oct 13 - Oct 14
Luxury Designer Home • Disney, Universal & Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

14. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is ￥48,918
￥61,754 total
includes taxes & fees
Oct 12 - Oct 13
Spacious 5-bedroom house in welcoming Winter Park
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

15. 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 ￥47,493
￥59,999 total
includes taxes & fees
Oct 12 - Oct 13
Cute 5-bedroom,6bed house in superb Winter Park.
A modern bedroom with a large bed, a bedside table, a wooden dresser, and a hanging light fixture.

16. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (336 reviews)
"The check in process was smooth and did not require any front desk it was perfect for a quick stay! The room was pretty big for the price! and very clean. The property itself was cute and cozy they had a very cool common area! Love this stay"
United States
Dustin
The price is ￥12,111
￥13,626 total
includes taxes & fees
Oct 26 - Oct 27
Suites by The Wellborn
A modern kitchen with grey cabinets, a wooden countertop, and a built-in stove.

17. Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park
South Eola
10.0 out of 10, Exceptional, (15 reviews)
"Clean and quiet spot with an easy check-in process. Super close to the lake with lots of restaurants within walking distance. Parking was easy to access and made getting in and out quite easy."
United States
Caroline V.
The price is ￥12,310
￥26,632 total
includes taxes & fees
Oct 13 - Oct 14
Lake Eola view 1 bedroom Thornton Park
A swimming pool with lounge chairs and palm trees.

18. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,404 reviews)
"Convenient to parks and good value."
United States
Tracy
The price is ￥9,688
￥12,858 total
includes taxes & fees
Oct 25 - Oct 26
The Point Hotel & Suites Orlando
A bedroom with a bed, a ceiling fan, and artwork on the walls.

19. Downtown Private Efficiency Lake Eola Central Business District

Downtown Private Efficiency Lake Eola Central Business District
Downtown Orlando
9.6 out of 10, Exceptional, (68 reviews)
"It's a nice spot tucked right in the heart of Orlando! Perfect for solo travelers or couples. It's bigger and better than the hotels nearby. Plus it includes free parking and is cheaper than a hotel!"
United States
Noah
The price is ￥11,113
￥25,285 total
includes taxes & fees
Oct 20 - Oct 21
Downtown Private Efficiency Lake Eola Central Business District
A two-story house with a front porch, a driveway, and a well-maintained lawn.

20. ⛲️Walk to Lake Eola & restaurants

⛲️Walk to Lake Eola & restaurants
Thornton Park
9.2 out of 10, Wonderful, (51 reviews)
"Very well situated."
United States
Al F.
The price is ￥13,393
￥28,920 total
includes taxes & fees
Oct 19 - Oct 20
⛲️Walk to Lake Eola & restaurants
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
"Loved the space inside. Disappointed the ceiling fan in screened in porch didn’t work. Staff all friendly. Close drive to attractions Loved back door with outside access right to pool."
Mary 3-night trip
Posted 3 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
  • Use the map to find apartments and other holiday homes in the Winter Park neighbourhood you prefer
  • 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?

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !: Visitors like this Winter Park vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Winter Park?

Expedia has 55 vacation rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, whereas Lake Mizell and Kraft Azalea Gardens 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.