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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
$320 nightly
The price is $362
Sep 30 - Oct 1
Total with taxes and fees
Winter Park Spacious Unit - 118
A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

2. 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.
$240 nightly
The price is $268
Oct 6 - Oct 7
Total with taxes and fees
Funky Remodeled Otown Bungalow Sleeps 8
A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

3. 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, (4 reviews)
"The home is beautiful!! The place was clean, comfortable, and exactly as described. The host was friendly, responsive, and made everything easy. I would definitely stay here again and recommend it to others."
United States
Breasia J.
$325 nightly
The price is $361
Sep 24 - Sep 25
Total with taxes and fees
The Canopy on Periwinkle- A Home Away From Home
A modern kitchen with white cabinets, stainless steel appliances, and a black dining chair.

4. 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.
$263 nightly
The price is $292
Sep 24 - Sep 25
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
A modern bathroom with a wooden door, a white sink, and a mirror.

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
$186 nightly
The price is $207
Sep 24 - Sep 25
Total with taxes and fees
Comfy Tiny Home @WP. Large Private Deck+Queen bed

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

Apartment. Downtown Orlando 10 min & Disney 25 min
Fairview Shores
$152 nightly
The price is $168
Sep 28 - Sep 29
Total with taxes and fees
Apartment. Downtown Orlando 10 min & Disney 25 min
A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

7. 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.
$238 nightly
The price is $264
Sep 24 - Sep 25
Total with taxes and fees
Charming home @wp. Patio +Gazebo. close to highwys
A recreational vehicle with a covered awning, a small table, and a wooden fence.

8. 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.
$111 nightly
The price is $122
Oct 2 - Oct 3
Total with taxes and fees
OASIS UNDER THE OAK TREE.
A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.

9. 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.
$148 nightly
The price is $164
Oct 4 - Oct 5
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

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

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
$260 nightly
The price is $289
Sep 24 - Sep 25
Total with taxes and fees
Cozy home 5min to Park Ave and Downtown Orlando
A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

11. 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.
$298 nightly
The price is $331
Oct 7 - Oct 8
Total with taxes and fees
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.

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.
$234 nightly
The price is $259
Sep 24 - Sep 25
Total with taxes and fees
Spacious 5-bedroom house in gorgeous Winter Park
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

13. 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.
$275 nightly
The price is $305
Sep 24 - Sep 25
Total with taxes and fees
Cute 5-bedroom house in peaceful Winter Park
A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

14. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
$582 nightly
The price is $647
Sep 27 - Sep 28
Total with taxes and fees
Luxury Designer Home • Disney, Universal & Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

15. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
$340 nightly
The price is $377
Sep 24 - Sep 25
Total with taxes and fees
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.

16. 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.
$331 nightly
The price is $367
Sep 24 - Sep 25
Total with taxes and fees
Cute 5-bedroom,6bed house in superb Winter Park.
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.
$152 nightly
The price is $168
Sep 24 - Sep 25
Total with taxes and fees
Lake Eola view 1 bedroom Thornton Park
A living room with a green sofa, a wooden coffee table, and a patterned rug. There are three framed artworks on the wall and a large plant to the left.

18. Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location
South Eola
10.0 out of 10, Exceptional, (18 reviews)
"Great location and home! "
United States
Emma D.
$157 nightly
The price is $174
Sep 24 - Sep 25
Total with taxes and fees
Renovated Condo Lake Eola View Great Location
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, (66 reviews)
"Great place to stay"
United States
James P.
$137 nightly
The price is $152
Sep 24 - Sep 25
Total with taxes and fees
Downtown Private Efficiency Lake Eola Central Business District
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

20. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (58 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
$222 nightly
The price is $246
Sep 24 - Sep 25
Total with taxes and fees
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
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

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

10/10 Excellent
"Super bien situé et avec un bon resto en plus mc coy! Bien pratique pour les cols très töt!"
Pascal 1-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport

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 $87 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?

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 Albin Polasek Museum and Sculpture Gardens and Rollins Museum of Art, whereas Kraft Azalea Gardens and Virginia S. Nelson Rose 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.