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

Winter Park Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winter Park vacation rentals

A modern bathroom with a wooden door, a white sink, and a mirror.

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
$159 nightly
The price is $178
Nov 17 - Nov 18
Total with taxes and fees
Comfy Tiny Home @WP. Large Private Deck+Queen bed
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.
$225 nightly
The price is $251
Nov 22 - Nov 23
Total with taxes and fees
Funky Remodeled Otown Bungalow Sleeps 8
A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.

3. 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.
$160 nightly
The price is $178
Nov 18 - Nov 19
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
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.
$236 nightly
The price is $264
Nov 11 - Nov 12
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

5. 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.
$249 nightly
The price is $278
Nov 22 - Nov 23
Total with taxes and fees
Cozy home 5min to Park Ave and Downtown Orlando
A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

6. 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.
$218 nightly
The price is $244
Nov 17 - Nov 18
Total with taxes and fees
Charming home @wp. Patio +Gazebo. close to highwys
A wooden gate with a metal latch, a clear plastic barrier, and a bicycle parked nearby.

7. 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.
$112 nightly
The price is $125
Dec 5 - Dec 6
Total with taxes and fees
OASIS UNDER THE OAK TREE.
A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

8. 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.
$268 nightly
The price is $299
Nov 11 - Nov 12
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.

9. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (5 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.
$262 nightly
The price is $292
Nov 11 - Nov 12
Total with taxes and fees
Spacious 5-bedroom house in gorgeous Winter Park
A living room with a sofa, coffee table, and decorative wall art.

10. 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
9.6 out of 10, Exceptional, (5 reviews)
"Nice and roomy!"
United States
Ashley C.
$366 nightly
The price is $408
Nov 17 - Nov 18
Total with taxes and fees
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

11. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
$270 nightly
The price is $301
Nov 11 - Nov 12
Total with taxes and fees
Spacious 5-bedroom house in welcoming Winter Park
A modern bathroom with a wooden vanity, a round mirror, and a potted plant.

12. Top 1% Modern Japandi Retreat - Jacuzzi No Fee

Top 1% Modern Japandi Retreat - Jacuzzi No Fee
Winter Park
10.0 out of 10, Exceptional, (8 reviews)
"Clean house, good location to where we wanted to be!"
United States
Jennifer M.
$597 nightly
The price is $665
Nov 22 - Nov 23
Total with taxes and fees
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
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, (2 reviews)
"Great place"
United States
Christian H.
$540 nightly
The price is $605
Nov 12 - Nov 13
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.

14. 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.
$263 nightly
The price is $293
Nov 30 - Dec 1
Total with taxes and fees
Cute 5-bedroom,6bed house in superb Winter Park.
A sign with 'The Wellborn' written on it, surrounded by lush greenery and a building in the background.

15. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (344 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
$68 nightly
The price is $76
Nov 23 - Nov 24
Total with taxes and fees
Suites by The Wellborn
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

16. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (22 reviews)
"It was a cute property and in a great location to get anywhere in the area"
United States
Devan S.
$314 nightly
The price is $352
Nov 12 - Nov 13
Total with taxes and fees
Stylish & Cozy King Bed Retreat @ Baldwin Park
A swimming pool with lounge chairs and palm trees.

17. The Point Hotel & Suites Orlando

The Point Hotel & Suites Orlando
4.0 star property
Florida Center
8.6 out of 10, Excellent, (1,497 reviews)
"This is a great place to stay"
United States
Susan
$81 nightly
The price is $91
Nov 12 - Nov 13
Total with taxes and fees
The Point Hotel & Suites Orlando
A resort pool area with palm trees, lounge chairs, and umbrellas.

18. Marriott's Grande Vista

Marriott's Grande Vista
4.0 star property
Orlando
9.0 out of 10, Wonderful, (5,414 reviews)
"Clean room, friendly staff, beautiful property"
United States
Francesco
$96 nightly
The price is $108
Dec 1 - Dec 2
Total with taxes and fees
Marriott's Grande Vista
A bedroom with a bed, a ceiling fan, a stained glass window, and a door leading to another room.

19. TINY unit in cottage in the middle of Downtown

TINY unit in cottage in the middle of Downtown
Downtown Orlando
9.8 out of 10, Exceptional, (24 reviews)
"The unit was nice and clean. It was a close walk to the Kia Center. In a pretty quiet area."
United States
Paula
$149 nightly
The price is $167
Nov 17 - Nov 18
Total with taxes and fees
TINY unit in cottage in the middle of Downtown
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 Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"."
Melissa Jo 3-night trip
Posted 1 hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

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 $86 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 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.