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
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 kitchen with white cabinets, stainless steel appliances, and a black dining chair.

1. 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.
$243 nightly
The price is $271
Nov 12 - Nov 13
Total with taxes and fees
Quiet and safe neighborhood come to this great place with lots of room for relax
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 modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

3. 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 two-story building with a wooden deck and a black railing.

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
$164 nightly
The price is $183
Nov 17 - Nov 18
Total with taxes and fees
Comfy Tiny Home @WP. Large Private Deck+Queen bed
A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

5. 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.
$224 nightly
The price is $250
Nov 17 - Nov 18
Total with taxes and fees
Charming home @wp. Patio +Gazebo. close to highwys
A swimming pool with a curved edge, surrounded by a concrete deck and a brick border.

6. 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.
$164 nightly
The price is $182
Nov 18 - Nov 19
Total with taxes and fees
1-bedroom vacation room just 12 minutes from University of Central Florida
A compact kitchen with wooden cabinets, a stove, a microwave, and a sink.

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 living room with hardwood flooring, a grey sofa, a glass coffee table, and a kitchen area with wooden cabinets and a stainless steel refrigerator.

8. 3-bedroom house in quaint Winter Park with cool vibes

3-bedroom house in quaint Winter Park with cool vibes
Hannibal Square
$356 nightly
The price is $397
Dec 7 - Dec 8
Total with taxes and fees
3-bedroom house in quaint Winter Park with cool vibes
A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

9. 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.
$275 nightly
The price is $307
Nov 17 - Nov 18
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.

10. 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.
$270 nightly
The price is $300
Nov 12 - Nov 13
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.

11. 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.

12. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
$278 nightly
The price is $309
Nov 12 - Nov 13
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.

13. 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.
$592 nightly
The price is $660
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.

14. 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.
$556 nightly
The price is $621
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.

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.
$271 nightly
The price is $301
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.

16. 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 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, (1,500 reviews)
"This is a great place to stay"
United States
Susan
$83 nightly
The price is $93
Nov 29 - Nov 30
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, (5,422 reviews)
"Wonderful stay!"
United States
Christina
$96 nightly
The price is $108
Dec 2 - Dec 3
Total with taxes and fees
Marriott's Grande Vista
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

19. 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.
$340 nightly
The price is $381
Nov 18 - Nov 19
Total with taxes and fees
Stylish & Cozy King Bed Retreat @ Baldwin Park
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, (53 reviews)
"Very well situated."
United States
Al F.
$176 nightly
The price is $196
Nov 18 - Nov 19
Total with taxes and fees
⛲️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

Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

10/10 Excellent
"My daughter loved the resort"
Michael Daniel 3-night trip
Posted 6 hours ago
Coco Key Hotel & Water Park Resort

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 $81 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.