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

Our top choices for Winter Park vacation rentals

A patio with a table and chairs, a potted plant, and a blue umbrella.

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.
The price is AED 459
AED 1,000 total
includes taxes & fees
16 Nov - 17 Nov
Quiet and safe neighborhood come to this great place with lots of room for relax
A modern kitchen with stainless steel appliances, a marble island, and pendant lighting.

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.
The price is AED 675
AED 1,113 total
includes taxes & fees
12 Dec - 13 Dec
Funky Remodeled Otown Bungalow Sleeps 8
A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

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.
Cozy home 5min to Park Ave and Downtown Orlando
A small building with a green door and two vertical light fixtures on either side.

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

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is AED 374
AED 676 total
includes taxes & fees
19 Nov - 20 Nov
Comfy Tiny Home @WP. Large Private Deck+Queen bed
A wooden exterior with a brown door, a black mat at the entrance, and a small plant to the left.

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.
The price is AED 465
AED 924 total
includes taxes & fees
17 Nov - 18 Nov
Charming home @wp. Patio +Gazebo. close to highwys
A swimming pool with a brick patio, surrounded by a fence and a building with large windows.

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.
The price is AED 278
AED 670 total
includes taxes & fees
17 Nov - 18 Nov
1-bedroom vacation room just 12 minutes from University of Central Florida
A backyard with a grill, patio furniture, and a covered area.

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.
The price is AED 397
AED 459 total
includes taxes & fees
5 Dec - 6 Dec
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
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.
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.
The price is AED 918
AED 1,106 total
includes taxes & fees
16 Nov - 17 Nov
Spacious 5-bedroom house in gorgeous Winter Park
A modern kitchen with white cabinets, a dining area with a wooden table, and a view of the living room through an archway.

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.
The price is AED 654
AED 1,499 total
includes taxes & fees
17 Nov - 18 Nov
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
The price is AED 951
AED 1,143 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AED 1,451
AED 2,423 total
includes taxes & fees
22 Nov - 23 Nov
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
A bedroom with a bed, bedside tables, a ceiling fan, a large mirror, and a window with blinds.

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.
The price is AED 977
AED 2,290 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AED 918
AED 1,106 total
includes taxes & fees
30 Nov - 1 Dec
Cute 5-bedroom,6bed house in superb Winter Park.
A brick pathway leading through a lush garden with various plants and a statue.

16. Suites by The Wellborn

Suites by The Wellborn
4.0 star property
Lake Cherokee
8.2 out of 10, Very good, (346 reviews)
"Very clean and nice stay"
United States
Wade
The price is AED 248
AED 279 total
includes taxes & fees
29 Nov - 30 Nov
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, (1,511 reviews)
"This is a great place to stay"
United States
Susan
The price is AED 225
AED 298 total
includes taxes & fees
29 Nov - 30 Nov
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, (5,434 reviews)
"Wonderful stay!"
United States
Christina
The price is AED 353
AED 397 total
includes taxes & fees
2 Dec - 3 Dec
Marriott's Grande Vista
A covered patio with wicker furniture and a glass table, overlooking a residential street with houses and palm trees.

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.
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, (54 reviews)
"Very well situated."
United States
Al F.
The price is AED 374
AED 720 total
includes taxes & fees
18 Nov - 19 Nov
⛲️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

Avanti International Resort

Avanti International Resort

10/10 Excellent
"Good food, overall clean, could use some updating."
David 6-night trip
Posted less than an hour ago
Avanti International Resort

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.