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

Holiday Homes in Winter Park

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winter Park holiday homes

1. 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 AU$370
includes taxes & fees
1 Dec - 2 Dec
Funky Remodeled Otown Bungalow Sleeps 8

2. 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 AU$407
includes taxes & fees
1 Dec - 2 Dec
Cozy home 5min to Park Ave and Downtown Orlando

3. 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 AU$394
includes taxes & fees
1 Dec - 2 Dec
Charming home @wp. Patio +Gazebo. close to highwys

4. 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 AU$447
includes taxes & fees
1 Dec - 2 Dec
Mills House @WP. Sleeps 11 Renovated. Queen beds

5. 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

6. 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 AU$433
includes taxes & fees
17 Nov - 18 Nov
Spacious 5-bedroom house in gorgeous Winter Park

7. 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 AU$589
includes taxes & fees
17 Nov - 18 Nov
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

8. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
Spacious 5-bedroom house in welcoming Winter Park

9. 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 AU$981
includes taxes & fees
22 Nov - 23 Nov
Top 1% Modern Japandi Retreat - Jacuzzi No Fee

10. 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 AU$900
includes taxes & fees
1 Dec - 2 Dec
Luxury Designer Home • Disney, Universal & Downtown

11. 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.
Cute 5-bedroom,6bed house in superb Winter Park.

12. 2/1 with private backyard in the heart of Ivanhoe

2/1 with private backyard in the heart of Ivanhoe
Ivanhoe Village
8.0 out of 10, Very good, (16 reviews)
"Great location"
United States
Josh H.
The price is AU$359
includes taxes & fees
16 Nov - 17 Nov
2/1 with private backyard in the heart of Ivanhoe

13. 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

14. Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
8.6 out of 10, Excellent, (21 reviews)
"The location worked perfect for our needs in a quiet and safe area. The host was very pleasant and we had a wonderful experience dealing with him and any concerns were met and promptly taken care of. We would definitely stay there again "
United States
Robin R.
The price is AU$239
includes taxes & fees
17 Nov - 18 Nov
Sunshine Escape Guesthouse ☀

15. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
College Park
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location, easy access to many amenities.Host genuinely cares about the clienteles well being and that needs are accommodated for if required."
Canada
Kevin G.
The price is AU$253
includes taxes & fees
16 Nov - 17 Nov
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

16. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"This cute lil place is perfect for a few nights for one person or a couple. It’s quiet, private and safe, and appointed with everything you need. The bed is comfy and the coffee was great. "
United States
Lindsay W.
The price is AU$254
includes taxes & fees
17 Nov - 18 Nov
CUTE and COZY studio w/ jacuzzi!

17. Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is AU$220
includes taxes & fees
16 Nov - 17 Nov
Studio in the heart of Orlando

18. Private Luxury Pool / Swim up bar / Smart-home

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.6 out of 10, Exceptional, (90 reviews)
"It's a absolute vibe. I enjoyed myself completely lovely setup easy access to everything so many things provided for you and your comfort. I'm sure we'll do it again."
United States
Mayah Y.
The price is AU$702
includes taxes & fees
17 Nov - 18 Nov
Private Luxury Pool / Swim up bar / Smart-home

19. “The Clementine” Boho Home in Orlando’s Food Scene

“The Clementine” Boho Home in Orlando’s Food Scene
Park Lake - Highland
9.6 out of 10, Exceptional, (27 reviews)
"A phenomenal stay!"
United States
Samuel S.
The price is AU$336
includes taxes & fees
29 Nov - 30 Nov
“The Clementine” Boho Home in Orlando’s Food Scene

20. Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool

Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool
College Park
9.6 out of 10, Exceptional, (15 reviews)
"Property was great, and host extremely responsivewould go back there anytime"
United States
Tom47 D.
The price is AU$1,283
includes taxes & fees
1 Dec - 2 Dec
Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Park Hotel Reviews

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
144
Accommodation
5530 Holiday Homes
Lowest Price
AU$220
Highest Price
AU$1,283