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

Search Vacation 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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Winter Park vacation homes

Interior

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 ￥19,983
￥40,556 total
includes taxes & fees
Aug 20 - Aug 21
Funky Remodeled Otown Bungalow Sleeps 8
Interior

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

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is ￥18,150
￥37,537 total
includes taxes & fees
Aug 19 - Aug 20
Cozy home 5min to Park Ave and Downtown Orlando
Interior

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 ￥15,623
￥35,790 total
includes taxes & fees
Aug 20 - Aug 21
Charming home @wp. Patio +Gazebo. close to highwys
Smart TV, video games

4. 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
10.0 out of 10, Exceptional, (4 reviews)
"Nice and roomy!"
United States
Ashley C.
The price is ￥23,913
￥62,772 total
includes taxes & fees
Aug 23 - Aug 24
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Coffee/tea maker, fridge, microwave, oven

5. 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 ￥27,683
￥53,702 total
includes taxes & fees
Aug 19 - Aug 20
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

6. 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.
The price is ￥39,855
￥50,377 total
includes taxes & fees
Aug 19 - Aug 20
Cute 5-bedroom house in peaceful Winter Park
Private kitchen

7. Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (3 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 ￥45,116
￥56,747 total
includes taxes & fees
Sep 10 - Sep 11
Spacious 5-bedroom house in gorgeous Winter Park
Smart TV, fireplace, stereo

8. 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, (3 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.
The price is ￥38,596
￥67,610 total
includes taxes & fees
Sep 1 - Sep 2
The Canopy on Periwinkle- A Home Away From Home
Smart TV

9. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
The price is ￥40,174
￥101,511 total
includes taxes & fees
Aug 21 - Aug 22
Luxury Designer Home • Disney, Universal & Downtown
Private kitchen

10. 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 ￥47,826
￥60,420 total
includes taxes & fees
Aug 19 - Aug 20
Cute 5-bedroom,6bed house in superb Winter Park.
Desk, WiFi, bed sheets

11. 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 ￥7,576
￥25,112 total
includes taxes & fees
Aug 26 - Aug 27
Studio in the heart of Orlando
Exterior

12. “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, (26 reviews)
"A phenomenal stay!"
United States
Samuel S.
The price is ￥14,826
￥30,629 total
includes taxes & fees
Aug 19 - Aug 20
“The Clementine” Boho Home in Orlando’s Food Scene
3 bedrooms, desk, iron/ironing board, WiFi (free)

13. 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, (54 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is ￥20,791
￥40,399 total
includes taxes & fees
Aug 19 - Aug 20
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Dining

14. PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark

PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Orlando
10.0 out of 10, Exceptional, (4 reviews)
"Nice place , will book again "
United States
Kadijah J.
The price is ￥26,902
￥61,815 total
includes taxes & fees
Aug 19 - Aug 20
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Terrace/patio

15. Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.

Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
West Lakes District
10.0 out of 10, Exceptional, (4 reviews)
"Tammie is an amazing host! Super comfy and cute tiny home! Definitely booking again!"
United States
chelsea
The price is ￥11,105
￥21,952 total
includes taxes & fees
Aug 31 - Sep 1
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
Coffee/tea maker, fridge, microwave, oven

16. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (46 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is ￥17,217
￥51,805 total
includes taxes & fees
Sep 16 - Sep 17
Florida Vacation with pool fun for families
Outdoor pool, a heated pool

17. Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
9.8 out of 10, Exceptional, (69 reviews)
"Love the location. "
United States
Jolyn W.
The price is ￥17,935
￥41,998 total
includes taxes & fees
Aug 19 - Aug 20
Large, beautiful, very comfortable one bedroom on small lake
Interior

18. Tiny tropical Orlando Univesal-Disney

Tiny tropical Orlando Univesal-Disney
Orlando
6.8 out of 10, (39 reviews)
"Great stay!"
United States
Allison C.
The price is ￥10,043
￥18,971 total
includes taxes & fees
Aug 19 - Aug 20
Tiny tropical Orlando Univesal-Disney
Smart TV

19. NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando

NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Lancaster Park
10.0 out of 10, Exceptional, (19 reviews)
"Clean, good location, easy check in/check out"
United States
Chris
The price is ￥19,370
￥49,789 total
includes taxes & fees
Aug 19 - Aug 20
NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Smart TV, table tennis

20. Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (25 reviews)
"Quiet neighborhood, good location."
United States
River
The price is ￥25,109
￥43,951 total
includes taxes & fees
Aug 19 - Aug 20
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Clean rooms and staff were very pleasant."
Andrea 6-night trip
Posted less than an hour ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
238
Accommodation
5348 Vacation Homes
Lowest Price
￥18,971
Highest Price
￥101,511