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

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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 ￥19,971
￥40,372 total
includes taxes & fees
Sep 15 - Sep 16
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 ￥18,322
￥37,721 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 ￥15,773
￥35,948 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 ￥24,695
￥63,630 total
includes taxes & fees
Aug 25 - Aug 26
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 ￥27,666
￥53,669 total
includes taxes & fees
Aug 18 - Aug 19
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 ￥39,830
￥50,345 total
includes taxes & fees
Aug 18 - Aug 19
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 ￥44,928
￥56,533 total
includes taxes & fees
Sep 17 - Sep 18
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
￥67,292 total
includes taxes & fees
Sep 16 - Sep 17
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 ￥40,149
￥101,447 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 ￥47,796
￥60,382 total
includes taxes & fees
Aug 18 - Aug 19
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 ￥7,915
￥25,440 total
includes taxes & fees
Sep 7 - Sep 8
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, (25 reviews)
"A phenomenal stay!"
United States
Samuel S.
The price is ￥14,817
￥30,610 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 18 - Aug 19
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 ￥26,885
￥65,974 total
includes taxes & fees
Aug 18 - Aug 19
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 ￥17,924
￥41,972 total
includes taxes & fees
Aug 18 - Aug 19
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, (38 reviews)
"Great stay!"
United States
Allison C.
The price is ￥10,037
￥18,959 total
includes taxes & fees
Aug 18 - Aug 19
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
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 ￥25,093
￥44,978 total
includes taxes & fees
Aug 18 - Aug 19
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.
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Top Winter Park Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"My fav !!"
Erica 3-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
4
Accommodation
5348 Vacation Homes
Lowest Price
￥60,604
Highest Price
￥108,593