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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Winter Park vacation homes

Smart TV, video games

1. 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 AED 624
AED 1,518 total
includes taxes & fees
6 Aug - 7 Aug
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Interior

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 465
AED 928 total
includes taxes & fees
6 Aug - 7 Aug
Funky Remodeled Otown Bungalow Sleeps 8
Interior

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

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is AED 435
AED 888 total
includes taxes & fees
9 Aug - 10 Aug
Cozy home 5min to Park Ave and Downtown Orlando
Interior

4. 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 360
AED 828 total
includes taxes & fees
2 Sep - 3 Sep
Charming home @wp. Patio +Gazebo. close to highwys
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 AED 642
AED 1,227 total
includes taxes & fees
5 Aug - 6 Aug
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, (2 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 AED 918
AED 1,146 total
includes taxes & fees
5 Aug - 6 Aug
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 AED 1,084
AED 1,364 total
includes taxes & fees
30 Aug - 31 Aug
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 AED 988
AED 1,832 total
includes taxes & fees
5 Aug - 6 Aug
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 AED 926
AED 2,309 total
includes taxes & fees
5 Aug - 6 Aug
Luxury Designer Home • Disney, Universal & Downtown
Smart TV

10. Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park Charmer - Heated Pool Home - Close to everything
Winter Park
8.2 out of 10, Very Good, (19 reviews)
"Fabulous place with incredible value "
United States
Kyle C.
The price is AED 623
AED 1,510 total
includes taxes & fees
8 Aug - 9 Aug
Winter Park Charmer - Heated Pool Home - Close to everything
Private kitchen

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.
The price is AED 1,102
AED 1,377 total
includes taxes & fees
5 Aug - 6 Aug
Cute 5-bedroom,6bed house in superb Winter Park.
Pool

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

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.6 out of 10, Exceptional, (82 reviews)
"Host was very responsive to our needs"
United States
Thomas S.
The price is AED 694
AED 1,464 total
includes taxes & fees
5 Aug - 6 Aug
Private Luxury Pool / Swim up bar / Smart-home
Exterior

13. “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 AED 342
AED 706 total
includes taxes & fees
5 Aug - 6 Aug
“The Clementine” Boho Home in Orlando’s Food Scene
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 AED 620
AED 1,561 total
includes taxes & fees
5 Aug - 6 Aug
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Desk, WiFi, bed sheets

15. 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 AED 175
AED 579 total
includes taxes & fees
5 Aug - 6 Aug
Studio in the heart of Orlando
3 bedrooms, desk, iron/ironing board, WiFi (free)

16. 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 AED 479
AED 920 total
includes taxes & fees
5 Aug - 6 Aug
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Smart TV

17. 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 AED 446
AED 1,092 total
includes taxes & fees
6 Aug - 7 Aug
NEW! Spacious designer 2-Bed/2.5-Bath townhome near Downtown Orlando
Coffee/tea maker, fridge, microwave, oven

18. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (44 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is AED 441
AED 1,254 total
includes taxes & fees
10 Aug - 11 Aug
Florida Vacation with pool fun for families
Property grounds

19. *Travel Themed Property with Backyard Oasis*

*Travel Themed Property with Backyard Oasis*
Maitland
9.8 out of 10, Exceptional, (39 reviews)
"Great stay with plenty of space. Family was down for a wedding so space was a need and the home delivered. The pool was an added plus along with the backyard. Great stay!"
United States
Roy W.
The price is AED 1,532
AED 2,766 total
includes taxes & fees
7 Aug - 8 Aug
*Travel Themed Property with Backyard Oasis*
Outdoor pool, a heated pool

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

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
10.0 out of 10, Exceptional, (68 reviews)
"Love the location. "
United States
Jolyn W.
The price is AED 579
AED 1,161 total
includes taxes & fees
8 Aug - 9 Aug
Large, beautiful, very comfortable one bedroom on small lake
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

Caribe Royale Orlando

Caribe Royale Orlando

10/10 Excellent
"I enjoyed the room and the gym facility "
Wendy 3-night trip
Posted 1 hour ago
Caribe Royale Orlando