Holiday Homes in Winter Park

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Check prices for these dates

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 NZ$453
includes taxes & fees
10 Nov - 11 Nov
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 NZ$522
includes taxes & fees
23 Nov - 24 Nov
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 NZ$449
includes taxes & fees
17 Nov - 18 Nov
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 NZ$535
includes taxes & fees
11 Nov - 12 Nov
Mills House @WP. Sleeps 11 Renovated. Queen beds

5. 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 NZ$541
includes taxes & fees
10 Nov - 11 Nov
Spacious 5-bedroom house in gorgeous Winter Park

6. 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 NZ$766
includes taxes & fees
17 Nov - 18 Nov
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

7. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is NZ$559
includes taxes & fees
10 Nov - 11 Nov
Spacious 5-bedroom house in welcoming Winter Park

8. 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 NZ$1,210
includes taxes & fees
22 Nov - 23 Nov
Top 1% Modern Japandi Retreat - Jacuzzi No Fee

9. 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 NZ$1,081
includes taxes & fees
10 Nov - 11 Nov
Luxury Designer Home • Disney, Universal & Downtown

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 NZ$538
includes taxes & fees
30 Nov - 1 Dec
Cute 5-bedroom,6bed house in superb Winter Park.

11. Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
8.8 out of 10, Excellent, (20 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 NZ$293
includes taxes & fees
10 Nov - 11 Nov
Sunshine Escape Guesthouse ☀

12. 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.
The price is NZ$639
includes taxes & fees
10 Nov - 11 Nov
Stylish & Cozy King Bed Retreat @ Baldwin Park

13. Modern Oasis in Orlando | Private Yard | Cabana

Modern Oasis in Orlando | Private Yard | Cabana
Fairview Shores
8.6 out of 10, Excellent, (8 reviews)
"It was nice place to stay!"
United States
Jason A.
The price is NZ$410
includes taxes & fees
10 Nov - 11 Nov
Modern Oasis in Orlando | Private Yard | Cabana

14. 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 NZ$310
includes taxes & fees
10 Nov - 11 Nov
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!

15. 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 NZ$307
includes taxes & fees
10 Nov - 11 Nov
CUTE and COZY studio w/ jacuzzi!

16. *Travel Themed Property with Backyard Oasis*

*Travel Themed Property with Backyard Oasis*
Maitland
9.8 out of 10, Exceptional, (42 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 NZ$1,131
includes taxes & fees
10 Nov - 11 Nov
*Travel Themed Property with Backyard Oasis*

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 NZ$272
includes taxes & fees
17 Nov - 18 Nov
Studio in the heart of Orlando

18. “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 NZ$409
includes taxes & fees
16 Nov - 17 Nov
“The Clementine” Boho Home in Orlando’s Food Scene

19. 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, (58 reviews)
"Everything about the house was great. Great house for the price!"
United States
Charles T.
The price is NZ$434
includes taxes & fees
10 Nov - 11 Nov
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

20. 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 NZ$1,016
includes taxes & fees
10 Nov - 11 Nov
Private Luxury Pool / Swim up bar / Smart-home
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.

Learn more about Winter Park

Stroll through the Morse Museum to see the world's largest collection of Tiffany glass, then boat through the Winter Park Chain of Lakes. Charming Park Avenue offers upscale shopping and outdoor cafés where you can people-watch before catching a sunset concert in Central Park.

A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.