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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winter Park vacation homes

A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

1. 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 ￥21,719
￥43,393 total
includes taxes & fees
Nov 18 - Nov 19
Charming home @wp. Patio +Gazebo. close to highwys
A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

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 ￥21,543
￥41,796 total
includes taxes & fees
Nov 1 - Nov 2
Funky Remodeled Otown Bungalow Sleeps 8
A modern kitchen with white cabinets, a wooden dining table set with white plates and a knife, and a potted plant.

3. 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 ￥27,378
￥49,149 total
includes taxes & fees
Oct 31 - Nov 1
Cozy home 5min to Park Ave and Downtown Orlando
A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

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 ￥26,663
￥51,674 total
includes taxes & fees
Nov 11 - Nov 12
Mills House @WP. Sleeps 11 Renovated. Queen beds
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

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 ￥39,415
￥49,190 total
includes taxes & fees
Nov 1 - Nov 2
Spacious 5-bedroom house in gorgeous Winter Park
A living room with a sofa, coffee table, and decorative wall art.

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 ￥28,852
￥67,775 total
includes taxes & fees
Nov 1 - Nov 2
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

7. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is ￥40,992
￥51,429 total
includes taxes & fees
Nov 10 - Nov 11
Spacious 5-bedroom house in welcoming Winter Park
A modern bathroom with a wooden vanity, a round mirror, and a potted plant.

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 ￥62,276
￥112,538 total
includes taxes & fees
Nov 22 - Nov 23
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

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 ￥41,938
￥101,928 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Designer Home • Disney, Universal & Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

10. Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
8.0 out of 10, Very good, (4 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 ￥39,415
￥49,190 total
includes taxes & fees
Nov 2 - Nov 3
Cute 5-bedroom house in peaceful Winter Park
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

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 ￥39,415
￥49,190 total
includes taxes & fees
Nov 1 - Nov 2
Cute 5-bedroom,6bed house in superb Winter Park.
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

12. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (21 reviews)
"It was a cute property and in a great location to get anywhere in the area"
United States
Devan S.
The price is ￥23,649
￥57,270 total
includes taxes & fees
Nov 1 - Nov 2
Stylish & Cozy King Bed Retreat @ Baldwin Park
A front door with a glass panel, a wreath, and a doormat with a welcoming message.

13. 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, (3 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 ￥11,391
￥29,273 total
includes taxes & fees
Nov 3 - Nov 4
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

14. 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 ￥9,223
￥26,832 total
includes taxes & fees
Nov 2 - Nov 3
Sunshine Escape Guesthouse ☀
A modern bedroom with a yellow bed, a dark door, and a green wall with a neon sign.

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 ￥9,967
￥28,256 total
includes taxes & fees
Nov 1 - Nov 2
CUTE and COZY studio w/ jacuzzi!
A single-story house with a covered porch, a brick pathway leading to the entrance, and a fenced backyard.

16. “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 ￥18,131
￥33,247 total
includes taxes & fees
Nov 1 - Nov 2
“The Clementine” Boho Home in Orlando’s Food Scene
A hot tub with a waterfall feature, a covered seating area, and a bar with outdoor seating.

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

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.8 out of 10, Exceptional, (87 reviews)
"Best VRBO thus far, the host were great and the smart house offered much more than expected, I’d recommend this house to any family! I’d definitely stay again!"
United States
Dennis P.
The price is ￥36,735
￥70,941 total
includes taxes & fees
Nov 2 - Nov 3
Private Luxury Pool / Swim up bar / Smart-home
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

18. 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 ￥20,575
￥39,663 total
includes taxes & fees
Nov 9 - Nov 10
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A bed with white bedding and two blue pillows with a coral reef design, a tall green plant beside the bed, and a window with grey curtains in the background.

19. 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 ￥8,077
￥25,420 total
includes taxes & fees
Nov 17 - Nov 18
Studio in the heart of Orlando
A modern kitchen with white cabinets, a stainless steel sink, and a dining area with a table and chairs.

20. 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 ￥29,561
￥70,661 total
includes taxes & fees
Nov 3 - Nov 4
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
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 Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"Room was clean and comfortable. Property was clean and well maintained."
Nicole 1-night trip
Posted 1 hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
243
Accommodation
5507 Vacation Homes
Lowest Price
￥25,420
Highest Price
￥112,538