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

Our top choices for Winter Park holiday homes

A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

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 £208
includes taxes & fees
1 Nov - 2 Nov
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.

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 £235
includes taxes & fees
29 Oct - 30 Oct
Cozy home 5min to Park Ave and Downtown Orlando
A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

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 £217
includes taxes & fees
30 Oct - 31 Oct
Charming home @wp. Patio +Gazebo. close to highwys
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 £244
includes taxes & fees
17 Nov - 18 Nov
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 £228
includes taxes & fees
1 Nov - 2 Nov
Spacious 5-bedroom house in gorgeous Winter Park
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

6. 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 £234
includes taxes & fees
2 Nov - 3 Nov
Cute 5-bedroom house in peaceful Winter Park
A living room with a sofa, coffee table, and decorative wall art.

7. 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 £329
includes taxes & fees
2 Nov - 3 Nov
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

8. 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 £472
includes taxes & fees
10 Nov - 11 Nov
Luxury Designer Home • Disney, Universal & Downtown
A modern bathroom with a wooden vanity, a round mirror, and a potted plant.

9. 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 £539
includes taxes & fees
22 Nov - 23 Nov
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

10. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is £237
includes taxes & fees
11 Nov - 12 Nov
Spacious 5-bedroom house in welcoming 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 £228
includes taxes & fees
1 Nov - 2 Nov
Cute 5-bedroom,6bed house in superb Winter Park.
A modern living room with a dining area, featuring a wooden floor, a gray sofa, a dining table with chairs, and a wall-mounted plant.

12. 2/1 with private backyard in the heart of Ivanhoe

2/1 with private backyard in the heart of Ivanhoe
Ivanhoe Village
8.0 out of 10, Very good, (16 reviews)
"Great location"
United States
Josh H.
The price is £181
includes taxes & fees
29 Oct - 30 Oct
2/1 with private backyard in the heart of Ivanhoe
A modern kitchen with wooden cabinets, a black countertop, a stainless steel refrigerator, a microwave, and a coffee maker.

13. 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 £259
includes taxes & fees
1 Nov - 2 Nov
Stylish & Cozy King Bed Retreat @ Baldwin Park
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 £131
includes taxes & fees
2 Nov - 3 Nov
Sunshine Escape Guesthouse ☀
A front door with a glass panel, a wreath, and a doormat with a welcoming message.

15. 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 £139
includes taxes & fees
3 Nov - 4 Nov
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
A hot tub with a waterfall feature, a covered seating area, and a bar with outdoor seating.

16. 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 £354
includes taxes & fees
2 Nov - 3 Nov
Private Luxury Pool / Swim up bar / Smart-home
A modern bedroom with a yellow bed, a dark door, and a green wall with a neon sign.

17. 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 £139
includes taxes & fees
1 Nov - 2 Nov
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.

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 £170
includes taxes & fees
1 Nov - 2 Nov
“The Clementine” Boho Home in Orlando’s Food Scene
A bedroom with a bed, a mirror, a wardrobe, and a floral artwork on the wall.

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)
"This home was just what we needed, it was clean and comfortable. Great communication with the owner. Nice, safe neighborhood."
United States
Angie P.
The price is £194
includes taxes & fees
2 Nov - 3 Nov
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
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 £339
includes taxes & fees
29 Oct - 30 Oct
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

8/10 Good
"Good water pressure."
Thomas 3-night trip
Posted 4 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
253
Accommodation
5412 Holiday Homes
Lowest Price
£131
Highest Price
£539