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

Holiday Homes in Winter Park

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winter Park holiday homes

A modern living room with a ceiling fan, a flat-screen TV, and a dining area with a white table and chairs.

1. 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, (4 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 NZ$631
includes taxes & fees
29 Sept - 30 Sept
The Canopy on Periwinkle- A Home Away From Home
A modern kitchen with stainless steel appliances, a grey sofa, and a dining area with a floral rug.

2. 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$470
includes taxes & fees
28 Sept - 29 Sept
Charming home @wp. Patio +Gazebo. close to highwys
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
The price is NZ$497
includes taxes & fees
29 Sept - 30 Sept
Cozy home 5min to Park Ave and Downtown Orlando
A modern kitchen with a marble countertop, built-in appliances, and a dining area with a green sofa.

4. 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$478
includes taxes & fees
6 Oct - 7 Oct
Funky Remodeled Otown Bungalow Sleeps 8
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, (4 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$601
includes taxes & fees
27 Sept - 28 Sept
Spacious 5-bedroom house in gorgeous Winter Park
A modern kitchen with dark wooden cabinets, a stainless steel refrigerator, a microwave, and an oven.

6. 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$581
includes taxes & fees
27 Sept - 28 Sept
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.

7. 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 NZ$541
includes taxes & fees
27 Sept - 28 Sept
Cute 5-bedroom house in peaceful Winter Park
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
The price is NZ$1,110
includes taxes & fees
8 Oct - 9 Oct
Luxury Designer Home • Disney, Universal & Downtown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a glass dining table with chairs.

9. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is NZ$682
includes taxes & fees
27 Sept - 28 Sept
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.

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$662
includes taxes & fees
27 Sept - 28 Sept
Cute 5-bedroom,6bed house in superb Winter Park.
A compact room with a bed, a small table with plates, a microwave, and a green wall with a neon sign.

11. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (10 reviews)
"Pet friendly, all you need for a quick trip to Orlando with a couple and their pet"
United States
Jackson K.
The price is NZ$313
includes taxes & fees
27 Sept - 28 Sept
CUTE and COZY studio w/ jacuzzi!
A modern hotel room with a wooden bed, a desk with chairs, a patterned wall, and a window with blinds.

12. 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$301
includes taxes & fees
27 Sept - 28 Sept
Sunshine Escape Guesthouse ☀
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.

13. 2/1 with private backyard in the heart of Ivanhoe

2/1 with private backyard in the heart of Ivanhoe
Ivanhoe Village
8.2 out of 10, Very good, (15 reviews)
"Great location"
United States
Josh H.
The price is NZ$400
includes taxes & fees
27 Sept - 28 Sept
2/1 with private backyard in the heart of Ivanhoe
A front door with a glass panel, a wreath, and a doormat with a welcoming message.

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, (2 reviews)
"Very nice location in a quiet residential neighborhood. There is only street parking but usually plenty of space."
United States
rimma
The price is NZ$274
includes taxes & fees
29 Sept - 30 Sept
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
A modern kitchen with wooden cabinets, a central island, and a built-in oven. There is a dining area with a blue sofa and a TV on the wall.

15. Charming Heated Pool home in Altamonte Springs

Charming Heated Pool home in Altamonte Springs
Altamonte Springs
9.2 out of 10, Wonderful, (30 reviews)
"Everything was awesome "
United States
Kyle T.
The price is NZ$650
includes taxes & fees
26 Sept - 27 Sept
Charming Heated Pool home in Altamonte Springs
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 NZ$339
includes taxes & fees
5 Oct - 6 Oct
“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.

17. 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)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is NZ$445
includes taxes & fees
1 Oct - 2 Oct
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
A modern kitchen with a black countertop, two stools, a wooden cabinet, and a TV displaying a mountain landscape.

18. “Downtown Orlando Comfy House”

“Downtown Orlando Comfy House”
Lawsona - Fern Creek
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time during our stay. The property is beautiful, the host is friendly and helpful, and the location is perfect. "
United States
Courtanie C.
“Downtown Orlando Comfy House”

19. Florida Vacation with pool fun for families

Florida Vacation with pool fun for families
Casselberry
9.4 out of 10, Exceptional, (48 reviews)
"Awesome location, nice home, and great pool"
United States
Daniel W.
The price is NZ$585
includes taxes & fees
27 Sept - 28 Sept
Florida Vacation with pool fun for families

20. 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 NZ$255
includes taxes & fees
29 Sept - 30 Sept
Orlando Tiny Home retreat Near Downtown with garden, with animals and AC.
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
"So much to do here and see. The property is fantastic and family friendly. We will be back."
DANIEL 2-night trip
Posted 11 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
168
Accommodation
5516 Holiday Homes
Lowest Price
NZ$255
Highest Price
NZ$1,110