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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winter Park holiday homes

Interior

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 £188
includes taxes & fees
16 Sept - 17 Sept
Funky Remodeled Otown Bungalow Sleeps 8
Smart TV, fireplace, stereo

2. 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 £266
includes taxes & fees
21 Sept - 22 Sept
The Canopy on Periwinkle- A Home Away From Home
Interior

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 £178
includes taxes & fees
12 Oct - 13 Oct
Charming home @wp. Patio +Gazebo. close to highwys
Interior

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

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is £180
includes taxes & fees
17 Sept - 18 Sept
Cozy home 5min to Park Ave and Downtown Orlando
Private kitchen

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 £192
includes taxes & fees
13 Sept - 14 Sept
Spacious 5-bedroom house in gorgeous Winter Park
Coffee/tea maker, fridge, microwave, 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 £249
includes taxes & fees
13 Sept - 14 Sept
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

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 £226
includes taxes & fees
14 Sept - 15 Sept
Cute 5-bedroom house in peaceful Winter Park
Private kitchen

8. Luxury Designer Home • Disney, Universal & Downtown

Luxury Designer Home • Disney, Universal & Downtown
College Park
The price is £489
includes taxes & fees
22 Sept - 23 Sept
Luxury Designer Home • Disney, Universal & Downtown
Private kitchen

9. 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 £266
includes taxes & fees
15 Sept - 16 Sept
Cute 5-bedroom,6bed house in superb Winter Park.
Private kitchen

10. Spacious 5-bedroom house in welcoming Winter Park

Spacious 5-bedroom house in welcoming Winter Park
Winter Park
The price is £294
includes taxes & fees
13 Sept - 14 Sept
Spacious 5-bedroom house in welcoming Winter Park
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 £129
includes taxes & fees
13 Sept - 14 Sept
Sunshine Escape Guesthouse ☀
Fridge, microwave, oven, stovetop

12. Stylish & Cozy King Bed Retreat @ Baldwin Park

Stylish & Cozy King Bed Retreat @ Baldwin Park
Orlando
10.0 out of 10, Exceptional, (17 reviews)
"The house was beautiful and the host was very responsive! "
United States
Dawn H.
The price is £224
includes taxes & fees
20 Sept - 21 Sept
Stylish & Cozy King Bed Retreat @ Baldwin Park
Pool

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

Private Luxury Pool / Swim up bar / Smart-home
College Park
9.6 out of 10, Exceptional, (85 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 £300
includes taxes & fees
14 Sept - 15 Sept
Private Luxury Pool / Swim up bar / Smart-home
Exterior

14. “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 £146
includes taxes & fees
14 Sept - 15 Sept
“The Clementine” Boho Home in Orlando’s Food Scene
Coffee/tea maker, fridge, microwave, oven

15. Charming Heated Pool home in Altamonte Springs

Charming Heated Pool home in Altamonte Springs
Altamonte Springs
9.4 out of 10, Exceptional, (29 reviews)
"Everything was awesome "
United States
Kyle T.
The price is £256
includes taxes & fees
13 Sept - 14 Sept
Charming Heated Pool home in Altamonte Springs
Dining

16. 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 £341
includes taxes & fees
13 Sept - 14 Sept
PROMO NOW: 3brdrm home near Downtown Orlando and Winterpark
Desk, iron/ironing board, WiFi, bed sheets

17. CUTE and COZY studio w/ jacuzzi!

CUTE and COZY studio w/ jacuzzi!
Azalea Park
8.6 out of 10, Excellent, (9 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 £136
includes taxes & fees
28 Sept - 29 Sept
CUTE and COZY studio w/ jacuzzi!
3 bedrooms, desk, iron/ironing board, free WiFi

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, (56 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is £191
includes taxes & fees
16 Sept - 17 Sept
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Exterior

19. Modern Zen + Downtown Orlando +Hot Tub + Grill + Movie Room + Patio + Aquarium

Modern Zen + Downtown Orlando +Hot Tub + Grill + Movie Room + Patio + Aquarium
Colonialtown South
10.0 out of 10, Exceptional, (20 reviews)
"Everything was perfect! Absolutely would stay again and looking forward to it!"
United States
Gghost
The price is £327
includes taxes & fees
14 Sept - 15 Sept
Modern Zen + Downtown Orlando +Hot Tub + Grill + Movie Room + Patio + Aquarium
Coffee/tea maker, fridge, microwave, oven

20. Renovated Peaceful Luxury Walk to Mall Park Publix

Renovated Peaceful Luxury Walk to Mall Park Publix
Altamonte Springs
9.0 out of 10, Wonderful, (22 reviews)
"Host responded quickly to our texts.Location was excellent for our needs."
United States
Angie Y.
The price is £143
includes taxes & fees
16 Sept - 17 Sept
Renovated Peaceful Luxury Walk to Mall Park Publix
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 Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"The room was clean. The resort is well kept. It is kid friendly. Its location from Disney World is perfection. We did not have to fight with I-4. Would definitely stay again at this resort with my family."
Margarita 2-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
232
Accommodation
5515 Holiday Homes
Lowest Price
£129
Highest Price
£489