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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Winter Park holiday homes

Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is HK$1,528
HK$2,644 total
includes taxes & fees
22 Feb - 23 Feb
Cozy home 5min to Park Ave and Downtown Orlando
Fridge, microwave, oven, stovetop

Sleek, Spacious & Central – Your Ideal Getaway

Sleek, Spacious & Central – Your Ideal Getaway
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Great location in Winter Park! So many quality restaurants and things to do close by. The home is easily accessible with plenty of space. The host, Wendy was very hospitable. We left a toiletry bag and she was kind enough to let us know so we could come back. We enjoyed our one night stay!"
United States
Adam A.
The price is HK$946
HK$1,704 total
includes taxes & fees
23 Feb - 24 Feb
Sleek, Spacious & Central – Your Ideal Getaway
TV, offices

Cozy home w/working space & kitchen

Cozy home w/working space & kitchen
College Park
8.0 out of 10, Very good, (2 reviews)
"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."
United States
Danielle H.
The price is HK$613
HK$1,987 total
includes taxes & fees
25 Feb - 26 Feb
Cozy home w/working space & kitchen
Property grounds

Charming home @wp. Patio +Gazebo. close to highwys

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Very clean and location was great"
United States
Vicki V.
The price is HK$977
HK$2,023 total
includes taxes & fees
22 Feb - 23 Feb
Charming home @wp. Patio +Gazebo. close to highwys
Private kitchen

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
The price is HK$2,165
HK$3,190 total
includes taxes & fees
3 Mar - 4 Mar
Spacious 5-bedroom house in gorgeous Winter Park
Smart TV, video games

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
The price is HK$1,524
HK$3,387 total
includes taxes & fees
24 Feb - 25 Feb
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Exterior

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
The price is HK$1,213
HK$2,251 total
includes taxes & fees
22 Feb - 23 Feb
Funky Remodeled Otown Bungalow Sleeps 8
Fridge, microwave, oven, stovetop

Mills House @WP. Sleeps 11 Renovated. Queen beds

Mills House @WP. Sleeps 11 Renovated. Queen beds
Fairview Shores
6.0 out of 10, (1 review)
"The air fresheners plug ins were too powerful, we had to put them outside while we stayed in the house. Not enough power outlets. Hanging lamps on master bedroom are not practical, didn’t find the switch to turn them off. Spot light outside kept me up. The motion triggered the light to go on and off constantly. "
United States
Monica E.
The price is HK$1,339
HK$2,573 total
includes taxes & fees
22 Feb - 23 Feb
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

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 HK$2,610
HK$5,163 total
includes taxes & fees
1 Mar - 2 Mar
Cute 5-bedroom,6bed house in superb Winter Park.
Outdoor dining

Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
9.6 out of 10, Exceptional, (13 reviews)
"The property was immaculately clean, stylish, roomy and private! It was so convenient to everything yet on the outskirts in a quiet peaceful neighborhood. "
United States
KELLY Z.
The price is HK$457
HK$1,330 total
includes taxes & fees
23 Feb - 24 Feb
Sunshine Escape Guesthouse ☀
Pool

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (22 reviews)
"Great location , Very enjoy , private space, would book in the future for sure "
United States
Matt B.
The price is HK$860
HK$2,090 total
includes taxes & fees
22 Feb - 23 Feb
Spacious & Private Guest Pool House Oasis
Children’s area

Tiny home near downtown w/ outdoor patio

Tiny home near downtown w/ outdoor patio
College Park
10.0 out of 10, Exceptional, (2 reviews)
"Cute tiny house, comfy bed, nice shower, great little place to stay"
United States
Megan L.
The price is HK$524
HK$1,633 total
includes taxes & fees
1 Mar - 2 Mar
Tiny home near downtown w/ outdoor patio
1 bedroom, iron/ironing board, free WiFi, bed sheets

1x1 Guest Suite 10 minutes from UCF

1x1 Guest Suite 10 minutes from UCF
Union Park
9.2 out of 10, Wonderful, (7 reviews)
"The room was clean, quiet and very convenient. It is more spacious than what it looks in photos, a nice alternative to a hotel room. Parking was easy and the area feels safe. "
United States
Michael
The price is HK$461
HK$983 total
includes taxes & fees
22 Feb - 23 Feb
1x1 Guest Suite 10 minutes from UCF
Smart TV

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.4 out of 10, Exceptional, (13 reviews)
"Great stay! "
United States
Ash L.
The price is HK$682
HK$1,188 total
includes taxes & fees
25 Feb - 26 Feb
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Desk, WiFi, bed sheets

Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.0 out of 10, Wonderful, (4 reviews)
"Very nice and clean and comfortable "
United States
Kahari
The price is HK$371
HK$1,231 total
includes taxes & fees
22 Feb - 23 Feb
Studio in the heart of Orlando
Property grounds

Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748

Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748
Kissimmee
9.8 out of 10, Exceptional, (16 reviews)
"The place was in a great community. We felt very safe and right at home. Very well maintained with so many things to do on property. Great communication from the property owner. You can’t go wrong booking a stay here! We will definitely be back!"
United States
Emily D.
Spacious 2-Bedroom House 5 Star Near Disney Mill Creek Resort 2748
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (96 reviews)
"Nice place!"
United States
Anonymous traveller
The price is HK$1,133
HK$2,561 total
includes taxes & fees
3 Mar - 4 Mar
Eastpark. Pet friendly! Lake Nona
3 bedrooms, desk, iron/ironing board, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.8 out of 10, Exceptional, (23 reviews)
"Beautiful place to stay near the airport "
United States
Rodney
The price is HK$1,125
HK$2,136 total
includes taxes & fees
22 Feb - 23 Feb
Tranquil 3-bedroom house in Sanford with AC, WiFi
Smart TV, ping pong

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!

Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Azalea Park
9.6 out of 10, Exceptional, (17 reviews)
"Place was clean and had plenty of space for us. Check-in was easy and the host is very responsive and helpful."
United States
Ryan V.
The price is HK$1,062
HK$1,938 total
includes taxes & fees
23 Feb - 24 Feb
Quiet retreat 15 minutes from downtown Orlando, Orlando Airport International!
Dining

Brand NewPainted Vacation Hse NrUCF PetsOK Fenced

Brand NewPainted Vacation Hse NrUCF PetsOK Fenced
Orlando
9.6 out of 10, Exceptional, (16 reviews)
"My family stayed here with our pup and it was great. Plenty of room for everyone and a great yard space for all of us to enjoy. "
United States
Olivia S.
The price is HK$1,336
HK$2,629 total
includes taxes & fees
24 Mar - 25 Mar
Brand NewPainted Vacation Hse NrUCF PetsOK Fenced
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

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

10/10 Excellent
"Check-in was excellent, stayed for 3 days. Room was great. After they changed it. I They make the beds and give fresh towels daily. Heated pool and 2 jacuzzis were excellent. Applebees, which is physically connected to hotel, did not disappoint. The front desk people were excellent when you called with issues. Would stay again."
MICHELLE 3-night trip
Posted 1 day ago
Holiday Inn Resort Orlando - Lake Buena Vista by IHG

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
217
Accommodation
5893 Vacation Homes
Lowest Price
HK$983
Highest Price
HK$5,163

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