Search Vacation Homes in Winter Park

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Our top choices for Winter Park holiday homes

Magic Studio

9.4 out of 10, Exceptional, (3)
"Clean, roomy for two, comfortable bed, Met all our needs. Plan to stay there again."
Magic Studio

Mills House @WP. Sleeps 11 Renovated. Queen beds

10.0 out of 10, Exceptional, (1)
"This was a quaint little place with plenty of sleeping. The fenced in back yard with a canopy cover and chairs was a nice bonus. The kitchen was sufficiently stocked and newly remodeled. There were new smart TV ‘s in each room. There was a Publix right up the road as well as lots of great restaurants. We also enjoyed an antique mall (in the Publix plaza). We would highly recommend this place to others ."
The price is HK$1,000
HK$2,200 total
includes taxes & fees
2 Sept - 3 Sept
Mills House @WP. Sleeps 11 Renovated. Queen beds

Winter Park Gem, 2BR Near Parks, 3MI to Downtown

The price is HK$717
HK$2,172 total
includes taxes & fees
1 Sept - 2 Sept
Winter Park Gem, 2BR Near Parks, 3MI to Downtown

SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W

9.6 out of 10, Exceptional, (14)
"pet friendly resort "
The price is HK$554
HK$1,589 total
includes taxes & fees
31 Aug - 1 Sept
SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2772 W

Charming 2-bedroom apartment in house with AC, WiFi included

10.0 out of 10, Exceptional, (3)
"Very nice place. Very clean. Would stay again"
The price is HK$737
HK$1,072 total
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom apartment in house with AC, WiFi included

Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

8.8 out of 10, Excellent, (95)
"This home was right where we needed, clean, spacious and the pool was lovely. "
The price is HK$765
HK$3,685 total
includes taxes & fees
31 Aug - 1 Sept
Mi Casa Es Su Casa!!🏡 4 Bdrm home with pool

Charming 3-bedroom home away from home.

9.8 out of 10, Exceptional, (17)
"Perfect stay while visiting local family. "
The price is HK$1,161
HK$2,907 total
includes taxes & fees
31 Aug - 1 Sept
Charming 3-bedroom home away from home.

Sunshine Escape Guesthouse ☀

9.6 out of 10, Exceptional, (10)
"Great place to stay to get away for the weekend. Quiet neighborhood not far fromPark Ave "
The price is HK$456
HK$1,239 total
includes taxes & fees
31 Aug - 1 Sept
Sunshine Escape Guesthouse ☀

The Cozy Crash Pad: Tiny House Experience

9.2 out of 10, Wonderful, (19)
"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."
The price is HK$449
HK$1,100 total
includes taxes & fees
31 Aug - 1 Sept
The Cozy Crash Pad: Tiny House Experience

Pet Friendly!✰ Charming home with big patio!

10.0 out of 10, Exceptional, (16)
"Beautiful place to stay, clean and peaceful. Definitely recommend this place "
The price is HK$933
HK$2,790 total
includes taxes & fees
12 Sept - 13 Sept
Pet Friendly!✰ Charming home with big patio!

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

9.8 out of 10, Exceptional, (7)
"This place is a great size guest suite on a scenic property in a rural area close to the suburbs, very nice getaway, we enjoyed our short stay! It's very clean and cozy, and the hosts are very helpful, thank you!"
The price is HK$737
HK$1,248 total
includes taxes & fees
7 Sept - 8 Sept
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Cozy House in Orlando w/ a Large Fenced Yard 15m to Downtown

9.6 out of 10, Exceptional, (7)
"Nice home and location. "
The price is HK$828
HK$1,916 total
includes taxes & fees
8 Sept - 9 Sept
Cozy House in Orlando w/ a Large Fenced Yard 15m to Downtown

Exquisite Newly Renovated Minutes to Disney and Great Shopping

9.2 out of 10, Wonderful, (79)
"The property needs a little TLC but is clean and has everything you need. The beds are very comfortable. Being on the first/ground floor the property needed more privacy, sheer curtains would help."
Exquisite Newly Renovated Minutes to Disney and Great Shopping

8 ppl•Beautiful House Near Universal Studios and Attractions

2.0 star property
7.4 out of 10, Good, (3)
"My friend and I enjoyed our stay. The beds were very comfortable and the home was immaculate! Thank you so much for hosting an incredible home."
The price is HK$1,091
HK$1,384 total
includes taxes & fees
2 Sept - 3 Sept
8 ppl•Beautiful House Near Universal Studios and Attractions

Tranquil 3-bedroom house in Sanford with AC, WiFi

9.8 out of 10, Exceptional, (18)
"Beautiful place to stay near the airport "
The price is HK$1,052
HK$2,060 total
includes taxes & fees
2 Sept - 3 Sept
Tranquil 3-bedroom house in Sanford with AC, WiFi

THE CHLOE by EVRH

9.0 out of 10, Wonderful, (65)
"This house was great for our stay. The decor and cleanliness was great. "
The price is HK$772
HK$3,919 total
includes taxes & fees
8 Sept - 9 Sept
THE CHLOE by EVRH

Spacious & Private Guest Pool House Oasis

9.6 out of 10, Exceptional, (14)
"Great location , Very enjoy , private space, would book in the future for sure "
The price is HK$818
HK$2,088 total
includes taxes & fees
15 Sept - 16 Sept
Spacious & Private Guest Pool House Oasis

6-bedroom 3bath "Clue" Themed home near parks

2.0 star property
9.0 out of 10, Wonderful, (9)
"Close to where we need to work."
The price is HK$1,179
HK$3,212 total
includes taxes & fees
3 Sept - 4 Sept
6-bedroom 3bath "Clue" Themed home near parks

Renovated Peaceful Luxury Walk to Mall Park Publix

9.4 out of 10, Exceptional, (11)
"Very nice little place walking distance to Advent Health."
The price is HK$667
HK$1,478 total
includes taxes & fees
2 Sept - 3 Sept
Renovated Peaceful Luxury Walk to Mall Park Publix

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

10.0 out of 10, Exceptional, (30)
"Great property and host "
The price is HK$1,130
HK$2,088 total
includes taxes & fees
24 Sept - 25 Sept
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Park Hotel Reviews

Find out more about Winter Park

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
Accommodation
6116 Vacation Homes
Lowest Price
HK$631
Highest Price
HK$1,949