Search Holiday Homes in Winter Park

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Winter Park holiday homes

Private kitchen

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
The price is £294
includes taxes & fees
19 Apr - 20 Apr
Cute 5-bedroom house in peaceful Winter Park
Interior

Cozy home 5min to Park Ave and Downtown Orlando. Dedicated office.

Cozy home 5min to Park Ave and Downtown Orlando. Dedicated office.
Fairview Shores
The price is £188
includes taxes & fees
12 May - 13 May
Cozy home 5min to Park Ave and Downtown Orlando. Dedicated office.
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
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed our stay! Everything was clean, comfortable, and quiet. Very easy access to local restaurants and shopping, and a short drive to theme parks. We would definitely stay here again! Thank you! "
United States
Megan J.
The price is £287
includes taxes & fees
19 Apr - 20 Apr
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Property grounds

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

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
7.0 out of 10, Good, (2 reviews)
"Very clean and location was great"
United States
Vicki V.
The price is £168
includes taxes & fees
19 Apr - 20 Apr
Charming home @wp. Patio +Gazebo. close to highwys
Exterior

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
The price is £195
includes taxes & fees
19 Apr - 20 Apr
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
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 £229
includes taxes & fees
19 Apr - 20 Apr
Mills House @WP. Sleeps 11 Renovated. Queen beds
Private kitchen

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (1 review)
"The house was clean, in a quiet neighborhood. Everything you could need was close and traffic was not bad at all. The host answers any and all questions quick and made the experience hassle free."
United States
Stephanie S.
The price is £272
includes taxes & fees
1 May - 2 May
Spacious 5-bedroom house in gorgeous Winter Park
Living area

WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS

WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS
Winter Park
9.0 out of 10, Wonderful, (2 reviews)
"We had a great time! Home was clean, roomy and all we had hoped for. The hosts were very communicative and quick to answer all our questions prior to our stay! Would definitely recommend!"
United States
Rita C.
WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS
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 £398
includes taxes & fees
5 May - 6 May
Cute 5-bedroom,6bed house in superb Winter Park.
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
9.4 out of 10, Exceptional, (8 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 £88
includes taxes & fees
19 Apr - 20 Apr
1x1 Guest Suite 10 minutes from UCF
Desk, WiFi, bed sheets

Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
The price is £119
includes taxes & fees
12 May - 13 May
Studio in the heart of Orlando
Terrace/patio

Historic Hotspot • Walk to Downtown Fun • Luxury Beds

Historic Hotspot • Walk to Downtown Fun • Luxury Beds
Sanford
10.0 out of 10, Exceptional, (13 reviews)
"Ideal location, easy walk to food and fun."
United States
Steven H.
The price is £182
includes taxes & fees
19 Apr - 20 Apr
Historic Hotspot • Walk to Downtown Fun • Luxury Beds
Fridge, microwave, oven, stovetop

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!

Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Buena Ventura Lakes
10.0 out of 10, Exceptional, (33 reviews)
"Clean spacious very cozy & relaxing"
United States
Nicky B.
The price is £245
includes taxes & fees
20 Apr - 21 Apr
Escape to Paradise!Luxury Waterfront Heated Pool House with Game Room and Piano!
Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (97 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is £253
includes taxes & fees
21 Apr - 22 Apr
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, (25 reviews)
"Beautiful place to stay near the airport "
United States
Rodney
The price is £204
includes taxes & fees
19 Apr - 20 Apr
Tranquil 3-bedroom house in Sanford with AC, WiFi
Fridge, microwave, oven, stovetop

Orlando Vacation homeAway near Universal with hot/tub

Orlando Vacation homeAway near Universal with hot/tub
Oak Ridge
8.8 out of 10, Excellent, (22 reviews)
"So nice, we stayed here twice! Very close to Universal and so much more...."
United States
Matthew J.
The price is £171
includes taxes & fees
21 Apr - 22 Apr
Orlando Vacation homeAway near Universal with hot/tub
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, (16 reviews)
"Great stay! "
United States
Ash L.
The price is £109
includes taxes & fees
29 Apr - 30 Apr
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Terrace/patio

-A Sweet Home Near Theme Parks!-

-A Sweet Home Near Theme Parks!-
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"The house was very clean and well organized. All appliances were working and in great condition. Check in and check out was so simple. And it had the absolute biggest selection of coffee. We had a great stay"
United States
Barbara
The price is £269
includes taxes & fees
22 Apr - 23 Apr
-A Sweet Home Near Theme Parks!-
Private kitchen

Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
10.0 out of 10, Exceptional, (12 reviews)
"Perfect! Place was clean. Parking was easy. ( Business travel)"
United States
Matt S.
The price is £213
includes taxes & fees
19 Apr - 20 Apr
Charming 2-bedroom Florida Getaway! Sleeps 6
Terrace/patio

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
9.0 out of 10, Wonderful, (24 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
The price is £113
includes taxes & fees
11 May - 12 May
The Cozy Crash Pad: Tiny House Experience
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

8/10 Good
"Nice place but the second Waterpark was still under construction ( can't blame them for that) The only real negative thing I can think of was the lack of working ice machines. I had to go 2 floors down and to the adjacent building."
Roberto 2-night trip
Posted 3 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
244
Accommodation
5449 Holiday Homes
Lowest Price
£88
Highest Price
£398