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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Winter Park holiday rentals

Fridge, microwave, oven, stovetop

Quiet and safe neighborhood come to this great place with lots of room for relax

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
10.0 out of 10, Exceptional, (2 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
The price is £217
includes taxes & fees
13 May - 14 May
Quiet and safe neighborhood come to this great place with lots of room for relax
Outdoor pool

1-bedroom vacation room just 12 minutes from University of Central Florida

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic Host"
United States
Marek K.
The price is £128
includes taxes & fees
13 May - 14 May
1-bedroom vacation room just 12 minutes from University of Central Florida
Exterior

Comfy Tiny Home @WP. Large Private Deck+Queen bed

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is £144
includes taxes & fees
20 May - 21 May
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is £203
includes taxes & fees
27 May - 28 May
Cozy home 5min to Park Ave and Downtown Orlando
Property grounds

Virbo Host Website is not working for me. Do not book this property. Thank you

Virbo Host Website is not working for me. Do not book this property. Thank you
Fairview Shores
The price is £83
includes taxes & fees
10 May - 11 May
Virbo Host Website is not working for me. Do not book this property. Thank you
Exterior

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 £196
includes taxes & fees
9 Jun - 10 Jun
Funky Remodeled Otown Bungalow Sleeps 8
Private kitchen

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
The price is £225
includes taxes & fees
1 Jun - 2 Jun
Cute 5-bedroom house in peaceful Winter Park
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 £263
includes taxes & fees
12 May - 13 May
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 £278
includes taxes & fees
13 May - 14 May
Spacious 5-bedroom house in gorgeous Winter Park
Property grounds

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 £166
includes taxes & fees
20 May - 21 May
Charming home @wp. Patio +Gazebo. close to highwys
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 £288
includes taxes & fees
1 Jun - 2 Jun
Cute 5-bedroom,6bed house in superb Winter Park.
Exterior

Hilton Vacation Club Grand Beach Orlando

Hilton Vacation Club Grand Beach Orlando
3.0 star property
Orlando
9.4 out of 10, Exceptional, (1,514 reviews)
"Spacious rooms and clean. Great resort!!!"
United States
Javier
The price is £106
includes taxes & fees
17 May - 18 May
Hilton Vacation Club Grand Beach Orlando
2 outdoor pools, open 7:00 AM to 11:00 PM, free pool cabanas

Magical Moment Vacation Condos

Magical Moment Vacation Condos
4.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"Very Clean room staff were great !! Definitely would stay again !"
United States
stephanie
The price is £247
includes taxes & fees
13 May - 14 May
Magical Moment Vacation Condos
Apartment (1 Bedroom) | Interior

Suite Near Universal Studios w Pool & Hot Tub

Suite Near Universal Studios w Pool & Hot Tub
3.0 star property
International Drive District
10.0 out of 10, Exceptional, (1 review)
"The room was clean and service was great!"
United States
Daija
The price is £112
includes taxes & fees
12 May - 13 May
Suite Near Universal Studios w Pool & Hot Tub
2 bedrooms, desk, free WiFi

The Front Porch

The Front Porch
3.0 star property
Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The price is £153
includes taxes & fees
10 May - 11 May
The Front Porch
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is £167
includes taxes & fees
17 May - 18 May
The Blue Aztec
Beach

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (67 reviews)
"Great place, found the heater, thank you!Would stay again, just pull the bed away from the wall for us old folk "
United States
Susan J.
The price is £113
includes taxes & fees
11 May - 12 May
Tiny Hidden Cottage
Outdoor pool

“Best Stay Ever” – Recent Guest

“Best Stay Ever” – Recent Guest
Lake Mary
9.8 out of 10, Exceptional, (52 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is £186
includes taxes & fees
27 May - 28 May
“Best Stay Ever” – Recent Guest
Apartment, Patio

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
4.0 star property
Kirkman North
The price is £303
includes taxes & fees
11 May - 12 May
Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly
Interior

Cozy studio in fabulous Orlando close to everything

Cozy studio in fabulous Orlando close to everything
Orlando
9.8 out of 10, Exceptional, (19 reviews)
"The host is wonderful and the place was exactly what I needed. The bed was extremely comfortable and the neighborhood really quiet. I will definitely be back and stay here again."
United States
Robin L.
The price is £125
includes taxes & fees
11 May - 12 May
Cozy studio in fabulous Orlando close to everything
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Loved the retro details down to the soap bars and shampoo bottles. Cool ! A trip through time. Lively. Awesome extensive pools and minutes away to Universal parks by shuttle"
Martin 1-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort

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Frequently asked questions

Can I find holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Kraft Azalea Gardens, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Winter Park. Make sure you have time to check out the university setting and gardens during your trip.

What are some of the best holiday rentals that Winter Park has to offer?

Grand Luxury Lakes 3BR Townhouse near Disney: This holiday home rental outside of Winter Park is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms and a kitchen with a dishwasher.

How many holiday rentals are there in Winter Park?

Expedia has 58 holiday rentals for your stay in Winter Park.

What can I see and do in Winter Park?

Cultural attractions include Casa Feliz Historic Home Museum and Winter Park History Museum, whereas Lake Virginia and Mead Garden are a couple of picturesque spots to enjoy the outdoors. Universal Studios Florida and Universal Orlando Resort are other popular places to visit in the area.

What are holiday rentals like in Winter Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Park. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.