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

Next weekend
In two weeks
In one month
In two months

Compare 5864 Vacation Homes in Winter Park with updated reviews, rates, and availability.

Marriott's Sabal Palms

4.0 star property
9.6 out of 10, Exceptional, (192)
"Great property for families with access to hotel amenities"
The price is AED 988
AED 1,112 total
includes taxes & fees
5 Jun - 6 Jun
Marriott's Sabal Palms

Marriott's Imperial Palm Villas

4.0 star property
9.2 out of 10, Wonderful, (55)
"Well run property, loved the 2 or three bedroom layout, with a lounge, dining and kitchen area. "
The price is AED 1,392
AED 1,566 total
includes taxes & fees
3 Jun - 4 Jun
Marriott's Imperial Palm Villas

Exquisite Luxury Villa with Pool in Prime Location

2.0 out of 10, (1)
Exquisite Luxury Villa with Pool in Prime Location

Vista Cay Resort by Casiola Vacation Homes

3.5 star property
8.8 out of 10, Excellent, (180)
"Excellent "
The price is AED 855
AED 1,856 total
includes taxes & fees
3 Jun - 4 Jun
Vista Cay Resort by Casiola Vacation Homes

Quiet Oasis in Lovely Neighborhood

9.8 out of 10, Exceptional, (137)
"Very nice and quiet. "
The price is AED 331
AED 693 total
includes taxes & fees
3 Jun - 4 Jun
Quiet Oasis in Lovely Neighborhood

Vacation USA LTD

3.5 star property
6.8 out of 10, (155)
"Great location and proximity to the airport, Disney parks and Universal Studios. Place was clean, easy to access and had all the amenities we needed. "
The price is AED 863
AED 1,527 total
includes taxes & fees
2 Jul - 3 Jul
Vacation USA LTD

Family Townhome near Disney! Patio w/Pvt Splash Pool, Modern Decor,Free wifi, Resort w/waterpark!

9.6 out of 10, Exceptional, (14)
"Great location, nice place."
Family Townhome near Disney! Patio w/Pvt Splash Pool, Modern Decor,Free wifi, Resort w/waterpark!

Splendid 5Bd Close to Disney at Storey Lake 4251

5.0 star property
9.0 out of 10, Wonderful, (10)
"Home was great super clean and very cozy and comfortable. "
Splendid 5Bd Close to Disney at Storey Lake 4251

Upstay Resort Retreat w Private Pool & Hot Tub

10.0 out of 10, Exceptional, (5)
"Everything was exactly as described…an absolutely perfect property for our large family or family reunion, could be better if some basic cleaning products were there like dishwasher pods, garbage bags, towels, laundry pods. "
Upstay Resort Retreat w Private Pool & Hot Tub

Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen

10.0 out of 10, Exceptional, (33)
"Very nice stay"
Luxury 5 BR at Disney Universal free heated pool high chair stroller playpen

LUXE Disney Home! Priv Heated Pool/Spa, 3000ft2, 6 bed/5.5bath, Sleeps 13!

9.4 out of 10, Exceptional, (6)
"My family of 6 stayed here and enjoyed every bit of it!"
The price is AED 853
AED 1,871 total
includes taxes & fees
13 Jun - 14 Jun
LUXE Disney Home! Priv Heated Pool/Spa, 3000ft2, 6 bed/5.5bath, Sleeps 13!

Beautiful and cozy home at Sonoma Resort

9.2 out of 10, Wonderful, (9)
"The home is just beautiful! The upstairs tv area was so nice to sit and just watch a movie. The hot tub and pool were great for relaxing after a day out walking around. Highly recommend this beautiful home! "
Beautiful and cozy home at Sonoma Resort

Home 6BR - Prime Location

8.4 out of 10, Very Good, (27)
"Great stay"
Home 6BR - Prime Location

New Mansion Mins to Universal. 5830

9.2 out of 10, Wonderful, (9)
"All of the rooms were great the home was close to the parks and restaurant's. Also the beds were really comfortable."
New Mansion Mins to Universal. 5830

Lake-View Home w/ Game Room in Orlando!

9.0 out of 10, Wonderful, (55)
"We were going to Disney World for the weekend and this was a great location only 22 minutes away from magic Kingdom parking. The view from the living room was amazing, overlooking the pool and the lake. "
Lake-View Home w/ Game Room in Orlando!

Family & Pet Friendly (*additional pet fee applies), Charming Orlando Home!

10.0 out of 10, Exceptional, (153)
"Excellent Host, Great Home."
Family & Pet Friendly (*additional pet fee applies), Charming Orlando Home!

(IG4933) STOREY LAKE Home 4/3 Private Pool & Free Waterpark

9.2 out of 10, Wonderful, (22)
"Beautiful place to stay along with the close proximity to parks."
(IG4933) STOREY LAKE Home 4/3 Private Pool & Free Waterpark

Brand New 6BD Luxury Home w/ Pool, Best Location.

Brand New 6BD Luxury Home w/ Pool, Best Location.

Family Friendly home with Fenced in Backyard to enjoy with kids & pets

10.0 out of 10, Exceptional, (142)
"Our family stayed here for our son’s UCF graduation and it was a perfect place for us. Being able to bring our dog was wonderful, and she enjoyed the fenced back yard. The neighborhood was quiet, the beds were comfortable, and there was enough room for everyone. We would stay here again. "
Family Friendly home with Fenced in Backyard to enjoy with kids & pets

Entire Lakefront House in Orlando with Boat & Fish, close to Disney, Universal

8.8 out of 10, Excellent, (6)
Entire Lakefront House in Orlando with Boat & Fish, close to Disney, Universal
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