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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Featured Vacation Homes in Winter Park

Marriott's Sabal Palms
Surrounded by lush greenery and a serene body of water, this resort offers a central swimming pool with multiple access points.

Marriott's Sabal Palms

4.0 star property
9.6 out of 10, Exceptional, (193)
"Great stay with the family "
The price is P11,862
P13,345 total
includes taxes & fees
Aug 8 - Aug 9
Marriott's Sabal Palms
Marriott's Imperial Palm Villas
Relax by the resort's central pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas at your disposal.

Marriott's Imperial Palm Villas

4.0 star property
9.2 out of 10, Wonderful, (56)
"Well run property, loved the 2 or three bedroom layout, with a lounge, dining and kitchen area. "
The price is P14,903
P16,765 total
includes taxes & fees
Aug 15 - Aug 16
Marriott's Imperial Palm Villas
Westgate Blue Tree
2 outdoor pools

Westgate Blue Tree

3.5 star property
The price is P9,150
P13,118 total
includes taxes & fees
Jul 16 - Jul 17
Westgate Blue Tree
Stunning Game Room & Pool Jacuzzi Storey Lake 2799
Water park

Stunning Game Room & Pool Jacuzzi Storey Lake 2799

2.0 star property
10.0 out of 10, Exceptional, (1)
Stunning Game Room & Pool Jacuzzi Storey Lake 2799
Stunning 4Bd W/ Pool @ Storey Lake 5019
Water park

Stunning 4Bd W/ Pool @ Storey Lake 5019

2.0 star property
Stunning 4Bd W/ Pool @ Storey Lake 5019
Vacation USA LTD
Relax by the pool surrounded by lounge chairs and a patio.

Vacation USA LTD

3.5 star property
6.8 out of 10, (157)
"Loved the place. We had a mini family vacation, and the house was very well kept."
The price is P12,531
P22,640 total
includes taxes & fees
Jul 16 - Jul 17
Vacation USA LTD
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Relax by the pool with a clear view of the sky through the glass ceiling.

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

5.0 star property
8.8 out of 10, Excellent, (3)
"Nice "
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
4 Bd Sleeps 10 w/ GameRoom Close to Disney 5147
Enjoy cooking and relaxing in this stylish kitchen and living space, featuring a central island, stainless steel appliances, and a large window with a view.

4 Bd Sleeps 10 w/ GameRoom Close to Disney 5147

4.0 star property
8.0 out of 10, Very Good, (12)
"The home proved to be incredibly spacious and accommodating. One drawback, however, was the parking situation, which became increasingly crowded in the evenings, making it difficult to navigate the slim driveway. Nevertheless, I was pleased with the location's accessibility, featuring a range of nearby stores, restaurants, and gas stations. The host's ongoing communication was also a significant aspect of my stay. Moreover, the unit's close proximity to the trash area was a convenient feature....
4 Bd Sleeps 10 w/ GameRoom Close to Disney 5147
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
Relax by the resort's multiple pools and lounging areas, featuring sun loungers and shaded spots.

Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653

5.0 star property
10.0 out of 10, Exceptional, (2)
"Everything was excellent. I like the property was really cozy and nice. The only thing I didn’t like was that more concerned about when you leaving?"
Gorgeous 4 Bd w/ Pool @ Storey Lake Resort 2653
Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161
Enjoy cooking in the kitchen with a central island, dishwasher, microwave, and oven, complemented by cabinetry and a countertop.

Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161

4.0 star property
7.4 out of 10, Good, (3)
"Convenient to the parks, shopping, restaurants"
Amazing 4 Bedroom Close to Disney @Compass Bay Resort 5161
Stunning 4 Bd Close to Disney w/ Pool @ Storey Lake Resort 4369
Private kitchen

Stunning 4 Bd Close to Disney w/ Pool @ Storey Lake Resort 4369

4.5 star property
Stunning 4 Bd Close to Disney w/ Pool @ Storey Lake Resort 4369
Vista Cay Resort by Casiola Vacation Homes
Relax by the pool surrounded by palm trees and enjoy a refreshing swim or lounge on the sun-kissed deck.

Vista Cay Resort by Casiola Vacation Homes

3.5 star property
8.8 out of 10, Excellent, (181)
"Excellent "
The price is P7,776
P22,196 total
includes taxes & fees
Aug 3 - Aug 4
Vista Cay Resort by Casiola Vacation Homes
Family Friendly Four Bedroom w GameRoom @Disney 5145
Relax in this stylish living room with a sofa, coffee table, and dining area.

Family Friendly Four Bedroom w GameRoom @Disney 5145

5.0 star property
7.4 out of 10, Good, (6)
"It was fantastic!"
Family Friendly Four Bedroom w GameRoom @Disney 5145
Upstay - Waterside Home With Pool and Hot Tub
Enjoy meals in this dining area with a round table and wicker chairs, surrounded by a pool and patio view.

Upstay - Waterside Home With Pool and Hot Tub

2.0 star property
Upstay - Waterside Home With Pool and Hot Tub
Stunning 4Bd With Pool At Storey Lake Resort 4821
Golf

Stunning 4Bd With Pool At Storey Lake Resort 4821

5.0 star property
Stunning 4Bd With Pool At Storey Lake Resort 4821
Family Friendly 4 Bd w/GameRoom near Disney 5103
Relax by the oval-shaped pool surrounded by lush greenery and mature trees.

Family Friendly 4 Bd w/GameRoom near Disney 5103

3.5 star property
9.4 out of 10, Exceptional, (6)
"House was exactly as pictured. Great location- near stores and Disney parks. Great communication from staff - responded to texts and emails quickly. "
Family Friendly 4 Bd w/GameRoom near Disney 5103
Gorgeous 4 Bd w/ Pool Close to Disney @ Storey Lake 2963
Relax by the resort's central pools and water play area, surrounded by lounge seating and umbrellas.

Gorgeous 4 Bd w/ Pool Close to Disney @ Storey Lake 2963

4.5 star property
9.0 out of 10, Wonderful, (4)
"It was really nice and my family was able to enjoy it. The beds were very comfortable and the pool was so much fun! "
Gorgeous 4 Bd w/ Pool Close to Disney @ Storey Lake 2963
Family Friendly 4Bd Near Disney @ Compass Bay 5116
Enjoy cooking in this well-equipped kitchen with a central island, gas stove, and stainless steel appliances.

Family Friendly 4Bd Near Disney @ Compass Bay 5116

3.5 star property
Family Friendly 4Bd Near Disney @ Compass Bay 5116
Family Friendly 4Beds Close to Disney @Compass Bay Resort Orlando 5102
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and dishwasher, complemented by white cabinetry and a granite countertop.

Family Friendly 4Beds Close to Disney @Compass Bay Resort Orlando 5102

4.0 star property
8.0 out of 10, Very Good, (3)
"This place was great, close to everything, perfect amenities and wonderful communication. We will definitely try and stay here again."
Family Friendly 4Beds Close to Disney @Compass Bay Resort Orlando 5102
Sonoma Resort
Relax by the tranquil pool surrounded by palm trees and a soothing water feature.

Sonoma Resort

3.5 star property
7.6 out of 10, Good, (18)
"Aco vacation resort requires copy of license and credit card with permission to charge whatever they wanted. I didn’t like that. Expedia said not to share that info but they requested it."
Sonoma Resort
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
Sign in
Sign up, it's free