Best Resorts in Winter Park

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May 14 - May 15
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May 15 - May 16
This weekend
May 17 - May 19
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May 24 - May 26

Compare Resorts in Winter Park with updated reviews, rates, and availability.

6 Bedroom Estate with Pool and Theater | 4 bedrooms, premium bedding, pillowtop beds, desk
Villatel Orlando Resort
4.0 star property
10.0 out of 10, Exceptional, (16)
"Amazing place and location "
Villatel Orlando Resort
Indoor pool, a heated pool
Resort Inside Disney Gates, Lazy River, Mini Golf +Spacious Suite+Full Kitchen
10.0 out of 10, Exceptional, (23)
"Outside and inside of this place is amazing. We will be back!! Fun available for all ages."
Resort Inside Disney Gates, Lazy River, Mini Golf +Spacious Suite+Full Kitchen
Indoor pool, a heated pool
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
10.0 out of 10, Exceptional, (20)
"We had a great stay. The condo was perfect for our family, the pools and restaurants were convenient, and the proximity to the parks made for a stress free trip."
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
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Indoor pool, a heated pool
Family Bliss: 3BR Dlx inside Disney Gates, Lazy rivers
10.0 out of 10, Exceptional, (2)
"Amazing location, beautiful resort. After a long day at the park it was nice to relax at this resort; the lazy river was a good way to wind down the day. Will be staying here again in the future. I highly recommend this location for anyone that is looking to have their dream Disneyworld / Universals Studios vacation. This was more price friendly than staying within the park but offered a lot of convenience due to the proximity to the parks."
Family Bliss: 3BR Dlx inside Disney Gates, Lazy rivers
Indoor pool, a heated pool
Family Bliss: 1BR Dlx inside Disney Gates, Lazy rivers
10.0 out of 10, Exceptional, (41)
"Club Wyndham and this VRBO were fantastic and proved right for a family!"
Family Bliss: 1BR Dlx inside Disney Gates, Lazy rivers
Indoor pool, a heated pool
Family Friendly+Mini Golf+Outdoor Pools+Stunning Grounds-2 Bd. Dlx
10.0 out of 10, Exceptional, (5)
"Super easy booking process and a seamless experience. The property is fabulous. We couldn’t have been happier!"
Family Friendly+Mini Golf+Outdoor Pools+Stunning Grounds-2 Bd. Dlx
Indoor pool, a heated pool
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
10.0 out of 10, Exceptional, (20)
"We had a great stay. The room was clean and the property had so much to keep us all entertained."
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
Indoor pool, a heated pool
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
10.0 out of 10, Exceptional, (7)
"We love this place every time we come. It has so many fun things to do, great food options, and so close to everything."
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
Smart TV
1 BEDROOM WITH LOFT DISNEY AREA VACATION RENTAL AWARD WINNING MILL CREEK RESORT
10.0 out of 10, Exceptional, (3)
"We enjoyed this property. Quiet area and perfect for our dog"
The price is $79
$208 total
includes taxes & fees
May 18 - May 19
1 BEDROOM WITH LOFT DISNEY AREA VACATION RENTAL AWARD WINNING MILL CREEK RESORT
Pool
2 BEDROOM DISNEY AREA VACATION RENTAL IN AWARD WINNING "MILL CREEK RESORT"
10.0 out of 10, Exceptional, (2)
"this is a cute little tiny home. it was very clean and the neighborhood was quite It's perfect for a couple and its cheaper than a hotel room."
2 BEDROOM DISNEY AREA VACATION RENTAL IN AWARD WINNING "MILL CREEK RESORT"
Property grounds
Brand New Lakefront 18th FL - .8 miles from Disney
10.0 out of 10, Exceptional, (31)
"We were so pleased with our stay in Josh and Amy’s condo. The condo is clean, the view is amazing, and it was perfectly located near everything we wanted to visit. We watched the Disney fireworks out the front door of the condo and the Universal fireworks from the private balcony. The sunrise view over Lake Bryan is breathtaking. Josh and Amy could not have been more attentive and quick to respond. Perfect stay!!!"
Brand New Lakefront 18th FL - .8 miles from Disney
Indoor pool, a heated pool
Family Bliss: 3BR Dlx inside Disney Gates, Lazy rivers
9.8 out of 10, Exceptional, (18)
"The resort was wonderful, great pools, responsive staff, wonderful rooms. The kitchen was well stocked with anything you need. Only drawback is as a timeshare, you are pushed a bit to attend sales meetings for “free” incentives. Once I was very firm, they left us alone. Everything else was excellent!!!"
Family Bliss: 3BR Dlx inside Disney Gates, Lazy rivers
Indoor pool, a heated pool
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
9.8 out of 10, Exceptional, (23)
"Really enjoyed the condo and the grounds. Good location to restaurants and activities."
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
Indoor pool, a heated pool
Family Bliss: 3BR Dlx inside Disney Gates, Lazy rivers
9.8 out of 10, Exceptional, (50)
"Great"
Family Bliss: 3BR Dlx inside Disney Gates, Lazy rivers
Indoor pool, a heated pool
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
9.8 out of 10, Exceptional, (19)
"The unit and the facilities were wonderful. Clean and spacious and well furnished. The only annoying part was check in with Wyndam who tried to push us into a vacation ownership sales presentation."
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
3 outdoor pools, cabanas (surcharge), pool umbrellas
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
5.0 star property
9.6 out of 10, Exceptional, (781)
"Lovely Property "
The price is $1,135
$1,277 total
includes taxes & fees
May 28 - May 29
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Waterslide
Evermore Orlando Resort
4.0 star property
9.6 out of 10, Exceptional, (40)
"Beautiful, clean property. Staff was excellent service was great too! Would go back!"
Evermore Orlando Resort
Exterior
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
9.6 out of 10, Exceptional, (25)
"They really came through on all their promises. Room was as advertised, clean, updated enough, plenty of utensils in kitchen. Beds super comfortable. Grounds are kept beautifully. No problem parking."
Family Bliss: 2BR Dlx inside Disney Gates, Lazy rivers, Parks
Exterior
JW Marriott Orlando Bonnet Creek Resort & Spa
4.0 star property
9.2 out of 10, Wonderful, (366)
"It was fantastic. Staff was friendly and helpful. Clean , modern and very comfortable. Close to everything"
The price is $305
$393 total
includes taxes & fees
May 28 - May 29
JW Marriott Orlando Bonnet Creek Resort & Spa
Front of property - evening/night
Arnold Palmer's Bay Hill Club & Lodge
4.0 star property
9.2 out of 10, Wonderful, (1000)
"Loved it! Beautiful area, wonderful staff, will definitely be returning! "
The price is $265
$298 total
includes taxes & fees
May 19 - May 20
Arnold Palmer's Bay Hill Club & Lodge
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See all available properties in Winter Park
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.

Other property types in Winter Park

Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4810)
"Very convenient. We stayed before our Disney Cruise. "
The price is $199
$224 total
includes taxes & fees
May 29 - May 30
Hyatt Regency Orlando International Airport
Exterior
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
3.5 star property
8.6 out of 10, Excellent, (3118)
"Excellent receptionist… will come back for sure ..!!!!"
The price is $82
$122 total
includes taxes & fees
Jun 10 - Jun 11
Holiday Inn Resort Orlando - Lake Buena Vista, an IHG Hotel
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very Good, (7180)
"pool was great , room was large 2 bedroom condo very nice only complaint was our key cards kept not working had to go to front desk 3 times to get new cards cause none of the 4 cards we had would open the door "
The price is $156
$202 total
includes taxes & fees
May 16 - May 17
Lake Buena Vista Resort Village & Spa
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.

Frequently asked questions

What can I expect from a resort vacation in Winter Park?
Longing for a relaxing getaway? Indulge in all the comforts of a resort, where you can find everything you need for your vacation from tasty dining options to activities and shopping. One of the 1518 comfortable resorts in the area might be just what you’re looking for, whether you’re hoping for great restaurants on site, shopping possibilities, or activities for the kids.
What's the best resort for my stay in Winter Park?
Our top-rated resorts around Winter Park: Wyndham Garden Lake Buena Vista Disney Springs® Resort Area - Family-friendly resort less than 10 minutes from Disney Springs™. 18.8 mi (30.2 km) from Winter Park. Features 2 outdoor pools, 3 restaurants, and 2 bars. Highly rated for its proximity to shopping. Rosen Centre Hotel - Spa resort. 14.4 mi (23.1 km) from Winter Park. Has 7 restaurants, 3 bars, and a full-service spa. Wyndham Grand Orlando Resort Bonnet Creek - Family-friendly resort. 20.6 mi (33.1 km) from Winter Park. Enjoy the 5 outdoor pools, 4 restaurants, and lazy river. Evermore Orlando Resort - Beach resort. 17.7 mi (28.6 km) from Winter Park. Amenities include 3 outdoor pools, 3 restaurants, and a private beach. JW Marriott Orlando Bonnet Creek Resort & Spa - Spa resort. 20.2 mi (32.5 km) from Winter Park. Access to 2 outdoor pools, 6 restaurants, and a full-service spa.
What can I do in Winter Park?
Travelers enjoy the shopping and other activities in Winter Park, and also have good things to say about the dining options here. Check out the interesting exhibits at Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, or grab your golf clubs for a game at Winter Park Country Club or Winter Pines Golf Club. Other top attractions in the area include Universal Studios Florida and Universal Orlando Resort.
What's the seasonal weather like in Winter Park?
The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall.
What's the best way to get to and around Winter Park?
Fly into Orlando Intl. Airport (MCO), which is located 11.8 mi (19 km) from the city center. Otherwise, look for flights into Orlando Sanford Intl. Airport (SFB), which is 13.4 mi (21.6 km) away. To venture out into the surrounding area, hop aboard a train at Winter Park Station.