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Compare 772 Vacation Homes in Winter Park with updated reviews, rates, and availability.

Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI

10.0 out of 10, Exceptional, (75)
"Really enjoyed our stay. Plenty of room for us to spread out. "
Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI

Perfect mountain getaway any time of year!

9.4 out of 10, Exceptional, (64)
"Property was in great shape. Very roomy and comfortable. Highly recommend."
Perfect mountain getaway any time of year!

Beautiful townhome in the heart of Town of Winter Park w/PRIVATE HOT TUB

9.8 out of 10, Exceptional, (41)
"Spacious townhome and in a great location! "
The price is AEDĀ 918
AEDĀ 3,373 total
includes taxes & fees
1 Jul - 2 Jul
Beautiful townhome in the heart of Town of Winter Park w/PRIVATE HOT TUB

Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily

9.6 out of 10, Exceptional, (34)
"The property is very nice with a good location to the bus stop, close to many places to eat and easy access. We have stayed in several VRBO properties and this is a good one."
Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily

Luxe Downtown Winter Park Private Hot Tub 4 BR

9.8 out of 10, Exceptional, (68)
"We stayed here for a family wedding. Great accommodations and Bob was great to work with!"
Luxe Downtown Winter Park Private Hot Tub 4 BR

Indulge | Majestic Views | Teepee | Hot Tub

9.4 out of 10, Exceptional, (19)
"The home is beautiful and accommodated our group well. "
The price is AEDĀ 941
AEDĀ 2,847 total
includes taxes & fees
17 Jun - 18 Jun
Indulge | Majestic Views | Teepee | Hot Tub

Stunning townhome. Few minutes from Winter Park Ski Resort and Town of WP

9.6 out of 10, Exceptional, (91)
"Amazing place to stay and close to the winter pak"
Stunning townhome. Few minutes from Winter Park Ski Resort and Town of WP

'Snow Dream'- the Ultimate Family Retreat

10.0 out of 10, Exceptional, (151)
"Great property would rent again"
'Snow Dream'- the Ultimate Family Retreat

Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!

9.8 out of 10, Exceptional, (71)
"Great place for two families. Nice location. "
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!

Tree-Lined Home with Private Hot Tub, Gas Fireplace, Shuffleboard & WiFi

9.8 out of 10, Exceptional, (36)
"Plenty of space, en suite bathrooms, fire pit, hot tub, lots of outdoor space the kids, just can’t say enough, it’s a great spot."
Tree-Lined Home with Private Hot Tub, Gas Fireplace, Shuffleboard & WiFi

Base Camp 480 | Gorgeous Mountain Townhome On Slopes | Private Hot Tub | Dreamy Luxe Decor

9.8 out of 10, Exceptional, (60)
"Everything they did was great."
Base Camp 480 | Gorgeous Mountain Townhome On Slopes | Private Hot Tub | Dreamy Luxe Decor

New River Front Luxury Villa 244 I Hot Tub I Great Views I Best Price I FREE Adventures Daily

9.8 out of 10, Exceptional, (26)
"We had a group trip and stayed at this townhouse and it was absolutely beautiful just like the photos. The house has stunning views and a lot of places are in walking distance. The only thing that I wish was different was the amount of stairs but the overall house was great."
New River Front Luxury Villa 244 I Hot Tub I Great Views I Best Price I FREE Adventures Daily

Spectacular Modern Lodge with on-site Concierge! Amazing Views!

9.8 out of 10, Exceptional, (47)
"Excellent location just a few miles away from Winter Park, which you can see from the living room windows. Loved the views. Close to shopping, groceries and the bus line to Winter Park resort. Great communication with property manager. Property stocked well with towels, blankets, etc. "
Spectacular Modern Lodge with on-site Concierge! Amazing Views!

Luxury Home 270 I Next To Resort I Hot Tub I Great Views I Best Price I FREE Adventures Daily

10.0 out of 10, Exceptional, (43)
"Our adult children and our three grandchildren stayed in this beautiful home for a week in Jan. The home way over surpassed our expectations. By far the best VRBO home we have rented. The home was very well stocked to help our stay more enjoyable. We would stay here again!"
Luxury Home 270 I Next To Resort I Hot Tub I Great Views I Best Price I FREE Adventures Daily

New Luxury Pond Chalet 11 I Great Views I Best Price I FREE Adventures Daily

New Luxury Pond Chalet 11 I Great Views I Best Price I FREE Adventures Daily

Spacious remodeled home w/Yoga Studio, private hot tub, mountain views.

9.6 out of 10, Exceptional, (52)
"A great place to stay. While close to neighbors, they are out of sight with amazing views of the neighboring mountains. "
Spacious remodeled home w/Yoga Studio, private hot tub, mountain views.

Luxury villa with private hot tub and just minutes to WP Resort

9.8 out of 10, Exceptional, (16)
"We loved our stay! The location is close to all activities! The house has everything you need. We definitely will be going back."
Luxury villa with private hot tub and just minutes to WP Resort

Townhome near hiking/fishing/skiing with private hot tub & mountain views

10.0 out of 10, Exceptional, (11)
"Great stay and location "
Townhome near hiking/fishing/skiing with private hot tub & mountain views

Luxurious 3 bedroom private hot tub, mt views

9.0 out of 10, Wonderful, (12)
"Easy check-in process, very clean, beautiful home"
Luxurious 3 bedroom private hot tub, mt views

New Headwaters Condo 206 I Great Views I Best Price I FREE Adventures Daily

7.0 out of 10, Good, (2)
"Lovely place we did have some issues with the door not locking and took over 24 hours to get a resolution which resulted in missing certain activities on our trip since we were not able to leave the site since the door wouldn't lock"
New Headwaters Condo 206 I Great Views I Best Price I FREE Adventures Daily
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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