Search Vacation Homes in Winter Park

Compare 675 Vacation Homes in Winter Park with updated reviews, rates, and availability.

Trailhead 524 Clubhouse w/ Hot tub | Pool
View of dining and living room with the fireplace

Trailhead 524 Clubhouse w/ Hot tub | Pool

9.8 out of 10, Exceptional, (39)
"The listing stated it slept 8 and it actually slept 8 in beds! (Sometimes the listing says it sleeps 8 and 2 people are relegated to pull out couches, not the case here which was amazing!). The kitchen was beautiful and location was close to “Downtown” which was very convenient and in walking distance. The views were also just gorgeous. The place looks out to the mountain and greenery and we even saw a mama moose and her baby one morning! Very peaceful and serene. One comment there weren’t basic...
Trailhead 524 Clubhouse w/ Hot tub | Pool
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Exterior

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

9.8 out of 10, Exceptional, (64)
"We had a great stay. The place was very comfortable, it’s well maintained and has the most well appointed kitchen of any place we have stayed. Thank you! "
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Cozy Chalet with Mountain Views & Large Balcony - Steps to Shuttle

Cozy Chalet with Mountain Views & Large Balcony - Steps to Shuttle

8.4 out of 10, Very Good, (8)
"The description of the property documented a fireplace after paying a notice appeared that that the fireplace has been removed. Vacasa refunded us only one hundred dollars. We requested to be refunded one hundred per night. We were never given an answer just a complete run around. Also, there was no laundry detergent. I requested it to be sent. I was then told the washer and dryer is not an amenity so laundry detergent will not be provided. I mentioned that it is noted that you would like us to...
Cozy Chalet with Mountain Views & Large Balcony - Steps to Shuttle
Luxury Home 270 I Next To Resort I Hot Tub I Great Views I Best Price I FREE Adventures Daily
beautiful front exterior with ski 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, (40)
"Great time staying at house. Amazing location and finishes were impressive. House accommodated a large group and we had a great time"
Luxury Home 270 I Next To Resort I Hot Tub I Great Views I Best Price I FREE Adventures Daily
NEW 2 bedroom private home private hot tub, walk to downtown
45 Idlewild Pic 26

NEW 2 bedroom private home private hot tub, walk to downtown

10.0 out of 10, Exceptional, (1)
"Property was very clean and comfortable, we enjoyed our stay. The layout of the house is a little wonky, and the hot tub is right on the roadside, but we adapted. Good for a couple nights, not we'd want to stay a whole week. Recommend adding a wine opener. :)"
The price is SAR 787
SAR 1,791 total
includes taxes & fees
9 Jan - 10 Jan
NEW 2 bedroom private home private hot tub, walk to downtown
Winterfell at Winter Park Resort, New Luxury Home | Private Hot Tub | Stunning Views
Winterfell at Winter Park Resort | Winter is coming!!

Winterfell at Winter Park Resort, New Luxury Home | Private Hot Tub | Stunning Views

10.0 out of 10, Exceptional, (1)
"It was a great property for our group of 10. Well stocked and plenty of room. Tim and Stacey, our hosts, provided lots of good local information and suggestions. The location, right across from the ski resort was ideal for us and close enough to watch the fireworks from the house. We highly recommend it."
Winterfell at Winter Park Resort, New Luxury Home | Private Hot Tub | Stunning Views
210 Sawyer with Private Hot Tub
Living Room

210 Sawyer with Private Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great place, great location !!! Close to the slopes . Planning our spring break ski trip asap. Clean place, and the hot tub was great .perfect weather snowed yesterday "
210 Sawyer with Private Hot Tub
Tree-Lined Townhome Downtown w/Private Hot Tub, Slope Views, Fireplace, WiFi

Tree-Lined Townhome Downtown w/Private Hot Tub, Slope Views, Fireplace, WiFi

9.2 out of 10, Wonderful, (35)
"We had such a great family stay in this condo unit! It had all we needed with the exception of sharp knives which is a small thing! Thanks for letting us enjoy your space!"
Tree-Lined Townhome Downtown w/Private Hot Tub, Slope Views, Fireplace, WiFi
Custom Mtn Home near downtown Winter Park, on Shuttle Route, Hot tub!!
Panoramic of front of house

Custom Mtn Home near downtown Winter Park, on Shuttle Route, Hot tub!!

9.8 out of 10, Exceptional, (15)
"We had a wonderful thanksgiving vacation! Check in was easy, communication was quick, and the house was absolutely gorgeous! "
The price is SAR 3,042
SAR 7,410 total
includes taxes & fees
14 Jan - 15 Jan
Custom Mtn Home near downtown Winter Park, on Shuttle Route, Hot tub!!
Indulge | Majestic Views | Teepee | Hot Tub

Indulge | Majestic Views | Teepee | Hot Tub

9.8 out of 10, Exceptional, (12)
"Home was well equipped and the location was perfect. Notified rental to have cleaner take care of oven that was full of debris from burned drippings. The home was clean in every other way and we fortunately did not need oven for our one night. I would definitely book again. "
The price is SAR 1,357
SAR 3,323 total
includes taxes & fees
21 Jan - 22 Jan
Indulge | Majestic Views | Teepee | Hot Tub
Condo with fireplace on shuttle route, offering scenic woodland views.
Living room - Big sofa, fire place and TV

Condo with fireplace on shuttle route, offering scenic woodland views.

9.2 out of 10, Wonderful, (20)
"Condo was clean and well equipped. We enjoyed our stay, would have like to have tv's in secondary bedrooms. would stay here again."
Condo with fireplace on shuttle route, offering scenic woodland views.
Downtown Townhome w/Free WiFi, Shuttle Service, Private Hot Tub, & Washer/Dryer

Downtown Townhome w/Free WiFi, Shuttle Service, Private Hot Tub, & Washer/Dryer

9.4 out of 10, Exceptional, (35)
"The unit was perfect for the family; however the smoke alarms were a little temperamental as they went off twice during our stay."
Downtown Townhome w/Free WiFi, Shuttle Service, Private Hot Tub, & Washer/Dryer
New River Front Luxury Villa 244 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Property Exterior

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

9.6 out of 10, Exceptional, (24)
"Our family stayed here for 5 days and it was the perfect getaway trip with enough space for everyone! Walking distance to many restaurants and shopping options!"
New River Front Luxury Villa 244 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
New Luxury Loft 24 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Beautiful open floor plan with great views

New Luxury Loft 24 I Hot Tub I Great Views I Best Price I FREE Adventures Daily

9.8 out of 10, Exceptional, (41)
"We had a great time at David’s place! We found it to be exactly as advertised. Clean and comfortable in a great location. We were able to walk to just about everything we wanted to do. We would definitely recommend and stay again!"
New Luxury Loft 24 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Four-story townhome with private hot tub, roof deck & big mountain views

Four-story townhome with private hot tub, roof deck & big mountain views

9.8 out of 10, Exceptional, (9)
"Great location, clean , modern"
Four-story townhome with private hot tub, roof deck & big mountain views
Stunning single standing home with Private Hot Tub & Byers Peak vistas
Living room - Gorgeous Atrium with beautiful and peaceful views located on the lower level

Stunning single standing home with Private Hot Tub & Byers Peak vistas

9.8 out of 10, Exceptional, (60)
"We stayed for our family vacation. Our teens and preteens had plenty of space to spread out and just relax. "
Stunning single standing home with Private Hot Tub & Byers Peak vistas
Luxury Winter Retreat in Winter Park: Steps to Main Street with Private Hot Tub
Our living room is the perfect place to relax and unwind. Cozy vibes only!

Luxury Winter Retreat in Winter Park: Steps to Main Street with Private Hot Tub

10.0 out of 10, Exceptional, (47)
"Great property! Good location!"
Luxury Winter Retreat in Winter Park: Steps to Main Street with Private Hot Tub
Luxury 4 BR Cabin: 2 King Suites on Shuttle Route
Winter Park Vacation Rental | 4BR | 3BA | 2,500 Sq Ft | Stairs Required

Luxury 4 BR Cabin: 2 King Suites on Shuttle Route

10.0 out of 10, Exceptional, (98)
"Great location, awesome property. The only issue was we didn’t allow ourselves a long enough Stay. look forward to visiting the area again and would consider this property again for a future visit "
Luxury 4 BR Cabin: 2 King Suites on Shuttle Route
Luxury, END UNIT townhome w/amazing views & privacy. High-end furnishings. Cozy.
Living area

Luxury, END UNIT townhome w/amazing views & privacy. High-end furnishings. Cozy.

10.0 out of 10, Exceptional, (8)
"Came up to stay for the weekend during the jazz festival, but just went horseback riding and had a quiet relaxing weekend. It was wonderful."
Luxury, END UNIT townhome w/amazing views & privacy. High-end furnishings. Cozy.
Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort
Living Room - Spacious, mountain modern design. All the comforts of home. Gas fireplace. Large windows for plenty of natural light.

Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort

9.6 out of 10, Exceptional, (45)
"Nice stay, nice location"
The price is SAR 1,502
SAR 4,204 total
includes taxes & fees
29 Jan - 30 Jan
Spacious Townhome with Private Hot Tub, minutes away from Winter Park 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.
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Other property types in Winter Park

Zephyr Mountain Lodge
Front of property - evening/night

Zephyr Mountain Lodge

3.5 star property
8.2 out of 10, Very Good, (645)
"We loved our stay there. The location could not be more convenient for skiing. "
The price is SAR 1,707
SAR 2,037 total
includes taxes & fees
10 Jan - 11 Jan
Zephyr Mountain Lodge
A Frame Club
Exterior

A Frame Club

3.5 star property
9.0 out of 10, Wonderful, (78)
"My husband and I stayed here for a night and it was a wonderful and quaint getaway from the hectic life. We have already recommended A-Frame Club to friends and family"
A Frame Club
Indian Peaks Resort
Exterior detail

Indian Peaks Resort

3.5 star property
9.2 out of 10, Wonderful, (117)
"Sin duda regresaré nos encanto Ami y a mi familia "
Indian Peaks 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.