Photo by Winter Park Resort

Winter Park holiday rentals

We found 2,166 holiday rentals — enter your dates for availability
Select from 341 houses, 479 flats and other holiday rentals to find the perfect place for your stay in Winter Park. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Winter Park

Showing deals for:22 Jan - 29 Jan

Interior
Outdoor dining
Interior
Living area
Exceptional
(185 reviews)

Beautiful Mountain Lodge-Ski,Hike,Bike,Relax-We Are Close to it All!

Tabernash

8% off
S$5,499
for 7 nights, 1 home
S$786 per night
includes taxes & fees
Beautiful Mountain Lodge-Ski,Hike,Bike,Relax-We Are Close to it All!
Plenty of natural light shines on the main level.
Private kitchen
Upstairs loft has the best views in the whole home.
Dining
Exceptional
(117 reviews)

Top of the Mountain Log Home with BREATHTAKING VIEWS near Winter Park, Granby

Tabernash

6% off
S$5,077
for 7 nights, 1 home
S$725 per night
includes taxes & fees
Top of the Mountain Log Home with BREATHTAKING VIEWS near Winter Park, Granby
Dining table adjacent to gas fireplace with 10-mile mountain views
Upper Living Room (access to private deck, 10-mile view, and 55' flat screen TV)
Kitchen island, bartop and breakfast area provides comfortable seating for 16
Wood hickory cabinets, double oven, large single basin stainless steel sink
Exceptional
(83 reviews)

Keystone Large Family Home - Amazing Views, Rustic Charm - Hot Tub, Game Room

Dillon

8% off
S$12,417
for 7 nights, 1 home
S$1,774 per night
includes taxes & fees
Keystone Large Family Home - Amazing Views, Rustic Charm - Hot Tub, Game Room
Great Room dining area, stairs to loft
Living area
Gourmet Kitchen with island bar
Outdoor dining
Exceptional
(165 reviews)

Snow Dream Family Retreat: Hot Tub, Game Room, Stocked Kitchen, Sparkling Clean!

Winter Park

6% off
S$6,820
for 7 nights, 1 home
S$974 per night
includes taxes & fees
Snow Dream Family Retreat: Hot Tub, Game Room, Stocked Kitchen, Sparkling Clean!
View from Living Room window
Over-sized kitchen island for easy meal prep and serving
Spacious Main floor living space w/ fireplace and 60" TV
Welcome to your mountain getaway!
Exceptional
(240 reviews)

5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle

Winter Park

8% off
S$7,034
for 7 nights, 1 home
S$1,005 per night
includes taxes & fees
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
Living area
Private kitchen
Dining
Interior
Exceptional
(17 reviews)

Cozy mountain escape in Empire

Empire

7% off
S$2,594
for 7 nights, 1 home
S$371 per night
includes taxes & fees
Cozy mountain escape in Empire
Exterior detail
Private kitchen
Pool
Fitness facility
Exceptional
(46 reviews)

Dog-friendly condo close to Winter Park shuttle with pool, hot tub, tennis, gym

Fraser

8% off
S$2,479
for 7 nights, 1 apartment
S$354 per night
includes taxes & fees
Dog-friendly condo close to Winter Park shuttle with pool, hot tub, tennis, gym
Bedroom 3
Terrace/patio
Private kitchen
Interior
Excellent
(66 reviews)

Spectacular 11BR Mountain Home for Large Groups

Fraser

12% off
S$9,768
for 7 nights, 1 home
S$1,395 per night
includes taxes & fees
Spectacular 11BR Mountain Home for Large Groups
Bar (on property)
Exterior
Interior
Interior
Wonderful
(22 reviews)

Large Upscale Retreat off Vasquez Rd. Sleeps 14

Winter Park

11% off
S$8,596
for 7 nights, 1 cabin
S$1,228 per night
includes taxes & fees
Large Upscale Retreat off Vasquez Rd. Sleeps 14
8 Person Jacuzzi on main floor deck
Vasquez Creek
Kitchen on Main Floor
Dining Room on Main Floor
Exceptional
(51 reviews)

Perfect Vacation Home for Every Season in Downtown Winter Park

Winter Park

7% off
S$7,736
for 7 nights, 1 home
S$1,105 per night
includes taxes & fees
Perfect Vacation Home for Every Season in Downtown Winter Park
Private kitchen
Living area
Property grounds
Living area
Wonderful
(7 reviews)

Cozy Mountain Cabin

Idaho Springs

8% off
S$1,783
for 7 nights, 1 cabin
S$255 per night
includes taxes & fees
Cozy Mountain Cabin
Welcome to Our Cozy Mountain Cabin!
The cabin looks magical with a little snow at twilight!
View towards the kitchen
En-suite bathroom
Exceptional
(141 reviews)

Charming Log Cabin for Peaceful Mountain Getaway!

Black Hawk

7% off
S$2,317
for 7 nights, 1 cabin
S$331 per night
includes taxes & fees
Charming Log Cabin for Peaceful Mountain Getaway!
Private kitchen
Terrace/patio
Exterior
Room
Exceptional
(36 reviews)

Beautiful view 2 miles above sea level

Idaho Springs

8% off
S$1,995
for 7 nights, 1 home
S$285 per night
includes taxes & fees
Beautiful view 2 miles above sea level
Miscellaneous
Private kitchen
Room
Dining
Exceptional
(6 reviews)

Hygge Haus - 2BD Lake View & Pet Friendly Retreat

Dillon

6% off
S$6,282
for 7 nights, 1 apartment
S$897 per night
includes taxes & fees
Hygge Haus - 2BD Lake View & Pet Friendly Retreat
4 hot tubs accessible to guests of Zephyr!
Snow and ski sports
Property grounds
Living area
Exceptional
(49 reviews)

FRONT ROW LUX Premium View - Gondola - SLOPESIDE BLDG Ski-In Ski-Out Updated 2BR

Winter Park

8% off
S$9,390
for 7 nights, 1 apartment
S$1,341 per night
includes taxes & fees
FRONT ROW LUX Premium View - Gondola - SLOPESIDE BLDG Ski-In Ski-Out Updated 2BR
Interior
Kitchen into Living Spaces
Deck
Open Floor Plan Living, Dining, Kitchen
Exceptional
(28 reviews)

Penthouse Cozy Condo in the heart of Downtown Winter Park

Winter Park

8% off
S$4,735
for 7 nights, 1 apartment
S$676 per night
includes taxes & fees
Penthouse Cozy Condo in the heart of Downtown Winter Park
Interior
Room
Interior
Property grounds
Exceptional
(15 reviews)

Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4

Winter Park

8% off
S$4,327
for 7 nights, 1 apartment
S$618 per night
includes taxes & fees
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Pool and hot tub at the clubhouse
Property grounds
Clubhouse
Dining and kitchen
Exceptional
(82 reviews)

Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!

Winter Park

8% off
S$3,925
for 7 nights, 1 apartment
S$561 per night
includes taxes & fees
Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
The view of Vasquez Territory at Winter Park from just out the front door.
Living area
Interior
Private kitchen
Exceptional
(83 reviews)

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

Winter Park

7% off
S$3,776
for 7 nights, 1 home
S$539 per night
includes taxes & fees
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Fully appointed kitchen with all you will need to prepare meals and eat in.
Interior
Outdoor spa tub
Interior
Exceptional
(21 reviews)

Heart of Downtown - Private Hot Tub, Heated Garage, Fireplace & Washer/Dryer

Winter Park

8% off
S$2,710
for 7 nights, 1 apartment
S$387 per night
includes taxes & fees
Heart of Downtown - Private Hot Tub, Heated Garage, Fireplace & Washer/Dryer
1 of 4 hot tubs in Slopeside and Riverside buildings
ZML
Living room with queen sleeper sofa and views.
Bedroom with king size bed and views of the mountains.
Exceptional
(30 reviews)

Zephyr Mountain Lodge - Beautifully Renovated

Winter Park

8% off
S$4,685
for 7 nights, 1 apartment
S$669 per night
includes taxes & fees
Zephyr Mountain Lodge - Beautifully Renovated
Beautiful fall leaves from the balcony
Lounge area with large screen TV, pool table, kids area, business center
Well stocked kitchen with everything you need
Indoor pool at clubhouse, plus two indoor hot tubs
Exceptional
(50 reviews)

Cozy and convenient family condo in heart of downtown Winter Park

Winter Park

8% off
S$2,922
for 7 nights, 1 apartment
S$417 per night
includes taxes & fees
Cozy and convenient family condo in heart of downtown Winter Park
Overall view from entry
Keystone Lake in the Summer
Comfy Pottery Barn sofa and chair, sofa features a queen sleeper
Upgraded kitchen cabinetry and granite counters with designer pendant lighting
Exceptional
(25 reviews)

Luxury Condo, Hot Tub, Balcony, Shuttle to Ski Slopes

Keystone

8% off
S$4,579
for 7 nights, 1 apartment
S$654 per night
includes taxes & fees
Luxury Condo, Hot Tub, Balcony, Shuttle to Ski Slopes
Interior
Kitchen with stools for additional seating, new appliances, and a large pantry
View of dining, kitchen, and living room area.
Exceptional
(100 reviews)

Slopeside Paradise--3 BR, 2.5 Bath 2 Minutes from the Slopes!

Winter Park

8% off
S$7,149
for 7 nights, 1 home
S$1,021 per night
includes taxes & fees
Slopeside Paradise--3 BR, 2.5 Bath 2 Minutes from the Slopes!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The cosy city of Winter Park awaits you

Enjoy the live music and other features of Winter Park. Renowned for its skiing, mountain views and snowboarding, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Winter Park

Do you want to find attractions to see during your stay? Travellers enjoy Winter Park for its skiing, snowboarding and hiking. Venture out of your cosy holiday rental and experience everything that makes Winter Park a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Winter Park Ski Resort (3.7 mi / 5.9 km)
  • Keystone Ski Resort (25.5 mi / 41.1 km)
  • Trestle Bike Park (2.5 mi / 4.1 km)
  • Pole Creek Golf Club (7.7 mi / 12.3 km)
  • Ski Granby Ranch (10.3 mi / 16.6 km)
  • Eldora Mountain Resort (10.7 mi / 17.3 km)

Exploring the mountains and other natural features in Winter Park

Whether you're an adventurous traveller or just want to appreciate the scenery, Winter Park is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Rocky Mountain National Park (29.7 mi / 47.9 km)
  • Saint Mary's Glacier (9.2 mi / 14.8 km)
  • Georgetown Lake (14.1 mi / 22.7 km)
  • Torreys Peak (16 mi / 25.8 km)
  • Lake Granby (16.4 mi / 26.3 km)
  • Loveland Pass (18.4 mi / 29.6 km)

Seasonal weather averages in Winter Park

Winter Park is well known for its skiing. If you're interested in winter sports, you might consider visiting in January, February, March or April, when snowfall averages 67 cm and temperatures average -8°C.

Travelling to and around Winter Park

The nearest airport is in Broomfield, CO (BJC-Rocky Mountain Metropolitan), located 35.7 mi (57.4 km) from the city centre.

If you'd prefer to travel by train, the main station is Winter Park Ski Resort Amtrak Station.

Frequently asked questions

What is the best area to stay in Winter Park when booking a holiday rental?
Old Town Winter Park is one of the more sought-after locations for a holiday property in Winter Park. Spend your stay here to savour the comfort and privacy that comes with having the entire place to yourself.
What is the most popular type of holiday rental accommodation in Winter Park?
The most desirable types of holiday rentals in Winter Park are condos. Prefer something different? Vrbo has numerous options to match our guests' unique requirements, so you'll see holiday homes in loads of sizes and shapes. The perfect fit is waiting for you — book yours today.
How much does it cost to rent a holiday rental in Winter Park?
Different factors affect the price of a holiday rental in Winter Park, such as the time of year, length of stay and property type. However, all our holiday homes have something in common — exceptional value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Winter Park?
When you travel and the style and size of the property will determine the cost of your beachside escape. Put in your Winter Park travel dates to see your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday rentals in Winter Park?
Pack a travel bag and a bone for the pup in your life because Winter Park has 598 stays that open their doors to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Winter Park?
Tick the "pool" box in our handy filter tool and select from 255 houses with private pools in Winter Park on Vrbo. Ball games, gentle soak or noodle joust? Free time is up to you when your Vrbo holiday home comes with a swimming pool.
What are popular rental amenities in Winter Park?
Some of the most popular rental amenities guests are looking for in Winter Park are tennis, a chef and a lake view. Whether you're travelling with family, buddies or even pets, Vrbo holiday properties feature the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday rentals in Winter Park?
Winter Park has 101 holiday properties that can fit 10 or more people. These properties come with the space and privacy you need to share good times with your nearest and dearest.
Are there holiday rentals in Winter Park that welcome kids?
With 598 family-friendly holiday rentals available in Winter Park, now is a fantastic time to introduce your children to the pleasures of travel. Simply check our "Properties good for families" filter box to view stays packed with amenities perfect for families on the move, such as multiple bedrooms, yards, bunk beds and entertainment areas.
What are the top attractions for families in Winter Park?
There are plenty of amazing things to see and do with the family in Winter Park, including:
  • Amazen Maze Winter Park
  • Moffat Tunnel West Portal
  • Trestle Bike Park
Are there one-bedroom holiday rentals in Winter Park?
You'll find 106 one-bedroom properties in Winter Park to choose from. A one-bedroom holiday home is a wonderful choice if it's just you and your partner or if you're holidaying alone. Toss in more convenience, space and privacy compared to a hotel, and you're bound to have a memorable trip.
Can I find two-bedroom holiday rentals in Winter Park?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 221 two-bedroom holiday properties Winter Park has to offer.
Are there holiday rentals with WiFi in Winter Park?
Whether you want to keep up with the headlines, reply to emails or surf your social networks, there are 157 holiday homes with WiFi in Winter Park. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Winter Park?
You can pick from 27 Vrbo holiday homes with air conditioning in Winter Park giving you that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then use our filter tool to search for stays with air conditioning.
How old do you have to be to rent a holiday rental in Winter Park?
We recommend checking with the Winter Park holiday rental you'd like on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Winter Park for?
How long you can rent a holiday rental in Winter Park is down to the property. Simply enter your chosen travel dates to look at a list of options offering extended stays. With loads of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Winter Park.

More holiday ideas