Family-Friendly Vacation Rentals in Pioneer Express Ski Lift, CO: Compare 10+ Sites & Save

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1273 Best Family Vacation Rentals in Pioneer Express Ski Lift (Starting from $140)

Viking Alpine Haven
Viking Alpine Haven
Apartment
Winter Park, CO, USA
2.3k from Pioneer Express Ski Lift center

Apartments, Accommodations, Lodgings, Places to stay, Family, Ski resorts

3 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$313
Average price / night
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Beautiful Ski-In Home, with Hot Tub!
Beautiful Ski-In Home, with Hot Tub!
House
Winter Park, CO, 80482, United States
2.2k from Pioneer Express Ski Lift center

Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms18 Guests
9.6

Exceptional

14 reviews

$954
Average price / night
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Trailside Mountain Retreat with Private Hot Tub
Trailside Mountain Retreat with Private Hot Tub
House
Winter Park, CO, USA
2.3k from Pioneer Express Ski Lift center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay, Family

4 Bedrooms9 Guests
New to Booking
$450
Average price / night
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Borders Nat'l Forest at a Trailhead.  3.3 Miles to Winter Park Resort. Sleeps 12
Borders Nat'l Forest at a Trailhead. 3.3 Miles to Winter Park Resort. Sleeps 12
House
Winter Park, CO, 80482, United States
2.3k from Pioneer Express Ski Lift center

Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
9.8

Exceptional

110 reviews

$459
Average price / night
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Winter Park Cozy Condo
Winter Park Cozy Condo
Apartment
Winter Park, CO, USA
2.3k from Pioneer Express Ski Lift center

Apartments, Accommodations, Lodgings, Places to stay, Ski resorts, Condos

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$140
Average price / night
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Hot Tub | Mountain Views | Steps to Trails
Hot Tub | Mountain Views | Steps to Trails
Apartment
Winter Park, CO, 80482, United States
2.4k from Pioneer Express Ski Lift center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
New to Booking
$546
Average price / night
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Hideaway Village Columbine 7
Hideaway Village Columbine 7
Apartment
Winter Park, CO, USA
2.5k from Pioneer Express Ski Lift center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$169
Average price / night
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Downtown WP Timber Top Home I Hot Tub I Great Views I Game Room I Discounted Attractions
Downtown WP Timber Top Home I Hot Tub I Great Views I Game Room I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.4k from Pioneer Express Ski Lift center

Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms14 Guests
9.8

Exceptional

36 reviews

$1219
Average price / night
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Winter Park Ski Haus
Winter Park Ski Haus
House
Winter Park, CO, USA
2.5k from Pioneer Express Ski Lift center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom19 Guests
New to Booking
$690
Average price / night
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Winter Park Mountain Townhome
Winter Park Mountain Townhome
House
Winter Park, CO, 80482, United States
2.5k from Pioneer Express Ski Lift center

Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$420
Average price / night
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Luxury 4 BR Cabin 2 King Suites on Shuttle Route
Luxury 4 BR Cabin 2 King Suites on Shuttle Route
House
Winter Park, CO, USA
2.5k from Pioneer Express Ski Lift center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$530
Average price / night
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Immaculate Winter Park Home Hot Tub and Views!
Immaculate Winter Park Home Hot Tub and Views!
House
Pioneer Express Ski Lift, Winter Park, Colorado, USA
2.5k from Pioneer Express Ski Lift center

Hot Tub, Wheelchair Accessible, Internet, Parking, Child Friendly

4 Bedrooms12 Guests
New to Booking
$517
Average price / night
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New creek side chateau guest suite!  Booking for Ski Season NOW! With hot tub!
New creek side chateau guest suite! Booking for Ski Season NOW! With hot tub!
House
Winter Park, CO, 80482, United States
2.5k from Pioneer Express Ski Lift center

Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
10.0

Exceptional

56 reviews

$485
Average price / night
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Mountain View Retreat, Walk to Winter Park Gondola
Mountain View Retreat, Walk to Winter Park Gondola
House
Winter Park, CO, USA
2.5k from Pioneer Express Ski Lift center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$437
Average price / night
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3 Mi to Winter Park Resort: Cozy Ski Condo
3 Mi to Winter Park Resort: Cozy Ski Condo
Condo
Winter Park, CO, 80482, United States
2.5k from Pioneer Express Ski Lift center

Dryer, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, Patio

2 Bedrooms6 Guests
9.8

Exceptional

21 reviews

$167
Average price / night
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Cozy Mtn Hideaway, 4 Mi to Winter Park Resort!
Cozy Mtn Hideaway, 4 Mi to Winter Park Resort!
House
Pioneer Express Ski Lift, Winter Park, Colorado, USA
2.5k from Pioneer Express Ski Lift center

Internet, Wheelchair Accessible, Parking, Child Friendly

1 Bedroom4 Guests
New to Booking
$146
Average price / night
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Slopeside Chalet 106 I Hot Tub I Great Views I Bunk Room I Discounted Attractions
Slopeside Chalet 106 I Hot Tub I Great Views I Bunk Room I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.6k from Pioneer Express Ski Lift center

Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$459
Average price / night
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Cozy-Chic Condo with Mtn Views 3 Mi to Slopes!
Cozy-Chic Condo with Mtn Views 3 Mi to Slopes!
Apartment
Winter Park, CO, USA
2.5k from Pioneer Express Ski Lift center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Ski resorts, Condos

2 Bedrooms8 Guests
New to Booking
$147
Average price / night
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Fantastic Creekside Condo in the town of Winter Park
Fantastic Creekside Condo in the town of Winter Park
Condo
winter park, CO, 80482, United States
2.6k from Pioneer Express Ski Lift center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

50 reviews

$309
Average price / night
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Slopeside 204 Kinney Townhouse
Slopeside 204 Kinney Townhouse
House
Pioneer Express Ski Lift, Winter Park, Colorado, USA
2.6k from Pioneer Express Ski Lift center

Kitchen, Breakfast, Hot Tub, Internet, Parking, Child Friendly

3 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$342
Average price / night
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Slopeside Chalet 97A I Hot Tub I Great Views I Bunk Room I Discounted Attractions
Slopeside Chalet 97A I Hot Tub I Great Views I Bunk Room I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.6k from Pioneer Express Ski Lift center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Extra Bed, Fireplace, Free Parking

2 Bedrooms8 Guests
10.0

Exceptional

29 reviews

$343
Average price / night
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Slopeside Chalet 113D I Hot Tub I Great Views I Bunk Room I Discounted Attractions
Slopeside Chalet 113D I Hot Tub I Great Views I Bunk Room I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.6k from Pioneer Express Ski Lift center

Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms8 Guests
9.8

Exceptional

22 reviews

$385
Average price / night
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Slopeside Villa 125 I Private Hot Tub I Ski Views I Arcade I Discounted Attractions
Slopeside Villa 125 I Private Hot Tub I Ski Views I Arcade I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.7k from Pioneer Express Ski Lift center

Arcade, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Free Parking, Heater

3 Bedrooms8 Guests
6.0

Review score

3 reviews

$471
Average price / night
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Winter Park condo minutes from everything
Winter Park condo minutes from everything
Condo
Winter Park, CO, 80482, United States
2.7k from Pioneer Express Ski Lift center

Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$273
Average price / night
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Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Game Room I Discounted Attractions
Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Game Room I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.7k from Pioneer Express Ski Lift center

Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms14 Guests
9.6

Exceptional

5 reviews

$1110
Average price / night
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Downtown WP Villa 835 I Private Hot Tub I Great Views I Discounted Attractions
Downtown WP Villa 835 I Private Hot Tub I Great Views I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.7k from Pioneer Express Ski Lift center

Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$620
Average price / night
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Downtown WP Villa 745 I Private Hot Tub I Great Views I Discounted Attractions
Downtown WP Villa 745 I Private Hot Tub I Great Views I Discounted Attractions
House
Winter Park, CO, 80482, United States
2.7k from Pioneer Express Ski Lift center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$531
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Pioneer Express Ski Lift.

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Frequently Asked Questions

You can explore 1273 verified family-friendly vacation rentals in Pioneer Express Ski Lift. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Pioneer Express Ski Lift vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $140 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Pioneer Express Ski Lift offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Pioneer Express Ski Lift are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Pioneer Express Ski Lift often include amenities such as Child Friendly, Fireplace/Heating, and Laundry. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.