Family-Friendly Vacation Rentals in Headwall, MT: Compare 10+ Sites & Save

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346 Best Family Vacation Rentals in Headwall (Starting from $125)

Whitefish Mountain Condo Balcony and Resort Access!
Whitefish Mountain Condo Balcony and Resort Access!
Apartment
Whitefish, MT, USA
0.5k from Headwall center

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

1 Bedroom4 Guests
7.0

Good

1 reviews

$1607
Average price / night
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Ski in-Ski out Morning Eagle 3-bedroom condo in Whitefish
Ski in-Ski out Morning Eagle 3-bedroom condo in Whitefish
Condo
Whitefish, MT, 59937, United States
0.1k from Headwall center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms8 Guests
9.0

Fabulous

6 reviews

$585
Average price / night
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Morning Eagle 207
Morning Eagle 207
House
Whitefish, MT, USA
0.5k from Headwall center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
8.3

Very Good

10 reviews

$125
Average price / night
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Comfortable Condo in Whitefish Mountain Resort Village
Comfortable Condo in Whitefish Mountain Resort Village
Condo
Whitefish, MT, 59937, United States
0.3k from Headwall center

Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$379
Average price / night
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Morning Eagle 209
Morning Eagle 209
House
Whitefish, MT, USA
0.5k from Headwall center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Ski resorts

1 Bedroom4 Guests
7.0

Good

2 reviews

$125
Average price / night
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The Trailblazer - Luxe Ski-In/Ski-Out townhome on Whitefish Mountain
The Trailblazer - Luxe Ski-In/Ski-Out townhome on Whitefish Mountain
House
Whitefish, MT, 59937, United States
0.4k from Headwall center

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

5 Bedrooms12 Guests
10.0

Exceptional

10 reviews

$612
Average price / night
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Morning Eagle 304
Morning Eagle 304
House
Whitefish, MT, USA
0.5k from Headwall center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Ski resorts

1 Bedroom6 Guests
7.0

Good

1 reviews

$331
Average price / night
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Spacious Condo with Mountain Views
Spacious Condo with Mountain Views
Condo
Whitefish, MT, 59937, United States
0.4k from Headwall center

Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
9.4

Superb

9 reviews

$300
Average price / night
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Whitefish Mountain Ski-InandOut Condo with Views!
Whitefish Mountain Ski-InandOut Condo with Views!
Apartment
Whitefish, MT, USA
0.5k from Headwall center

Apartments, Cheap, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
7.5

Good

2 reviews

$739
Average price / night
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Comfortable Condo Near Slopes
Comfortable Condo Near Slopes
Condo
Whitefish, MT, 59937, United States
0.4k from Headwall center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

2 Bedrooms6 Guests
New to Booking
$287
Average price / night
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Ski-InandSki-Out Whitefish Escape with Balcony!
Ski-InandSki-Out Whitefish Escape with Balcony!
Apartment
Whitefish, MT, USA
0.5k from Headwall center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay, Family

2 Bedrooms5 Guests
9.2

Superb

4 reviews

$647
Average price / night
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Cozy Studio Near Slopes
Cozy Studio Near Slopes
Apartment
Whitefish, MT, 59937, United States
0.4k from Headwall center

Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$278
Average price / night
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Slopeside 103
Slopeside 103
House
Whitefish, MT, USA
0.6k from Headwall center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Ski resorts

1 Bedroom12 Guests
8.0

Good

1 reviews

$347
Average price / night
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Nicely Furnished Condo with Valley Views
Nicely Furnished Condo with Valley Views
Condo
Whitefish, MT, 59937, United States
0.4k from Headwall center

Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
9.4

Superb

6 reviews

$398
Average price / night
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Slopeside 117
Slopeside 117
House
Whitefish, MT, USA
0.6k from Headwall center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Ski resorts

1 Bedroom10 Guests
New to Booking
$356
Average price / night
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Charming Condo with Mountain Rustic Decor
Charming Condo with Mountain Rustic Decor
Condo
Whitefish, MT, 59937, United States
0.4k from Headwall center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$375
Average price / night
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Slopeside 129
Slopeside 129
House
Whitefish, MT, USA
0.6k from Headwall center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Ski resorts

1 Bedroom9 Guests
New to Booking
$365
Average price / night
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Mountain Rustic Condo with Valley Views
Mountain Rustic Condo with Valley Views
Condo
Whitefish, MT, 59937, United States
0.4k from Headwall center

Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$295
Average price / night
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Alpine Glow Ski Haus
Alpine Glow Ski Haus
House
Whitefish, MT, USA
0.6k from Headwall center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Ski resorts

1 Bedroom14 Guests
New to Booking
$726
Average price / night
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Slopeside 111
Slopeside 111
House
Whitefish, MT, USA
0.6k from Headwall center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom12 Guests
9.5

Superb

2 reviews

$357
Average price / night
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Cozy Condo Near Lifts
Cozy Condo Near Lifts
Condo
Whitefish, MT, 59937, United States
0.4k from Headwall center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

2 Bedrooms6 Guests
New to Booking
$396
Average price / night
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Black Diamond #1B
Black Diamond #1B
Apartment
Vista, MT, USA
0.6k from Headwall center

Apartments, Accommodations, Pet-friendly, Lodgings, Hot tubs, Places to stay, Accessible hotels

3 Bedrooms8 Guests
8.0

Good

5 reviews

$582
Average price / night
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Updated Condo Just a Short Walk to the Slopes
Updated Condo Just a Short Walk to the Slopes
Condo
Whitefish, MT, 59937, United States
0.4k from Headwall center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$289
Average price / night
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Spacious 3 bedroom condo with incredible ski access / hot tub / gym / underground parking
Spacious 3 bedroom condo with incredible ski access / hot tub / gym / underground parking
Condo
Whitefish, MT, 59937, United States
0.5k from Headwall center

AC, Balcony, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$328
Average price / night
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Ski In/Ski Out, Pool Table + Hot Tub & VIEWS!
Ski In/Ski Out, Pool Table + Hot Tub & VIEWS!
House
Whitefish, MT, 59937, United States
0.5k from Headwall center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms19 Guests
10.0

Exceptional

6 reviews

$2101
Average price / night
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Mid-Mountain Ski In/Ski Out with Game Room + Hot Tub + Pet Friendly
Mid-Mountain Ski In/Ski Out with Game Room + Hot Tub + Pet Friendly
House
Whitefish, MT, 59937, United States
0.5k from Headwall center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

6 Bedrooms22 Guests
9.6

Exceptional

19 reviews

$1865
Average price / night
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Slope Side Condo with Plenty of Room
Slope Side Condo with Plenty of Room
Condo
Whitefish, MT, 59937, United States
0.5k from Headwall center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms9 Guests
9.8

Exceptional

6 reviews

$418
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 Headwall.

Headwall Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 346 verified family-friendly vacation rentals in Headwall. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Headwall vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $125 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Headwall 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 Headwall 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 Headwall often include amenities such as Fireplace/Heating, Child Friendly, and Wellness Facilities. 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.