
Family-friendly holiday rentals in Gypsum
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Top-rated family-friendly rentals in Gypsum
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Popular amenities for Gypsum family-friendly rentals
Family-friendly home rentals with a hot tub

Premier Location in Lionshead
This place was by far the best location in Vail we have ever stayed at and we have been coming for 20 years off and on. The view itself cannot be beat! The patio/ porch is amazing. You will have a view of the Bavarian inspired Village and feel like you hav been transported to Europe. Walk out the door and you are steps away from Skiing/ Gondola or Events like we were just at for the GoPro MountainGames. Parking at Lionshead Garage was convenient but not cheap. We will definitely be back!

Beautiful Log Home -4 Master Suites! Fishing! Ski!
Mark & Nancy were on top of everything before we got to the cabin. From vehicle recommendations to all of the info we needed to get in. The airbnb was stocked with everything we needed along with fun card and board games to keep everyone entertained. One couple on the trip even got engaged at the top of the hill right by the airbnb with the beautiful mountains in the background! 10/10 would recommend.

Cozy 1 bedroom Granby Ranch condo
My dog and I really enjoyed our stay at Scott’s! We were doing a long road trip so it was nice to have a comfortable and clean place to stay during our trip to recharge.

Modern Luxury - 4 Mins To Lifts - Jacuzzi - Sauna
Stylish, comfy and well-stocked with everything we needed. Easy drive into Aspen, making it an affordable alternative. Super responsive hosts. Recommend.

Fun & Cozy Cabin without the Woods
We loved our stay! It was a very unique place very close everything. I loved the story behind the house, and the book of the history of the cabin. Of course, my girls loved the hot tub, and were in it every night we were there. We would love to come back someday!

Ski-In/Out Beaver Creek Townhome!
We really enjoyed our stay at Reid's place. The home was comfortable and in a quiet neighborhood close to everything. We enjoyed the catwalk in and out for skiing. The hot tub was a nice feature and the kitchen cabinet was well stocked with basic spices/baking needs. We would absolutely go back next year if it wasn't already booked for the week we need.

Lakeside w/ Mtn Views, Access Ski & Sport NO PETS
Great place to stay to see a show at the amphitheater. The place was clean and has a great view of the lake and mountains. Plan on there again.

Hot Tub - Amazing Views - Family/Groups - Private
Absolutely amazing home. Just sitting on the back deck with the view of the mountain is worth everything. The home was clean host was great. Can't wait to stay again.
Family- and pet-friendly home rentals

Tranquil Log Cabin- ALL King Beds/10% off Summer!
Stayed here with 6 people total and everyone was very comfortable. Tara provided helpful instructions and was always responsive to any questions I had. The property requires a gate code and has very little traffic once off the main road. Kitchen was spacious and the loft bedroom upstairs was super cool. We got snowed on pretty good our first night so we were very glad to be able to use the fireplace at the home! The place was very clean and couldn’t have been happier with our stay.

Eagle Vail house on golf course- 4/4
Was perfect for our group. Will stay again.

Our Dream Ranch Guest Home
Jody went above and beyond to check in with us to make sure we had everything we needed, she took the time to demonstrate how her cooling system worked to keep us cool and comfortable. The bunkhouse had everything we needed for our stay.

Views of Golf & Ski On/Off Condo/ W&D/Hottub/Grill
Great place with easy access to the slopes!

Spring has arrived!
Lisa’s place was perfect for what I needed - a simple, peaceful accommodation to spend the night as I was passing through the area. Everything was exactly like the description and Lisa was proactive in communicating instructions prior to check in. The Murphy bed was comfortable, the kitchen was well-stocked, and even though the suite is attached to the main house, it felt very private. Would definitely stay there again!

The Cricket- An amazing Tiny House!
We thought this place was marvelous. Nature all around, but close to amenities and adventure. 6 deer in front yard. mountain bluejays . beds oh so comfy, shower great. I slept on the porch.. excellent use of space. really good lighting for reading. rushing Creek out kitchen window. glorious.

Magic Getaway in the Mountains, Fairplay, CO
Jonathan and Kelly’s place was a wonderful place to relax. Views were incredible and we had two moose come to visit! The stars at night were amazing, and the kitchen and grill provided everything needed to cook a great meal after a day of exploring. Lots of great hiking options nearby, and a superlative tub for soaking after that hike. Can’t recommend enough.

Dreamy Yurt “1 of 23 Best Glamping Spots in U.S”
The Yurt was so much fun. It is camping, or glamping I should say, so keep that in mind. But it did have everything we needed. It was a little cold at night, but Pam got us extra heating blankets to help. Pam was very responsive to our needs and she went out of our way to make sure we were comfortable and happy, which I really appreciated. The bathroom was shared with one other Yurt and the water was warm (not hot) but, remember, you are GLAMPING so that should be expected. The microwave and the wifi are in the "barn," which is a short walk away. I have AT&T and had no service in the Yurt. We loved our time there and will definitely consider coming back again. It is in such an amazing location and you do get away from all the crazy of city life.
Family-friendly home rentals with a pool

Peaceful riverside 2+bdrm Condo in EagleVail
the house was comfortable, the surroundings were nice, and the common hot tub after skiing was great. the house had some minor glitches, but the space is well used and the sleeping space is very nice. I'd say, ideal for a family of four or two couples with a kid. the beds are; two queens and two twins (a couch and a bed under the couch)

Perfect Summertime Pool Amenities 1 Bed Peak 7
My husband and I took a quick getaway to Breck after spending time in Denver. This is my third time staying in Breck. Out of all of the Airbnbs that I’ve stayed at in Breck, this has definitely been my favorite. The Airbnb was spacious, clean and had great amenities. My husband and I loved making use of the hot tub, pool, shuttle and pool table. It was off season so a bonus was that it was so quiet. Anyways, we miss it already. Definitely stay with Scott if you are looking for a Breck Airbnb.

Frisco One Bed One Bath Condo
Perfectly situated to Frisco area and surrounding towns. Easy under a mile walk to main strip of Frisco with shops, restaurants, outdoor beer garden and music, marina and Mountain View. My boyfriend and I walked home after night out on the town and felt very safe. Tara was very flexible and responsive - perfect for our stay - would stay again!

East Vail Condo steps from Hot Tub/Pool on Busline
Great stay in Vail! Such a well decorated and stocked condo on the bus line! One of the most proactive and responsive management teams as well!

The Perfect Mountain Getaway
This place was perfectly centralized to many Summit County activities. The condo was spacious, comfortable, well stocked, and very clean. The beds were comfy too. We really enjoyed our time here.

Vail Valley Condo:Pool/Hot Tub,Walk to Everyrthing
Perfect Ski Getaway – Amazing Location & Amenities! I had an incredible stay at this Airbnb! The location was absolutely perfect, just minutes away from the ski resort, making it super convenient to hit the slopes. The balcony was amazing, offering stunning views that made for the perfect spot to relax after a long day with a grill to make an amazing dinner after a long day. The place itself was spacious, well-equipped, and had all the amenities needed for a comfortable stay. Everything was clean, well-maintained, and thoughtfully set up to make guests feel right at home. Plenty of room for everyone, and the host was great with communication. Would definitely stay here again—highly recommend for anyone looking for the perfect ski retreat! ⛷️

Aspen Mountain Residences Saturday Studio
Great experience staying at this property . The room was great and the staff was first class and very accommodating. Will definitely look to book again

COZY CHALET CHIC' ON THE SLOPES
Great location. The apartment is actually smaller than I expected but it was well-arranged. It’s more like a studio than a one-bedroom as there’s only curtain separating the bedroom and the living room. Living room was spacious. The location beats everything. Hand soap was not provided, also bring your own grounded powder if you are a coffee person.
Quick stats about holiday rentals that are family-friendly in Gypsum
Total rentals
40 properties
Nightly prices starting at
$100 NZD before taxes and fees
Total number of reviews
440 reviews
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wi-Fi availability
40 properties include access to Wi-Fi
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- Breckenridge Ski Resort
- Beaver Creek Resort
- Aspen Mountain
- Snowmass Ski Resort
- Vail Ski Resort
- Rifle Falls State Park
- Buttermilk Ski Resort
- Sunlight Mountain Resort
- Glenwood Caverns Adventure Park
- Ski Cooper
- Beaver Creek Golf Club
- Breckenridge Nordic Center
- Maroon Creek Club
- Aspen Highlands Ski Resort
- Leadville Ski Country
- Mountain Top Children's Museum