Family-friendly vacation rentals in Gypsum

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Gypsum family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A spacious living area features a high ceiling with large windows, allowing natural light to illuminate the space. A comfortable sofa faces a stone fireplace and a mounted television. Cozy seating options include two armchairs. A wooden coffee table is centered in the room, complemented by a dining table nearby.
Townhouse in Keystone
4.85 out of 5 average rating, 190 reviews

2 BR, 2 BA Mountain View Family Friendly BCA-45499

CoryRating, 5 stars1 month ago
It was a great stay with almost everything we could want from the condo. We had a family of 5 and slept comfortably in the condo and within close proximity to the mountain of Keystone. Overall good stay
Guest favorite
Cabin in Fairplay
4.98 out of 5 average rating, 193 reviews

Beautiful Log Home -4 Master Suites! Fishing! Ski!

JasmineRating, 5 stars2 months ago
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.
Guest favorite
Home in Fraser
4.89 out of 5 average rating, 133 reviews

Big Views, Big House, Hot Tub, Close to town

SamanthaRating, 5 stars1 week ago
I can’t say enough good things about this home. 10/10 recommend! Very easy check in and clear instructions, accommodating of early checkin if available! The home came stocked with everything you can think of and even the things you didn’t think of. The home was open and spacious, my favorite part was the large table that sat the whole family of 11 for a nice meal together. Conveniently located near outdoor activities, a grocery store, coffee shop and a quick bite. As if that wasn’t enough, we were offered a discount on a future stay that we will definitely be taking advantage of! Thank you so much for sharing your home with us!
Guest favorite
The exterior of a two-story red chalet is surrounded by tall pine trees and natural landscaping. A spacious deck with railings extends from the side of the house, providing outdoor access. The home features varied rooflines and large windows allowing for natural light.
Home in Breckenridge
4.92 out of 5 average rating, 101 reviews

Slalom Chalet - Luxury Mountain Home

DominicRating, 5 stars1 month ago
Really enjoy our stay in Breckenridge and at this home. Had everything we needed and Adam was super responsive. Enjoyed the hot tub and views.
Guest favorite
A spacious living area features a red seating arrangement with a comfortable sofa and armchair, complemented by light streaming through multiple windows. A kitchen island with a sink is visible, alongside a dining area that includes four chairs. A stone fireplace adds a touch of warmth to the space.
Condo in Granby
4.85 out of 5 average rating, 405 reviews

Cozy 1 bedroom Granby Ranch condo

AlexandraRating, 5 stars1 month ago
Great spot, as described, very comfortable and peaceful, and has everything you need for a getaway including a well stocked kitchen! Also appreciated the bonus snacks left by previous folks. :) Hot springs were close enough that I didn't end up using the hot tub but if staying longer, that would have a been a great perk. (Cleaning up, vacuuming, and washing + drying the laundry is requested so just make sure you can budget that time in the morning.) Would definitely recommend Scott's place!
Guest favorite
A spacious living area features large windows that allow natural light to fill the room. A flat-screen TV is mounted above a wooden mantle, with a cozy fireplace below. Comfortable seating options include a sectional sofa and a lounge chair, complemented by a wooden coffee table.
Condo in Keystone
4.91 out of 5 average rating, 188 reviews

Bright, spacious, extra clean condo in Keystone!

CorrinneRating, 5 stars1 month ago
We loved our stay at Mary and Alan's condo. The property was so beautiful and had lovely pathways and trees. The community pool and hot tub was so pristine and so close we enjoyed a hot soak after skiing. The condo was so bright and spacious we loved the space. Had many lovely nights in the large living room with the fire. We would love to come back and stay here hopefully next year!! Thanks again Mary and Alan!
Superhost
A welcoming entryway is illustrated, featuring a tiled floor and practical matting for outdoor gear. Wall hooks are available for coats and bags, while large windows provide natural light and a view of the outdoors.
Home in Crested Butte
4.88 out of 5 average rating, 155 reviews

Mountain House with Mt. Crested Butte views!

ScottRating, 5 stars1 month ago
We had a great time with our kids and grandkids. The beds were very comfortable and the house is warm and toasty. The kitchen is well stocked and Maria is just a text away if you need anything. If there is one thing that could be improved it would be the cleanliness of the water in the hot tub. While we were there the maintenance person came by to maintain it but the water is very cloudy and needed to be changed. I don't like making negative public comments but that is what we experienced yet we still had a great time at her place.
Top guest favorite
Townhouse in Granby
4.94 out of 5 average rating, 115 reviews

Beautiful Townhome in Granby Ranch

CarolineRating, 5 stars1 month ago
We had a very positive experience. Our host was very responsive at booking, before arrival, and once we were in the home. They had a notebook full of instructions by room which made everything work as it should.

Family- and pet-friendly home rentals

Superhost
A private deck features a patio table with an umbrella, surrounded by chairs. Lush greenery and flowers are visible in the background, with a fence providing privacy. A grill is positioned nearby, creating an inviting outdoor space for dining and relaxation.
Home in Glenwood Springs
4.84 out of 5 average rating, 323 reviews

Down town Glenwood Springs Cottage.

AliseRating, 5 stars1 month ago
We loved this place so much... It was very cute & clean and had everything you could possibly need. It was the perfect location for walking to town.
Guest favorite
A modern kitchen is showcased with natural wood cabinetry and granite countertops. Stainless steel appliances are prominently featured, along with a dining table surrounded by four chairs. Soft lighting creates a warm atmosphere, enhancing the functionality of the space.
Condo in Dillon
4.88 out of 5 average rating, 141 reviews

2 Bed 2 Bath Family Ski Condo (Pet Friendly!)

JimRating, 5 stars1 week ago
Such a great location between Silverthorn and A Basin… so easy to get to the mountain, without breaking the bank. Highly recommend!
Top guest favorite
A clean and functional bathroom is equipped with a light-colored vanity featuring wooden cabinetry and a spacious countertop. A large mirror reflects the bright lighting above, while decorative framed photos line the walls. Soft blue rugs are positioned on the tiled floor, adding a touch of color.
Home in Breckenridge
4.92 out of 5 average rating, 218 reviews

3 BR / 2 Bath, Everything Close, Beautiful Views!

KatelynRating, 5 stars1 month ago
The pictures don't do this place justice! The home is wonderful, sturdy, and full of high quality furniture throughout. The couch and beds were very nice! We were more than comfortable with 5 people and a dog here; there was plenty of space and seating. The kitchen was well equipped, the bathrooms were well-supplied, and the backyard (even covered in snow) was a real treat. Great space for a dog, and in warmer weather it would be a great space to hangout. The location was quiet and peaceful, and with the proximity to the bus stop it was very easy to get anywhere in town without driving. Mike was a wonderful host; always responsive, always friendly, and his welcome packet has tons of local suggestions for things to do/places to go!
Guest favorite
An inviting bathroom features tiled walls and a modern shower enclosed by a patterned curtain. A toilet and shelving with neatly arranged towels are visible in the background, creating a functional and organized space.
Home in Eagle Vail
4.88 out of 5 average rating, 104 reviews

Eagle Vail house on golf course- 4/4

MonicaRating, 5 stars1 month ago
Was perfect for our group. Will stay again.
Guest favorite
A firepit is surrounded by a brick circle, offering a view of expansive green fields and distant mountains bathed in soft sunset light. Tree lines and gentle hills add to the serene landscape, creating an inviting outdoor space for relaxation.
Farm stay in Parachute
4.93 out of 5 average rating, 180 reviews

Our Dream Ranch Guest Home

KathieRating, 5 stars1 month ago
This was such a lovely place to stay. Jody is very kind which made it easy to communicate with her. She was very responsive to my messages. We felt at home while we were there. We were able to easily cook our own meals. The house was stocked with basic things like kitchenware, spices, and such. Everything we needed in the kitchen was there. The beds were very comfortable and inviting. Jody has put a lot of time and thought into the decorating of the house. We very much enjoyed the artwork on the walls. I can not began to share how lovely the views were outside the windows. The electric fireplace was very cozy on the snowy days. My family outside of Colorado is wanting to stay here again when they visit later on. I'd definitely stay here again! Thank you for providing such a lovely retreat.
Guest favorite
A snow-covered exterior showcases a home with a wooden deck and steps leading to a spacious entrance. The surroundings are surrounded by snow-blanketed ground and mountain landscapes in the background, under a clear blue sky.
Home in Frisco
4.89 out of 5 average rating, 176 reviews

Cool Frisco One Bedroom Home

AliciaRating, 5 stars1 month ago
Place was perfect for a ski weekend! Location to downtown Frisco was ideal, and the place itself was actually nicer in person than it appears on pics
Top guest favorite
An aerial view of Villa Panda showcases its spacious structure nestled among snow-covered terrain. The landscape features gentle hills and valleys beneath a bright sky, enhancing the home's isolated hilltop location. The circular driveway leads to an outdoor seating area, emphasizing a serene winter retreat.
Home in Summit County
4.96 out of 5 average rating, 105 reviews

Stunning Mtn Views; next to Ski/hike/fly fishing

HowardRating, 5 stars1 month ago
Pablo’s place has everything! We did some gourmet cooking with the breville sous vide and enjoyed unlimited espresso and cappuccino! Great location. Pablo was very responsive.
Top guest favorite
A dining area features a glass table surrounded by brown leather chairs. A wooden serving tray is placed centrally. The kitchen in the background includes modern appliances and shelving with glassware, with natural light streaming through a window.
Home in Leadville
4.98 out of 5 average rating, 147 reviews

Lodge on Leiter ~ with hot tub!

DanielRating, 5 stars2 months ago
We booked this space for a long ski weekend and it was perfect for what we needed. Located in the middle of Leadville and convenient to everything nearby. The house was clean and well equipped and the hot tub was a nice way to unwind after a day on the mountain. Would rent again!

Family-friendly home rentals with a pool

Top guest favorite
A well-appointed bathroom features a dual-sink vanity with modern fixtures. A small refrigerator and stacked washer/dryer are positioned near the doorway. Light-colored cabinetry complements the dark tile flooring, while a spacious shower is visible through a frosted glass door.
Condo in Breckenridge
4.99 out of 5 average rating, 274 reviews

GORGEOUS REMODELED CONDO..Walk to Lift/Town/Trails

VictorRating, 5 stars4 weeks ago
Brian and his beautiful condo were both great. We have stayed in this condo before and were glad to be able to come back. Location is excellent, condo decor is beautiful, and equipment [humidifiers, fans, blankets, clothing hooks, etc] was just what we needed. Brian was very responsive to our questions with effective answers and actions as needed. This is a great place for 6 people. All three generations enjoyed our stay!! Don’t hesitate to try Columbine 205!!!
Top guest favorite
Cabin in Granby
5 out of 5 average rating, 119 reviews

Ski Cabin! | 5 mi to Granby Ranch | 25 mi to WP

AliciaRating, 5 stars1 month ago
I absolutely loved this cabin! Melany and Blake have the house set up perfectly, anything you need this house has it. The views were amazing and I will definitely be back here. Felt like home.
Top guest favorite
A heated swimming pool is surrounded by a spacious patio adorned with lounge chairs. The clear blue water reflects the cloudless sky, while trees provide gentle shade nearby. The pool area is enclosed with a fence, allowing for a private and relaxing environment.
Apartment in Winter Park
4.97 out of 5 average rating, 259 reviews

Beautifully Furnished Modern Condo In Downtown WP

YaniRating, 5 stars3 weeks ago
Had a lovely stay at Roger & Sharon’s place! Everything was as described, we had everything we needed, and felt right at home. Extremely clean and well maintained, well stocked kitchen, comfortable bed. Thank you for a great stay!
Guest favorite
An aerial view showcases the Club Meadowridge complex, highlighting a centrally located clubhouse with a heated outdoor pool and two tennis courts. Surrounding mountains and lush greenery create a scenic backdrop, while nearby lodgings are visible in the distance.
Condo in Fraser
4.86 out of 5 average rating, 229 reviews

Beautiful Condo with Hot Tub on Ski Bus Route

SarahRating, 5 stars2 weeks ago
The location was perfect for my family. We took the Amtrak train to and from Fraser. The local bus system was super convenient from the station to the condo, grocery,and winter park for skiing. We also enjoyed convenient access to the pool, hot tubs, and laundry facilities.
Top guest favorite
A vibrant blue tennis court is shown, featuring a well-maintained net at the center. Surrounding trees and mountains provide a scenic backdrop, while green fencing encloses the space. The court is ready for play, with clear lines marking the boundaries.
Condo in Avon
4.97 out of 5 average rating, 156 reviews

Hot Tub, Pool, Sauna, Shuttle to Vail & The Westin

CraigRating, 5 stars3 weeks ago
Amazing place to stay with family! Plenty of room to spread out and great gathering space for everyone to be together. A true chefs kitchen. Avon rec center is right across the street and the free Westin gondola is less than a 5 min walk. You can enjoy the slopes or a beautiful stroll along the river walk. We loved our time here!
Guest favorite
Townhouse in Frisco
4.91 out of 5 average rating, 220 reviews

Frisco townhome getaway with fantastic views

RandyRating, 5 stars1 month ago
Marsha’s place was the perfect place for us. It was conveniently located near several ski resorts and comfortable for our family from the moment we got there. Beds are often a top concern of ours when we travel and we were happy because we all slept comfortably and well while there. It was nice to have a garage both in that we did not have to worry about parking, and for loading our things in and out. We enjoyed the community center and the pool/hot tubs. The kitchen had the tools we needed to be able to cook for ourselves for the week. We found Marsha’s place to be clean, cozy and as advertised. We wish that we always could stay at a place that brought us this type of ease while away from home. The cherry on top of our stay was Marsha herself. We got ourselves into quite the pickle during our stay and with no other options, we called Marsha. She was kind, steady, and helped find a quick solution. We are so thankful!
Guest favorite
A spacious dining area features a large wooden table set for dinner, adorned with plates and glasses. A rustic fireplace and a decorative antler mount enhance the ambiance. A spiral staircase leads to an upper level, adding architectural interest to the warm, inviting space.
Townhouse in Breckenridge
4.9 out of 5 average rating, 195 reviews

Deer Lodge - Penthouse Ski Condo in Breckenridge

BobbiRating, 5 stars1 month ago
We had a wonderful stay at Andrew’s condo! The condo was just as described. Very cozy with wonderful views of the mountain. We loved the ease of walking to the slopes and to downtown. We hope to come back someday!
Guest favorite
Townhouse in Avon
4.82 out of 5 average rating, 150 reviews

Ski-In/Out Beaver Creek Townhome!

ErinRating, 5 stars1 month ago
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.

Quick stats about vacation rentals that are family-friendly in Gypsum

  • Total rentals

    40 properties

  • Nightly prices starting at

    $60 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

  • Wifi availability

    40 properties include access to wifi

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