Family-friendly vacation rentals in Woodland Park

A spacious living area features a ceiling fan and large sectional sofa arranged around a coffee table. The floor is wood-like, complemented by an area rug. Natural light enters through multiple windows, and an adjacent dining area is visible in the background.

4.85 out of 5 average rating, 103 reviews

Mountain Sanctuary - Family Retreat

Mountain town getaway and sanctuary! In Pike National Forest with great hiking/running trails walking distance from the home. Camping, fishing, picnics, and hiking trails within a short drive. Old town Woodland Park has family entertainment and restaurants. Short drives include Manitou Springs, Santa's Workshop, Cave of the Winds, Garden of the Gods, and Pike's Peak! Cozy up with two woodburning fireplaces and large family rooms. Outdoor patio with private hot tub, firepit, grill, & dining table

4.9 out of 5 average rating, 340 reviews

Mountain View Tiny Home | Woodland Park CO

Retreat to your Woodland Park tiny home! With mountain views from the porch, this tiny house is tucked among the trees in a quiet tiny home community. Located just off the main road and about ½ mile from coffee, groceries, and local dining, it offers both convenience and a peaceful feel. Spend your days exploring nearby hiking, Rampart Reservoir, and Cripple Creek, then settle in with fast WiFi, a full kitchen, Roku TV, and easy self check-in. A 4.9★ Guest Favorite. 4WD/AWD recommended Sept–May.

The living area showcases a pair of comfortable gray sofas arranged around a coffee table. A large television displays a virtual fireplace, creating a cozy ambiance. A light fixture casts a warm glow, and a dining area with a wooden table provides additional seating.

4.92 out of 5 average rating, 182 reviews

Little Woody's Hideaway-(4)DownTown - 329662

License 329662. Cozy little 2 story home with 1 bedroom, 1 bath with a pull out sofa sleeper in the center of downtown Woodland Park. It has so much charm you will never want to leave! You have shops and restaurants a hop skip and jump away and the memorial park in your backyard and you can walk to almost EVERYTHING. You will enjoy the farmers market in the spring and summer that is a block away or sit outside and BBQ. Beautiful hikes are 5-20 mins away, we have a guide for all your adventures!

The exterior of a tiny house features a combination of green and wood paneling. Large windows allow ample natural light, while a welcoming door with steps leads inside. Gravel surrounds the house, enhancing the natural setting among surrounding trees.

4.93 out of 5 average rating, 581 reviews

Wabi Sabi Tiny House - No Cleaning Fees!

I designed and built this Tiny House a few years ago! As such, it's still an ongoing work in progress and so not quite as picturesque as the finished homes you may see on TV, but it's still fully functional, cozy, and homey. To sleep, you'll have the choice of a queen size loft bed (must climb narrow stairs to access) or a queen size (comfortable!) sofa bed on the ground floor. Located in Woodland Park, CO you have an AMAZING view of Pike's Peak and close proximity to so many adventures 🤗

Guest suite in Woodland Park

A mountain home is set among Ponderosa pine trees, featuring a spacious deck with outdoor seating. The lower level has large windows allowing for views of the surrounding nature. The well-maintained lawn and landscaped area add to the inviting atmosphere of the property.

4.99 out of 5 average rating, 273 reviews

Private Suite w/Trees & Awesome Peak View 328878.

Picture-perfect Pikes Peak views from your living room, bedroom, and patio of this stunning Colorado mountain home's guest suite with a classic Colorado feel. The suite includes the entire walk-out lower-level of our home. It is private, separate, and has its own entrance. With a full kitchen and central location, this is the perfect base-camp for a Colorado get-away; however, with the Ponderosa Pines, Aspen, and beautiful hiking trails right up the street, you may never want to leave.

The entrance of the cabin is displayed, featuring a welcoming red door adorned with a wreath. A wooden bench with two cushions sits on a stone pathway, surrounded by trees and planters, creating an inviting outdoor space.

4.88 out of 5 average rating, 419 reviews

Cabin with Pikes Peak View in WP License#329434

Our Cabin was built in 1947, it is a bit of Country but was recently updated with a modern flair with cool interior barn doors and decor, but we kept the nuts and bolts of the 1940's design. It has an incredible view of Pikes Peak, Woodland Park has many restaurants, family-friendly activities. Only 25 Minutes to Colorado Springs. The Cabin is good for couples, solo adventurers, and furry friends. The cabin is cute and cozy and located just off Main Street in Woodland Park. License # 329434

Treehouse in Cascade-Chipita Park

The unique octagon structure of the Treehouse is surrounded by lush greenery, with tall trees and fog creating a serene atmosphere. The design elevates the home above the forest floor, showcasing wooden supports and inviting outdoor stairs leading up to the entrance.

4.99 out of 5 average rating, 301 reviews

Luxury Treehouse Escape | Near Pikes Peak+Views

Welcome to the Treehouse - Your Colorado Getaway. Perched high in the trees with panoramic views, a HUGE bathtub, coffee bar with local coffee, two decks, and KING sized bed, you’ll never want to leave. This completely remodeled, octagon treehouse is just 15 minutes from most attractions in Colorado Springs and 5 minutes from the famous Pikes Peak Highway and gorgeous hiking trails - you are right in the middle of plenty to do while also being tucked away in your own little forest paradise.

A firepit table is featured in the foreground, with a steaming mug resting on its surface. In the background, a scenic view of snow-covered mountains and a wooden fence can be seen under a partly cloudy sky.

4.92 out of 5 average rating, 132 reviews

Pikes Peak BrightStar Boutique!

Kick back and relax in this calm, stylish Boutique Tiny Home. Pikes Peak Brightstar Boutique is a unique one-of-a-kind Tiny Home with many creature comforts such as AC/Dual Heating system, internet connected TV, Washer/Dryer, vibrant lighting and a gorgeous loft with magnificent views of Pike Peak from the moment you wake up. The unit also features a spacious Tiny Home bathroom, stocked K-Cup Coffee maker and full kitchen to cook home cooked meals. Extremely cozy, quiet and entertaining!

A cozy living room features a brown leather sofa and a handmade wooden table. Natural light floods the space through large windows, illuminating a relaxing nook with patterned poufs and a guitar hung on the wall. Outdoors, a porch with rocking chairs offers a view of the surrounding trees.

4.99 out of 5 average rating, 153 reviews

Sunny Treetop Tiny Home! Beautiful Pikes Peak View

Welcome to Treetop Tiny Home! My home is nestled in an adorable close knit Tiny Home community in the lovely town of Woodland Park, Colorado! Come and escape the hustle of this busy world, and enter into the peaceful tranquility of tiny home living... in the woods. Woodland Park is centrally located to some of the finest attractions Colorado has to offer: Just minutes to Rampart Reservoir, Pikes Peak, The North Pole, Cave of the Winds, and so many beautiful hikes! Insta @treetoptinyhome

The living area features a comfortable gray sofa paired with a distinctive black wingback chair. A decorative coffee table is centered on a soft area rug, while elegant light fixtures hang above. Natural light pours in through clerestory windows, enhancing the airy ambiance.

4.96 out of 5 average rating, 203 reviews

Charming Mountain Retreat with private HOT TUB

Welcome to Mini Maison, the coziest tiny home in Woodland Park! Whether you're looking to unwind and refresh or explore the natural beauty the area has to offer, our beautifully decorated home was curated with comfort and luxury in mind. We're located just 10 minutes from Pikes Peak, the most visited mountain in the USA. Garden of the Gods, Manitou Springs and Cave of the Winds are also nearby. Come enjoy the Colorado mountains, our private and peaceful retreat is waiting for you!

The A-frame tiny home is surrounded by a serene winter landscape, with snow-covered trees and a dusting of snow on the porch railing. A few deer are seen near the entrance, adding to the tranquil atmosphere of the setting.

4.96 out of 5 average rating, 180 reviews

A-frame, Tiny home, Hot tub, 3 acres, Sleeps 4!

Kick back and relax in this stylish tiny home A-frame on 2 acres for a romantic getaway or time with your family. • Hot tub • Sleeps 4 • Indoor fire place & outdoor propane fire pit • Fully stocked coffee bar provided • Board games • Off-road trails & rentals in town all year • 15 minutes to Pikes Peak Entrance • 25 mins to Cave of the Winds • 35 mins to Garden of the Gods • Secluded & outside of city limits, yet minutes to town • 45 minutes to CO Springs Airport

4.97 out of 5 average rating, 124 reviews

A modern kitchen space features a sleek white countertop with seating for six, beside a warm fireplace integrated into a black feature wall. A cozy brown armchair is positioned nearby, and ample natural light filters through the window, creating an inviting ambiance.

Cabin in Divide

Romantic Lakefront Cabin - Hot Tub-VIEWS!

Whether you’re a couple seeking a romantic escape or a small group looking for a relaxing retreat, our lakefront cabin offers the perfect blend of cozy charm and stunning mountain views. Unwind with serene lake vistas from the deck and take in breathtaking sunsets that light up the sky each evening—creating unforgettable moments together. Located just 45 minutes from Colorado Springs, the cabin is also near exciting attractions. Book NOW!

Popular amenities for Woodland Park family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern cabin features a stone and wood exterior, accented by a spacious deck with seating and string lights. A set of wooden stairs leads up from the ground to the deck, surrounded by natural landscaping and trees.

4.97 out of 5 average rating, 365 reviews

Luxury Mountain Cabin w/ Views, Hot Tub, Fireplace

Cabin in Green Mountain Falls

A charming blue cabin features a triangular roof and a spacious balcony, surrounded by pine trees. Two kayaks are securely mounted on the side, and the entryway is framed by flower decorations. The backdrop showcases a scenic mountain view beneath a clear blue sky.

4.92 out of 5 average rating, 181 reviews

Cabin in the Woods*Hot Tub*Fireplace*Foosball

4.94 out of 5 average rating, 359 reviews

The exterior of a charming cabin is depicted during twilight, showcasing a red metal roof and brick accents. Large windows offer a warm glow from inside, while the surrounding greenery provides a natural backdrop. A wooden deck invites relaxation as the sun sets in the distance.

Cabin in Divide

Mountain charm -Hot Tub, pups, mtn. views

4.92 out of 5 average rating, 170 reviews

Beautiful Cabin w/ Decks/Views/sauna/hot tub!

4.98 out of 5 average rating, 106 reviews

A modern A-frame cabin is nestled in a snowy landscape, showcasing a spacious deck and a luxurious hot tub. Nearby, a geodesic dome offers a unique stargazing experience. The backdrop features a starry sky, enhancing the serene mountain setting.

Cabin in Florissant

New! A-Frame w/ Hot Tub + Stargazing Dome

4.95 out of 5 average rating, 129 reviews

A private outdoor area is shown, featuring a hot tub and a cozy seating arrangement with two chairs surrounding a fire pit. The space is surrounded by natural grass and trees, providing a tranquil ambiance near the modern a-frame cabin.

Cabin in Divide

Aspen Grove AFrame | Hot Tub | Firepit

4.95 out of 5 average rating, 106 reviews

A shaded area with a hot tub is visible beside large glass doors leading into the tent interior. Light filters through the wooden beams above, illuminating a cozy space with comfortable seating. A person is seated at the edge of the hot tub, enjoying the serene surroundings.

Tent in Monument

Luxury Creekside Glamping Tent w/ Hot Tub & Views

The exterior of the mountain home is portrayed, featuring wood siding and a large deck that wraps around the structure. Surrounding pine trees and natural landscape are visible, enhancing the privacy of the property. The sloping mountains in the background complete the serene setting.

4.92 out of 5 average rating, 208 reviews

Lost Antler Lodge(6)-hottub/3acres/near town/views

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 296 reviews

The exterior of a charming A-frame cabin features a sloped roof and a welcoming blue facade. A small porch is adorned with potted plants, while a pathway of stone slabs leads through landscaped greenery. Sunlight filters through surrounding trees, enhancing the inviting atmosphere.

Cabin in Palmer Lake

𓃲A-Frame on Palmer Lake𓃲 Firepit┃Foosball┃Grill

4.92 out of 5 average rating, 103 reviews

The log cabin is elevated on a sturdy foundation, surrounded by a wooded area. Steps lead up to a welcoming deck, which offers views of the forest. Sunlight filters through the trees, illuminating the natural stone path that surrounds the property.

Cabin in Florissant

Timberwood Cabin

Cottage in Green Mountain Falls

A welcoming living area features a cozy seating arrangement with a black leather sofa, a colorful floral armchair, and wooden coffee table. Large glass doors provide natural light and showcase mountain views. A stone fireplace adds warmth to the space, complemented by orange curtains.

4.8 out of 5 average rating, 127 reviews

Moose Cabin – Lake Views & Private Hot Tub

The cozy cabin exterior is surrounded by tall evergreen trees, featuring a red facade and large windows. A green lawn filled with wild grass leads up to the entrance, while a small patio area is visible beside the house.

4.97 out of 5 average rating, 147 reviews

Chipita Park Creekside Retreat

4.93 out of 5 average rating, 622 reviews

Tiny home in Florissant

Enjoy a Rocky Mountain winter escape

Superhost

A scenic view reveals rolling hills adorned with evergreen trees. Snow-dusted peaks stretch across the horizon, complemented by a diverse landscape featuring both dense forests and open spaces. The atmosphere reflects tranquility, with soft light casting a gentle glow over the vast wilderness.

Cabin in Florissant

4.93 out of 5 average rating, 216 reviews

Red Door Cabin

Superhost

The log cabin is surrounded by snow-covered ground, showcasing a welcoming facade with a sloped roof and overhanging eaves. Two large windows are visible, providing a glimpse into the interior. A wooden chair is positioned on the covered porch, offering a comfortable spot to enjoy the serene surroundings.

4.77 out of 5 average rating, 194 reviews

Log Cabin Mountains of Woodland Park/Pet Friendly

A warm living area features large windows framing scenic views of surrounding trees. The space includes a leather sofa, a loveseat, and an accent chair arranged around a coffee table, complemented by a patterned area rug and a lamp that adds soft lighting.

4.92 out of 5 average rating, 130 reviews

The HeartRock House in Cascade

Family-friendly home rentals with a pool

5 out of 5 average rating, 5 reviews

The exterior of a rustic adobe cottage is featured, showcasing a shaded porch with seating. Lush greenery surrounds the property, and a neat stone border defines the garden area. The soft sunlight illuminates the peaceful yard, creating a calm outdoor setting.

Cabin in Manitou Springs

2 Bedroom Cottage with Kitchen on 3 acres

5 out of 5 average rating, 35 reviews

A serene outdoor patio area features a table complemented by comfortable chairs, surrounded by lush greenery. A small waterfall pond is visible in the background, framed by tall trees and a clear sky, offering a peaceful natural setting.

Home in Larkspur

Forest Retreat, 2 floors, 3 bedrooms w/Hot Tub Spa

Guesthouse in Colorado Springs

An indoor pool area features a 35 ft heated swimming pool underneath a spacious glass enclosure. Two swan-shaped pool floats rest on the water, while lounge chairs are positioned along one side, providing a relaxing atmosphere. Natural light streams through the large glass walls.

4.91 out of 5 average rating, 126 reviews

Urban Float - Private Heated Pool/HotTub & Firepit

Apartment in Colorado Springs

A bright living area is furnished with a green sofa and a white slipcovered couch. A wooden coffee table sits in front. A dining table is positioned near a window, allowing natural light to illuminate the space. Decorative plates and a world map adorn the wall.

4.92 out of 5 average rating, 256 reviews

Quite Spacious Apt w/ Game Table, Bball Court

4.94 out of 5 average rating, 18 reviews

A well-maintained grassy yard is framed by a white picket fence. A large tree and decorative plants are visible, alongside a small swing set. The exterior of the house features large windows and is accompanied by a storage shed in the background.

Guest suite in Fountain

Settlers Pass apartment to experience Colorado

An outdoor patio area is highlighted by a wooden frame, providing shelter over a dining table and seating. A hot tub is situated nearby, surrounded by lush greenery and tall trees, creating a serene environment for relaxation.

4.88 out of 5 average rating, 132 reviews

Sunshine Mountain , experience true Colorado!

A rustic log cabin is set against a backdrop of lush greenery, featuring a wrap-around deck adorned with vibrant flower pots. Sturdy wooden stairs lead to the entry, surrounded by natural stone accents and shaded by tall pine trees.

4.97 out of 5 average rating, 161 reviews

Rustic Historic Colorado Mountain Cabin Pikes Peak