Family-friendly holiday rentals in Woodmoor

4.96 out of 5 average rating, 292 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

★Overlooking Palmer Lake, walkable to the downtown ★Location: 1 mi to Pinecrest Event Center, 20 mins to the Air Force Academy ★Outdoors: kayaking, paddle boarding, fishing, hiking ★YARD: Fenced in w/fire pit, grill, hammock, corn hole, ladder golf, yard dice ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys! ★55" Smart TV w/ access to apps like Hulu + Netflix ★Fast Wifi ★Keyless Entry ★Comfortable beds ★Equipped kitchen w/waffle maker, blender + more! ★Free Colorado beer

4.99 out of 5 average rating, 179 reviews

Cabin in Monument

Cozy A-Frame Retreat “Hot Tub”w-Views, Monument CO

Experience a true Colorado getaway with this custom built Scandinavian inspired A-frame, nestled on the Palmer Divide, located only 15 min to Colorado Springs & 30 min to S Denver. You will feel secluded within the pines and views to die for. You might see wildlife walking by while enjoying a cup of coffee or glass of wine in the hot tub or cozied up in a blanket on the deck. First bottle of wine on us! Hiking trails are minutes drive from cabin. Make sure to relax & make lots of memories. 😊

A light-filled living area features a comfortable gray sofa adorned with decorative cushions, alongside an accent chair with a floral pattern. A dark coffee table centers the space, placed on a plush gray area rug. Art with vibrant colors is displayed on the wall above.

4.9 out of 5 average rating, 163 reviews

The Adventurer’s Retreat

Are you looking for the perfect place to come back to after a day of adventure or just a quite serene getaway with your family? The large open space offers 2 very comfortable king beds, one is a 100% organic non-toxic pillow top mattress. You will feel like you're at home with a well equipped kitchenette, breakfast nook, and large living space along with a pool table. The apartment will make your stay not only relaxing but also fun. Our property has a playground for kids and pikes peak views!

Guest suite in Palmer Lake

An outdoor patio area features a round table with four chairs, shaded by a large blue umbrella. Lush green vegetation and a small stone pathway are visible, with a deck and grill in the background, offering a connection to the serene natural surroundings.

4.97 out of 5 average rating, 287 reviews

Studio@The Spring - a Mountain Town Oasis!

Relax and unwind in Mountain serenity. Away from it all - Near everything! Cool temps & fresh Mountain air abound in this mountain studio. Adventure on the trail's accessible just footsteps from the door. The lake and restaurants are within walking distance. Enjoy your own private patio, parking and entrance - A year-round spring runs through the backyard. Centrally located- you're close to Denver, Colorado Springs, Pueblo, the Air Force Academy and Ft. Carson. All amenities are within 10min.

A decorative stone bird figurine sits beside a vintage-style sign that spells 'RELAX' with mirrored letters. A small green plant in a textured glass vase adds a touch of nature to the rustic wooden shelf.

4.94 out of 5 average rating, 326 reviews

Windsong Suite~15 min to USAFA~2bed/2bath

New name, new furniture, same wonderful Peaceful Forest Retreat! Mother-in-law suite attached to our home in Pike National Forest! Serene living space complete w/ 2 bed, 2 bath, living room, kitchenette (no stove), deck, TV, internet & deer! Enjoy our secluded forest setting with easy access to the fun sites in Colorado Springs & the Urban delights of Denver. Relax on the deck of our wooded retreat with your morning coffee or while you grill & play corn hole after a fun day of exploring.

4.94 out of 5 average rating, 157 reviews

A cozy loft space features a spacious bed adorned with a colorful floral comforter and accent pillows. A white armoire stands nearby, complemented by a small kitchenette area with wood cabinetry. Soft lighting illuminates the room, enhancing a relaxed atmosphere.

Loft in Palmer Lake

The Little Brown House (that grew).

Light, airy, bright & fresh decor; cozy space with a view of Mt. Chautauqua; near Pinecrest wedding venue. Full amenities: king bed, fridge, coffee maker, microwave. Designated parking. Unlimited hiking right out the door. Variety of cuisine within walking distance: steak house, Mexican, bistro, quaint coffee bar, historic ice cream shop, full-menu restaurant overlooking the lake. Shops stocked with local artisans' works. The loft does not accommodate more than two persons--no exceptions.

Guest house in Colorado Springs

A charming yellow A-frame structure is seen amidst a snowy environment, surrounded by tall pine trees. A deck with black railing extends from the entrance, leading to a door framed in green. A warm light fixture hangs beside the door, enhancing the welcoming appearance.

4.86 out of 5 average rating, 219 reviews

Cozy, private, serene getaway in the woods

Serene studio apartment, stand alone structure in a beautiful ponderosa pine forest. This quiet apartment has a king sized bed, full bath with bathtub, a kitchenette with Keurig coffee maker, microwave, toaster oven, mini fridge, sink, dishes etc. There is a desk/ dedicated work space and Wifi. A TV, love seat and coffee table. A private neighborhood walking trail one block away that goes to a pond. Free on site parking. Coded door entry. Provided toiletries and snacks. And sunset view.

A spacious bedroom features a comfortable queen bed with crisp white linens and a green throw blanket. Natural light floods through a window dressed with sheer curtains. A wooden dresser and a small table are also present in the room, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 278 reviews

Private Lower Level Suite with Peak Views

Clean, cozy, and comfortable private walkout basement apartment with gorgeous views of Pikes Peak and the Air Force Academy. Large bedroom with comfortable queen bed, recently updated full bathroom, kitchenette (please note, no oven or cook top), and large living space with Roku tv, fireplace, and room for more to sleep and hang out. Located in a quiet neighborhood approx. 2 miles from the Air Force Academy, with easy highway access for activities in both Denver and Colorado Springs.

4.95 out of 5 average rating, 195 reviews

Flat in Monument

Serene Stay w/ Mountain Views in Downtown Monument

Welcome to your serene private apartment overlooking the mountains in Historic Downtown Monument. This updated, upper unit has 2 bedrooms each with its own en-suite bath, and an open-concept living room/ kitchen. The deck is spacious w/ beautiful Mountain views, perfect for enjoying the Colorado sunshine! Within walking distance of Downtown Monument’s shops and restaurants as well as the Santa Fe Hiking Trail! While USAFA, N CO Springs & other attractions are all a short drive away!

A rustic wooden sign displaying the text 'Cutthroat Cove' is mounted on a textured wall. The sign features a simple fish graphic, contributing to a natural and welcoming ambiance.

4.99 out of 5 average rating, 150 reviews

Cutthroat Cove- Air Force Academy

Completely relax! Even if you are here for business. Cutthroat Cove is near the entrance to the Air Force Academy but feels like you are living in the woods. Private entrance (with stairs), parking space, one bedroom, one bath with a large living room area. The mini kitchen features a dishwasher, mini-fridge, toaster oven and microwave. The fireplace makes it cozy and warm and sometimes we are visited by large wildlife. Minutes from restaurants and hiking trails.

4.96 out of 5 average rating, 210 reviews

Flat in Monument

"Private Suite in the Forest"

This private unshared 1 bedroom suite is in a home near Monument, the US Air Force Academy, Ford Amphitheatre in Colorado Springs, Castle Rock, Denver Tech Center, Restaurants/Coffee Shops/Brewery, Spruce Mountain, Fox Run Regional Park, Pike Nat. Forest, and many hiking/Nordic trails. It has great I-25 access and is comfortable, quiet, private, on a beautiful treed lot in the residential community of Woodmoor. It features a private entrance and unshared space.

4.91 out of 5 average rating, 331 reviews

A bright sleeping area features a spacious bed adorned with decorative pillows and a soft throw blanket. Two bedside tables with lamps flank the bed, and a piece of wall art adds an aesthetically pleasing touch. Natural light enters through a window, enhancing the light-colored walls.

Flat in Briargate

Simply Gorgeous, Private, Walkout Suite 1 bedroom

A home away from home, this newly renovated, modern 1 bedroom apartment and all the amenities you’d want in your own place. From the peaceful backyard with stunning mountain views, to the gorgeous and comfortable interior equipped with a functional kitchen, this private basement apartment is the perfect getaway. Nestled in a quiet and lovely neighborhood, our central location offers some of the best access to Colorado Springs. City Permit # A-STRP-25-0143

Popular amenities for Woodmoor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 139 reviews

The kitchen features white cabinetry with sleek silver handles and a granite countertop. An island with a wooden accent provides additional workspace. Modern appliances, including a refrigerator and oven, are visible. Soft lighting illuminates the space, creating a bright and functional cooking area.

Home in Monument

HOT TUB! Amazing Mountain views! Newly Remodeled

4.98 out of 5 average rating, 107 reviews

The chalet's A-frame structure is framed by tall pine trees, showcasing large windows that invite natural light. A gentle plume of smoke is rising from the chimney, indicating a warm interior. The outdoor deck offers a seating area for relaxation amidst a scenic mountain setting.

Cabin in Woodland Park

Fireplace, Hot Tub, 2 Decks, Scenic Vws, Dogs YES

Guest suite in Castle Rock

A spacious living area features a large, dark leather sectional sofa arranged around a wooden coffee table with a storage compartment. Natural light enters through the window, complemented by soft curtains. A dining area with a table and chairs is visible in the background.

4.98 out of 5 average rating, 173 reviews

Boho Basement - Private Entrance - Hot Tub

The exterior of a modern two-story guest house is shown, featuring large windows and a combination of light and dark materials. The structure is situated amidst tall pine trees on a gravel driveway, with a single carport located beneath the upper level.

4.99 out of 5 average rating, 191 reviews

Private Guest House in the Forest

Guest suite in Colorado Springs

A spacious hot tub is situated under a wooden pergola, surrounded by a wooden deck. Bubbling water reflects natural light, and distant mountain views are visible through trees in the background, providing a serene atmosphere.

4.9 out of 5 average rating, 283 reviews

✔Pets✔ ♕King Bed/Bath/Kitchen ♨Hot Tub♨ w views 🏞

A spacious deck area is furnished with comfortable seating, including a cozy sectional and armchairs. A table sits at the center, with the surrounding view showcasing a forested landscape and distant mountains under a softly lit sky.

4.95 out of 5 average rating, 188 reviews

✔️Clean★Quiet Home★King Bed★Hot Tub★Scenic Views✔️

Guest suite in Colorado Springs

A hot tub is illuminated with soft blue light, set on a private patio. String lights decorate the area, enhancing the outdoor atmosphere. In the background, a staircase leads to a spacious wooden deck surrounded by trees, creating a serene setting at dusk.

4.97 out of 5 average rating, 271 reviews

The Black Forest Estate

A single-story home features a light-colored exterior with a contrasting blue entrance door. A paved driveway leads to a two-car garage. The well-maintained front yard includes green grass and decorative shrubs, while a small seating area is positioned near the front porch.

4.9 out of 5 average rating, 442 reviews

Rockrimmon Retreat Hottub - FirePit - Dog Friendly

Family- and pet-friendly home rentals

Guest house in Colorado Springs

A modern living area features a large window that allows natural light to brighten the space. A comfortable leather sofa is complemented by a stylish coffee table and a cozy armchair. A television is positioned nearby, against a backdrop of light-colored walls and decorative artwork.

4.99 out of 5 average rating, 233 reviews

New Luxury 1 - Bed Near Downtown

Tiny home in Woodland Park

A charming tiny home is shown, featuring a welcoming front porch with white railings and steps leading up to the entrance. A gravel driveway accommodates two cars, and natural surroundings with trees enhance the property’s serene setting.

4.95 out of 5 average rating, 256 reviews

Pikes Peak Tiny Home

Tiny home in Woodland Park

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, 577 reviews

Wabi Sabi Tiny House - No Cleaning Fees!

Guest suite in Colorado Springs

An open-concept living area is showcased, featuring a dark leather sofa and a stylish wooden coffee table centered on a patterned area rug. Large windows allow natural light to fill the space, while light curtains provide privacy. A comfortable chair adds to the inviting seating arrangement.

4.94 out of 5 average rating, 734 reviews

Cozy Suite w/ Kitchen, Laundry | Downtown, CC, OTC

4.97 out of 5 average rating, 104 reviews

Huge family Home w/Hot Tub/Views/Location!

4.88 out of 5 average rating, 415 reviews

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.

Cabin in Woodland Park

Cabin with Pikes Peak View in WP License#329434

A bright bedroom features a spacious bed adorned with an orange quilt and various decorative pillows. Soft lighting comes from pendant fixtures, adding warmth. A window, partly covered by light curtains, allows natural light to fill the room, while a small bedside table complements the decor.

4.94 out of 5 average rating, 359 reviews

Wildflower Cottage | Fenced Yard | 1 mile D-Town

Farm stay in Woodland Park

A single-story bunkhouse is nestled within a natural setting, featuring large sliding glass doors that open to a patio area. Comfortable seating is arranged outside, with potted plants adding greenery to the landscape. Surrounding pine trees enhance the woodland atmosphere.

4.99 out of 5 average rating, 166 reviews

Bunkhouse In The Pines

Family-friendly home rentals with a pool

5 out of 5 average rating, 33 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

Guest house 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, 123 reviews

Urban Float - Private Heated Pool/HotTub & Firepit

4.92 out of 5 average rating, 250 reviews

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.

Flat in Colorado Springs

Quite Spacious Apt w/ Game Table, Bball Court

4.94 out of 5 average rating, 17 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

4.89 out of 5 average rating, 84 reviews

A spacious living area features a comfortable sectional sofa, a flat-screen smart TV mounted on the wall, and a coffee table. Fresh greenery adds a touch of nature, while a ceiling fan provides airflow. The adjoining kitchen space is subtly visible in the background.

Flat in Castle Rock

Rocky Mountain Haven w/ king bed | pool & hot tub

4.88 out of 5 average rating, 132 reviews

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.

Home in Woodland Park

Sunshine Mountain , experience true Colorado!

5 out of 5 average rating, 23 reviews

The exterior of a two-story home is displayed, showcasing a well-maintained backyard with a semi-inground heated pool surrounded by white lounge chairs. A deck with stairs leads to the entrance, while a sunroom is visible beneath the windows. Neatly trimmed greenery frames the area.

Home in Monument

Spacious, Mountain Views, Heated Pool, & Sunroom!