Family-friendly holiday rentals in Woodmoor

4.96 out of 5 average rating, 288 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, 173 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. 😊

4.9 out of 5 average rating, 163 reviews

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.

Guest suite in Monument

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, 285 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.

4.94 out of 5 average rating, 323 reviews

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.

Guest suite in Monument

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, 217 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.

4.95 out of 5 average rating, 192 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!

4.99 out of 5 average rating, 148 reviews

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.

Guest suite in Monument

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

The exterior of the home is softly illuminated at night, highlighting the entrance with wooden doors and porch. A welcoming pathway of stone leads to the porch, bordered by lush landscaping and decorative pumpkins. Tall trees surround the area, creating a serene atmosphere.

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.

A cozy basement suite is presented, featuring a sectional couch and a wall-mounted television. Shelves filled with books occupy one wall, while a dry bar with seating is visible nearby. Soft lighting contributes to a relaxed ambiance within the space.

4.94 out of 5 average rating, 303 reviews

Private, Spacious Basement Suite in N CO Springs

Relaxing, affordable, cozy basement suite in private home with dedicated parking spot. Easy access to I-25 that affords direct travel to Colorado Springs, the AF Academy, Manitou, Castlerock and Denver. Furnished bedroom with walk-in closet, queen bed; additional queen inflatable mattress if needed. Full bathroom, tv, sectional couch w/recliners, dry bar incl microwave, water cooler, toaster oven, dorm fridge, electric kettle and coffee maker.

Guest house in Palmer Lake

A rustic wooden cabin is nestled among snow-covered trees, presenting a serene winter scene. The building features a sloped roof and a single satellite dish, surrounded by a blanket of snow on the ground. The town of Palmer Lake is visible in the background.

4.95 out of 5 average rating, 257 reviews

Quaint and Historic Studio Cabin

Rustic and eco-friendly this studio guesthouse overlooks the quaint town of Palmer Lake. Within walking distance of all sorts of outdoor recreation and wonderful restaurants. We're a short driving distance from Colorado Springs and the US Air Force Academy, Garden of the Gods and Pikes Peak region. It's the perfect place to relax and recreate while maintaining distance and privacy. We look forward to hosting you! Becky and Phil

Popular amenities for Woodmoor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 286 reviews

Lake~Paddleboards~Hot Tub~Firepit~BBQ

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, 170 reviews

Boho Basement - Private Entrance - Hot Tub

4.98 out of 5 average rating, 105 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

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

4.93 out of 5 average rating, 135 reviews

A private hot tub is visible on the deck, surrounded by trees with distant mountain views in the background. The bubbling water reflects the sky, creating a serene retreat for relaxation.

Home in Monument

HOT TUB, Stunning Mountain views!

The living area features a comfortable teal sofa adorned with various pillows, complemented by a rustic wooden accent wall. Natural light streams through large windows, while a fan provides air circulation. A coffee table with a glass top sits in front of the sofa.

4.89 out of 5 average rating, 517 reviews

Private 2BR Hideaway Suite w/ Hot Tub & Firepit!

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, 184 reviews

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

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, 268 reviews

The Black Forest Estate

4.96 out of 5 average rating, 307 reviews

A cozy outdoor seating area features a fire pit surrounded by comfortable chairs, offering views of the expansive landscape and mountains in the distance. A hot tub is located nearby, providing an inviting space for relaxation amidst nature.

Townhouse in Palmer Lake

The Mountain Hideaway- Views, Spa, Adventure

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 702 reviews

A charming exterior view of a cabin-inspired home is surrounded by lush greenery and vibrant flowers. Stone pathways lead to a welcoming entrance, accentuated by light blue walls and a small patio featuring two chairs. Mature trees provide shade and enhance the natural setting.

Guest suite in Broadmoor

Cheyenne Canyon Getaway

A welcoming living space features a stone fireplace beneath a mounted television. Comfortable seating is arranged around a wooden table, and the open kitchen is equipped with stainless steel appliances and a large island for group gatherings.

4.9 out of 5 average rating, 110 reviews

Air Force proximity, fire pit, pool table

Flat in Old Colorado City

A spacious backyard features a fenced area with a children's climbing structure and outdoor dining space. Comfortable chairs are positioned around a grill, alongside a pebbled path leading through the yard, surrounded by greenery and trees.

4.93 out of 5 average rating, 514 reviews

★OCC Getaway★ Firepit, Grill, Backyard + Firestick

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, 231 reviews

New Luxury 1 - Bed Near Downtown

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, 571 reviews

Wabi Sabi Tiny House - No Cleaning Fees!

A living area features warm wooden flooring with a neutral color palette. An orange armchair complements a white sectional sofa adorned with textured pillows. A wooden cabinet is positioned beside a plant in a decorative pot, and wall art adds a modern touch to the space.

4.84 out of 5 average rating, 327 reviews

Cozy Bungalow, Pet friendly, big backyard, Trail!

4.94 out of 5 average rating, 124 reviews

Natural light fills a spacious living area with large windows, showcasing greenery outside. A comfortable sofa adorned with blankets is complemented by two modern armchairs. A wooden dining table is set nearby, with decorative touches including a potted plant and a wall-mounted shelf.

Home in Monument

Secluded Chalet in the Pines Hot tub Wrapped porch

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, 277 reviews

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

Family-friendly home rentals with a pool

Superhost

A spacious living area is furnished with a leather sofa and two easy chairs adjacent to a wooden accent table. Floor-to-ceiling windows offer expansive views of the surrounding landscape, while sliding glass doors provide direct access to the L-shaped terrace.

Flat in Colorado Springs

4.55 out of 5 average rating, 69 reviews

Mountain Views From L-Shaped Terrace

5 out of 5 average rating, 32 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.

4.92 out of 5 average rating, 120 reviews

Urban Float - Private Heated Pool/HotTub & Firepit

4.92 out of 5 average rating, 247 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, 83 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!