Family-friendly holiday rentals in Woodmoor

4.96 out of 5 average rating, 228 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.

Apartment in Monument

"Private Suite in the Forest"

This quiet unshared 1 bedroom suite is in a home 1 mile from Monument. Near hiking, the USAF Academy, Ford Amphitheatre, Colorado Springs, Castle Rock, Restaurants/Coffee Shops/Brewery, Spruce Mountain, Fox Run Regional Park, Pike Nat. Forest, and many hiking/Nordic trails. 45 miles so. of Denver. It's squeaky clean, 1 mile from I-25, comfortable, quiet, private, on a beautiful treed lot in the residential community of Woodmoor. Has a private entrance and is unshared space. Guests love it!

4.99 out of 5 average rating, 219 reviews

A custom A-frame cabin is surrounded by tall pines, featuring a sloped roof and large glass windows. A spacious deck with steps leads to outdoor seating and a hot tub, while natural stone landscaping adds to the serene setting.

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 with views to die for. You might see wildlife 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 is on us! Hiking trails are only minutes drive from the cabin. Make sure to relax & make lots of memories. 😊

Guest suite in Colorado Springs

The image showcases a rustic mountain retreat nestled in a colorful landscape of autumn foliage. The structure features a red roof and is surrounded by rolling hills and sparse trees, with a winding dirt path leading to the property.

4.99 out of 5 average rating, 265 reviews

Fall Special! Epic Views-Unique Mtn Getaway!

Epic panoramic mountain/city views-complete serenity! Your private retreat & basecamp for CO adventure! One-of-a-kind tranquil & modern mountain getaway on 40 acres bordering National Forest. *Enjoy morning coffee on your private deck or the sunset next to the fire pit w/ dramatic city & mountain vistas *At night enjoy sparkling stars & the glow of city lights below *Private hiking trails lead to a bubbling creek in the forest & feels a world away-yet it’s 8 min from town-best of both worlds

A cozy living area features two comfortable blue armchairs positioned alongside a small dark table. A decorative painting of deer adorns the wall, complemented by a light-colored backdrop. Natural light filters through partially sheer curtains, enhancing the warm wood flooring.

4.98 out of 5 average rating, 138 reviews

Spacious 2 Bedroom Basement w/ Kitchenette & Patio

Comfy, private, & spacious basement apartment w/separate keyless entrance for easy check-in. Relax on our covered, lit patio with firepit or enjoy breathtaking mountain views from our upstairs deck. Eat & cook in our well-stocked basement kitchenette, where breakfast items, cooking ingredients, spices, & condiments will be provided. Washer/dryer & complimentary laundry supplies provided. After a great night's sleep, explore Colorado Springs or Denver with access to i25 just 5 minutes away.

4.9 out of 5 average rating, 177 reviews

A rustic outdoor seating area features a round wooden table surrounded by four metal-framed chairs, all placed on a flagstone patio. A red umbrella adorned with string lights provides shade, while tall pine trees create a natural backdrop.

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!

5.0 out of 5 average rating, 120 reviews

Guest suite in Monument

The Fly-by! Mountain&Lake view; Hot Tub+MiniGolf

Escape to your private mountain retreat! This stunning 2020-built walkout suite offers the perfect blend of seclusion and convenience. Wake to breathtaking lake and Front Range views, then unwind by your private patio fire watching spectacular sunsets. The entire lower level is exclusively yours with separate access—no shared spaces. Parking in-garage (no snow scraping!) and modern amenities. Located minutes from the Academy and Garden of the Gods, yet peaceful enough to truly relax. Book now!

A modern kitchen and dining area features green cabinets, stainless steel appliances, and a large dining table with bench seating. Red chairs add a pop of color, while natural light fills the space through sliding glass doors leading to an outdoor area.

4.98 out of 5 average rating, 119 reviews

Family Friendly Charming +Clean 5 Bedroom House,

This 5 bedroom house has families and vacation amenities in mind! A small sitting room for coffee or conversation greets you when you walk in the door. The floor plan opens up to the living area that has a cozy couch to watch movies on and an eating area to share a meal. The kitchen is fully stocked with everything you need to prepare a meal together. The upper level has 4 bedrooms and a laundry room. There is a master suite with a king bed and a walk in closet. (no rooms on main level).

A two-story house features a combination of stone and stucco exterior, standing prominently against a cloudy sky. A three-car garage is integrated into the facade, with a porch area highlighted by decorative stonework. The surrounding yard includes low-maintenance landscaping with gravel accents.

4.96 out of 5 average rating, 101 reviews

Mountain Views, AF Academy, Hot tub, Fire Pit

Relax with the whole family at this peaceful place to stay. Great views and location. Close to shopping , restaurants, Air Force Academy, trails, and hiking . Easy access to I-25 to get to Colorado Springs or Denver . Master Suite with vaulted ceiling, double sided fireplace, large soaking tub, and walk-in closet. Enjoy the gourmet kitchen and coffee bar. Sit outside on the patio and enjoy the views next to the fire pit. You can walk across the street to walk or run on the trails. Safe area.

4.96 out of 5 average rating, 332 reviews

A spacious living area features high ceilings with large arched windows allowing ample natural light. Comfortable seating includes two patterned armchairs and a sofa, complemented by a coffee table on a cowhide rug. A stone fireplace adds a cozy touch, enhancing the wood-paneled walls.

Cabin in Palmer Lake

✷Kayak Cabin✷ Hot Tub┃Firepit┃Games┃Movie Room

★Location: 1 mi to Pinecrest Event Center, 20 mins to the Air Force Academy ★Outdoors: 0.7 mi to the lake for kayaking, 1 mi to hiking ★YARD: Fenced in w/fire pit, hot tub, hammock & games ★GARAGE w/kayaks & tennis rackets ★PORCH: Dining area, rocking chairs & grill ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys! ★70" Smart TV in living room & 70" Smart TV in movie room w/Apps + Cable ★Fast Wifi ★Keyless Entry ★Comfortable beds ★Equipped kitchen ★Free Colorado beer

An outdoor seating area is furnished with a spacious sectional sofa, surrounding a fire pit with glowing flames. Warm ambient lighting from string lights enhances the serene surroundings of trees and nature visible through large glass doors.

4.99 out of 5 average rating, 126 reviews

Contemporary Mtn 4BR + Hot Tub & Fire Pit & Views

• Resort‑style setting with expansive decks, fire-pits, hammocks, and a hot tub, creating elegant indoor‑outdoor spaces for relaxing, connecting, and taking in the mountain air and night sky • Architecturally interesting contemporary mountain 4‑bedroom home sleeping up to 10 just 2 exits north of the US Air Force Academy and near 6+ wedding venues • Gourmet kitchen for effortless entertaining with plenty of room to gather and play games or head out for a hike on beautiful nearby trails.

4.97 out of 5 average rating, 131 reviews

The living area is designed with a cozy sectional sofa facing a stone fireplace and a wall-mounted TV. Natural light fills the space, highlighting the wooden floors. A modern light fixture hangs above the open-concept dining area, which connects effortlessly to the kitchen.

Cabin in Palmer Lake

Pinecrest Perch | Creekside | Firepit | Fireplace

Welcome to Pinecrest Perch--a modern creekside retreat nestled in Pinecrest, a charming historic neighborhood in Palmer Lake, CO. This cozy cabin offers hillside views and easy access to town. Indulge in the local charm with nearby cafes and restaurants. Planning a wedding? The Pinecrest Event Center is just a half mile away. For day trips, explore the Air Force Academy (20 minutes), Garden of the Gods (35 minutes), or Denver (45 minutes). Your perfect mountain getaway awaits!

4.91 out of 5 average rating, 247 reviews

Peaceful Forest feel/Hidden but close/10mi USAFA

3bd 1ba Mountain themed home surrounded by Tall Ponderosa Pines trees frequented by deer/private walk-out onto deck/fire-pit seating area/BBQ grill/Play corn-hole, horseshoes jump on trampoline or kick-back. LOCAL: Beautiful hiking trails, unique shops, quaint eateries, Pubs, 2 Lakes, New amphitheater WEDDING VENUES: Palmer Lake, Monument, Larkspur & Flying Horse/Close to Colorado Springs, Manitou Spgs & CastleRock easy access i-25 Denver Airport 1hr.

Popular amenities for Woodmoor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 141 reviews

The exterior of the chalet is illuminated by warm string lights at dusk, showcasing a wood and glass structure surrounded by trees. A soothing hot tub is visible on the deck, offering a perfect spot for relaxation under the evening sky.

Cabin in Woodland Park

Aframe, Hot Tub, Scenic Views, 2 decks, Dogs YES

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.

4.98 out of 5 average rating, 162 reviews

HOT TUB! Amazing Mountain views! Newly Remodeled

Expansive mountain views are showcased, featuring the snow-capped peaks of Pikes Peak against a clear blue sky. The foreground includes rooftops of houses, blending naturally with the surrounding landscape, which highlights rolling hills and lush greenery.

4.99 out of 5 average rating, 255 reviews

Breathtaking Mountain Views | Hot Tub | Near USAFA

Cabin in Cascade-Chipita Park

4.95 out of 5 average rating, 243 reviews

Riverside Retreat: Hot Tub, Sauna, & Cold Plunge

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, 219 reviews

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

5.0 out of 5 average rating, 274 reviews

Home in Divide

Private Luxury Spa Retreat: Hot Tub, Sauna & Views

5.0 out of 5 average rating, 306 reviews

A two-story, contemporary mountain retreat is surrounded by tall trees. The exterior features a black facade, large windows illuminated warmly, and a spacious deck with steps leading to the landscape. The sky presents a subtle gradient of pink and blue hues at dusk.

Home in Woodland Park

Views, views, VIEWS I Hot tub I Peaceful 3 acres

Cabin in Colorado Springs

5.0 out of 5 average rating, 194 reviews

15 min to Downtown I Romantic I Hiking I Forest

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 313 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

Guesthouse in Colorado Springs

A uniquely shaped cottage is surrounded by tall trees, with soft lighting highlighting its architectural features. A stone pathway leads to the entrance, while decorative outdoor lights add a touch of charm to the serene woodland setting.

4.98 out of 5 average rating, 124 reviews

The Enchanted Hobbit Cottage

Earthen home in Colorado Springs

The exterior of a unique earthship home is framed by lush greenery and tall pine trees. Large glass windows reflect the surrounding landscape, allowing natural light to illuminate the earth-toned structure. A black door is visible at the front, alongside a small seating area.

5.0 out of 5 average rating, 221 reviews

Off-grid, Earthen home in the forest!

4.85 out of 5 average rating, 317 reviews

A scenic view captures the surrounding landscape, featuring rolling hills and distant mountains under a partly cloudy sky. Lush greenery and wild grasses fill the foreground, with trees framing the edges of the image. A peaceful natural setting is evident.

Cottage in Palmer Lake

Completely Remodeled Historical Cottage

Guesthouse 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, 277 reviews

Quaint and Historic Studio Cabin

4.96 out of 5 average rating, 461 reviews

A three-story home featuring a unique eyebrow design is surrounded by greenery and tall trees. The exterior showcases a blend of stone and wood accents, with two garage doors and a round, welcoming front door that leads into the property.

Home in Palmer Lake

★Comfortable Nature Retreat★ Trails, Lake & Dining

Guest suite in Colorado Springs

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.

4.95 out of 5 average rating, 347 reviews

Private, Spacious Basement Suite in N CO Springs

Guesthouse in Colorado Springs

A spacious living area showcases a cozy sofa adorned with colorful textiles, set against wooden log walls and warm lighting. A staircase made of natural wood curves upward, leading to the sleeping loft. Windows allow natural light to fill the space, offering views of the surrounding forest.

4.94 out of 5 average rating, 213 reviews

Rustic Bunkhouse in Black Forest

Family-friendly home rentals with a pool

An expansive home showcases a contemporary Southwestern design, surrounded by lush greenery. Large windows and multiple deck areas provide scenic views. An inset image reveals an indoor heated pool, framed by large windows that invite natural light and emphasize the tranquil indoor space.

4.98 out of 5 average rating, 132 reviews

Hidden Gem⋆Heated Pool⋆Gorgeous Views⋆2.4 ac⋆AC⋆EV

4.94 out of 5 average rating, 263 reviews

A lit hot tub is nestled on a spacious deck, surrounded by trees. Soft blue lights illuminate the water, and string lights hang overhead, creating a serene evening atmosphere. Furnished lounge areas are visible in the background, inviting relaxation.

Cabin in Divide

Hot tub, mtn views, massage chair, & steam shower!

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, 299 reviews

Quite spacious Apt w/Game Table, Pool, Bball court

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, 161 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

Guest suite in Manitou Springs

A welcoming entrance archway labeled 'Historic Manitou Springs' is set against a backdrop of snow-capped mountains. The arch is flanked by tall evergreen trees, and charming buildings are visible below, creating an inviting view of the historic town.

4.97 out of 5 average rating, 385 reviews

Manitou Terrace Place - clean, cozy & convenient!

The covered deck features a spacious seating area with comfortable furniture and a large outdoor kitchen equipped with a grill and a 36” griddle. A smart TV is mounted on the wall, and patio heaters are positioned for warmth. The pool and hot tub are visible in the background.

4.97 out of 5 average rating, 155 reviews

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