Family-friendly holiday rentals in Woodmoor

4.97 out of 5 average rating, 230 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!

FamilyIndoor spacesOutdoor spaces

4.99 out of 5 average rating, 222 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, Cabin Retreat/Hot Tub/w-Views

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. 😊

FamilyKitchenHospitality

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, 140 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.

KitchenFamilyBiking

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!

KitchenIndoor spacesLayout

4.9 out of 5 average rating, 178 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!

FamilyKitchenLong stay

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, 120 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).

KitchenFamilyCheckout

4.96 out of 5 average rating, 334 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 soda

KitchenFamilyCondition

4.96 out of 5 average rating, 103 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.

Indoor spacesKitchenAccess

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, 164 reviews

HOT TUB! Amazing Mountain views! Newly Remodeled

MOUNTAIN VIEWS! PRIVATE HOT TUB! Recently remodeled, professionally decorated throughout. Patio & sitting area around the outdoor fireplace. Walking distance to the Hearth House event center, Downtown Monument & locally owned restaurants. A few blocks to Monument lake to enjoy fishing, kayaking, flat boarding or soaking up the sun. Amazing mountain biking is close. Few minutes to the Air Force Academy, quick drive to Colorado Springs, Garden of the Gods, Broadmoor Hotel, Denver and more!

FamilyKitchenLaundry

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, 127 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.

FamilyIndoor spacesComfort

4.95 out of 5 average rating, 213 reviews

Apartment 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!

FamilyIndoor spacesHospitality

4.86 out of 5 average rating, 214 reviews

Guest suite in Monument

Scenic 2 bedroom with hot tub

Retreat to a space surrounded by trees and a Colorado get-a-way vibe, while still having close access to the highway, food, trails and more! We are located less than 40 minutes from the Colorado Springs airport and less than 20 minutes from the Air Force Academy. 15 mins Ford Amphitheater concert venue . Monument is a charming town that is worth exploring! There are many hiking and walking trails within miles of our home that radiate the beauty of Colorado !

KitchenFamilyComfort

Popular amenities for Woodmoor family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a 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, 228 reviews

Private House in the Forest

Indoor spacesFamilyCondition

An aerial view of a spacious Colorado home is presented, showcasing its modern architecture against a backdrop of expansive fields and distant mountains. The large backyard features a covered swim spa, outdoor seating areas, and a patio, all surrounded by scenic natural beauty.

4.95 out of 5 average rating, 113 reviews

Amazing Swim Spa | 5 Acres + Hot Tub + Games

FamilyIndoor spacesSleep quality

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, 257 reviews

Breathtaking Mountain Views | Hot Tub | Near USAFA

FamilyKitchenAccuracy

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.

4.94 out of 5 average rating, 223 reviews

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

FamilyKitchenView

4.94 out of 5 average rating, 122 reviews

Home in Woodland Park

Pikes Peak View-modern-spacious-hot tub-Sleeps 8

FamilyKitchenNearby

4.95 out of 5 average rating, 110 reviews

Fall Retreat~Sleeps 14+ Hot Tub~Theater~Fire Pits

FamilyIndoor spacesTV

4.97 out of 5 average rating, 165 reviews

The image showcases a breathtaking view of snow-capped mountains under a soft glow, framed by trees in the foreground. The varying shades of green and the snow highlight the majestic peaks, creating a serene and tranquil landscape.

Home in Woodland Park

Purple Mountain Chalet, Views, Hot Tub, Game Room

KitchenIndoor spacesBackyard

4.96 out of 5 average rating, 128 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

KitchenIndoor spacesHeating

Family- and pet-friendly home rentals

Superhost

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.

4.89 out of 5 average rating, 134 reviews

Air Force proximity, fire pit, pool table

KitchenFamilyCheck-in

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

Indoor spacesFamilyCheckout

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.

4.88 out of 5 average rating, 245 reviews

Cozy, private, serene getaway in the woods

Indoor spacesFamilyParks

5.0 out of 5 average rating, 101 reviews

The family room features a comfortable arrangement of soft couches and decorative pillows, centered around a large flat-screen TV mounted above a stone-topped media console. Shelving units display various decorative items, and natural light is allowed in through recessed ceiling lights.

Guest suite in Larkspur

Views Galore & Mountain Luxury Near Palmer Lake

KitchenIndoor spacesDecor

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, 225 reviews

Off-grid, Earthen home in the forest!

FamilyKitchenLocation

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, 217 reviews

Rustic Bunkhouse in Black Forest

KitchenFamilyBackyard

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.

4.94 out of 5 average rating, 353 reviews

Private, Spacious Basement Suite in N CO Springs

KitchenFamilyParking

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, 126 reviews

The Enchanted Hobbit Cottage

Indoor spacesFamilyDecor

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, 133 reviews

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

FamilyKitchenSkiing

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, 304 reviews

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

Indoor spacesKitchenComfort

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, 165 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

KitchenFamilyNearby

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

Staycation

KitchenFamilyParks

Superhost

A spacious living area features a comfortable dark sofa and two patterned armchairs surrounding a glass coffee table. Natural light fills the room through large windows, highlighting the open concept layout that connects to the dining area and kitchen in the background.

Townhouse in Colorado Springs

4.87 out of 5 average rating, 196 reviews

Resort-Style Townhome | Pool, Hot Tub & Gym Access

KitchenFamilyParks

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!

FamilyIndoor spacesNearby

4.88 out of 5 average rating, 133 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!

Indoor spacesFamilyBackyard