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!

KitchenIndoor spacesLayout

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. 😊

Indoor spacesKitchenParking

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, 139 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.

Indoor spacesFamilyPets

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!

Indoor spacesFamilyCleanliness

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!

FamilyIndoor spacesDecor

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

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.

FamilyKitchenView

4.94 out of 5 average rating, 356 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.

Indoor spacesFamilyBathroom

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.

FamilyIndoor spacesDecor

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!

FamilyIndoor spacesBathroom

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.

Indoor spacesKitchenAccuracy

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

Splash, play and make memories together on this beautiful 5-acre Colorado property with unobstructed mountain views. Enjoy the covered 19-ft swim spa, air hockey, Foosball and spacious 4-car garage hangout area. Families will appreciate the Pack ’n Play and highchair, while a dedicated workspace adds convenience. Just 5 min to USAFA, 9 min to Ford Amphitheater, 20 min to Downtown Colorado Springs and 25 min to Garden of the Gods.

KitchenIndoor spacesSkiing

Popular amenities for Woodmoor family-friendly rentals

Kitchen

Wifi

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, 225 reviews

Private House in the Forest

KitchenFamilyWi-Fi

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, 220 reviews

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

KitchenIndoor spacesLayout

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

Indoor spacesKitchenComfort

A stone fire pit is surrounded by several lounge chairs on a sunlit patio. The area features lush landscaping and a turf putting green with expansive mountain views in the background under a clear blue sky.

4.88 out of 5 average rating, 139 reviews

Falcon's Nest | hot tub/games/mins to USAFA&hiking

FamilyIndoor spacesSleep quality

4.97 out of 5 average rating, 106 reviews

Mountain Retreat | 5 Acres, Hot Tub, Views

FamilyKitchenQuiet

4.97 out of 5 average rating, 308 reviews

Cabin in Divide

Secluded Mountain Home w/ Hot Tub, Deck & Fire Pit

Indoor spacesFamilyBackyard

4.98 out of 5 average rating, 142 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

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

Indoor spacesFamilyParks

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

FamilyIndoor spacesAccuracy

Family- and pet-friendly home rentals

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, 223 reviews

Off-grid, Earthen home in the forest!

KitchenFamilyHeating

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, 133 reviews

Air Force proximity, fire pit, pool table

FamilyKitchenTV

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

FamilyIndoor spacesCheck-in

Guesthouse in Colorado Springs

A cozy cabin features a distinctive sloped roof and is surrounded by tall trees. The exterior is constructed from natural wood, complementing the forest setting. A stone fire pit and several outdoor benches are positioned in front of the cabin, providing a welcoming outdoor space.

4.95 out of 5 average rating, 146 reviews

Cozy Fishing Cabin in Black Forest

KitchenIndoor spacesAir conditioning

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

KitchenIndoor spacesComfort

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

Indoor spacesKitchenLaundry

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, 349 reviews

Private, Spacious Basement Suite in N CO Springs

FamilyIndoor spacesCleanliness

4.93 out of 5 average rating, 126 reviews

A bright living area is highlighted by large windows allowing natural light to fill the space. Comfortable seating is positioned near the windows, while a round dining table is set for meals. A well-equipped kitchen is visible in the background, featuring modern appliances.

Loft in Palmer Lake

Crow's Nest

FamilyKitchenCleanliness

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

KitchenFamilyView

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, 301 reviews

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

Indoor spacesFamilyPool

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, 387 reviews

Manitou Terrace Place - clean, cozy & convenient!

FamilyKitchenBreakfast

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, 163 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

Indoor spacesKitchenAir conditioning

4.88 out of 5 average rating, 112 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.

Apartment in Castle Rock

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

Indoor spacesFamilyGetting around

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!

KitchenFamilyLayout

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

FamilyIndoor spacesGetting around