Family-friendly holiday rentals in Gleneagle

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, 222 reviews

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

Stay in our Newly Built Family Home ✔ 4,800 sq ft Home, Perfect for Longer Stays & Families ✔ Professionally Cleaned & Sanitized ✔ 6-person Hot Tub, Gas Fire Pit & deck with Mountain Views ✔ King Size Bed 🗲Fast WiFi - Ideal for Working Remotely ✔ Fully Equipped Kitchen Upstairs, Kitchenette Downstairs ✔ In-Suite Washer & Dryer ✔ Theater Room with Complementary Netflix on all TVs ✔ 15 Minutes from USAF Academy We know you'll love your stay. Book today to reserve our beautiful home in the woods!

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, 266 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

4.98 out of 5 average rating, 103 reviews

USAFA area/Private & Spacious Suite/Self Check-in

Perfect location for US Air Force Academy families and visitors. Spacious suite/high-quality finishes. Private entrance through the back door patio. Safe & friendly community. Abundant choice of restaurants, outdoor entertainment, and shopping. Built with the comfort of our guests in mind. Bedrooms: premium, comfortable mattresses+pillows, blackout curtains, closets. Kitchenette: microwave, coffee maker, mini-fridge. Free snacks, coffee, creamer, tea. Patio sitting. COS Permit # A-STRP-23-1492.

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

Every 10th stay is donated to Habitat for Humanity to help build homes across the Country. Have fun with the whole family at this spacious place. There are 7 bedrooms that comfortably sleep 14 people PLUS a crib and pack and play for your little ones. We have stocked the house to include everything you need for a large group to cook, entertain, and enjoy your time together. Enjoy time in our backyard with our fire pit or grill and outdoor dining for your crew. Must be 25+ to book. No parties.

4.96 out of 5 average rating, 102 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.

Superhost

A spacious dining area features a long wooden table surrounded by six chairs, complemented by a wooden bench. Large windows provide ample natural light and forest views, while a staircase with decorative railings leads to the upper level. A deer mount is displayed on the wall.

4.93 out of 5 average rating, 194 reviews

Majestic Tall Pines Home w/Hot Tub + 3.8m to USAFA

Welcome to the impeccably styled Tall Pines! Located in a quiet neighborhood that offers the full getaway experience, this beautiful home is less than 4 miles to USAFA. Great family activities & restaurants are minutes away plus Fox Run Park is within walking distance. Inside, the spacious residence offers plenty of room for the entire group with a cozy living room, large kitchen, 4 inviting bedrooms and 2.5 baths. Outdoor living includes a hot tub, firepit, Adirondack patio, & forest views.

4.92 out of 5 average rating, 298 reviews

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.

Guest suite in Monument

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.

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, 352 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. No large dogs are allowed.

4.98 out of 5 average rating, 106 reviews

4 BDRM Spacious Mountain Retreat w/ Hot Tub

• 🌄 Spacious mountain retreat with large deck, hammocks, fire table, outdoor grill and private hot tub for starry Colorado nights. • 🏡 Roomy multi‑bedroom home to sleep up to 14 with open kitchen, big dining table, and multiple living areas so everyone can spread out. • 🎓 Minutes to the US Air Force Academy, 💍 near several wedding venues, and 🚗 a short drive to Garden of the Gods, top local hikes and close to dining, shopping, breweries, and groceries.

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.

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, 256 reviews

Breathtaking Mountain Views | Hot Tub | Near USAFA

Amazing mountain views of Pikes Peak and the Air Force Academy Chapel from almost every room in this beautiful home! 7-person hot tub on paver patio! Located at the edge of the forest in Northern Colorado Springs on the border of Monument. 10 minutes from USAFA! Sleeps 12 in beds (up to 16 with queen air mattress and two pack 'n plays). We are family friendly with two pack 'n plays and a highchair. Home is also air-conditioned!

4.99 out of 5 average rating, 103 reviews

Your COLORADO Home, 5 Min from AIR FORCE ACADEMY

Less than 5 minutes from the Air Force Academy North Gate entrance, great restaurants, coffee shops, grocery stores & shopping. Ranch Style Home with 5 bedrooms & 3 full bathrooms. Great place to stay for USAFA events, multi-family vacations, business travelers, holidays, weddings and more. Located in a quiet neighborhood with CLOSE & EASY access to I-25!

Popular amenities for Gleneagle family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 120 reviews

Guest suite in Monument

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

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, 479 reviews

Rockrimmon Retreat Hottub - FirePit - Dog Friendly

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

4.97 out of 5 average rating, 107 reviews

Mountain Retreat | 5 Acres, Hot Tub, 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.

4.95 out of 5 average rating, 296 reviews

The Black Forest Estate

4.98 out of 5 average rating, 163 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

The kitchen features wood cabinetry and granite countertops with a modern stainless-steel refrigerator and microwave. A double oven is installed beneath the countertop. The adjacent dining area showcases a wooden dining table surrounded by curved-back chairs, providing a welcoming space for meals.

4.98 out of 5 average rating, 362 reviews

The Memory Maker! 2 King Beds + Garage & Hot Tub!

4.97 out of 5 average rating, 127 reviews

Mountainview, 6 Kings, 5 baths, Hot Tub, Sleeps 14

Family- and pet-friendly home rentals

Guest house 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, 215 reviews

Rustic Bunkhouse in Black Forest

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.

4.88 out of 5 average rating, 245 reviews

Cozy, private, serene getaway in the woods

4.95 out of 5 average rating, 325 reviews

Briargate Retreat, Minutes USAFA, Food & Shopping

4.98 out of 5 average rating, 140 reviews

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.

Home in Monument

Spacious 2 Bedroom Basement w/ Kitchenette & Patio

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!

Camper van/Motorhome in Colorado Springs

A vintage 1960s camper is positioned amid a forested area, featuring a small outdoor deck with potted plants. A grill is placed nearby, and trees provide a natural backdrop, enhancing the tranquil setting.

4.9 out of 5 average rating, 373 reviews

Vintage Camping in Black Forest

4.95 out of 5 average rating, 400 reviews

Pet-Friendly - Game Room+Arcade - Mountain Views

The exterior view captures a spacious home nestled among the pines, highlighted by a wraparound deck. The design features a combination of red wood and grey siding. Surrounding natural landscapes provide a serene backdrop, enhancing the secluded feel of the property.

4.93 out of 5 average rating, 180 reviews

Sleeps 12 w/ Hot Tub! Hiking!

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

4.92 out of 5 average rating, 304 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, Pool, Bball court

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, 164 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

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

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!

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!

Home in Garden of the Gods

4.98 out of 5 average rating, 40 reviews

Indoor POOL, Hot Tub, Sauna! Garden of the Gods

An open living space showcases wooden cabinetry and a high ceiling with exposed beams. A spacious seating area includes a sectional couch and a coffee table. A dining table that seats six is visible, along with a wood-burning stove providing warmth.