Family-friendly vacation rentals in Gleneagle

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, 268 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 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✔️

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!

4.98 out of 5 average rating, 105 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, 104 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.

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, 128 reviews

The Enchanted Hobbit Cottage

An extraordinarily special place. Serene & Peaceful - Seclusion while only a few miles to Colo Springs & attractions. Pet & everything friendly. Your cottage sits on your own 3 acres, 10 acres to explore. Everything you need for a solo or couples retreat. There are playful touches everywhere (you’ll have to see it to understand). Specifically designed and built by your host – to enhance inspiration and vision. Not just pretty words, that’s the truth. Ron is first and foremost, an artist.

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

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.

4.92 out of 5 average rating, 299 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, 355 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.

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, 258 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

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, 483 reviews

Rockrimmon Retreat Hottub - FirePit - Dog Friendly

5.0 out of 5 average rating, 121 reviews

Guest suite in Monument

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

4.96 out of 5 average rating, 335 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

4.99 out of 5 average rating, 224 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

Secluded A-Frame Retreat/Hot Tub/ Cabin w-Views

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, 363 reviews

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

4.97 out of 5 average rating, 108 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, 300 reviews

The Black Forest Estate

4.97 out of 5 average rating, 129 reviews

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

Family- and pet-friendly home rentals

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, 218 reviews

Rustic Bunkhouse in Black Forest

4.98 out of 5 average rating, 141 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

4.98 out of 5 average rating, 106 reviews

4 BDRM Spacious Mountain Retreat w/ Hot Tub

4.95 out of 5 average rating, 325 reviews

Briargate Retreat, Minutes USAFA, Food & Shopping

Camper/RV 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.

Vintage Camping in Black Forest

4.9 out of 5 average rating, 373 reviews

A stone pathway meanders through a grassy yard, bordered by flowering plants. Lush greenery complements the landscape, with two clusters of blooming irises standing out. Residential homes are visible to the right, creating a peaceful neighborhood setting.

4.83 out of 5 average rating, 366 reviews

Private Studio on urban homestead Central #0633

4.95 out of 5 average rating, 250 reviews

Home in Briargate

America's Mountain Retreat

A studio apartment is shown, featuring a spacious bed with a neutral-toned blanket. A small dining area with two chairs and a table is visible. A kitchenette is equipped with essential appliances, and natural light enters through the window beside the private entrance.

4.88 out of 5 average rating, 634 reviews

Private Studio Comfort with a view

Family-friendly home rentals with a pool

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.

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

4.92 out of 5 average rating, 304 reviews

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.

4.99 out of 5 average rating, 134 reviews

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

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, 166 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

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, 157 reviews

Staycation

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.

Manitou Terrace Place - clean, cozy & convenient!

4.97 out of 5 average rating, 392 reviews

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

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

4.87 out of 5 average rating, 197 reviews

4.94 out of 5 average rating, 264 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!