Family-friendly holiday 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, 264 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

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Tiny home in Colorado Springs

An outdoor seating area is positioned under a wooden pergola, featuring a swing and a small table with two chairs. A BBQ grill is nearby on a grassy surface, with expansive sky views and surrounding grassy fields visible in the background.

4.89 out of 5 average rating, 136 reviews

Peaceful tiny home.

This memorable place is anything but ordinary. You will not regret choosing this modern tiny container home with amazing mountain views. Quiet, rural location but not too far for day trips to Colorado Springs.20 mins. to AFA, restaurants and many activities. You will have all the amenities Wi-Fi, kitchenette & BBQ grill. You will enjoy beautiful sunsets & sunrises while sitting by the fire pit. This tiny home is located on our 5 Acer property, we have a strict no pet policy. Sorry no fur babies.

Indoor spacesKitchenHospitality

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, 110 reviews

Amazing SWIM SPA, 5b/4b, FUN! 5 acres, HOT TUB!

Splash & make memories with loved ones! The gorgeous 5 acre lot boasts unobstructed mountain views. Loaded with amenities, this beautiful Colorado home has everything you need. Our newly installed 19ft long COVERED swim spa will provide endless hrs of fun for guests of all ages. 5 mins to Air Force Academy, shop & attractions, 9 mins to Ford Amphitheater, 20 mins to downtown Col Springs, 25 mins to Garden of the gods. Fantastic hangout space in the 4-car garage with air hockey, Foosball, & more!

Indoor spacesKitchenAccuracy

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.

4.9 out of 5 average rating, 131 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.

Indoor spacesFamilyLaundry

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, 120 reviews

The Enchanted Hobbit Cottage

An extraordinarily special place. Serene & Peaceful - Seclusion while still 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 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‘s first and foremost, an artist.

Indoor spacesKitchenCleanliness

Campervan/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.

4.9 out of 5 average rating, 367 reviews

Vintage Camping in Black Forest

Escape to the forest & live in a vintage 1960's camper! Featuring a kitchen with fridge, stovetop, full bed, and access to shower and laundry onsite! Conveniently located just minutes north of Colorado Springs. You are only a short drive from everything- Air Force Academy, beautiful hiking trails, & Regional Parks to name a few. Top attractions in Colorado Springs such as, Garden of the Gods, Manitou Springs, Pikes Peak & many more are only a 30 minute drive from your front door.

FamilyIndoor spacesWalkability

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, 343 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.

KitchenFamilyDecor

A dining table is set with a wooden tray displaying a bottle of wine, glasses, and a small plant. A cozy leather chair is visible in the background, with soft lighting provided by a lamp. Artwork is displayed on the wall beyond.

4.97 out of 5 average rating, 146 reviews

Peaceful Private Basmt Suite - USAFA North Springs

Entire basement suite with private entrance + lake view! This is a beautiful, clean and quiet space with self check-in. Queen size bed in large bedroom with barn door leading to living area with a eating table, mini fridge, microwave & toaster for easy meals + wet bar/sink. Large bathroom with walk-in shower. This space is perfect for 2 adults (+one baby in pack & play, available on request). Just minutes to Air Force Academy & so many restaurants!

FamilyIndoor spacesValue

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, 253 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!

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Shipping container in Monument

An outdoor deck features a private hot tub and a grill, surrounded by wooden panels and greenery. The container home is shown with large windows, reflecting natural light. Soft evening tones illuminate the space, providing a tranquil setting for relaxation.

4.96 out of 5 average rating, 107 reviews

'Honeycomb' Luxury Container w/ Sauna & Hot Tub

All-inclusive glamping retreat—no hidden fees other than taxes. The Honeycomb is a 10×20 container with queen bed, kitchenette, shower, toilet, TV, electric fireplace & private sauna. On your deck: hot tub, lounge chairs, sauna & fire pit with creek views. Enjoy $450 in free enhancements—propane, cooler & ice, outdoor bath, cold plunge, homemade wine or kombucha (you'll love it!), early check-in/out, pet & cleaning, and more.

FamilyIndoor spacesSleep quality

Cottage in Colorado Springs

An aerial view of the guest house is presented, showcasing a well-maintained exterior with a patio area featuring lounge chairs and an umbrella. Surrounded by lush greenery, the property includes a grassy lawn and a wooden fence, offering a sense of seclusion.

5.0 out of 5 average rating, 189 reviews

Black Forest Serenity

Black Forest Serenity is new guest house in the north end of Colorado Springs close to the USAFA. This beautiful, private and secluded guests house has its own driveway and access. If you are looking for some peaceful time away with time spent with loved ones, this is it! In addition there is another Airbnb guest house on the same property. Black Forest Tranquility Link is below https://abnb.me/QmYI2mTNs9

Indoor spacesKitchenGetting around

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, 210 reviews

Rustic Bunkhouse in Black Forest

Retreat from civilization in this beautiful log bunkhouse in the forest. Stroll among the ponderosa pines or sit by the lake on our sprawling 40 acres. Only 10 minutes northeast of Colorado Springs and 20 minutes to the heart of the Air Force Academy. This 1 bedroom (queen), 1 bath also has a 5-bed sleeping loft that sleeps 8 (one queen futon, two double, two single top bunks) and a full kitchen.

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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, 471 reviews

Rockrimmon Retreat Hottub - FirePit - Dog Friendly

KitchenFamilyLocation

5.0 out of 5 average rating, 120 reviews

Guest suite in Monument

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

FamilyIndoor spacesSleep quality

4.99 out of 5 average rating, 216 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

Indoor spacesKitchenLayout

4.96 out of 5 average rating, 329 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

FamilyKitchenParking

5.0 out of 5 average rating, 111 reviews

New build, private yard, CEDAR hot tub

Indoor spacesKitchenQuiet

A private hot tub is situated on a stone patio surrounded by tall trees. Comfortable seating is placed nearby, enhancing the outdoor relaxation space. The modern home's exterior is partially visible in the background, blending with the natural surroundings.

4.81 out of 5 average rating, 110 reviews

Whispering Pines Home w/ Hot Tub, 3.8m to USAFA

FamilyIndoor spacesValue

4.88 out of 5 average rating, 137 reviews

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.

Home in Monument

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

Indoor spacesFamilyParks

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, 216 reviews

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

Indoor spacesFamilyBathroom

Family- and pet-friendly home rentals

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, 240 reviews

Cozy, private, serene getaway in the woods

Indoor spacesFamilyLayout

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, 219 reviews

Off-grid, Earthen home in the forest!

Indoor spacesFamilyView

Bungalow in Colorado Springs

4.98 out of 5 average rating, 167 reviews

Luxury Escape at 5-Star Madison House in Colorado

Indoor spacesKitchenHospitality

Apartment in Old Colorado City

A spacious backyard features a fenced area with a children's climbing structure and outdoor dining space. Comfortable chairs are positioned around a grill, alongside a pebbled path leading through the yard, surrounded by greenery and trees.

4.93 out of 5 average rating, 561 reviews

★OCC Getaway★ Firepit, Grill, Backyard + Firestick

KitchenFamilyCleanliness

4.98 out of 5 average rating, 103 reviews

4 BDRM Spacious Mountain Retreat w/ Hot Tub

KitchenFamilyParking

A spacious hot tub is situated under a wooden pergola, surrounded by a wooden deck. Bubbling water reflects natural light, and distant mountain views are visible through trees in the background, providing a serene atmosphere.

4.91 out of 5 average rating, 310 reviews

✔Pets✔ ♕King Bed/Bath/Kitchen ♨Hot Tub♨ w views 🏞

Indoor spacesFamilyBathroom

Cottage in Old Colorado City

A modern kitchen features sleek gray cabinetry and a stylish backsplash with a mosaic pattern. An island with seating is complemented by pendant lighting. Appliances include a microwave and refrigerator, and natural light fills the space through a window.

4.97 out of 5 average rating, 601 reviews

Walk | Shop | Dine | Cottage @ Garden of the Gods

KitchenFamilyComfort

4.98 out of 5 average rating, 282 reviews

Cabin in Florissant

Retreat at Mydnyt Mountain•Hot Tub•No Chores

Indoor spacesKitchenCheckout

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.

4.92 out of 5 average rating, 296 reviews

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

Indoor spacesKitchenPets

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

FamilyKitchenHeating

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

FamilyKitchenLocation

Townhouse in Colorado Springs

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.

4.87 out of 5 average rating, 195 reviews

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

FamilyIndoor spacesPool

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, 153 reviews

Staycation

KitchenFamilyNearby

4.94 out of 5 average rating, 259 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!

KitchenIndoor spacesBarbecue

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!

FamilyKitchenLaundry

An aerial view of the private mansion highlights its spacious layout, surrounded by greenery and outdoor recreation areas. In another image, the indoor heated pool area is shown with large windows, allowing natural light and showcasing views of the surrounding landscape. A hot tub is featured with a serene backdrop of rolling hills and sunset colors. The final image displays stunning views of the mountains from a deck, emphasizing the tranquil environment.