Family-friendly vacation rentals in Gleneagle

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Gleneagle

  • Total vacation rentals

    Explore 30 vacation rentals in Gleneagle

  • Nightly prices starting at

    Gleneagle vacation rentals start at G$16,705 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,250 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Gleneagle vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Gleneagle rentals

  • 4.9 Average rating

    Gleneagle stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Gleneagle

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A tiny container home is illuminated at dusk, showcasing a cozy entrance beneath a wooden pergola with string lights. The surrounding landscape features grassy areas and a distant wooden fence, set against a dramatic blue sky with clouds.
Tiny home in Colorado Springs
4.9 out of 5 average rating, 170 reviews

Charming Tiny Home Getaway

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.

Guest favorite
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.
Home in Colorado Springs
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!

Top guest favorite
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.
Guest suite in Colorado Springs
4.99 out of 5 average rating, 263 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

Guest favorite
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.
Home in Colorado Springs
4.91 out of 5 average rating, 129 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.

Top guest favorite
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.
Guesthouse in Colorado Springs
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.

Guest favorite
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.
Home in Colorado Springs
4.81 out of 5 average rating, 110 reviews

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

Welcome to Whispering Pines! Located in a quiet neighborhood that offers the full Colorado 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, 3 inviting bedrooms, 2.5 baths & Game Room. Outdoor living includes a hot tub, firepit, deck & amazing forest views.

Top guest favorite
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.
Guesthouse in Colorado Springs
4.87 out of 5 average rating, 238 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.

Top guest favorite
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.
Guest suite in Colorado Springs
4.94 out of 5 average rating, 342 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.

Top guest favorite
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.
Guest suite in Colorado Springs
4.97 out of 5 average rating, 145 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!

Top guest favorite
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.
Home in Colorado Springs
4.99 out of 5 average rating, 252 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!

Top guest favorite
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.
Cottage in Colorado Springs
5 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

Guest favorite
Cottage in Colorado Springs
4.94 out of 5 average rating, 609 reviews

Visit Co Spngs at Country Cottage 'Cross the Creek

This bright and beautiful farm country Cottage is perfect for relaxing with family and friends. Surrounded by towering trees, a creek and nature, this guest house is Colorado country close to the city. High ceilings, newly renovated everything and charming brocante decor create a serene, welcoming atmosphere. Come experience the best of Colorado Springs while staying in this one of a kind property!

Popular amenities for Gleneagle family-friendly rentals

When is the best time to visit Gleneagle?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$45,105 GYDG$41,555 GYDG$48,237 GYDG$45,105 GYDG$46,984 GYDG$71,416 GYDG$62,854 GYDG$55,963 GYDG$42,181 GYDG$46,984 GYDG$54,502 GYDG$70,998 GYD
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