Family-friendly holiday rentals in Gleneagle

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 30 holiday rentals in Gleneagle

  • Nightly prices starting at

    Gleneagle holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,250 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Gleneagle holiday rentals include wifi 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 favourite
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.

Top guest favourite
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.
Home in Colorado Springs
4.95 out of 5 average rating, 215 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!

Top guest favourite
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, 262 reviews

Summer Deall! 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 favourite
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, 128 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 favourite
A spacious living room features a modern sectional couch in a neutral tone, arranged for comfort. A large TV is placed on a small console, while natural light floods the space through dual glass doors, which open to an outdoor area. A potted plant adds a touch of greenery.
Home in Colorado Springs
4.99 out of 5 average rating, 265 reviews

Family-Friendly | Cozy Modern | Convenient | USAFA

Beautifully renovated, spacious private basement suite w/ high ceilings! ☆ Enjoy two bedrooms w/ comfortable sleeping for six (king bed, queen bed & twin bunks) when you book with us! ☆ Clean & family-friendly; safe/quiet neighborhood ☆ Convenient to restaurants, shopping, attractions, & USAFA w/ easy access to I-25. Air Force Academy South Gate - 5 mins Garden of the Gods - 18 mins Cheyenne Mountain Zoo - 25 mins ☆ We are 1 mile from Chapel Hills Mall as a landmark for planning your stay.

Top guest favourite
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.
Guest house in Colorado Springs
4.98 out of 5 average rating, 119 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 favourite
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.
Camper van/Motorhome in Colorado Springs
4.9 out of 5 average rating, 364 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.

Top guest favourite
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, 339 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 favourite
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 favourite
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 favourite
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

Top guest favourite
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.
Guest house in Colorado Springs
4.94 out of 5 average rating, 208 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.

Popular amenities for Gleneagle family-friendly rentals

When is the best time to visit Gleneagle?

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Avg. price$279 SGD$257 SGD$299 SGD$300 SGD$403 SGD$330 SGD$389 SGD$346 SGD$261 SGD$291 SGD$337 SGD$439 SGD
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