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 $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,390 verified reviews to help you choose

  • 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
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.
Tiny home in Colorado Springs
4.89 out of 5 average rating, 134 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.

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, 241 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

Top guest favourite
Guest suite in Colorado Springs
4.99 out of 5 average rating, 162 reviews

Two Bedrooms Plus Full Kitchen—Steps to City Park!

Welcome to Arborview! We love living in the heart of Colorado and would love to share this amazing place with you. Enjoy your morning coffee on the private deck overlooking Cottonwood park, and then walk, ride, or take a short drive to many of the amazing sights Colorado Springs has to offer. At night, come back to your private space to unwind with a favorite dinner prepared in the full kitchen. The apartment takes up the entire lower level of our home and we live on the floors above. #STR-0627

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, 119 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 collage of charming farm animals is displayed, featuring a close-up of a dog, a pig beside a sunflower, a basket filled with eggs, a goat with kids, and a duck swimming peacefully in water. The background reveals scenic views of Pikes Peak.
Flat in Briargate
5 out of 5 average rating, 383 reviews

URBAN FARM • KING BED • no cleaning fee/no chores

Private entry, to clean and bright, lower level of home! Views of Pikes Peak! Briar Patch Urban Farm welcomes guests to a quaint homestead on 1/3 acre. Dwarf Goats, Chickens, Call Ducks, and Piggy, are some of the charming characters here - plus our Great Danes, Benny & Cowboy! 👉🏻READ ENTIRE LISTING 👉🏻ALL ADULT GUESTS MUST BE LISTED ON RESERVATION BY NAME 👉🏻$20/ADDITIONAL GUEST after 1st two 👉🏻HOST WILL CONTACT YOU UPON BOOKING 👉🏻”CHECK-IN” REQUIRES RESPONSE DAY BEFORE CHECKING IN

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
4.99 out of 5 average rating, 100 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.

Top guest favourite
A spacious, modern home with a combination of white siding and stone accents is visible. The structure features a three-car garage and an attractive, manicured front yard with landscaping elements. The surrounding area showcases wide driveways and open spaces, contributing to a serene atmosphere.
Loft in Colorado Springs
4.98 out of 5 average rating, 122 reviews

Appointed loft apt|Stunning Views|Close to USAFA

Relax in this calm, stylish space. It has its own separate entrance and is above the garage of the house. It is inviting and charming with all the comforts of home. Fully appointed with the needed items for a full kitchen, bathroom, living room and bedroom with a washer and dryer. This location is just a couple of miles from the North Gate entrance to the Air Force Academy with great views of Pikes Peak, Rampart Range, Academy Chapel. Very convenient to lots of Co Springs activities!

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, 319 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
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.
Earthen home in Colorado Springs
4.99 out of 5 average rating, 199 reviews

Off-grid, Earthen home in the forest!

*PLEASE READ FULL DESCRIPTION BEFORE BOOKING!* An eco friendly, self sustaining, off-grid Earthship home nestled into the Black Forest of Colorado Springs. A place to ground, disconnect, and fully immerse yourself in the beauty that is Colorado. This plant filled, handcrafted home is pure magic and unlike any other stay you've experienced and we are honored to share her with you. 🤗 "The richness I achieve comes from nature, the source of my inspiration" -Monet

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
4.96 out of 5 average rating, 136 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
The exterior of a modern two-story guest house is shown, featuring large windows and a combination of light and dark materials. The structure is situated amidst tall pine trees on a gravel driveway, with a single carport located beneath the upper level.
Home in Colorado Springs
5 out of 5 average rating, 201 reviews

Private Guest House in the Forest

Our family has lived on this gorgeous, treed 5-acre property for over twenty years. Back then we were considered the outskirts of town. Now we have amazing amenities just a couple of miles up the road. We've dreamed of building this guest house for years and are now proud to announce "We're open for business!" I've been designing and building custom homes for 25 years. This home represents all of my best ideas and style. You're going to love it!

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, 238 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!

Popular amenities for Gleneagle family-friendly rentals

When is the best time to visit Gleneagle?

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Avg. price$280 SGD$282 SGD$300 SGD$297 SGD$399 SGD$327 SGD$385 SGD$343 SGD$259 SGD$288 SGD$334 SGD$435 SGD
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