Family-friendly vacation rentals in Castle Pines

Apartment in Colorado Springs

A charming exterior of a single-story home is displayed, featuring a front porch with white railings and steps leading to a welcoming entrance. Lush green grass and well-maintained shrubbery create a pleasant outdoor space, framed by trees under a partly cloudy sky.

4.92 out of 5 average rating, 426 reviews

Inviting English Basement Apartment

Feel very much at home on a quiet street in downtown Colorado Springs. Enjoy your private side door entrance to the apartment, a porch swing and rockers, a fire in the outdoor fireplace or a comfy leather couch in front of the big screen. Easily accommodate five and bring the kids. Parks, trails, a restaurant and coffee houses just steps away! Free and ample street parking for up to 2 vehicles. The apartment is in compliance with the Colo Spgs Short term rental ordinance, permit number STR-0115

A dedicated office nook is positioned near the staircase, featuring a modern desk with a computer monitor and a comfortable chair. A collection of board games is displayed beside the desk, providing entertainment options. Natural light is abundant, creating a bright and functional workspace.

5 out of 5 average rating, 147 reviews

Mt Views, Deck & Grill. Walk to Coffee & Ice Cream

Currently ranked in the top 5% in Colorado Springs, this vacation rental offers exceptional value & excellent ratings! Watch the video tour & see for yourself why guests love staying here. Enjoy stunning Views of the Front Range Mtns. from this spacious, duplex-style property w/ easy access to the Powers corridor, featuring a numerous of shops, restaurants & exciting recreational activities; Climbing gym, Miniature golf & an IMAX theater! Conveniently located near a Greenbelt & Pocket Parks.

Guest suite in Colorado Springs

A living area is presented with a wall-mounted television displaying streaming options. A comfortable black sofa and a red ottoman are visible. Natural light enters from a nearby window, illuminating a small desk with a chair. A cozy electric fireplace provides warmth to the space.

4.96 out of 5 average rating, 312 reviews

The Haven at Ivywild

Enjoy staying in a modern hideaway nestled in the heart of the Ivywild neighborhood. Walk just 1 block down to the popular Ivywild School. Drive 5 minutes to downtown, and less than 10 minutes to Cheyenne Cañon, the Broadmoor, the zoo, Old Colorado City and Manitou. You're in an ideal spot to explore much of the fantastic food, drink, hiking, and sights that CO Springs has to offer. Or sit back and enjoy a beautiful view of the front range mountains while relaxing on the patio. Permit: STR-0691

A family-friendly park is shown with a playground equipped with colorful structures set against a backdrop of tall pine trees and open grassy areas. Picnic tables are scattered throughout, inviting outdoor gatherings in a serene environment.

4.99 out of 5 average rating, 272 reviews

Little Modern Ranch I Garden of the Gods

The Little Modern Ranch at Garden of the Gods is tailored for the perfect vacation! This home has backyard access to a 6 acre family-friendly park which has stunning, unobstructed views of Pikes Peak! It is a perfect home to entertain including a spacious kitchen with an open living plan and every modern convenience. Just a seven minute walk to the Historic Rockledge Ranch and Garden of the Gods and only a five minute drive to Old Colorado City and Manitou Springs! (PERMIT 0390)

Home in Old Colorado City

The exterior of a charming home is visible, featuring a welcoming front porch with wooden steps and a bench. Lush greenery surrounds the property, and the colorful façade blends harmoniously with the natural landscape.

4.95 out of 5 average rating, 192 reviews

Family-friendly with stunning views & great yard

No cleaning fee! Welcome to The Purple Cottage. Fully-stocked craftsman kitchen, spacious and private backyard, and beautiful views await you. 5 minutes to downtown Colorado Springs and Old Colorado City, 11 min to Garden of the Gods, 20 min to Colorado Springs airport and the Air Force Academy. Two bedrooms and one bathroom on each floor. Perfect for a family vacation or getaway with friends. Discounts for week-long and month-long stays! Colorado Springs permit STR-0467

4.93 out of 5 average rating, 288 reviews

A spacious living area features large windows framing expansive mountain views and a wooden ceiling. A comfortable sectional sofa and a unique wooden coffee table provide seating, while a cozy armchair invites relaxation. Natural light fills the space, enhancing the warm atmosphere.

Cabin in Idaho Springs

Mountain Vacation Home with Amazing views

This cozy cabin is close to family-friendly activities. You’ll love your stay because of the the views, high ceilings, privacy and the location. The cabin is great for couples, solo adventurers, and families (with kids) There are TVs with cable in the bedrooms and living room, a hot tub to soak in and enjoy how close the stars shine. PLEASE NOTE: This Vacation home's elevation is 10800 feet. The weather is unpredictable- From September to May 4 wheel drive is required!

4.87 out of 5 average rating, 263 reviews

2 King Masters! Mtn Views *Close To AF Academy

Beautiful Custom Colorado Springs Home On 3 Acres. 2 King Master Bedrooms - separate areas of the house. Gourmet Kitchen, Large Dining & Relaxing Private Patio. 12 Minutes To Air Force Academy, 25 Minutes To Garden Of The Gods, 45 Minutes To Denver. Just north of the Air Force Academy. We often have guests here that are going to weddings/events at the Flying Horse, Younger Ranch, Spruce Mountain and Larkspur. Xbox, Foosball, Movies and board games. You'll love it!

4.91 out of 5 average rating, 428 reviews

5BR Retreat w/ Hot Tub, Gym, & Cheyenne Mtn Views!

This is the ideal 5 BDRM vacation rental on a 0.51-acre lot with stunning mountain views. Remodeled for vacationers, this property accommodates up to 12 guests. Enjoy amenities like a gym, hot tub, BBQ grill, firepit, scenic viewpoint, smoker’s patio, and playground. We’ve been awarded Super-Host status 25 times in 7 years with hundreds of glowing guest reviews. There must be a reason for that—please check the reviews! Short-Term Rental Permit Number: STR-0110

A spacious living area features a large flat-screen TV mounted on the wall, facing a comfortable seating area. The open kitchen is visible, showcasing sleek cabinetry and modern appliances, with stylish bar seating nearby. A wooden dining table accommodates several guests.

4.9 out of 5 average rating, 252 reviews

Hot Tub Springs Dream House w/ 5 KINGS - Sleeps14!

Experience a fun immaculate dream home designed with trendy mid-century decor. You'll find this home with lots of space for both kids & adults! This home was completely remodeled from head to toe, everything is new, clean, & cozy. Enjoy our 65" TV, Foosball, Ping Pong, Xbox one, & Arcade game station. No fighting over who gets the king bed - we have 5 (also 2 other bunk beds)! Duvet covers are washed after each guest stay!

4.87 out of 5 average rating, 102 reviews

A spacious outdoor deck features a collection of wooden furniture, including tables and chairs, beneath vibrant red and green umbrellas. A barbecue grill is visible in the corner, surrounded by potted plants and a view of the surrounding trees.

Home in Boulder

PERFECT GETAWAY, MOUNTAIN RETREAT WITHIN TOWN!!

Beautiful updated home in idyllic location with exceptional furnishings and fixtures with granite, stainless and amazing views. This home sits on a dead end road with privacy and modern conveniences and high speed internet.. Enjoy this mountain oasis that is just miles and minutes to town. 3 acres with Deer and Wild Turkeys roaming the property daily. The home sits at the base of the Ann U. White Hiking Trail.