Family-friendly vacation rentals in Security-Widefield

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)

Superhost

4.84 out of 5 average rating, 361 reviews

Family Nature Retreat ★Equipped Kitchen★ ★Firepit★

★Five Star cleaning team trained in disinfecting and sanitation ★LOCATION: On ten acres in COS towards the Royal Gorge and Canon City. Minutes to Fort Carson & Olympic shooting range. Short drive to downtown, Garden of the Gods, Pikes Peak, USAFA ★Grill & gas firepit ★Movie projector w/Apple TV ★Game room w/dart board, games, books and toys ★Wood stove fireplace ★Equipped kitchen: coffee maker, waffle maker, popcorn maker, mixer, blender, pots, pans, toaster & more ★Garage

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

4.87 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 bright and airy entryway features light-colored walls complemented by warm wood flooring. A painting of autumn trees hangs above a railing, which overlooks a cozy living area. A stylish trash bin is positioned nearby, contributing to the home's modern design.

4.92 out of 5 average rating, 175 reviews

Peaceful Perfectly Located Updated 3 Bed Home

Newly updated 3 bedroom home in quiet cul-de-sac that can sleep up to 8 people. The home is in an ideal location on the central west side. Easy access to I-25 and downtown. 5-10 to Old Colorado City, Manitou Springs and Garden of the Gods. Attractions such Pikes Peak, Cave of the Winds,Air Force Academy are less than 20 minutes away. Great patio with mountain views. Dog friendly no cats please. Short term rental permit #456.

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!

Superhost

A modern bathroom features a glass-enclosed shower with textured tile walls, creating a clean and contemporary look. A white vanity with silver fixtures complements the space. A framed sign with the phrase 'Rise + Shine' is displayed on the wall above the sink.

Townhouse in Old Colorado City

4.93 out of 5 average rating, 153 reviews

Winter SALE! Beautiful Farmhouse Retreat

Casa Claudio Colorado is centrally located and close to downtown Colorado Springs, Air Force Academy, Garden of The Gods, Manitou Springs, located in Old Colorado City, and only 20 minutes to the Colorado Springs airport. You’ll love this completely renovated condo. It is great for couples, solo adventurers, business travelers, and families (with kids).