Family-friendly holiday rentals in Security-Widefield

4.96 out of 5 average rating, 180 reviews

Turquoise Door, Spacious Duplex, 3 Kings near AFA

Thank you for considering our 3-bedroom duplex conveniently located near the Air Force Academy and other Colorado Springs attractions & restaurants. Sleeps 8 with 3 king and 2 twin beds. Before hitting that "book now" button, pretty please, read the ENTIRE listing. Yep, the whole thing! We promise it’s not War and Peace. As committed hosts, we want your stay in Colorado Springs to be terrific from start to finish. Reading the full listing is key to a relaxing stay and less stress for us both! 😁

4.92 out of 5 average rating, 427 reviews

Flat in Colorado Springs

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

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

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

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

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

4.88 out of 5 average rating, 264 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, 429 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

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.