Family-friendly vacation rentals in Security-Widefield

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Security-Widefield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Colorado Springs

4.97 out of 5 average rating, 381 reviews

Private Carriage House, walk to downtown Co Spgs

Permit# A-STRP-22-0164 The Carriage House is located on a beautiful property adjacent to an 1889 Queen Anne Victorian, loaded with charm and character. It's two blocks south of Colorado College, walkable to downtown Colorado Springs, restaurants and dining, nightlife, public transportation nearby, and a 5-min drive to Old Colorado City. You’ll love the neighborhood, walkable to the urban city center, and private entrance. Our place is good for couples, solo adventurers, and business travelers.

Jan 31 – Feb 7

G$17,288 GYD per night

Guest favorite

Guest suite in Colorado Springs

4.97 out of 5 average rating, 258 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

Oct 13 – 20

G$18,540 GYD per night

Guest favorite

Guest suite in Colorado Springs

4.91 out of 5 average rating, 362 reviews

Hiking | Dining | Nightlife in Historic Ivywild

★ 2 miles to Downtown ★ 2 miles to Cheyenne Canon (tons of hiking) ★ 1.3 miles to 5 star Broadmoor Hotels (conference center) ★ 10 minute walk to the Historic Ivywild School (restaurants, cocktails, and local beer) ★ Quick drive to CO College, Garden of the Gods, Pikes Peak, USAFA, UCCS ★ Equipped kitchen w/ coffee maker, water kettle, coffee/tea and more! ★ Family Friendly: Pack 'n play, Baby monitor, and booster seat ★ WORK TRAVEL: FAST WIFI and designated desk space ★ 5 star cleaning rating

Oct 17 – 24

G$24,493 GYD per night

Guest favorite

Guesthouse in Colorado Springs

4.91 out of 5 average rating, 198 reviews

Coal Train Inn

Fort Carson! This cute, newly remodeled, 1 bedroom guesthouse is conveniently located near Ft Carson, and just minutes to downtown Colorado Springs. Lots of restaurants and shopping nearby and just 3 minutes from I-25, the gateway to the Rockies. Hike Cheyenne Canyon, Helen Hunt Falls, or Garden of the Gods. Visit the 5 Star Broadmoor Resort, or gamble in Cripple Creek (1 hr). So much to see and do! Our guest guide found inside the guesthouse will give you more ideas of things to do nearby.

Jan 13 – 20

G$26,308 GYD per night

Guest favorite

Home in Colorado Springs

4.9 out of 5 average rating, 402 reviews

Springs Hideaway 2 BR Spacious suite

Welcome to our lower-level Airbnb retreat! Nestled in a quiet area near most popular attractions, this space offers two bedrooms: one with a full-size bunk bed, the other with a cozy queen bed. Enjoy modern amenities like a washer/dryer, fully equipped kitchen, and dining area. We have private entry and digital lock for easy check-in/out. Check-in at 4:00 pm, check-out at 11:00 am. We observe quiet time from 10:00 pm to 6:00 am, ensuring a peaceful stay. The kitchen is ready for your needs!

Sep 26 – Oct 3

G$16,016 GYD per night

Guest favorite

Apartment in Colorado Springs

4.95 out of 5 average rating, 129 reviews

Quiet apartment with a view! STR-0944

Very clean private space! Area is cleaned and wiped down with disinfectant after every stay. Kitchen (private not shared), living and dining area is open concept. Kitchen has a full refrigerator, stove/oven, and dishes. Refrigerator will have fresh eggs to enjoy. Located on the east side of the Colorado Springs near many restaurants and stores. 1/2 mile from Walmart, across the street from a playground, 5.4 miles from Colorado College, 17 miles from Air Force Academy. Non smoking/non 420

Apr 13 – 20

G$22,991 GYD per night

Guest favorite

Guesthouse in Colorado Springs

4.97 out of 5 average rating, 812 reviews

Cozy Solar Cottage on the West Side

My cottage is centrally located, close to downtown--within walking distance. Garden of the Gods, road to Pikes Peak, & Colorado College are minutes away. The interior is quaint and cozy, but has a roomy kitchen, fully stocked for preparing food. The outdoor space is peaceful and relaxing. I have a detailed list of restaurants & things to do. You'll love the access to an urban trail (Monument Valley), comfy queen bed, & coffee. A coffee shop and breakfast place are within walking distance.

Apr 4 – 11

G$15,690 GYD per night

Guest favorite

Apartment in Colorado Springs

4.92 out of 5 average rating, 332 reviews

Creek's Edge Apt & Big Mtn Views rare for downtown

A creek runs through it! 1888 Victorian garden level walkout w/ private entrance. Upstairs Apt is a separate listing. (See extra photos/info on IG @red.house.green.roof). Your own patio & clover lawn for chillaxing, complete with very comfortable hammocks. Unusual XXL property feels very secluded. Bikes, firepit, cornhole, massive grape arbors. Nice balance of city/nature on the creek, train, bike path greenway & I-25 corridor. *SUPER CLEAN*SUPER CUTE*SUPER HOST* 420 friendly (outdoors)

Oct 21 – 28

G$25,175 GYD per night

Guest favorite

Cottage in Colorado Springs

4.96 out of 5 average rating, 157 reviews

Nestled in scenic Bear Creek Canyon.

This cozy cabin in the foothills is only minutes from Old Coloado City, Manitou Springs, Garden of the Gods and down town Colorado Springs. Located just a few minute walk from section 16 trail head on one side and Bear Creek Regional Park on the other. Built in 1899 this is one of only 22 homes in Bear Creek Canyon. This cabin has high speed internet and cable, 50 inch TV and dvd player for nights inside. A great seating area and green house for enjoying beautiful views outside.

Nov 11 – 18

G$28,826 GYD per night

Guest favorite

Guest suite in Colorado Springs

4.95 out of 5 average rating, 592 reviews

Quiet 2 BR w/ Kitchen, Near CC, OTC & Downtown

Unwind in the open concept of this loft-style apartment where mountain views await you on the balcony, only a mile or so from Downtown and Colorado College. The Olympic Training Center is under 1.5 miles away, too! Take a morning stroll to a nearby café and enjoy the peace and quiet of our neighborhood. You'll have the place to yourself, with a full kitchen and enough space to stretch out after a day exploring Colorado Springs. We hope you enjoy your visit to Colorado Springs!

Jan 13 – 20

G$25,497 GYD per night

Guest favorite

Guest suite in Downtown Colorado Springs

4.89 out of 5 average rating, 226 reviews

Modern Downtown Escape

This freshly updated dual family home was originally built in 1890. The 800 sq/ft upper unit is independent of the lower unit. This two BR/1 BA fully furnished home is ready for your next visit to CO. Located four blocks east of downtown, with quick access to I-25 and Hwy 24 you will be poised to adventure the region's many attractions in minutes. If relaxing at your home away from home is your goal; enjoy this beautiful modern style getaway. A-STRP-22-0189.

Nov 24 – Dec 1

G$23,749 GYD per night

Guest favorite

Home in Colorado Springs

4.95 out of 5 average rating, 155 reviews

Welcome Home: Vintage 1894 centrally located

We are pleased to welcome you to Colorado Springs! Our place is ideal for a vacation getaway, business trip, or home base for adventure! Be treated to vintage-inspired décor with just the right touches of modern. The home is centrally located with easy access to highways, very close to Colorado College, and just minutes from the extensive trail system and outdoor recreation opportunities. Our place is not appropriate for children, pets, or parties of any kind.

Aug 17 – 24

G$23,766 GYD per night