Family-friendly vacation rentals in Security-Widefield

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Security-Widefield

  • Total vacation rentals

    Explore 80 vacation rentals in Security-Widefield

  • Nightly prices starting at

    Security-Widefield vacation rentals start at G$6,274 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,950 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Security-Widefield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Security-Widefield rentals

  • 4.8 Average rating

    Security-Widefield stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Security-Widefield

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

1 of 1 pages1 / 1
Top guest favorite
The open living area showcases a stylish leather sofa paired with a wooden coffee table, complemented by decorative cushions. Natural light floods the space through skylights and windows. A fully equipped kitchen is visible in the background, along with a cozy dining area.
Guesthouse in Broadmoor
4.98 out of 5 average rating, 119 reviews

Earthy Chic Casita in Prime Location

Escape to Cheyenne Casita, a newly-built, stylish, cozy, 1 bed/1 bath home. Perfectly nestled near the mountains in a vibrant, historic neighborhood in a prime location. Whether you are looking for ideal hikes, historic landmarks, or want to indulge in the best local cuisine, you are near it all. Ideal for couples, business visitors, or solo travelers—this inviting space offers the perfect blend of convenience and tranquility. Cheyenne Casita is a safe space for everyone. Permit ASTRP23-1224

Top guest favorite
A gravel driveway leads to a single-story house, which features a covered front porch with steps. The house is surrounded by trees and open space, providing a sense of privacy. A BBQ grill is positioned nearby for outdoor cooking.
Home in Colorado Springs
4.96 out of 5 average rating, 247 reviews

2 bedroom 2 bath house. Pets ok. 420 Friendly.

Cozy & Private 2 bedroom/2 bathroom house! 420 & Pet Friendly! Has a smaller sized dog door leading to fenced in area. Bigger dogs ok, just can't fit through dog door. Private off street parking. Less than 5 mins from anything you need! (Walmart, many restaurants and fast food, gas, pet store, and more) CLEAN 6 person Hot Tub. Nice massage chair. 3 TV's w/ROKU. Washer/Dryer. Queen bed, Full bed, single fold out bed. Couch lays down too. Full kitchen use w/cookware. Coffee supplied. WIFI

Guest favorite
A cozy living room is presented with two comfortable sofas adorned with a variety of decorative pillows. A low wooden coffee table is positioned on a vibrant area rug, with a television mounted on the wall opposite. Natural light filters through the window, enhancing the welcoming atmosphere.
Home in Colorado Springs
4.93 out of 5 average rating, 137 reviews

Spacious 4 Bed, Central AC, Fire Pit, Grill, Games

Spacious updated four bedroom home with two bathrooms and large yard with covered back porch, fire pit, & grill. ➜ Fully loaded updated kitchen with dishwasher, blender, mixer, waffle iron, crock pot, etc. ➜ 24 Hour Keyless Entry ➜ Pet Booking - 2x Dogs only (see rules below) ➜ 75" smart TV in living room w/streaming & local channels ➜ Close to I-25, Fort Carson, World Arena and a short drive to Garden of the Gods, Pikes Peak, Zoo and much more! ➜ Stocked with games and puzzles for family fun!.

Top guest favorite
A bright bedroom features a spacious bed adorned with an orange quilt and various decorative pillows. Soft lighting comes from pendant fixtures, adding warmth. A window, partly covered by light curtains, allows natural light to fill the room, while a small bedside table complements the decor.
Home in Colorado Springs
4.95 out of 5 average rating, 401 reviews

Wildflower Cottage | Fenced Yard | 1 mile D-Town

★ " What a beautiful cottage! A lot of effort was clearly made to make this space resonate homey comfort!" ☞ Pet friendly ☞ Fully fenced backyard w/ dog door ☞ Walk, Bike or Drive 1 mile downtown ☞ 5 mins walk → Memorial Hospital, USOTC, Memorial Park ☞ Fully fenced backyard ☞ Back patio dining, charcoal BBQ, hammock ☞ SmartTV ☞ 18 mins to Garden of the Gods, C/S Airport, Manitou ☞ Fully equipped kitchen ☞ Private parking Perfectly sized for 2 guests and a kiddo. Human and/or the furry kind!

Guest favorite
The exterior of a two-story home is shown, featuring a spacious fenced yard with green grass and decorative landscaping. A large patio area is visible, along with a second-story deck accessed by stairs. A shaded area with an umbrella is present, creating inviting outdoor space.
Home in Colorado Springs
4.91 out of 5 average rating, 191 reviews

Perfect for Families Fire Pit BBQ & Mountain Views

★Quiet Peaceful Centrally located ★Fast Wifi, keyless entry with cable TV ★5 Star cleaning disinfecting sanitation ★Short drive to Fort Carson, Cheyenne Zoo, Cheyenne State Park etc ★Walmart 10 min ★5 min. Drive to 1-25 ★Fenced in yard on Corner lot with great neighbors. ★Parking up to 6 vehicles ★Enjoy the park right across the street for morning or evening walks ★Fully equipped spacious kitchen with everything you'll need. ★Fire Pit! ★2nd story deck with amazing views of Cheyenne Mountains!

Top guest favorite
A vibrant blue house features a private outdoor hot tub, shaded by a large umbrella. Comfortable seating areas are positioned nearby on the decking, surrounded by a tall wooden fence providing privacy and a green backdrop of trees.
Cottage in Colorado Springs
4.98 out of 5 average rating, 239 reviews

The Loft House *Downtown*HOT TUB*A/C*Private House

This beautiful private home is located in a prime location, being only two blocks from downtown, yet a full neighborhood feel. Private hot tub!!Walk to dinner or coffee! Two beds are located upstairs. Fully equipped kitchen to make cooking away from home easy. Private fenced yard with seating and a grill. Smart TV and Wifi avail. Family friendly-kids items avail. upon request. Easy access to the highway and centrally located within the city will make being a tourist easy! *non smoking property*

Top guest favorite
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.
Guesthouse in Colorado Springs
4.99 out of 5 average rating, 112 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 favorite
Cabin in Colorado Springs
5 out of 5 average rating, 185 reviews

15 min to Downtown I Romantic I Hiking I Forest

Located beside a babbling creek, our 2-bed, 2.5-bath log cabin offers a unique blend of rustic charm and modern comfort. Whether you're an avid hiker or seeking a tranquil getaway, our cabin's allure lies in its intimate connection with nature. Immerse yourself in the soothing sounds of the river, explore nearby trails and unwind on the creekside deck surrounded by the forest. Warm up by the wood-burning stove in winter. Experience the magic of Cheyenne Canyon-book for an unforgettable stay!

Top guest favorite
A spacious living area features a large, light-colored couch and love seat, complemented by a coffee table with a cozy throw. Large windows allow natural light to fill the room, and the open kitchen showcases modern appliances and a dining table with chairs.
Home in Fountain
4.86 out of 5 average rating, 109 reviews

Game Room and Rooftop Deck, Stylish 3 Bedroom Home

Welcome to our beautiful and stylish home in peaceful Fountain, Co. Modern, luxurious, comfortablewith space for friends and family. Located close to Fort Carson and downtown Colorado Springs. Perfect for those looking to have all of the amenities of home while exploring Southern Colorado. Guests will be able to enjoy a relaxing environment complete with a rooftop deck and firepit. End your nights overlooking the neighborhood and scenery of the mountains enjoying fresh air and a cozy fire.

Top guest favorite
Bungalow in Colorado Springs
4.98 out of 5 average rating, 163 reviews

Luxury Escape at 5-Star Madison House in Colorado

Welcome to our charming, beautifully renovated 2BR/1BA retreat in the historic Old North End! Perfect for couples and pet lovers, our home features styled concrete flooring, luxury linens, a spa-style bathroom, arcade games, a fenced yard, and more. Walk to downtown, parks, and Colorado College! A $250 security deposit will be collected before arrival and refunded 2 days after checkout, provided there is no damage. Enjoy complimentary wine, chocolate, and a truly memorable stay!

Top guest favorite
A spacious living area is characterized by warm-toned walls and a wood ceiling, featuring large windows that invite natural light. A cozy seating arrangement includes a sofa and upholstered chairs, while a fireplace offers a central focal point. Decorative wooden elements enhance the rustic charm.
Home in Fountain
4.96 out of 5 average rating, 101 reviews

Country Barn House

Enjoy our country barn house close to city living. We have a beautiful location in fountain halfway between Pueblo CO and Colorado Springs CO. Not to far from Fort Carson and only 5 min from PPIR (Pikes Peak International raceway). Walking trails close by for a quick stroll. Fully equipped house with 2 queen beds for sleeping, fully equipped kitchen, and washer/dryer. The whole house is yours minus the garage but lots of outside parking. Enjoy the mountain view’s of pikes peak.

Top guest favorite
An outdoor seating area features a firepit surrounded by comfortable lounge furniture. A large umbrella provides shade for the dining table set with several chairs. Lush greenery is visible along the fence, and a partly cloudy sky adds to the serene ambiance.
Home in Colorado Springs
4.95 out of 5 average rating, 175 reviews

Dwntwn Bungalow w/ King Bed, Fenced Yard & Hot Tub

►Less than 1 mile from downtown ►Minutes to OTC, Short drive to Colorado College, Garden of the Gods, Pikes Peak, USAFA ►3 blocks to local coffee ►Fenced in yard with dining furniture, yard games, FIREPIT & GRILL ►Smart TVs in living room & bedroom ★BRAND NEW★ comfortable king & queen bed! ►FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys + more! ►Fully equipped kitchen ★WAFFLE MAKER★ ►BUSINESS TRAVEL: Fast WIFI, keyless entry, desk ►Free Colorado soda

Popular amenities for Security-Widefield family-friendly rentals

When is the best time to visit Security-Widefield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,933 GYDG$23,424 GYDG$26,979 GYDG$25,097 GYDG$28,652 GYDG$30,325 GYDG$30,953 GYDG$31,162 GYDG$28,025 GYDG$27,397 GYDG$27,606 GYDG$29,280 GYD
Avg. temp0°C1°C5°C9°C14°C20°C22°C21°C17°C10°C4°C0°C

Destinations to explore