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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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Top guest favorite

The historic Victorian house features a prominent turret, multiple gables, and a wrap-around porch. Lush green trees surround the property, complementing the blue exterior with shingled walls. A manicured lawn stretches in front, enhancing the classic architectural details.

Guesthouse in Colorado Springs

4.97 out of 5 average rating, 426 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.

A dining area is featured, with a wooden table and four chairs set against a stone fireplace. A cozy atmosphere is created by warm lighting and natural wood accents. The kitchenette can be seen in the background, providing easy access to meal preparation.

Home in Colorado Springs

4.88 out of 5 average rating, 446 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 kitchenette, and dining area. We have private entry and digital lock for easy check-in/out. Checkin 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!

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.

Apartment in Colorado Springs

4.92 out of 5 average rating, 429 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 cozy living room features a tufted blue sofa beside a wooden coffee table. A woven rug covers the floor, while a vibrant red door adds a pop of color. Natural light streams through nearby windows, enhancing the bright and airy atmosphere.

Cottage in Colorado Springs

4.91 out of 5 average rating, 580 reviews

▶Downtown Cottage◀ Waffle Maker┃Fast WIFI┃Grill

★Five Star cleaning team trained in disinfecting and sanitation ★Close to downtown ★Short drive to Colorado College, Garden of the Gods, Pikes Peak, USAFA ★3 blocks to local coffee, Switchback ★BRAND NEW★ comfy beds! ★Beautiful fenced in yard w/porch ★Fully loaded, spacious kitchen w/Keurig ★BUSINESS TRAVEL: FAST WIFI & KEYLESS ENTRY ★47” TV in living room w/Hulu, Netflix & Sling TV ★Beautifully designed modern space ★Family friendly ★Washer/dryer ★Driveway parking ★Free Colorado beer

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.

Guest suite in Colorado Springs

4.96 out of 5 average rating, 317 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

Top guest favorite

A cozy outdoor seating area features a round table surrounded by four chairs on a stone patio. A vibrant orange umbrella provides shade, while lush greenery and decorative elements create an inviting space. The fence adds privacy to the charming setting.

Guesthouse in Colorado Springs

4.97 out of 5 average rating, 889 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.

A hot tub is situated on the back patio, enclosed by a wooden pergola for privacy. Surrounding greenery and a well-maintained yard enhance the tranquil setting. Water bubbles invitingly within the tub, offering a serene spot for relaxation.

Guest suite in Colorado Springs

4.86 out of 5 average rating, 1,185 reviews

⫸Cozy Retreat⫷ Fire Pit┃Peloton┃Corn Hole┃Hot Tub

Cozy In-law apt perfect for just one or two people packing a punch: massive shower, fireplace, record player, Roku TV (Hulu/Netflix) & comfiest bed! ★Walk to OTC; Short drive Dwntwn, CC, Pikes Peak, USAFA, UCCS ★YARD: Hot tub, firepit, grill, speaker, yard games, Schwinn bike ★GYM: Peloton, Treadmill & Elliptical. Jump ropes, kettle bells, speaker, Roku TV+MORE! ★DESK: printer, fast WIFI, G00gle Mini & cocktail shaker ★FAMILY: PackNplay, toys, high chair ★Kitchenette: stovetop, blender+more!

An inviting entryway features a warm wooden door adorned with a glass panel. A round dining table with two wooden chairs is positioned beside a decorative wall hanging and a small wall shelf, enhancing the welcoming atmosphere of the studio.

Loft in Colorado Springs

4.9 out of 5 average rating, 145 reviews

Cozy furnished studio with all the amenities.

Nicely furnished freshly painted studio above 2 car detached garage located close to downtown, North Cheyenne Canon & Fort Carson in newer neighborhood with shared patio. Includes: central air and heat, washer and dryer in unit, full kitchen including built-in microwave, mini fridge, 2 burner cooktop, coffee maker & larger convection toaster/oven. Good sized bath with shower. Private setting with separate entrance. Great park 1 block away with picnic table, gazebo & fantastic mountain views!

A well-lit seating area features a gray armchair beside double glass doors allowing natural light. A decorative pillow rests on the chair, and a framed moose print hangs on the wall. A small table with a sign is positioned nearby.

Guesthouse in Colorado Springs

4.9 out of 5 average rating, 207 reviews

Coal Train Inn

Fort Carson is nearby!! Cute, 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!

A warm living area is presented with wood-paneled walls and a high ceiling. Two leather sofas are positioned around a wooden coffee table, while a lamp and framed artwork enhance the cozy atmosphere. Large windows allow natural light to brighten the space.

Cottage in Broadmoor

4.96 out of 5 average rating, 180 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.

Top guest favorite

A queen-sized bed with an ornate wooden headboard is positioned in the center of the room, adorned with floral bedding. Bedside tables with lamps sit on either side, and a framed landscape painting is displayed on the wall. A doorway leads to another room, enhancing the open feel.

Apartment in Colorado Springs

4.96 out of 5 average rating, 187 reviews

Golden Suite, 1BR, downtown/CC

Beautiful, spacious Victorian, private 1 bedroom suite to enjoy downtown Colorado Springs. Includes a workspace that is great for business travelers. 1 block from Colorado College, and 1 1/2 blocks from a 7-11 convenience store. Walking distance to Monument Valley Park, where you can walk, run or ride your bike! Close to the heart of downtown Colorado Springs restaurants and nightlife, and a 5-minute drive to Old Colorado City. Easy access to many attractions in Colorado Springs!

Home in Colorado Springs

4.85 out of 5 average rating, 368 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

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Popular amenities for Security-Widefield family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A hot tub is situated on a wooden deck, surrounded by tall, green trees. The bubbling water creates steam, adding a serene ambiance. Views of the forest can be glimpsed in the background, inviting relaxation and connection with nature.

Cabin in Divide

4.89 out of 5 average rating, 304 reviews

Pineridge Cabin

Guest suite in Colorado Springs

4.93 out of 5 average rating, 509 reviews

Dream Rental★Trail Access, Hot Tub, Firepit, Grill

Top guest favorite

An aerial view of two red structures highlights the Mountain Retreat guest house adjacent to the host's residence. Both buildings feature green roofs, surrounded by trees and landscaped outdoor areas. Patios with seating and vibrant flowers enhance the inviting outdoor setting.

Guesthouse in Colorado Springs

4.98 out of 5 average rating, 574 reviews

Mountain Retreat w/ Hot Tub - 500+ 5 star reviews!

A charming historic cottage is framed by a decorative iron fence. The front porch, painted in vibrant blue with red accents, invites guests to relax. Surrounding greenery and seasonal flowers enhance the cottage's appeal, while a tree provides shade to the inviting entrance.

Cottage in Broadmoor

4.98 out of 5 average rating, 177 reviews

Captain Jack's Cottage in Beautiful Cheyenne Cañon

Top guest favorite

The exterior of a charming guesthouse is displayed, featuring a welcoming covered patio adorned with vibrant flowers and hanging planters. A well-maintained garden frames the entrance, while large windows allow natural light to brighten the interior. The dual gabled roof adds character to the structure.

Guesthouse in Colorado Springs

4.99 out of 5 average rating, 275 reviews

Guesthouse 420 patio, romantic setting.

Top guest favorite

An open-concept living area is showcased, featuring a modern kitchen with granite countertops and stainless-steel appliances. Large windows offer sweeping views of the mountain landscape, while a cozy seating area invites relaxation. Natural light fills the space, enhancing its bright and airy feel.

Townhouse in Palmer Lake

4.95 out of 5 average rating, 275 reviews

The Mountain Hideaway- Views, Spa, Adventure

Top guest favorite

A charming outdoor deck area features a small table surrounded by two woven chairs, showcasing sweeping views of the surrounding mountains and clear blue sky. Lush greenery frames the scene, enhancing the inviting atmosphere for relaxation.

Home in Colorado Springs

4.97 out of 5 average rating, 382 reviews

Stunning Mtn Views, Spacious, Hot Tub, Fire Pit!

Top guest favorite

A well-equipped kitchen is shown, featuring modern stainless steel appliances and ample countertop space. Unique lighting fixtures hang above a large island, complemented by high-backed stools. Natural light filters through the windows, highlighting dark cabinetry and open shelving displaying various kitchen items.

Guesthouse in Colorado Springs

4.95 out of 5 average rating, 191 reviews

Rock Island Studio

Family- and pet-friendly home rentals

A charming log cabin is framed by lush greenery, displaying a welcoming front porch with hanging plants. The structure features natural wooden logs, a gray roof, and a stone pathway leading to it. Nearby trees provide a sense of privacy and seclusion.

Cabin in Manitou Springs

4.94 out of 5 average rating, 708 reviews

Keithley Pines Bristlecone Cabin

Top guest favorite

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.

Home in Colorado Springs

4.95 out of 5 average rating, 194 reviews

Family-friendly with stunning views and great yard

Top guest favorite

A rustic wooden cabin is nestled among snow-covered trees, presenting a serene winter scene. The building features a sloped roof and a single satellite dish, surrounded by a blanket of snow on the ground. The town of Palmer Lake is visible in the background.

Guesthouse in Palmer Lake

4.95 out of 5 average rating, 235 reviews

Quaint and Historic Studio Cabin

A spacious living area features a cozy brown leather sectional and a coffee table atop a textured rug. A wooden bookshelf filled with books is visible, along with a dining area that includes a table and chairs. Large windows provide natural light and a view of the outdoors.

Cottage in Broadmoor

4.89 out of 5 average rating, 327 reviews

Desirable Historic 1899 Cheyenne Canyon Cottage

Top guest favorite

The exterior of the house features a shaded front porch with steps leading up to the entrance. A gravel pathway extends around the home, complemented by natural landscaping and a fenced yard in the background. Tall trees provide greenery and shade.

Home in Colorado Springs

4.96 out of 5 average rating, 135 reviews

Old Colorado City Gem

The front exterior of the home is presented in evening light, showcasing a warm, welcoming entrance with steps leading up to the door. Lush landscaping features stone pathways, decorative shrubs, and a variety of plants, complemented by the glow from large windows.

Home in Colorado Springs

4.97 out of 5 average rating, 270 reviews

Excellent home and central location (STR1036)

The interior showcases an open layout with a view of the sleeping area through double doors. A cozy sofa with decorative pillows contrasts with the hardwood floors. A breakfast bar is complemented by three metal stools, and natural light streams in from a nearby window.

Guesthouse in Colorado Springs

4.95 out of 5 average rating, 254 reviews

Neighborhood Cottage

A neatly arranged bookshelf features a variety of books in multiple genres and colors. Small decorative items are placed among the books, including a potted plant and a metallic sculpture. Natural light filters through the nearby window, illuminating the space.

Guest suite in Colorado Springs

4.94 out of 5 average rating, 666 reviews

Cozy Suite w/ Kitchen, Laundry | Downtown, CC, OTC

Family-friendly home rentals with Wifi

The living room includes a comfortable brown couch, a green accent wall, and large windows allowing natural light. A chair and small table with a lamp are present, alongside a bookshelf filled with books. Decorative cushions and a light fixture add a cozy touch.

Home in Colorado Springs

4.88 out of 5 average rating, 402 reviews

Downtown Victorian Home, Fenced In Yard with Grill

A spacious living area showcases a cozy sofa adorned with colorful textiles, set against wooden log walls and warm lighting. A staircase made of natural wood curves upward, leading to the sleeping loft. Windows allow natural light to fill the space, offering views of the surrounding forest.

Guesthouse in Colorado Springs

4.93 out of 5 average rating, 182 reviews

Rustic Bunkhouse in Black Forest

A charming yellow ranch house is depicted with a welcoming front porch and contrasting blue door. Two large trees provide shade in the front yard, while a privacy fence encloses the backyard. A pathway leads to the entrance, surrounded by lush green grass.

Cottage in Colorado Springs

4.91 out of 5 average rating, 274 reviews

Updated cottage with private yard (STR-0949)

An outdoor seating area is presented, featuring a round table surrounded by six chairs. A large yellow umbrella provides shade, enhancing the comfort of the space. Light-colored walls and green trees create a refreshing backdrop for relaxation.

Home in Colorado Springs

4.9 out of 5 average rating, 123 reviews

Spacious Duplex near Olympic Training Center

Top guest favorite

A spacious bedroom features a comfortable queen bed with crisp white linens and a green throw blanket. Natural light floods through a window dressed with sheer curtains. A wooden dresser and a small table are also present in the room, enhancing the inviting atmosphere.

Guest suite in Monument

4.92 out of 5 average rating, 266 reviews

Private Lower Level Suite with Peak Views

A comfortable living area features two dark gray sofas adorned with patterned throw pillows. A light-colored coffee table sits centrally, accompanied by decorative items. Natural light fills the space through three large windows, enhancing the soft beige walls.

Apartment in Colorado Springs

4.85 out of 5 average rating, 403 reviews

Helen Hunt Hideaway - Downtown

The exterior of a charming house is presented, featuring a well-maintained lawn and attractive landscaping. Window shutters frame the front windows. A cozy seating area with two folding chairs is seen beside flower pots. Nearby, a pathway leads toward the entrance, bordered by pebbles.

Home in Colorado Springs

4.88 out of 5 average rating, 325 reviews

Cozy and convenient~ Downtown #STR-1307

The exterior of the cabin features a wooden façade with shingles, accented by green shutters and a red window. A stone pathway leads to the entrance, bordered by a small garden and mountain terrain in the background.

Cabin in Cascade-Chipita Park

4.92 out of 5 average rating, 374 reviews

Mountain Life but Close to Attractions

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

Total rentals
70 properties
Nightly prices starting at
G$10,492 GYD before taxes and fees
Total number of reviews
2.4K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi

Destinations to explore