Family-friendly vacation rentals in Security-Widefield

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.

4.96 out of 5 average rating, 244 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

Home in Old Colorado City

A fenced backyard showcases a cozy firepit surrounded by six woven chairs. A playset with a slide is visible, and warm patio lights add ambiance. The space is adorned with lush turf, providing a comfortable area for outdoor activities.

4.83 out of 5 average rating, 426 reviews

»Good Vibes Villa« HotTub┃Waffle Maker┃Fenced Yard

★Fenced in yard w/fire pit, grill, hot tub, play set + outdoor games★ ►72" Smart TV w/Apps like Netflix ►BRAND NEW comfortable beds ►FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys + more! ►BUSINESS: Fast wifi, keyless entry, charging cords + TWO desk areas ►Equipped kitchen: waffle maker, blender, coffee maker, bread maker, french press + more! ►4 min walk to local coffee shop ►1 mile to dwntwn COS ►Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA, UCCS

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.

4.95 out of 5 average rating, 394 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!

Apartment in Old Colorado City

A spacious backyard features a fenced area with a children's climbing structure and outdoor dining space. Comfortable chairs are positioned around a grill, alongside a pebbled path leading through the yard, surrounded by greenery and trees.

4.92 out of 5 average rating, 546 reviews

★OCC Getaway★ Firepit, Grill, Backyard + Firestick

★Attractively located on the west side, 1 mi to downtown OCC, 1.5 mi to downtown COS ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Fenced in Backyard with fire pit, children's climbing structure, outdoor dining & grill ★BRAND NEW★ comfortable beds! ★Fully equipped kitchen w/blender, toaster, coffee maker, etc ★BUSINESS TRAVEL: FAST WIFI, Alexa, phone charging station, keyless entry ★FAMILY FRIENDLY: Pack N Play, Toys/Games & High chair ★TV w/Amazon firestick (Hulu/Netflix)

4.96 out of 5 average rating, 191 reviews

The entrance features a bright yellow exterior with blue accents, including a door framed by two potted plants. A spacious wooden deck with stairs is shown, bordered by a white railing and surrounded by greenery, creating a welcoming outdoor space.

Bungalow in Broadmoor

The Cozy Yellow Cottage

Tucked away in a mostly quiet alley in a super eclectic neighborhood, this tiny house was built before 'Tiny Houses' were even a thing. This remodeled and charming 626.5 square foot house is ALL YOURS! Close to downtown Colorado Springs, Ivywild School, the Caffeinated Cow, a library, restaurants, shopping, hiking and biking trails, leisurely and safe neighborhood walks- the sky is truly the limit on what adventures await you! City of Colorado Springs Short Term Rental Permit #A-STRP-22-0086

A spacious living area is visible with a large sectional sofa, a coffee table, and a flat-screen TV. Natural light is allowed in through the windows, enhancing the welcoming environment. An elegant dining area is adorned with a wooden table and tasteful decor.

4.89 out of 5 average rating, 288 reviews

"Central Springs" 4BR/2Bath Home GREAT Location

You will LOVE your stay in this 4 bedroom, 2 bathroom, fully furnished, clean home. This house is perfect for big groups or small. It has Central Heat & Air, full kitchen, BBQ in back, & is in a safe neighborhood. ~11 mins: COS airport ~18 min: downtown Colorado Springs ~25 mins: Garden of the Gods ~25 mins: Manitou Springs ~3 mins: shopping/grocery ~35 mins: Air Force Academy ~18 mins: Cheyenne Mt State Park ~15 mins: Fort Carson ~15 min: Peterson Air Force Base ~2.5 hours: Ski Resorts

A private hot tub is positioned in a fenced yard, surrounded by green turf. Soft lighting from patio string lights and lanterns creates a serene evening atmosphere. Steam rises from the tub, indicating warmth and comfort.

4.96 out of 5 average rating, 206 reviews

Private Basement*HotTub*Washer+Dryer*Full Kitchen*

✔Attractively located on the east side, in a cozy neighborhood near parks, restaurants, shopping, & grocery stores ✔Walking distance to Vibes' field (local COS baseball team) ✔Short drive to Pikes Peak, USAFA, Fort Carson, Fort Peterson, UCCS, COS Airport ✔Private yard with hot tub ✔Private entrance & keyless entry ✔AC ✔70” & 42" Roku TVs in living & bedroom ✔Washer & Dryer ✔Full kitchen: Keurig, oven & range, microwave, dishwasher, toaster, etc. Short Term Rental Permit #: A-STRP-23-0389

4.85 out of 5 average rating, 428 reviews

Nature Retreat: Hot Tub, Fire Pit + Projector

★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 ★Hot Tub ★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

Cabin in Cascade-Chipita Park

4.99 out of 5 average rating, 250 reviews

Serene Riverside Cabin: Hot Tub, Fire Pit, Patio

With a river in the backyard next to the private hot tub and massive gas fire pit for all of your party, what more could you need?! If you love watching local wildlife cross over a creek on a luxurious back patio that’s perfect for all seasons, then you should book here. Enjoy the full amenities of a kitchen stocked with a curator’s touch, heated towel rack, remote control gas fireplace, gas grill, 2023 top-to-bottom remodel. Book RiverHouse North, by Forest & Peak Retreats, today!

Camper/RV in Colorado Springs

A vintage 1960s camper is positioned amid a forested area, featuring a small outdoor deck with potted plants. A grill is placed nearby, and trees provide a natural backdrop, enhancing the tranquil setting.

4.9 out of 5 average rating, 358 reviews

Vintage Camping in Black Forest

Escape to the forest & live in a vintage 1960's camper! Featuring a kitchen with fridge, stovetop, full bed, and access to shower and laundry onsite! Conveniently located just minutes north of Colorado Springs. You are only a short drive from everything- Air Force Academy, beautiful hiking trails, & Regional Parks to name a few. Top attractions in Colorado Springs such as, Garden of the Gods, Manitou Springs, Pikes Peak & many more are only a 30 minute drive from your front door.

Guesthouse in Colorado Springs

4.95 out of 5 average rating, 159 reviews

A-Frame Country Cabin

A-frame cabin is situated on a 5-acre rural property just beyond the city limits - it is a detached mother-in-law suite, located 200 ft from our main residence. The cabin includes a loft w/a queen-sized bed, a single pullout couch, & a mini kitchen. It faces eastward, away from the mountains. Ideal for those seeking a peaceful countryside retreat, note that access to the bedroom is via a spiral staircase, and the property is serviced by well water. Owner maintained & operated.

A secluded patio area features four Adirondack chairs arranged around a smokeless firepit, with a warm fire burning brightly. A stone wall provides privacy and greenery from nearby trees enhances the tranquil environment.

4.95 out of 5 average rating, 427 reviews

Historic Craftsman ★ Fire pit┃Waffle Maker┃Near CC

✓LOCATION: Walk to Switchback Coffee┃1.0 mi to Colorado College┃1.5 mi to downtown┃Short drive to Garden of the Gods, Pikes Peak, USAFA ✓OUTDOORS: Sit under the string lights on a private fenced in patio w/smokeless firepit & grill ✓ENTERTAINMENT: Movie loft & living room w/Roku TVs, fast WIFI & games ✓EQUIPPED KITCHEN: Keurig, Chemex, waffle maker, blender, etc ✓FAMILY FRIENDLY: Pack N Play, high chair, stroller, toys, monitors +more ✓Mountain views ✓Complimentary local soda

Popular amenities for Security-Widefield family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern living area features a sectional couch facing a wall-mounted television. A sleek fireplace below adds warmth, while natural light enters through glass doors leading to the outdoor space. Decorative plants are placed on shelves, enhancing the ambiance.

4.96 out of 5 average rating, 142 reviews

Cheerful 2 bedroom suite with hot tub.

4.89 out of 5 average rating, 731 reviews

The Ironwood & Lilac Cottage

Home in Old Colorado City

The exterior of a two-story home is highlighted by warm lighting along the perimeter. A hot tub is visible on the patio, complemented by outdoor seating. The landscape includes a barren gravel area and trees that add a natural element, creating a welcoming atmosphere.

4.98 out of 5 average rating, 121 reviews

*As Seen on TV* Luxury Home near Downtown & OCC

4.96 out of 5 average rating, 117 reviews

A shaded area with a hot tub is visible beside large glass doors leading into the tent interior. Light filters through the wooden beams above, illuminating a cozy space with comfortable seating. A person is seated at the edge of the hot tub, enjoying the serene surroundings.

Tent in Monument

Luxury Creekside Glamping Tent w/ Hot Tub & Views

Home in Downtown Colorado Springs

A hot tub is positioned in the backyard, surrounded by a wooden pergola and complemented by a patio seating area. The clear blue water of the hot tub is visible, with a backdrop of well-maintained greenery and nearby outdoor furniture.

4.82 out of 5 average rating, 560 reviews

Downtown | Hot Tub | Big Backyard | Pet Friendly

An inviting outdoor area features a hot tub surrounded by a private wooden fence. Comfortable seating options, including lounge chairs, are positioned on the neatly maintained grass. The sky above is bright with scattered clouds, enhancing the serene atmosphere.

4.92 out of 5 average rating, 203 reviews

Woodsy Wonder Retreat | Hot Tub & Golf Course View

The backyard features a private hot tub beside an outdoor dining table and firepit area, all under string lights that create a warm ambiance. A wooden fence provides seclusion, enhancing the tranquil setting surrounded by grassy areas and trees.

4.96 out of 5 average rating, 425 reviews

☆Hillside Haven☆ Hot Tub┃Fire Pit┃Dog Run

An outdoor fire pit surrounded by multiple adirondack chairs is visible on a patio. The area offers expansive views of the mountains and the landscape below, showcasing a variety of trees and homes bathed in warm evening light.

4.88 out of 5 average rating, 112 reviews

Mountain View Ranch with Hot Tub, Games

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 319 reviews

A circular wooden sauna sits on a raised deck surrounded by trees. Blue adirondack chairs are arranged around a fire pit with glowing flames. The natural setting creates a peaceful atmosphere for outdoor relaxation.

Cabin in Divide

𓃵Moose Cabin𓃵 Sauna┃Firepit┃Woodstove┃Corn hole

4.97 out of 5 average rating, 745 reviews

A charming exterior view of a cabin-inspired home is surrounded by lush greenery and vibrant flowers. Stone pathways lead to a welcoming entrance, accentuated by light blue walls and a small patio featuring two chairs. Mature trees provide shade and enhance the natural setting.

Guest suite in Broadmoor

Cheyenne Canyon Getaway

Tiny home in Woodland Park

The exterior of a tiny house features a combination of green and wood paneling. Large windows allow ample natural light, while a welcoming door with steps leads inside. Gravel surrounds the house, enhancing the natural setting among surrounding trees.

4.93 out of 5 average rating, 602 reviews

Wabi Sabi Tiny House - No Cleaning Fees!

A cozy living room area features a comfortable brown couch adorned with two large, plush pillows. An antique trunk serves as a coffee table, enhancing the space's character. Soft light is provided by a floor lamp, and framed art pieces are displayed on the wall.

4.94 out of 5 average rating, 239 reviews

The Stone Cutter’s Cottage * Walk to Downtown COS

Guest suite in Colorado Springs

A stone pathway meanders through a grassy yard, bordered by flowering plants. Lush greenery complements the landscape, with two clusters of blooming irises standing out. Residential homes are visible to the right, creating a peaceful neighborhood setting.

4.82 out of 5 average rating, 352 reviews

Private Studio on urban homestead Central #0633

Guesthouse in Colorado Springs

A cozy cabin features a distinctive sloped roof and is surrounded by tall trees. The exterior is constructed from natural wood, complementing the forest setting. A stone fire pit and several outdoor benches are positioned in front of the cabin, providing a welcoming outdoor space.

4.95 out of 5 average rating, 132 reviews

Cozy Fishing Cabin in Black Forest

4.94 out of 5 average rating, 101 reviews

2BR Cozy Basement Suite with Garage Parking

Townhouse in Garden of the Gods

4.96 out of 5 average rating, 292 reviews

Hot Tub * Patio | 5 mins: Manitou, Garden of Gods

Family-friendly home rentals with a pool

Apartment in Colorado Springs

A spacious living area is furnished with a leather sofa and two easy chairs adjacent to a wooden accent table. Floor-to-ceiling windows offer expansive views of the surrounding landscape, while sliding glass doors provide direct access to the L-shaped terrace.

4.55 out of 5 average rating, 74 reviews

Overlooking Mountain Views | Terrace | Pool access

Guesthouse in Colorado Springs

An indoor pool area features a 35 ft heated swimming pool underneath a spacious glass enclosure. Two swan-shaped pool floats rest on the water, while lounge chairs are positioned along one side, providing a relaxing atmosphere. Natural light streams through the large glass walls.

4.91 out of 5 average rating, 152 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

Apartment in Colorado Springs

A bright living area is furnished with a green sofa and a white slipcovered couch. A wooden coffee table sits in front. A dining table is positioned near a window, allowing natural light to illuminate the space. Decorative plates and a world map adorn the wall.

4.92 out of 5 average rating, 273 reviews

Quite spacious Apt w/Game Table, Pool, Bball court

4.95 out of 5 average rating, 20 reviews

A well-maintained grassy yard is framed by a white picket fence. A large tree and decorative plants are visible, alongside a small swing set. The exterior of the house features large windows and is accompanied by a storage shed in the background.

Guest suite in Fountain

Settlers Pass apartment to experience Colorado

An open living space showcases wooden cabinetry and a high ceiling with exposed beams. A spacious seating area includes a sectional couch and a coffee table. A dining table that seats six is visible, along with a wood-burning stove providing warmth.

4.91 out of 5 average rating, 89 reviews

Cheerful home w/pool & hot tub in quiet area

4.88 out of 5 average rating, 133 reviews

An outdoor patio area is highlighted by a wooden frame, providing shelter over a dining table and seating. A hot tub is situated nearby, surrounded by lush greenery and tall trees, creating a serene environment for relaxation.

Home in Woodland Park

Sunshine Mountain , experience true Colorado!

Cabin in Cascade-Chipita Park

A rustic log cabin is set against a backdrop of lush greenery, featuring a wrap-around deck adorned with vibrant flower pots. Sturdy wooden stairs lead to the entry, surrounded by natural stone accents and shaded by tall pine trees.

4.97 out of 5 average rating, 162 reviews

Rustic Historic Colorado Mountain Cabin Pikes Peak