Family-friendly holiday 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, 237 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

An open loft bedroom features a large queen bed adorned with crisp linens and vibrant accent pillows, situated on a geometric-patterned area rug. Two bedside tables with lamps flanking the bed provide illumination, while a small desk and chair are positioned nearby, enhancing the room's functionality.

4.94 out of 5 average rating, 171 reviews

Old North End Carriage Home: Grill, Playroom, Roku

★LOCATION - This rental is in the upscale, historic Old North End. Walkable to CC. 1.3 mi from downtown. Short drive to USAFA, UCCS + Garden of the Gods. Easy access to I-25 as well as shopping + dining. ★String lights over outdoor dining area with Grill ★King bedroom w/ 55” Roku TV + Living room w/ 46" TV. Roku access to log into Hulu/Netflix. ★Equipped kitchen w/waffle maker, blender + more! ★Families welcome! Playroom with toys + books, children's dishware, high chair, pack n play & baby gate

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.

4.9 out of 5 average rating, 189 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!

Bungalow in Colorado Springs

A serene bedroom features a spacious bed adorned with neutral linens and decorative pillows. Two windows provide natural light, complemented by light-filtering curtains. A bedside table with a lamp and a cozy area rug enhance the warm atmosphere. A potted plant adds a touch of greenery.

4.92 out of 5 average rating, 283 reviews

Dwntwn home w/playroom, Walk to coffee shop & park

★Close to downtown 3 blocks to local coffee, Switchback ★Short drive to Colorado College, Garden of the Gods, Pikes Peak, USAFA ★Family friendly: Pack n play, baby bath, high chair, baby monitors, toy room, board games + more! ★BUSINESS TRAVEL: Fast WIFI, desk, keyless entry & G00gle home ★65” Roku TV in family rm, 54" Roku TV in master ★Fenced in yard w/fire pit & grill ★Fully equipped kitchen w/Keurig & drip coffee maker, waffle maker, blender & more ★BRAND NEW★ comfy beds ★Free Colorado soda

The exterior of the home is displayed, featuring a modern two-story design with gray siding and stone accents. A light blue front door is framed by large windows. A neatly paved driveway leads to a two-car garage, surrounded by landscaped greenery.

4.86 out of 5 average rating, 126 reviews

4 Bdrm/Beautiful/Cozy/Family Getaway

You will bring the whole family to this beautiful home with lots of room for fun. This 4 bedroom, 2.5 bath home offers plenty of space and convenience for you and your 7 guests. You will be located in a sought after neighborhood with miles of dirt trails for bikes, runs, or walks. The neighborhood offers 4 playgrounds, all within walking distance. Home has close access to trails and sidewalks. Your home is located 15 minutes away from Colorado Springs Airport, Peterson SFB, and Fort Carson.

4.87 out of 5 average rating, 105 reviews

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

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.

Home in Old Colorado City

A covered porch is featured with two comfortable blue chairs positioned on a wooden deck. Natural light casts shadows on the floor, while vibrant yellow siding complements the colorful trim. A view of the surrounding residential area can be seen beyond the railing.

4.93 out of 5 average rating, 364 reviews

Walk to Old CO City, King Bed, Fenced in Hot Tub

★Attractively located on the west side, 0.7 mi to downtown OCC, 1.5 mi to downtown COS ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Fenced in yard with fire pit & grill and hot tub ★BRAND NEW★ comfortable beds! ★Fully equipped kitchen w/blender, toaster, coffee maker, etc ★BUSINESS TRAVEL: Desk area, FAST WIFI, Alexa, charging cables, keyless entry ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, monitors, toys + more! ★Large Smart TVs ★FREE Colorado soda

4.85 out of 5 average rating, 424 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

A spacious living room is presented, featuring high vaulted ceilings and large windows allowing natural light to fill the space. The area includes gray sofas with vibrant blue and green accents, a decorative area rug, and original artwork on the walls, enhancing the inviting atmosphere.

4.88 out of 5 average rating, 107 reviews

Mandala Manor Hot Tub Oasis

This stunning vacation home features super stylish decor, vaulted ceilings, custom paintings, covered patio, fenced backyard with built in dog-run, and extra amenities for families with children, pets* and 420 vacationers. Located minutes from the Colorado Springs Airport, Schriever and Peterson Air Force Bases, and 20 minutes to downtown Colorado Springs, this location is out of the way but still a great gateway to everything Colorado Springs has to offer. *pet fee applies

A hot tub bubbles gently under a covered patio, with a sturdy table and benches visible in the background. The inviting water reflects soft light, while the overhead covering provides shade and protection from the elements.

4.94 out of 5 average rating, 173 reviews

Cozy Family Home near Ft Carson/Broadmoor

Inviting & cozy family home + hot tub just 8 minutes from Fort Carson and 15 minutes to the beautiful Broadmoor area! Jump on I-25 and in just a short drive, get to Garden of Gods, Cave of Winds, Old Colorado City, Cheyenne Mtn Zoo & Manitou Springs (and more) This Single level 2 King Bedrooms/2 Full Bathroom home is perfect for your entire family! Jump in the Hot Tub or enjoy the firepit after a fun day outdoors! See www.visitcos for all the fun things during your stay!

A spacious hot tub is situated underneath a wooden pergola, surrounded by lush trees. Comfortable outdoor seating is visible in the background, offering a relaxed atmosphere for guests. Sunlight filters through the leaves, highlighting the inviting water of the hot tub.

4.91 out of 5 average rating, 624 reviews

Walk Downtown | Hot Tub | King Bed | Fire pit

★4 blocks to downtown & to local coffee ★Short drive to Colorado College, Garden of the Gods, Pikes Peak, USAFA ★Fenced in backyard w/Dining furniture, FIREPIT, HOT TUB & GRILL ★ comfortable beds! ★Fully equipped, spacious kitchen w/Keirug, blender + more! ★BUSINESS TRAVEL: FAST WIFI & KEYLESS ENTRY ★60” Apple TV w/ Hulu & Netflix ★FAMILY FRIENDLY: Pack n play, high chair & toys ★Modern space designed by fashion blogger Leah Behr @leah_behr ★Driveway parking

A two-story modern home is displayed, featuring gray siding and stone accents. The front porch is framed by a well-maintained lawn and small trees. A two-car garage is located on the right, with a concrete driveway extending to the street.

4.94 out of 5 average rating, 263 reviews

Mountain Majesty

Nestled against the majestic backdrop of the Rockies, our home boasts a cozy ambiance infused with farmhouse mountain decor. Relax in spacious bedrooms with black out blinds with their own tvs, unwind in the well-appointed living spaces, and savor the breathtaking views from our mountain-inspired haven. Perfect for families or groups seeking a serene escape with easy access to the wonders of Colorado Springs. Your mountain adventure begins here!

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 cozy outdoor seating area features a fire table surrounded by several cushioned chairs, all illuminated by soft string lights. In the background, a hot tub is visible, accompanied by a wooden fence that creates a private, inviting atmosphere.

4.92 out of 5 average rating, 178 reviews

Spruce House | Hot Tub | Fire Pit | Downtown

A spacious hot tub sits in the foreground, set against a backdrop of a charming home bordered by a landscaped yard. The inviting exterior features large windows and a staircase leading to the entrance. Warm evening light highlights the surrounding trees and patio area.

4.94 out of 5 average rating, 541 reviews

☀Hot Tub with Mtn Views☀ Fire pit┃Fire Place┃Grill

4.97 out of 5 average rating, 316 reviews

Lake~Paddleboards~Hot Tub~Firepit~BBQ

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, 137 reviews

Cheerful 2 bedroom suite with hot tub.

An outdoor space features a fire pit surrounded by several adirondack chairs on gravel. A private hot tub is visible in the background alongside a barbecue grill. String lights hang above, illuminating the scene as a pastel sunset colors the sky.

4.94 out of 5 average rating, 143 reviews

Dog Friendly Home w/ Hot Tub, Fire Pit, Grill

4.95 out of 5 average rating, 145 reviews

A fenced backyard offers a view of the surrounding mountains and autumn foliage. The grassy area is framed by trees, with a wooden gate visible, leading out to nature trails. The sky is partly cloudy, adding depth to the scenic landscape.

Home in Broadmoor

Stunning Cañon Retreat, views from backyard

Superhost

A spacious bedroom is highlighted by a large bed with crisp white bedding. Flanking the bed are two nightstands with blue lamps. A modern artwork piece hangs above the bed, complementing the muted blue wall. Natural light filters through the nearby window.

Home in Downtown Colorado Springs

4.82 out of 5 average rating, 552 reviews

Downtown | Hot Tub | Big Backyard | Pet Friendly

Cabin in Cascade-Chipita Park

4.99 out of 5 average rating, 246 reviews

Serene Riverside Cabin: Hot Tub, Patio, Fire Pit

Family- and pet-friendly home rentals

Guesthouse in Colorado Springs

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.

4.94 out of 5 average rating, 199 reviews

Rustic Bunkhouse in Black Forest

A private outdoor patio is furnished with Adirondack chairs arranged around a fire pit table. The dark exterior of the house is accented by warm wood details, and the space is surrounded by lush greenery, offering a peaceful atmosphere for gatherings.

4.97 out of 5 average rating, 240 reviews

Casita Noir | King Bed | Fireplace | Fenced Yard

A comfortable living space features a brown leather sofa and a recliner, arranged around a wooden coffee table. A patterned area rug lies beneath, while wall art and decorative items enhance the ambiance. A corner fireplace adds warmth to the room.

4.97 out of 5 average rating, 216 reviews

Cheyenne Mountain Getaway-Entire Lower Level

An outdoor seating area is showcased with modern furniture, featuring four comfortable chairs surrounding a wooden coffee table. The space is anchored by a natural fiber rug, complemented by a greenery wall adorned with cacti, and string lights overhead provide a welcoming ambiance.

4.89 out of 5 average rating, 247 reviews

Outdoor Lounge w/Mtn Views from Hot tub + Firepit

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, 389 reviews

Wildflower Cottage | Fenced Yard | 1 mile D-Town

A spacious game room features a pool table with cues and balls positioned for play. Large windows provide views of the mountains and outdoor space, while colorful walls add a vibrant touch. The room is well-lit, creating an inviting space for socializing.

4.97 out of 5 average rating, 153 reviews

Interstellar Villa with 180° Mountain Range Views

4.99 out of 5 average rating, 211 reviews

WALK Downtown|Pet Friendly|Fully Fenced Yard|BBQ

4.92 out of 5 average rating, 176 reviews

Entire Single Family Home

Family-friendly home rentals with a pool

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, 269 reviews

Quite Spacious Apt w/ Game Table, Bball Court

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.

4.9 out of 5 average rating, 146 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

4.95 out of 5 average rating, 19 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, 87 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

Townhouse in Colorado Springs

A sunlit bedroom showcases a spacious bed layered with crisp white linens and dark pillows. Light streams through large windows adorned with floral curtains, creating a warm ambiance. A bedside lamp complements the natural lighting, enhancing the inviting atmosphere of the space.

4.99 out of 5 average rating, 102 reviews

*King Bed*2CarGarage*Gym*Workspace*EVCharger*