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, 253 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

FamilyIndoor spacesQuiet

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, 192 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!

KitchenIndoor spacesCondition

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, 410 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!

FamilyKitchenBarbecue

4.87 out of 5 average rating, 101 reviews

A compact kitchen area features modern appliances, including a stove and oven, alongside white cabinetry. Cooking utensils are neatly arranged on hooks. A rustic wooden table is set with plates and woven placemats, while the living area offers a cozy couch under warm wood paneling.

Tiny home in Fountain

<3Underneath the Stars Romantic Retreat<3TinyHome

Get cozy and settle into this wonderfully equipped tiny home. This romantic little getaway is the perfect place to relax and unplug from the world. Rustic ranch feeling and is only 15 min. away from the city for night outings. Enjoy all the comforts of a regular home as well as your PRIVATE outdoor patio with a fire pit. Get the smores ready to go with a fuzzy blanket and cuddle up next to your loved one. Or come on over to the shared space where you can enjoy the hot tub underneath the stars.

Indoor spacesFamilyCondition

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.

4.87 out of 5 average rating, 137 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.

FamilyIndoor spacesWi-Fi

Guesthouse in Colorado Springs

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.

4.98 out of 5 average rating, 120 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.

Indoor spacesFamilyBathroom

Bungalow in Colorado Springs

4.99 out of 5 average rating, 222 reviews

Private Stay w/ A/C Near Downtown & Mem Hospital

Stay in a private 1920s bungalow blending historic charm, modern comfort, and thoughtful touches from local hosts who care about you! Enjoy original hardwood floors, a fully-equipped kitchen, fiber Wi‑Fi, dedicated workspace, A/C, walk-in shower, comfy Queen bed, and a privacy-fenced patio. Walk to coffee, parks, and trails, then relax in a quiet neighborhood minutes from downtown, Garden of the Gods, Manitou Springs, Olympic Training Center, CO College, and Memorial Hospital. Sleeps up to 4.

FamilyKitchenLocation

4.86 out of 5 average rating, 109 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.

FamilyIndoor spacesSleep quality

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.

4.86 out of 5 average rating, 124 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

Indoor spacesFamilySleep quality

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.

4.93 out of 5 average rating, 180 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!

KitchenIndoor spacesHospitality

An outdoor space features a hot tub surrounded by trees, with a fire pit and four white Adirondack chairs arranged around it. A mini putting green can be seen in the background, while string lights glow softly, creating a warm ambiance as the sun sets.

4.95 out of 5 average rating, 103 reviews

Hot Tub • Fire Pit • Mini Golf | Downtown Escape

Welcome to your private Colorado Springs retreat! Soak in the hot tub under the stars, gather around two fire pits, or challenge friends to giant chess, cornhole, putt-putt, and oversized yard games in your own backyard oasis. Just minutes from downtown, Garden of the Gods, Manitou Springs, and the Olympic Center, this family-friendly getaway combines fun, comfort, and convenience with gig-speed Wi-Fi, Smart TVs, and modern amenities.

Indoor spacesKitchenParking

The exterior of a two-story house is visible, featuring a green facade and large windows. A landscaped yard includes manicured grass and flower beds, while a driveway leads up to the garage. A sunny blue sky frames the charming home.

4.99 out of 5 average rating, 286 reviews

Beautiful family ready home.

This clean, well-thought out home has everything a family needs for a great stay in Colorado Springs. It’s a comfortable home away from home—perfect for relaxing and making memories. The home shares walls with a separate unit but has no shared spaces. Guests enjoy a private entrance and exclusive access to the spacious back patio. Hosts live onsite in an attached apartment and are available if needed, while respecting your privacy.

FamilyKitchenCleanliness

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

4.84 out of 5 average rating, 438 reviews

Nature Retreat: Hot Tub, Fire Pit + Projector

KitchenFamilyValue

Cabin in Colorado Springs

5.0 out of 5 average rating, 191 reviews

15 min to Downtown I Romantic I Hiking I Forest

Indoor spacesKitchenNearby

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, 559 reviews

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

KitchenIndoor spacesPets

The kitchen features wood cabinetry and granite countertops with a modern stainless-steel refrigerator and microwave. A double oven is installed beneath the countertop. The adjacent dining area showcases a wooden dining table surrounded by curved-back chairs, providing a welcoming space for meals.

4.98 out of 5 average rating, 355 reviews

The Memory Maker! 2 King Beds + Garage & Hot Tub!

FamilyIndoor spacesParks

A fully fenced backyard features a stone fire pit surrounded by red Adirondack chairs. Sunlight filters through the trees, highlighting the spacious outdoor area, which includes a gravel path and a grassy section, with mountains visible in the distance.

4.94 out of 5 average rating, 310 reviews

Mountain views! Hot Tub! Downtown! Pet friendly!

FamilyKitchenParking

Superhost

4.89 out of 5 average rating, 741 reviews

The Ironwood & Lilac Cottage

KitchenFamilyWi-Fi

The exterior of a modern two-story home is showcased, featuring a blend of white and natural wood siding. A front porch with seating overlooks a well-maintained lawn, while a gravel driveway leads to a garage. Lush greenery and trees provide additional privacy.

4.96 out of 5 average rating, 119 reviews

Private Modern Oasis • Hot Tub • Pikes Peak Views

Indoor spacesFamilyHot tub

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, 214 reviews

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

FamilyIndoor spacesHot tub

Family- and pet-friendly home rentals

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.

4.92 out of 5 average rating, 381 reviews

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

KitchenFamilyLong stay

4.96 out of 5 average rating, 174 reviews

Couples Getaway w/ Hot Tub, Fire Pit, Grill

KitchenFamilyView

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.

4.93 out of 5 average rating, 559 reviews

★OCC Getaway★ Firepit, Grill, Backyard + Firestick

FamilyKitchenValue

4.97 out of 5 average rating, 332 reviews

Lake~Paddleboards~Hot Tub~Firepit~BBQ

Indoor spacesFamilyHospitality

4.96 out of 5 average rating, 251 reviews

Centrally Located with 180° Mountain Range Views

KitchenIndoor spacesBathroom

4.91 out of 5 average rating, 187 reviews

Entire Single Family Home

KitchenIndoor spacesAmenities

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.

4.95 out of 5 average rating, 179 reviews

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

Indoor spacesFamilyCleanliness

The exterior of a modern black house is shown, featuring a metal roof and large windows. A concrete driveway leads up to the entrance, accompanied by an outdoor seating area with chairs and a fire pit. Surrounding greenery adds a natural touch.

4.97 out of 5 average rating, 259 reviews

Casita Noir | King Bed | Fireplace | Fenced Yard

Indoor spacesFamilyQuiet

Family-friendly home rentals with a pool

Superhost

A spacious living area features a comfortable dark sofa and two patterned armchairs surrounding a glass coffee table. Natural light fills the room through large windows, highlighting the open concept layout that connects to the dining area and kitchen in the background.

Townhouse in Colorado Springs

4.87 out of 5 average rating, 195 reviews

Resort-Style Townhome | Pool, Hot Tub & Gym Access

FamilyIndoor spacesCondition

An expansive home showcases a contemporary Southwestern design, surrounded by lush greenery. Large windows and multiple deck areas provide scenic views. An inset image reveals an indoor heated pool, framed by large windows that invite natural light and emphasize the tranquil indoor space.

4.98 out of 5 average rating, 131 reviews

Hidden Gem⋆Heated Pool⋆Gorgeous Views⋆2.4 ac⋆AC⋆EV

KitchenIndoor spacesBackyard

The covered deck features a spacious seating area with comfortable furniture and a large outdoor kitchen equipped with a grill and a 36” griddle. A smart TV is mounted on the wall, and patio heaters are positioned for warmth. The pool and hot tub are visible in the background.

4.97 out of 5 average rating, 151 reviews

Staycation

KitchenFamilyPool

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, 296 reviews

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

KitchenFamilyBiking

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, 161 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

KitchenFamilyOutdoor spaces

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!

KitchenFamilyGetting around

A private above-ground pool is featured in a fenced backyard surrounded by landscaped grass. The two-story home is visible in the background, with a wooden deck and patio furniture nearby. A swing set is also present, creating a family-friendly outdoor space.