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, 254 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

KitchenFamilyAmenities

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!

KitchenIndoor spacesOutdoor spaces

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, 193 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!

FamilyIndoor spacesParking

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.

KitchenIndoor spacesDecor

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, 138 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.

Indoor spacesKitchenNearby

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.

KitchenFamilyComfort

Cabin in Colorado Springs

5 out of 5 average rating, 191 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!

KitchenIndoor spacesSleep quality

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

★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

KitchenIndoor spacesValue

4.97 out of 5 average rating, 332 reviews

Lake~Paddleboards~Hot Tub~Firepit~BBQ

The closest you'll get to beach vibe with Pikes Peak Views! RARE lakeside home yet only 1 mile from downtown and central to the best in the Springs! 🌟 What you'll love • All king-sized beds • Outdoor glamp bedroom with lake views – guest favorite! • 7person hot tub with Pikes Peak & lake views! • Fully stocked kitchen + BBQ grill + wood-fired pizza oven • Large, fenced yard perfect for families or furry friends • Unlimited paddleboard access on the lake • 420 friendly (outside)

KitchenFamilySleep 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, 125 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

KitchenFamilyPets

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!

Indoor spacesFamilyGetting around

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, 104 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.

FamilyKitchenLong stay

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

5 out of 5 average rating, 111 reviews

New build, private yard, CEDAR hot tub

KitchenIndoor spacesSleep quality

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

Indoor spacesKitchenLong stay

4.98 out of 5 average rating, 138 reviews

Mini-Golf| HotTub| GameRoom| Views| 8 total beds!

KitchenIndoor spacesWi-Fi

Superhost

4.89 out of 5 average rating, 741 reviews

The Ironwood & Lilac Cottage

FamilyIndoor spacesWi-Fi

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*

Indoor spacesKitchenPets

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

FamilyKitchenComfort

4.84 out of 5 average rating, 439 reviews

Nature Retreat: Hot Tub, Fire Pit + Projector

FamilyIndoor spacesNearby

4.96 out of 5 average rating, 174 reviews

Couples Getaway w/ Hot Tub, Fire Pit, Grill

FamilyIndoor spacesWalkability

Family- and pet-friendly home rentals

Guesthouse in Colorado Springs

4.94 out of 5 average rating, 161 reviews

A-Frame Country Cabin

Indoor spacesKitchenCheck-in

4.97 out of 5 average rating, 760 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

Indoor spacesKitchenHiking

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

KitchenFamilyCheckout

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, 561 reviews

★OCC Getaway★ Firepit, Grill, Backyard + Firestick

FamilyIndoor spacesHeating

Home in Old Colorado City

A modern living space features a stylish gray sofa adorned with patterned cushions. A circular, wire base coffee table sits atop a textured area rug, complementing the wood flooring. Light from the window highlights a scenic artwork on the wall and the open kitchen area beyond.

4.92 out of 5 average rating, 370 reviews

Cozy Colo Cottage with love in Old Colorado City

Indoor spacesKitchenWalkability

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, 263 reviews

Outdoor Lounge w/Mtn Views from Hot tub + Firepit

Indoor spacesFamilyCheck-in

4.96 out of 5 average rating, 251 reviews

Centrally Located with 180° Mountain Range Views

KitchenIndoor spacesAccess

A bright living area features white leather sofas arranged around a glass coffee table. A ceiling fan is mounted above, and a piece of mountain artwork decorates the wall. The space opens up to a dining area and kitchen visible in the background.

4.97 out of 5 average rating, 102 reviews

ᨒStylish 4BR | Movie Lounge | 10 min to Ft Carsonᨒ

FamilyIndoor spacesSleep quality

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 18 reviews

Cabin in Manitou Springs

2 Bedroom Cottage with Kitchen on 3 acres

FamilyWalkabilityShared spaces

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

Indoor spacesFamilyNearby

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 spacesComfort

Cabin in Cascade-Chipita Park

An expansive wooden deck features seating with Adirondack chairs, inviting relaxation. A fire pit is positioned nearby, creating a cozy atmosphere for gathering. The cabin exterior showcases a combination of dark siding and stone accents, illuminated by warm outdoor lighting.

4.9 out of 5 average rating, 68 reviews

Cortland Cabin Getaway W/ Views & Hot Tub- Pets OK

FamilyIndoor spacesNearby

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, 92 reviews

Cheerful home w/pool & hot tub in quiet area

Indoor spacesFamilyBarbecue

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!

FamilyIndoor spacesCheckout