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, 252 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

Guest suite in Colorado Springs

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.

4.95 out of 5 average rating, 380 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

4.95 out of 5 average rating, 147 reviews

Charming Home with Mountain Views & Sunny Patio

Make your stay peaceful and refreshing in this inviting 3-bedroom home in beautiful Colorado Springs. Ideal for families, couples, business travelers, or a quiet seasonal getaway, this first-level retreat offers cozy comfort, mountain views, and a relaxed atmosphere just minutes from downtown. Designed for comfort and productivity, this home features high-speed 500 Mbps Wi-Fi (download & upload)—perfect for remote work, video calls, and streaming after a day of exploring. Permit A-STRP-25-1080

Flat 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, 558 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)

4.87 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.

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.

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, 123 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.

4.93 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!

Guest suite in Colorado Springs

4.81 out of 5 average rating, 113 reviews

Mountain Retreat With Hot Tub and Room To Relax

Escape to our private 1,400 sq. foot retreat at the base of Cheyenne Mountain! This spacious garden-level apartment comfortably sleeps 4 - 6 guests, has a private entrance and hot tub, perfect after a day out exploring. Enjoy a full kitchen, grill, living room, and a unique 'Bear Cave' for kids. Minutes from The Broadmoor and local trails with quick access to Old Colorado City, up to Manitou Springs and Woodland Park. Your home base for adventure!

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.

A private backyard oasis features a relaxed hot tub under a wooden pergola, surrounded by a wooden fence and landscaped with white gravel. Stairs lead up to the entryway of the home, illuminated by natural light.

4.98 out of 5 average rating, 388 reviews

Downtown Bungalow | Hot Tub | Pet Friendly | Patio

You won't want to miss out on this quaint space close to Shooks Run Park and Downtown Colorado Springs! This 1920s home has been recently updated. Soak in a luxurious spa in your own private fully-fenced backyard oasis. Enjoy free coffee, tea, and hot chocolate from a plumbed Keurig machine. Binge-watch your favorite Netflix show on 2 large screen HDTV's, or challenge your travel partner to a game of Foosball. A-STRP-22-0544

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

Enjoy a comfortable stay in this pet-friendly 2BR, 2.5BA end-unit townhome in a prime Colorado Springs location, just 7 minutes to downtown with easy access to major highways. With a garage, fast WiFi, and space to sleep up to 5, this home is ideal for short visits or monthly stays. Guests also enjoy access to a resort-style community clubhouse, pool, fitness center, and dog park.

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

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, 354 reviews

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

The bedroom features a spacious bed adorned with a soft green blanket and decorative pillows. Flanking the bed are two bedside tables with lamps. Above, three framed art pieces depict cacti, complementing the natural light streaming through the window.

4.89 out of 5 average rating, 283 reviews

Alpaca Adobe: Hot tub, Couples hammock & Fire pit!

4.91 out of 5 average rating, 192 reviews

180° Mountain Range Views and Centrally Located

Cabin in Colorado Springs

5.0 out of 5 average rating, 190 reviews

15 min to Downtown I Romantic I Hiking I Forest

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, 436 reviews

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

A single-story home features a light-colored exterior with a contrasting blue entrance door. A paved driveway leads to a two-car garage. The well-maintained front yard includes green grass and decorative shrubs, while a small seating area is positioned near the front porch.

4.9 out of 5 average rating, 471 reviews

Rockrimmon Retreat Hottub - FirePit - Dog Friendly

4.96 out of 5 average rating, 173 reviews

Couples Getaway w/ Hot Tub, Fire Pit, Grill

4.84 out of 5 average rating, 438 reviews

Nature Retreat: Hot Tub, Fire Pit + Projector

Family- and pet-friendly home rentals

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

Guest house 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, 119 reviews

The Enchanted Hobbit Cottage

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

Home in Old Colorado City

A spacious outdoor deck is shaded by a large fabric canopy, featuring comfortable wicker seating and a grill. The surrounding area includes gravel landscaping with flower planters and a privacy fence, creating a cozy and inviting space for relaxation.

4.84 out of 5 average rating, 330 reviews

The Clubhouse

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!

4.95 out of 5 average rating, 390 reviews

Pet-Friendly - Game Room+Arcade - Mountain Views

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*

4.94 out of 5 average rating, 772 reviews

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

Keithley Pines Bristlecone Cabin

Family-friendly home rentals with a pool

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

Guest house 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

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, 130 reviews

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

4.92 out of 5 average rating, 296 reviews

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.

Flat in Colorado Springs

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

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!

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.

4.96 out of 5 average rating, 49 reviews

King's Oasis