Pet-friendly holiday rentals in Security-Widefield

4.97 out of 5 average rating, 155 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

4.87 out of 5 average rating, 174 reviews

Outdoor Lounge w/Mtn Views from Hot tub + Firepit

Welcome to the Cactus Casita! ✩Fenced in DREAM yard with patio dining, fireplace, IG wall, cactus torches, firepit, grill, hot tub, hammocks + outdoor games ✩1 mile to Dwntwn ✩Walk to OTC; Short drive to CC, Pikes Peak, USAFA, UCCS, Garden of the Gods ✩48" TV w/Roku + sound system ✩BRAND NEW comfy King + Queen bed ✩FAMILY FRIENDLY: PackNplay, baby bath, high chair, baby monitors, toys + more! ✩BUSINESS: Fast wifi, keyless entry, G00gle Minis ✩Equipped kitchen: coffee, waffle maker, blender, etc

Superhost

4.85 out of 5 average rating, 186 reviews

Walk|Shop|Dine Ivywild Bungalow

☞ Walk Score 85 (Walk to Creekwalk shopping center, cafes, dining, etc.) ☞ Pet friendly (fenced in side-yard!) + views of Pikes Peak ☞ 50" Smart TV ☞ Primary King Bedroom ☞ Pull out sofa in livingroom (full size). Chair in Office Converts to Twin Sleeper ☞ Fast wifi & Private workspace 5 mins → Broadmoor Hotel 7 mins → Downtown Colorado Springs/Colorado College 10 mins → Hiking trails at Cheyenne Canyon 15 mins → Garden of the Gods / Manitou Springs / USAFA 20 mins →Colorado Springs Airport ✈

4.97 out of 5 average rating, 157 reviews

Casita Noir |King Bed|Fire Pit|Patio|Driveway

Casita Noir is a private house with high end furnishings, perfect for your next trip. Near Downtown and I25. Walkable to Prospect Lake/ Memorial Park, Hillside Gardens for concerts/ weddings, and Switchback Roasters. Custom built construction with thoughtful touches to enhance your stay. You'll wake up well rested in our very comfortable king size bed, and make yourself an espresso or tea to enjoy in front of the fireplace. After a day of sight seeing, enjoy a drink while relaxing on the patio.

Apartment in Colorado Springs

4.87 out of 5 average rating, 160 reviews

Lovely Apartment! Dog friendly - Sleeps 4

Our adorable 745 SQFT apartment is tucked away at the end of a cul de sac with a beautiful Pikes Peak view & is near many CO Springs attractions, grocery stores & shopping. You will be welcomed with a sparkling clean space & thoughtful touches including coffee, spices, & oil. The 2 bedrooms & 1 full bath have been freshly remodeled. Keeping your comfort in mind, we have included an LED Smart TV (w/YoutubeTV), radiant heat, private parking, & laundry (coin-op). We are excited to host your stay!

Guest house in Colorado Springs

4.92 out of 5 average rating, 162 reviews

Across from the Park with Fenced Yard and Hot Tub

★Directly across Memorial Park - Velodrome, Play Sets, ice skating, walking trail around lake, YMCA Rec Ctr w/swimming/fishing ★Walk 0.5 mi to local Switchback coffee ★1.3 mi to dwntwn COS ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Fenced in yard w/firepit, grill, hot tub + yard games ★New king bed ★55" Roku TV w/Apps ★Fast WIFI ★Equipped kitchen: Waffle maker, blender + more! ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys ★Free Colorado beer

Superhost

4.94 out of 5 average rating, 305 reviews

☀Family Fun☀✔Foosball ✔Air Hockey ✔Fenced backyard

✓Game room: air hockey, foosball table + games ✓Pet/Family Friendly: Pack 'n play, High chair, Baby monitors, Bouncer, Baby bath, Treehouse, Outdoor playset, toys, Dog yard ✓Equipped kitchen w/ waffle maker, blender + more! ✓ Fenced in yard w/patio furniture, string lights + grill ✓55" Smart TV w/Roku, log into apps like Hulu/Netflix ✓WORK TRAVEL: FAST WIFI, desk, G00gle Home ✓Washer/Dryer ✓5k to Olympic Training Ctr ✓Short drive to Downtown, CO College, Garden of the Gods, Pikes Peak, USAFA

4.99 out of 5 average rating, 333 reviews

Cabin in Divide

Rainbow Trail A-Frame Hot Tub |Firepit| StarGazing

This recently renovated A-frame cabin is nestled on 2 acres of tranquil, forested land surrounded by aspen and pine trees — the perfect mountain escape. Unwind in the private hot tub, warm up by the cozy wood-burning stove, or gather around the outdoor fire pit for a night under the stars. Plus, with the addition of our Star Gazing Net in June 2025. Near Divide, Florissant, and Woodland Park, 45-minute drive from Colorado Springs, 1.5 hours from Breckenridge skiing, and 2 hours from (DIA).

4.96 out of 5 average rating, 156 reviews

Cheyenne Mountain Getaway-Entire Lower Level

Our property is located right in the middle of almost everything you want to see when you come to Colorado Springs. Besides a beautiful view of Cheyenne Mountain with Pikes Peak visible in the distance, you’ll be a stone’s throw from The Broadmoor World Arena, Fort Carson, Cheyenne Mountain Zoo, The Olympic Training Center, and the Air Force Academy. You’ll want for nothing as there is a full kitchen, washer and dryer, and a shower and bathtub, as well as ample room for your family.

Superhost

4.84 out of 5 average rating, 370 reviews

Family Nature Retreat ★Equipped Kitchen★ ★Firepit★

★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

4.97 out of 5 average rating, 225 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)