Smoking friendly holiday rentals in Security-Widefield

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

The Ganja Getaway 420 Friendly

The perfect 420 relaxation destination just minutes from the heart of Old Colorado City and downtown Colorado Springs. Creative space, comfortable rooms, full kitchen, spacious living room and all your ganja smoking supplies make this the perfect lounge pad to feel at home while you enjoy and play in the Springs! LGBTQ+ friendly! Explore hiking, sightseeing, Garden of the Gods, cool shops, restaurants, dispensaries, and all the hidden gems of the Westside. Guests must be 21+ STR Permit #1658

Family Home| 3 Bedrooms+Loft| Deck+Firepit|Games

Welcome to Colorado Springs, enjoy our AirBnb house like it’s your own vacation getaway. You will find this 2-story family home just outside our thriving downtown scene! A short drive from Colorado Springs Airport, downtown, all the military bases, shopping, restaurants, entertainment, and all the local attractions. After a day of adventure, return home and enjoy the provided TVs, board games, books, and all the kitchen essentials. Relax out on the deck and end the night around the fire-pit.

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.

⫸Cozy Retreat⫷ Fire Pit┃Peloton┃Corn Hole┃Hot Tub

Cozy In-law apt perfect for just one or two people packing a punch: massive shower, fireplace, record player, Roku TV (Hulu/Netflix) & comfiest bed! ★Walk to OTC; Short drive Dwntwn, CC, Pikes Peak, USAFA, UCCS ★YARD: Hot tub, firepit, grill, speaker, yard games, Schwinn bike ★GYM: Peloton, Treadmill & Elliptical. Jump ropes, kettle bells, speaker, Roku TV+MORE! ★DESK: printer, fast WIFI, G00gle Mini & cocktail shaker ★FAMILY: PackNplay, toys, high chair ★Kitchenette: stovetop, blender+more!

✮Downtown Tiny House✮ ✓Fire pit ✓Grill ✓Roku TV

Stay in a converted tiny house that was once a 1900’s Carriage House. ★Five Star cleaning team trained in disinfecting and sanitation ★4 blocks from downtown COS ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Newly landscaped backyard with fire pit + grill. Shaded patio with seating ★32" TV with Roku w/apps ★Business Travel: Keyless entry + fast wifi ★Fully equipped kitchenette: hot plate, microwave, mini fridge, pots, pans, Keurig + more! ★FREE Colorado-made soda

Mountain Views and Close to Downtown Home

Welcome to your perfect Colorado Springs getaway! Start your mornings with breathtaking views of Pikes Peak from the main living spaces, then bask in over 300 days of sunshine in thoughtfully designed outdoor lounging areas. Inside, you’ll find a fully stocked kitchen, plush beds made for deep rest, and responsive hosts who are always here to help. Whether you’re hiking the trails, exploring downtown, or simply unwinding under the Colorado sky—this home was made for your kind of stay

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)

Colorado Garden Suite

city permit A-STRP-25-0666 We hope you enjoy our guest suite You will have space and privacy in the lower level of our home, located in NW Colorado Springs. The suite includes 2 bedrooms with Queen size beds; 1 full bathroom, living area; a Kitchenette handy for ordering in or heating up meals, mini fridge,coffeemaker and water kettle. You will have private use of the 2 person hotub, patio, 420 room and laundry room. Many other amenities are provided for your convenience.

Interstellar Villa with 180° Mountain Range Views

Welcome to our pet-friendly, ranch-style retreat, perfect for families and large groups! Enjoy an open-concept living, dining, and kitchen area, ideal for gathering. Take in breathtaking 180-degree views of Pikes Peak, unwind in two master suites with en suite baths, and stay cool with central AC. Have fun with the pool table and let your pets roam in the large fenced yard. Conveniently located near Colorado Springs’ east-side shopping and amenities, this home has it all!

The Element House of Wonder & Mystery *NoCleanFee*

Winner of The Springs magazine's "Top 25 Airbnbs in Colorado Springs," designator, this property was custom designed by award-winning interior designer Austin William Davidson. "The Element House" -- a place of Mystery and Wonder -- offers super comfortable beds, luxury linens, stunning décor, an amazing backyard and patio, a treasure hunt for guests, historical artifacts, and quality amenities, making this the most interesting and comfortable place to stay in the area!

WALK Downtown|Pet Friendly|Fully Fenced Yard|BBQ

We’re here to make your dream trip effortless and unforgettable. Whether you’re planning a family getaway, a spontaneous adventure, or celebrating a special occasion, our team is ready to assist every step of the way. With modern amenities, inviting spaces, and thoughtful touches designed for comfort and convenience, you’ll feel right at home. Relax, recharge, and create lasting memories during a stay that’s tailored to make every moment truly special.