Holiday rentals with a pool in Colorado Springs

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

Relax with the whole family at this peaceful place to stay. Enjoy the community pool during summer, Tennis, and walking trails. It is an independent family-friendly unit in the basement of the main house. It is a private space with its own entrance and separate from the main house. Free public parking or on the house driveway. Patio with table, grill, hammock, fire pit, and basketball court. Close to attractions, shopping, etc. Permit: A-STRP-25-0737 per Ordinance 7.5.1706 Rules and Regulations

Family · Value · Barbecue

Spacious, Mountain Views, Heated Pool, & Sunroom!

Welcome to your summer getaway in the picturesque city of Monument. Minutes from the Air Force Academy and Colorado Springs, this spacious home is an ideal retreat for those seeking a blend of relaxation and adventure. Enjoy your time in the beautiful sunroom, soaking in the heated pool (open Memorial Day- Labor Day), playing ping-pong, or watching a movie together. Boasting 6 bedrooms, 3.5 baths, full kitchen, & neighborhood parks, this home has everything you need for your family's next stay!

Family · Location · Layout

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

Cortland Cabin is a cozy, 931-square-foot mid-century modern mountain retreat just 15 minutes from CO Springs and 8 minutes from the Pikes Peak entrance and Santa's Workshop. Nestled between Manitou Springs and Woodland Park, it features stunning mountain views, a private hot tub, fire pit, and a bright open-concept layout with wraparound windows that bring the outdoors in. Dog-friendly and thoughtfully equipped, it's the perfect place to relax, explore, and enjoy cool mountain air year-round.

Family · Location · Nearby

2 Bedroom Cottage with Kitchen on 3 acres

Town-N-Country Cottages sits along Sutherland Creek and is situated on 3 quiet acres. We are less than a mile from Garden of the Gods, 2 mi from Red Rock Canyon Trail, 2.2 miles from Pikes Peak Cog Railway & 1 mile stroll to the historic town of Manitou Springs. Our 2 Bedroom cottages have fully equipped kitchens, living room, Wi-Fi & cable TV. Amenities include seasonal pool & hot tub, playground, covered pavilion w/BBQ grills, picnic tables, coin-operated laundry, and volleyball courts.

Family · Location · Outdoor spaces

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

NON-SMOKING PROPERTY. Located in Erindale Heights, one of the true hidden treasures of Colorado Springs. It is nestled away in a private 2.4 acres but surrounded by metropolitan amenities. Many of the area’s newest and most compelling restaurants, shopping outlets, and theaters are within 5 minutes away. It is adjacent to Austin Bluffs Open Space and Pulpit Rock Park. Garden of the Gods is within visible 8 miles distance and nearest to Air Force Academy. Non-owner-occupied permit STR-0085.

Location · Value · Sleep quality

Urban Float - Heated Indoor Pool/HotTub & Firepit

Discover your perfect Colorado Springs getaway – a stylish 2-bedroom guesthouse with an indoor pool/hot tub blending mountain views 🏔️ & urban convenience 🏖️. 🏊‍♀️ Enjoy a year-round dip in your 35 ft heated indoor pool, reserve time slots on our shared calendar. 🍽️ Cook delicious meals in the fully equipped kitchen. 🔥 Sit back and relax in your 7-person hot tub 🪵 Gather around the fire pit in the private backyard. 📍 Explore the Olympic Training Center, shops, & restaurants nearby.

Family · Location · View

Sunshine Mountain , experience true Colorado!

3 bed, 2 bath home in the shadow of Pike's Peak. Features a wheel chair ramp, 7.5 acres of shared property with wooded walking trails and an adults only swim spa patio area. The perfect spot to get away to a country setting but close to town. We have WIFI, 65" TV, soaking tub, new bedding, stocked kitchen/pantry, seasonal art studio, outdoor seating, fire pit & onsite parking. Base price is for 4 guests (Sleeps 8). For larger groups we also a RV site with hookups.

Family · Location · Backyard

Cheerful home w/pool & hot tub in quiet area

Relax with the whole family at this peaceful place to stay. We have everything needed to be your home away from home while you visit Colorado. Unwind in the hot tub (open year-round) and stay warm and toasty with the wood burning stove. Seasonal heated outdoor pool opening end of May 2026. Safety fence for the little kiddos-available upon request. Home is within 5 minutes of I-25, one mile from Pulpit Rock Park and Cottonwood Creek Trail. STR-26-0046

Value · Family · Laundry

Pikes Peak Views • A/C • Wildlife •Charis # 330886

Enjoy breathtaking Pikes Peak views from this modern Woodland Park townhouse! Rare for the area, this home offers central A/C for cool summer comfort. Watch for deer, foxes, wild turkeys & other wildlife. Perfect for families, couples & ministry travelers. Features 3 BR, 3 BA, full kitchen, fast Wi-Fi, stylish décor & 2-car garage. Walk to downtown & the Aquatic Center. Includes 1 FREE daily swim pass. Just 7 min to Charis & Andrew Wommack.

Value · Family · Cleanliness

King's Oasis

Family-friendly home just outside Colorado Springs city limits—only minutes from the airport! Located in a peaceful neighborhood, this cozy retreat features a private pool perfect for kids and a relaxing space for adults. With comfortable living areas, a fully equipped kitchen, and easy access to local parks and attractions, it’s the perfect spot for a relaxing getaway without the city noise. Your peaceful Colorado escape starts here!

Location · Family · Barbecue

Hot tub, mtn views, massage chair, & steam shower!

This home offers stunning views from a spacious wraparound deck, with a hot tub just off the master bedroom. Recently remodeled, it combines comfort and mountain charm. Inside, enjoy a wood stove, gas fireplace, massage chair, steam shower, and Jacuzzi tub, plus STARLINK WiFi and Roku TV. Large windows and skylights fill the home with light, and every room opens to the deck with seating areas and a propane BBQ.

Value · Family · Hospitality

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.

Family · Location · Kitchen