Holiday rentals with a pool in Pueblo

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

Location · Value · Nearby

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.

Location · Family · TV

Secluded Cabin Retreat: 41 Acres Near Royal Gorge

This beautiful authentic log cabin sits on 41 private acres for you to escape the hustle and relax in nature. The property backs to BLM land with access to the San Isabel National Forest that you can explore on foot, 4-wheelers, dirt bikes, or ATVs. Perfect for hunting on GMU 69. There is plenty of space at the log cabin for large or multiple families to gather. Cook in the large kitchen and dine outside with views of Pikes Peak. Enjoy the stars in the dark sky while soaking in the hot tub.

Location · Family · View

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 · Back garden

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 · Value · Layout

Retro vibes, modern comfort, pool. . .

Modern Comfort – A Palm Springs Retro Apartment. Step into a 1960s Palm Springs-inspired apartment at Starlite Vintage Resort. This spacious 2-bedroom unit features a queen bed, a second bedroom with queen + bunks, and a pull-out sofa. Enjoy a large kitchen, dining and living space, foosball table, vintage décor, and a private balcony with stunning mountain views. Guests also enjoy the seasonal pool, playground, fire pits, yard games, and our iconic vintage gas station photo spot.

Location · Family · View

The Overlook @ Royal Gorge

The Overlook Cabin is perfectly located to give you incredible views of the valley and on a clear day, the Sangre de Cristo mountain range beyond! Enjoy panoramic views of the countryside from the living area, a kitchenette and private bathroom and shower. Relax in the evening by a fire on your personal deck in Adirondack chairs. Located near the Royal Gorge at the Royal Gorge RV Resort & Cabins, you will have access to all resort amenities, including the hot tub and pool.

Location · Family · Decor

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.

Location · Value · Pets

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 · Back garden

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.

Family · Location · View

1BR Furnished Apartment Pet Friendly | Heated Pool

Stay in a fully furnished 1BR/1BA apartment in an upscale Colorado Springs community—perfect for long stays, relocations, or business travel. Enjoy a modern kitchen, high-speed WiFi, in-unit washer/dryer, and comfortable living area. Community amenities include a heated pool, hot tub, fitness center, clubhouse, grills, dog park, and pet spa. Convenient to Peterson AFB, downtown, trails, and dining.

Location · Decor · Walkability

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.

Location · Family · Cleanliness