Family-friendly holiday rentals in Castle Rock

4.96 out of 5 average rating, 296 reviews

The exterior of a charming A-frame cabin features a sloped roof and a welcoming blue facade. A small porch is adorned with potted plants, while a pathway of stone slabs leads through landscaped greenery. Sunlight filters through surrounding trees, enhancing the inviting atmosphere.

Cabin in Palmer Lake

𓃲A-Frame on Palmer Lake𓃲 Firepit┃Foosball┃Grill

★Overlooking Palmer Lake, walkable to the downtown ★Location: 1 mi to Pinecrest Event Center, 20 mins to the Air Force Academy ★Outdoors: kayaking, paddle boarding, fishing, hiking ★YARD: Fenced in w/fire pit, grill, hammock, corn hole, ladder golf, yard dice ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys! ★55" Smart TV w/ access to apps like Hulu + Netflix ★Fast Wifi ★Keyless Entry ★Comfortable beds ★Equipped kitchen w/waffle maker, blender + more! ★Free Colorado beer

4.99 out of 5 average rating, 190 reviews

A custom A-frame cabin is surrounded by tall pines, featuring a sloped roof and large glass windows. A spacious deck with steps leads to outdoor seating and a hot tub, while natural stone landscaping adds to the serene setting.

Cabin in Monument

Cozy A-Frame Retreat “Hot Tub”w-Views, Monument CO

Experience a true Colorado getaway with this custom built Scandinavian 🇸🇪 inspired A-frame, nestled on the Palmer Divide, located only 15 min to Colorado Springs & 30 min to S Denver. You will feel secluded within the pines with views to die for. You might see wildlife walking by while enjoying a cup of coffee or glass of wine in the hot tub or cozied up in a blanket. First bottle of wine on us! Hiking trails are minutes drive from the cabin. Make sure to relax & make lots of memories. 😊

4.88 out of 5 average rating, 121 reviews

A spacious living room is presented, featuring a comfortable seating area with a sectional sofa and armchair. A coffee table centers the space, while a television stands on a console nearby. Natural light fills the room through large windows, and a dining area is visible in the background.

Home in The Meadows

Spacious Cozy Walkout Basement.

Spacious and bright walkout basement with cozy bedroom, walk-in closet, small kitchenette, full bathroom, complete living room with queen sofa bed and large washer and dryer. Private entrance through the backyard with access to to the outdoor patio. Right in the heart of Castle Rock. 5 minutes from the Outlets, 45 min from the airport, 25 min from Denver. PLEASE NOTE - Our family lives upstairs including kids, some noise can be heard from below specially weekday mornings, evenings and weekends

Guest suite in The Meadows

An outdoor seating area is shown beneath a covered patio. Comfortable couches face a coffee table featuring a propane fire pit, surrounded by scenic views of open fields and distant hills. Potted plants contribute to the natural ambiance.

4.99 out of 5 average rating, 106 reviews

Newly renovated private downstairs cottage

Our downstairs apartment with a private entrance offers all the comforts of home in a newly remodeled and fully furnished space. Relax on the recliner sofas and watch a movie, or get some work done with scenic views of the open space and mountains. Sleep comfortably on our memory foam mattresses and wake up to a variety of hot drink options at the coffee bar or cook a meal in the fully-equipped kitchen. Within minutes of parks, trails, outlet shopping, dining, & Castle Rock Adventist Hospital.

An inviting exterior of a single-story home is displayed, featuring a well-maintained lawn and a paved driveway. The backdrop showcases the impressive 'castle rock' formation against a clear blue sky, emphasizing the serene setting of the property.

4.9 out of 5 average rating, 298 reviews

Under the ROCK

Guests have access to the entire main floor including 2 bedrms, 2 bathrms, Lg Kitchen, Family Rm, Gas Fireplace, Dining Rm, Laundry, and a large deck with hottub. Guests can walk just 2-blocks to the entrance of "The Rock Park" and climb the "castle rock". Downtown Castle Rock is just a 2-3 minute drive. The house is just 3 minutes to I-25 and about 15 minutes to the DTC (Denver Tech Center), about 25-minutes to the Air Force Academy, and about 35-minutes to Colorado Springs and Denver.

4.96 out of 5 average rating, 237 reviews

A comfortable living area features a spacious brown sofa adorned with decorative pillows. A light-colored ottoman sits in the center, with a small potted plant on top. Natural light floods in through multiple windows, and a door leads to the enclosed porch.

Bungalow in Castle Rock

1920's Historic House Short Walk to Downtown

Enjoy all the modern conveniences & updates while experiencing the charm of a 1920's historical house. Enjoy time together in the open concept living room, dinning, and kitchen. Watch the sunset in the enclosed front porch, and sleep in comfort on one of the 3 beds in the house. You will have plenty to do being 2 blocks from downtown Castle Rock; close to trails, restaurants, parks, the outlet malls, zip-lines, and so much more. Close to Denver and Co Springs. This house will not disappoint!

An inviting master bedroom features a spacious bed framed by a stylish metal headboard, complemented by a decorative bench at the foot. Soft blue curtains frame the windows, while rustic wooden beams enhance the cozy, warm atmosphere of the space.

4.98 out of 5 average rating, 482 reviews

The Dyer House Inn

Experience a luxurious and fully restored 1890s barn on the first homestead property in the heart of downtown Castle Rock. High-end finishes throughout ensure your complete comfort and relaxation. Coffee, antiques, restaurants, shopping, and Festival Park are only a two minute walk from your front door. Enjoy a taste of simple, country living as you walk past our garden, chickens, and wild rabbits. The large, 1/2 acre property is charming, spacious, and the perfect backdrop for your stay.

An expansive deck features a dining table with several chairs under a large umbrella, surrounded by greenery and a fenced yard. The view highlights natural landscapes and the Rock formation in the distance, offering a serene outdoor space for relaxation.

5 out of 5 average rating, 209 reviews

THE ROCK HOUSE-HotTub,Crib,PoolTable,5Bedroom3Bath

Experience Colorado to its fullest. Easy access to I-25 to visit Denver & Colorado Springs, walking distance to downtown Castle Rock and the trailhead to hike The Rock. Amazing location near hiking, Castlewood Canyon, golf, parks & shopping. Enjoy views while in the hot tub, shoot a game of pool, watch a movie on the 70” TV, warm up by the fireplace or cook dinner in our fully stocked kitchen. This spacious house is renovated and ready to host your trip with friends and family! Crib included!

Guest suite in Castle Rock

A spacious living area features a large, dark leather sectional sofa arranged around a wooden coffee table with a storage compartment. Natural light enters through the window, complemented by soft curtains. A dining area with a table and chairs is visible in the background.

4.98 out of 5 average rating, 176 reviews

Boho Basement - Private Entrance - Hot Tub

Welcome to Boho Basement - This charming one-bedroom walkout apartment is nestled in a prime location just minutes away from downtown Castle Rock, local parks, and hiking trails. Discover a warm and inviting space complete with a full kitchen, ample living space, and a luxurious king-size bed. A private hot tub awaits you outside, providing the perfect spot for unwinding. At Boho Basement, you can enjoy all the comforts of home while experiencing the beauty of Colorado. Book your stay today!

Guesthouse in Castle Rock

A modern kitchen features sleek white cabinetry and a spacious granite countertop. Full-sized stainless steel appliances include a refrigerator, oven, and microwave. Two place settings are set on the counter, enhancing the inviting cooking space, complemented by pendant lighting above.

5 out of 5 average rating, 273 reviews

Cozy and Comfortable Castle Rock Gem 2 Bedroom

Escape from the city to this cozy, private guesthouse. Our sleepy neighborhood sits high up on a ridge overlooking quaint Castle Rock. Minutes away is the historic town of Castle Rock with eclectic restaurants, boutique shopping, breweries, parks and the nearby outlet mall. Step out to gorgeous Colorado sunsets, mountain views, nearby walking trails and enjoy this peaceful setting. Perfect spot to call home while you explore all that Castle Rock, Denver and the Rocky Mountains have to offer.

A modern kitchen with gray cabinets and stainless steel appliances is complemented by wooden flooring. Natural light highlights the spacious area, featuring a large window above the sink. A staircase leads to the upper level, while a coat hook is positioned near the entryway.

4.98 out of 5 average rating, 125 reviews

Kroll Loft - Comfort & Fun!

Gormet full kitchen, comfortable king-sized bed, pullout queen-sized sleeper sofa, theater-like 85" TV & private outdoor patio with grill! Kids & adults alike will love the arcade complete with air hockey, skee-ball, and basketball. Fast WiFi, full laundry, private parking, and AC will insure a perfect stay! Incredible location just a short walk from Castle Rock's finest restaurants, retail, & recreation. Stand-alone house so you'll have the entire property for the ultimate in peace & quiet!

Guesthouse in Castle Rock

The exterior view displays a multi-level wooden building with a warm, natural finish. A wooden staircase leads to a second-floor entrance, with a black metal railing enhancing safety. A vehicle is parked in front of the garage, framed by greenery.

4.91 out of 5 average rating, 173 reviews

Downtown Studio Suite

Modern 1 bedroom apartment built in 2021. Located in downtown Castle Rock. Walking distance to restaurants,events,walking paths and parks. Street parking available in front of the property. AC. Inside is a full kitchen with essentials including coffee, cream, dining table & chairs. Full laundry with 2 pods provided. 1 bedroom with a queen bed, TV for streaming & elec fireplace & walk in closet. Main room has sofa/pull out queen bed and a recliner. Full bath with soaps. Sleeps 4

Popular amenities for Castle Rock family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cabin in Cascade-Chipita Park

A hammock is positioned under tall trees, providing a view of the cabin beyond. The backyard features a grassy area with cornhole boards set up for leisure activities. The surrounding trees and mountains add to the serene atmosphere.

4.95 out of 5 average rating, 213 reviews

RiverHouse South w/ Sauna, Hot Tub & Fireplace

Superhost

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.

Guesthouse in Colorado Springs

4.91 out of 5 average rating, 130 reviews

Urban Float - Private Heated Pool/HotTub & Firepit

Guesthouse in Palmer Lake

A cozy bedroom features a king size bed with patterned black and white pillows, complemented by a rattan headboard and bench. A decorative antler mount adorns the dark wood wall, while natural light streams in from large windows, enhancing the serene atmosphere.

4.95 out of 5 average rating, 146 reviews

A Retreat in the Woods by a Lake & Mountain Views!

4.98 out of 5 average rating, 112 reviews

The exterior of the chalet is illuminated by warm string lights at dusk, showcasing a wood and glass structure surrounded by trees. A soothing hot tub is visible on the deck, offering a perfect spot for relaxation under the evening sky.

Cabin in Woodland Park

Dogs YES, Scenic Vws, Fireplace, Hot Tub, 2 Decks

4.94 out of 5 average rating, 144 reviews

A private hot tub is visible on the deck, surrounded by trees with distant mountain views in the background. The bubbling water reflects the sky, creating a serene retreat for relaxation.

Home in Monument

HOT TUB, Stunning Mountain views!

4.93 out of 5 average rating, 136 reviews

Natural light fills a spacious living area with large windows, showcasing greenery outside. A comfortable sofa adorned with blankets is complemented by two modern armchairs. A wooden dining table is set nearby, with decorative touches including a potted plant and a wall-mounted shelf.

Home in Monument

Secluded Chalet in the Pines Hot tub Wrapped porch

4.98 out of 5 average rating, 144 reviews

A welcoming living room features a warm wood ceiling and large windows that fill the space with natural light. Comfortable seating includes a tan leather sofa and two upholstered chairs in a deep hue. A coffee table sits atop a textured rug, enhancing the cozy ambiance.

Cabin in Woodland Park

Luxury Cabin w/ Hot Tub, Private Trail&Dark Skies

4.95 out of 5 average rating, 194 reviews

A spacious deck area is furnished with comfortable seating, including a cozy sectional and armchairs. A table sits at the center, with the surrounding view showcasing a forested landscape and distant mountains under a softly lit sky.

Home in Colorado Springs

✔️Clean★Quiet Home★King Bed★Hot Tub★Scenic Views✔️

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 105 reviews

The log cabin is elevated on a sturdy foundation, surrounded by a wooded area. Steps lead up to a welcoming deck, which offers views of the forest. Sunlight filters through the trees, illuminating the natural stone path that surrounds the property.

Cabin in Florissant

Timberwood Cabin

4.96 out of 5 average rating, 435 reviews

A three-story home featuring a unique eyebrow design is surrounded by greenery and tall trees. The exterior showcases a blend of stone and wood accents, with two garage doors and a round, welcoming front door that leads into the property.

Home in Palmer Lake

★Comfortable Nature Retreat★ Trails, Lake & Dining

Guesthouse in Palmer Lake

A rustic wooden cabin is nestled among snow-covered trees, presenting a serene winter scene. The building features a sloped roof and a single satellite dish, surrounded by a blanket of snow on the ground. The town of Palmer Lake is visible in the background.

4.95 out of 5 average rating, 260 reviews

Quaint and Historic Studio Cabin

Guesthouse in Colorado Springs

A spacious living area showcases a cozy sofa adorned with colorful textiles, set against wooden log walls and warm lighting. A staircase made of natural wood curves upward, leading to the sleeping loft. Windows allow natural light to fill the space, offering views of the surrounding forest.

4.94 out of 5 average rating, 199 reviews

Rustic Bunkhouse in Black Forest

Cabin in Colorado Springs

The exterior of a rustic bunkhouse is captured, featuring a covered porch supported by wooden beams. A concrete patio provides outdoor seating options, while a gravel driveway leads to the property. Trees and open landscape can be seen in the background.

4.91 out of 5 average rating, 151 reviews

Still Water Ranch-Private quiet farm house

4.96 out of 5 average rating, 228 reviews

Cabin in Florissant

Whimsical Dreams Cabin | Firepit | Kids Fort

Earthen home in Colorado Springs

The exterior of a unique earthship home is framed by lush greenery and tall pine trees. Large glass windows reflect the surrounding landscape, allowing natural light to illuminate the earth-toned structure. A black door is visible at the front, alongside a small seating area.

4.99 out of 5 average rating, 198 reviews

Off-grid, Earthen home in the forest!

Guest suite in Colorado Springs

The image showcases a rustic mountain retreat nestled in a colorful landscape of autumn foliage. The structure features a red roof and is surrounded by rolling hills and sparse trees, with a winding dirt path leading to the property.

4.99 out of 5 average rating, 234 reviews

Summer special! Unique Mtn Getaway w/ Epic Views!

Family-friendly home rentals with a pool

A modern living area features a cozy sectional sofa adorned with throw pillows, situated around two circular coffee tables. A green accent chair complements the space, with soft lighting provided by a floor lamp. A fireplace adds warmth, while artwork and plants introduce touches of elegance.

4.94 out of 5 average rating, 230 reviews

Modern 2BD 2BA | DTC | Light Rail | Pool + Fire

Apartment in Greenwood Village

A modern kitchen features a spacious countertop with a stainless steel sink and a microwave mounted above. Natural light enters through the window, illuminating the area. Cabinets and appliances complement the overall functionality, while a cozy living space is visible in the background.

4.94 out of 5 average rating, 266 reviews

Modern 1 Bedroom apt, furnished, pool, gym | DTC

Superhost

A spacious living room features a ceiling fan and large windows that provide natural light. A television is mounted above a stone fireplace, while a green cabinet and a glass coffee table are positioned in front of a comfortable sofa. The open kitchen and dining area are visible in the background.

Apartment in Greenwood Village

4.89 out of 5 average rating, 135 reviews

*Home away from home* 1 Bedroom unit close to DTC

4.84 out of 5 average rating, 324 reviews

Cozy, Ground Floor Condo in DTC w/ Full Kitchen!

A modern kitchen and dining area are highlighted, featuring a round table with four chairs. Recessed lighting illuminates the space, and a sliding door provides access to an outdoor area. Stainless steel appliances are visible in the kitchen, accompanied by wooden cabinetry.

4.88 out of 5 average rating, 169 reviews

Modern 2BR in DTC | First Floor | Sleeps 5

4.93 out of 5 average rating, 121 reviews

Apartment in Centennial

Centrally Located Two Bedroom Condo in Centennial

A comfortable living area features a brown sofa, a television on a stand, and a glass-top coffee table. Natural light is invited through a skylight and sliding glass doors that lead to a patio. A dining table with wooden chairs is set in one corner.

4.89 out of 5 average rating, 129 reviews

Comfortable & Affordable condo w/Queen bed