Family-friendly holiday rentals in Castle Pines

An inviting outdoor space features a gas firepit surrounded by several seating options on a grassy area. A wooden deck leads to the house, with stairs ascending to the upper level. Scenic views of the open space and wildlife are visible in the background.

4.96 out of 5 average rating, 153 reviews

Large Luxurious Home Breathtaking Views w/ FirePit

Elevate your getaway experience at our exceptional Airbnb, where breathtaking views and modern amenities converge for the ultimate retreat. Situated just 5 minutes from downtown, our home offers the perfect blend of convenience and tranquility. Recharge your electric vehicle at our charging station and make the most of your stay with top-notch entertainment through our surround sound system. Book your stay today and discover a world where luxury, relaxation, and convenience harmoniously coexist.

4.99 out of 5 average rating, 512 reviews

A modern cabin is nestled among tall trees, showcasing a snow-covered landscape. Large windows provide views of the interior, where warm light glows from inside. A hot tub is visible on the deck, inviting relaxation amidst the serene winter setting.

Cabin in Black Hawk

Riverfront Cabin | Hot Tub, Fire Pit, Steam Shower

★★★★★ “The perfect blend of luxury and nature.” – Haley 💦 SPA BATHROOMS – Steam shower + jetted tub 🌿 HOT TUB & HAMMOCK – Soak creekside or sway in the trees 🔥 COZY EVENINGS – Fire pit, BBQ grill, fireplaces & in-floor heat ❄️ COOL COMFORT – Summer A/C 🐾 PET & FAMILY-FRIENDLY – Trails, Pack ’n Play, high chair 📶 FAST WI-FI – Stream, Zoom, or unplug 📍 10 min ⭆ Nederland — mtn town & adventure hub ➳ Breathe deep. Reconnect with what matters. ♡ Tap Save —unforgettable cabin stays start here

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.

4.88 out of 5 average rating, 126 reviews

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

4.97 out of 5 average rating, 478 reviews

The living area is highlighted by a gas fireplace and built-in shelving with decorative accents. A 55-inch flat-screen TV is mounted above the fireplace. Seating includes two dark leather sofas and a coffee table on a floral-patterned rug, with accent chairs in a complementary design.

Flat in Parker

Luxury 2BR Private Suite Retreat, Parker near I-25

This 2 BR luxury suite is located in a $1.5M home on the lower level with a private entrance, patio, large deck, and ample parking. This is a large private unit (~1500 sq. ft.) located on 2 acres in a rural setting, but minutes to restaurants and I-25 & Lincoln Ave. There is a private pickleball court on the property available upon request. We frequently host guests visiting Denver, Colorado Springs, and the acclaimed IVF facility in nearby Lone Tree. Guests find this a very desirable property.

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, 307 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, 248 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, 492 reviews

Historic 1890s Barn | Spa Bath - Steps to Downtown

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, 219 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!

4.88 out of 5 average rating, 101 reviews

A spacious living area features a comfortable sectional sofa, a flat-screen smart TV mounted on the wall, and a coffee table. Fresh greenery adds a touch of nature, while a ceiling fan provides airflow. The adjoining kitchen space is subtly visible in the background.

Flat in Castle Rock

Rocky Mountain Haven w/ king bed | pool & hot tub

Unwind in the stylish one-bedroom apartment in Castle Rock, located in Castle Rock and a short drive from Pikes Peak. City is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through the city easily from this prime location. Once you are ready to relax, retreat to your comfy apartment. ✔ Fully Equipped Kitchen ✔ Comfy King bed and sleep sofa ✔ Dining Table ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool (Seasonal) ✔ Hot Tub Learn more below!

4.98 out of 5 average rating, 199 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 Spring & 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. 😊

The sleeping area features a cozy queen bed with a warm, textured blanket. A barn-style door leads to a bathroom, while a small area rug adds color to the floor. Soft lighting is provided by wall-mounted fixtures, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 106 reviews

5 star *Cozy, Clean, and Bright! Private WalkOut*

*No outrageous cleaning fees or long cleaning lists. We really want you to stay! *Private walkout ground level basement with separate entrance and covered patio. Hosts live in the house above basement. *Ideal for 2 people sharing a bed. Queen bed and a small sofa (not big enough for an adult to sleep on). *About a mile to downtown Castle Rock with local restaurants *Walking distance to hiking at Rock Park *Quiet and Friendly Culdesac Neighborhood *Close to Castle Rock Outlet Mall

A well-lit living area features vaulted ceilings, providing an open feel. A round glass coffee table is centered between two comfortable sofas adorned with decorative pillows. Large windows allow natural light to fill the space, while a staircase leads to the upper level.