Family-friendly vacation rentals in Highland

5 out of 5 average rating, 236 reviews

An A-frame cabin stands amidst lush trees, illuminated by evening lights. A cedar hot tub, surrounded by natural boulders, emits steam, inviting relaxation. The exterior features large windows that bring the outdoors in, while a seating area is positioned nearby for enjoying the serene atmosphere.

Cabin in Running Springs

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Hiking

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings and high-end linens ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds No pets permitted

Guest suite in San Bernardino

A charming exterior of a single-story house is framed by lush palm trees and vibrant greenery. The front yard showcases a variety of plants, with a well-maintained pathway leading to the entrance. Clear blue skies provide a bright backdrop to this inviting structure.

4.99 out of 5 average rating, 158 reviews

Cozy independent Studio in Arrowhead Country Club!

SPACIOUS, BRAND NEW, INDEPENDENT STUDIO in the luxurious and peaceful Arrowhead Country Club. Independent with self-check in. 1 California bed plus 1 additional bed, kitchenette and huge shower. 500 sqft by the Golf course and 20 min. away from LAKE ARROWHEAD! Great for all seasons. Trees all around, all markets and restaurants you may need. Also 10 min. from San Manuel Casino. Close to Riverside and Redlands! We will only consider bookings for Registered ID Guests with reviews. Thank you!

4.95 out of 5 average rating, 196 reviews

The outdoor patio features a rustic fire pit surrounded by several Adirondack chairs, inviting relaxation. A wooden deck leads to the entrance of the cabin, set against lush greenery and shade provided by tall trees. The cabin's stone chimney adds character to the setting.

Cabin in Crestline

Cozy Cabin at LAKE Gregory- walk to shops and lake

A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

4.98 out of 5 average rating, 293 reviews

A spacious deck features a cozy wooden seating area with a light gray sofa and accent chair, surrounded by lush greenery and mountains in the distance. A small side table holds a decorative plant, adding a touch of nature to the serene outdoor space.

Cabin in Running Springs

@wild_olive_den • Serene Mountain Getaway Cabin

★ Featured in Condé Nast Traveler ★ Experience a designer escape at the Wild Olive Den. Perched above Running Springs with panoramic views, our cabin features a relaxing hot tub, EV charger, and 3 scenic decks. Perfect for families or a romantic getaway: 🏔 15min to Lake Arrowhead & Snow Valley Ski 🎡 7min to SkyPark / Santa’s Village 💻 Fast 370 Mbps Wi-Fi 🧸 Fully kid-equipped (Pack & Play/High chair) + Central A/C & Backup Generator! Relax by the fire or spin vinyl on the record player!

Guesthouse in San Bernardino

A spiral staircase leads to a lofted sleeping area, featuring a railing that offers safety. The main level displays a seating arrangement with a lamp beside a cozy sofa. A television is mounted on the wall, while decorative accents enhance the space.

4.84 out of 5 average rating, 287 reviews

Guesthouse with Loft & ICE COLD AC

This private and stylish guest house is perfect for group trips or the single traveler. Will sleep 4 adults and 1 kid with a Q bed, Q leather sofa fold out and a D futon. Quality bedding and pillow top mattress are very comfortable. K-Cups of coffee are provided along with bath sheets. Work at the desk or watch the game on the 50" big screen. Close to Yaamava Casino, Glen Helen Amphitheatre, Crestline, and three major hospitals. It's quiet and peaceful. Smoke outside only. Ice-cold A/C

5 out of 5 average rating, 97 reviews

Cabin in Big Bear

The Capricorn Cabin

Welcome to the Capricorn Cabin! Built in 1961, this cozy mid-century modern A-frame cabin in Big Bear blends historic charm with hygge comfort featuring vintage décor, a modern gel-fuel fireplace, vaulted ceilings, and king bed sleeping loft. Located in the historic Big Bear neighborhood Sugarloaf, this cabin is perfect for a romantic getaway, trip with your small family, or solo retreat. Just minutes from the lake, slopes, and village, with easy access by bus. We'd be happy to host you!

4.87 out of 5 average rating, 163 reviews

The living room is furnished with a dark brown sectional sofa, a white coffee table, and a pair of armchairs. A television is positioned against a gray wall, while natural light enters through the windows, which are adorned with navy blue curtains. Decorative elements enhance the space.

Home in Highland

Ray of sunshine Cottage.

Cozy and centrally-located home to relax, work, go to the casino, attend concerts or events near by. Down the street (1.2 miles) from Yaamava Resort & Casino. 14 min (6.8 miles) from National Orange Show Event center (NOS). 9 min (4.3 miles) from San Bernardino International Airport. 25 min (25 miles) from Ontario International Airport. Conveniently located as it’s at walking distance to restaurants, Starbucks, retail store; as well as food market, fast food places and more!

4.93 out of 5 average rating, 132 reviews

A modern living room features a sleek leather sofa and a cozy ottoman centered on a decorative area rug. A stylish light fixture hangs overhead, while a fireplace with an elegant mantel adds warmth. Large windows invite ample natural light, showcasing outdoor views.

Villa in San Bernardino

LUX 4BR near NOS & Yaamava with Private Backyard

Nestled on the foothills of the San Bernardino Mountains is our luxurious 4BR house, boasting a professionally designed interior that will capture your heart immediately! Only 5-minute drive to downtown, while the top destinations of Lake Arrowhead, Disneyland, and Palm Springs are within an hour's journey. 2300 sq. ft. of space awaits – a 55” HDTV, a foosball table, ultra-fast 500 MB/s Wi-Fi, and access to a private backyard with jacuzzi and BBQ (extra fee need to apply).

A bright sleeping area features a spacious bed with stylish linens and decorative pillows. A round mirror hangs above a modern sink in an adjoining area, complemented by floating shelves adorned with towels and greenery. A dining table with sleek chairs occupies the cozy kitchen space.

4.92 out of 5 average rating, 117 reviews

Bright Modern 2-Bd House in Quiet neighborhood!

This bright modern house was recently remodeled and it's ready for you to enjoy! The home is situated in a very quiet and safe neighborhood at the end of a cul-de-sac in the foothills of the San Bernardino mountains. This house is the perfect place to use as a basecamp when exploring San Bernardino (Yaamava Resort and Casino, NOS, the first McDonald's museum, Big Bear, Lake Arrowhead, Joshua Tree, Palm Springs, Orange County (Disneyland, Knotts), LA and so many more places.

Guest suite in Loma Linda

The exterior of a two-story home is presented, featuring a blend of neutral tones. A well-maintained landscape of low shrubs and decorative stones surrounds the property, enhancing the curb appeal. A driveway leads to a single-car garage, contributing to a welcoming street view.

4.97 out of 5 average rating, 306 reviews

Amazing Large 1 Bedroom, No Chores Home

Bring the whole family to this wonderful place in the heart of Loma Linda. The bedroom has its own retreat with a sleeper sofa for the kids or friends. Within a couple of miles you have Loma Linda University and Loma Linda VA. A couple miles East and you are in Downtown Redlands where you have entertainment, plentiful restaurants, and nightlife. Or enjoy the peaceful citrus trails this beautiful neighborhood offers which lead you to large parks where you can enjoy a picnic.

An outdoor space is presented, featuring a sparkling pool and a relaxing Jacuzzi under a wooden gazebo. Colorful murals adorn the surrounding wall, with warm light illuminating the area at dusk. Comfortable lounge chairs are positioned around the pool for leisure.

4.82 out of 5 average rating, 224 reviews

Hot Tub, Fire Pit/Game Room/ Near NOS Center

Welcome to our meticulously clean three-bedroom, two-bath haven in San Bernardino! This gorgeous house is designed for comfort and entertainment. Unwind in the game room with a pool table or gather around the patio's fire pit. Experience the charm of our outdoor space, featuring a second fire pit in the grass area. Create lasting memories surrounded by freshly painted murals near the inviting pool and brand-new Jacuzzi – perfect for starlit evenings with friends and family.

A spacious bedroom features a king-size bed covered in an orange quilt, accompanied by a white nightstand with a small plant. A bench sits at the foot of the bed, and an open closet with hanging space is visible, alongside a gray dresser against the wall.

4.91 out of 5 average rating, 157 reviews

2-King size bed: Hidden Gem

Join the fuss, come and relax in this NEW lively & stylish rear space. Here you have one master bedroom with a king-size bed and its private restroom, TV with Netflix. Send your guest to the second bedroom also king size bed & TV, and leave that one friend to sleep in the sofa bed joined by another TV. Fully stocked kitchen plus We offer free coffee ☕️ ◆15 minute drive to Yaamava' Resort & Casino ◆9 minute drive to National Orange Show (NOS) Center ig arbnbproperties

Popular amenities for Highland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 111 reviews

Cabin in Running Springs

Log Cabin w/Gorgeous Views, Hot Tub+King Beds

4.96 out of 5 average rating, 138 reviews

Home in Riverside

Casa de Agua Retreat

4.99 out of 5 average rating, 310 reviews

The cabin, set among tall trees, features a gray exterior with warm, glowing windows. A stone pathway leads to the entrance, framed by natural landscaping. The tranquil setting hints at a peaceful atmosphere, ideal for a quiet getaway, especially during evening hours.

Cabin in Forest Falls

Palisades View - Cabin With Spa

4.94 out of 5 average rating, 463 reviews

A modern chalet cabin is set against a backdrop of tall trees, featuring a sloped roof and large windows. A wooden deck extends from the front, furnished with two chairs and a small table for outdoor relaxation. The red brick chimney adds a rustic touch.

Cabin in Big Bear

Rancho Pines I Spruce, Skiing + Hiking + Hot Tub

4.97 out of 5 average rating, 234 reviews

The A-frame chalet showcases large wall-to-wall glass doors, inviting natural light. A spacious deck with comfortable outdoor seating surrounding a bright orange fireplace offers views of the surrounding wooded landscape and boulders.

Cabin in Big Bear

Modern Swiss Chalet | Sweeping Views | Hot Tub

4.91 out of 5 average rating, 172 reviews

Home in Grand Terrace

Riverside Serenity Spring Oasis|Spa/Pool/Mini Golf

A bubbling hot tub is viewed from the edge, with a patio area visible in the background. Soft lighting highlights the space, and a modern TV is mounted on the wall, adding to the cozy ambiance of the outdoor setting.

4.91 out of 5 average rating, 149 reviews

Luxury Home w/Private Jacuzzi & Firepit

Villa in Rancho Cucamonga

A private pool area features a natural stone water slide, surrounded by lush greenery and palm trees. A hot tub is positioned beside the pool, with colorful flowers in a planter nearby. Vibrant patio furniture adds a touch of comfort to the outdoor setting.

4.87 out of 5 average rating, 143 reviews

Gorgeous Resort Style Mountain view Pool Villa

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 149 reviews

A bright bedroom features a white wooden bed frame adorned with a blue and aqua bedding set. Colorful pillows add a touch of vibrancy. Soft lighting from two bedside lamps creates a warm glow, and a window with blinds allows for natural light to filter in.

Home in North Fontana

Cozy Quiet Private Rose House laundry cooking

Place to stay in Running Springs

4.96 out of 5 average rating, 150 reviews

Family friendly Modern A-Frame Chalet • Pets & EV

4.98 out of 5 average rating, 120 reviews

A charming cabin exterior is framed by a lush, wooded landscape. The structure features a dark wood exterior with red accents, including windows and a front door. A wooden deck extends from the entrance, nestled beside a large, aged tree.

Cabin in Lake Arrowhead

Storybook Nook- Romantic and Pet Friendly Cottage!

4.97 out of 5 average rating, 125 reviews

A spacious living area showcases high vaulted ceilings and large floor-to-ceiling windows framing expansive views of the mountains. A leather sofa sits atop a light-colored rug, adjacent to a stone fireplace with a warm glow. Rustic chandeliers provide soft ambient lighting, enhancing the inviting space.

Cabin in Lake Arrowhead

Modern Cabin with Stunning Views, Outdoor Firepit

4.99 out of 5 average rating, 130 reviews

Hilltop Escape | Heated Pool & Epic Views

4.9 out of 5 average rating, 224 reviews

The guest house features a welcoming entrance with a decorative front door and a small chair positioned by the entrance. Lush greenery surrounds the exterior, with tropical plants and palm trees enhancing the natural landscape. A clean pathway leads to the doorway.

Guesthouse in Colton

Oasis in the canyon

5 out of 5 average rating, 105 reviews

An expansive deck features a circular gas fire pit surrounded by four lounge chairs. String lights are hung above, creating a soft glow. Tall trees are visible in the background, enhancing the outdoor setting.

Cabin in Crestline

Fairy Forest Cabin - Walk to Lake, Dog-Friendly

Cabin in Idyllwild-Pine Cove

The A-frame cabin is nestled among towering trees, illuminated by soft exterior lights. The design features large windows, offering a glimpse of the interior. A gentle staircase leads up to the welcoming deck, creating a harmonious blend with the natural surroundings.

4.96 out of 5 average rating, 300 reviews

A-Frame Style Modern Cabin | ReWild

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 293 reviews

Two wooden lounge chairs are positioned by a poolside area, surrounded by lush greenery and tall cypress trees. A small metal table sits between the chairs, creating a inviting space for relaxation amid a gravel landscape.

Guesthouse in Claremont

Pool • Garden Patio • 5 Min to Village & Colleges

4.95 out of 5 average rating, 157 reviews

A spacious outdoor pool is surrounded by a concrete patio and palm trees, providing a relaxing area for guests. The lush greenery and well-maintained landscaping enhance the outdoor setting, while the house features a tiled roof and large windows that allow natural light.

Home in Riverside

Charming 5 bed, 3 bath home with pool

4.9 out of 5 average rating, 116 reviews

An outdoor living space features a large pool surrounded by sun loungers, with a cozy fire pit area nearby. The two-story estate is visible in the background, showcasing a blend of modern and rustic elements against a backdrop of mountainous scenery.

Home in Cherry Valley

Vineyard Retreat, Pool & Amazing Views!

4.99 out of 5 average rating, 336 reviews

The outdoor space features a sparkling swimming pool surrounded by a landscaped patio. The cottage is seen in the background with large glass doors, inviting natural light. Beautiful plants and greenery enhance the serene atmosphere, providing a pleasant space for relaxation.

Guesthouse in Redlands

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

4.78 out of 5 average rating, 120 reviews

A private, fenced pool is surrounded by lush greenery and palm trees. The water appears inviting, with some leaves floating on the surface. A rustic gazebo is visible in the background, and lounge chairs are placed nearby for relaxation.

Home in Rancho Cucamonga

Luxury 5BR Pool Home | ONT, Victoria Gdns & Mills

4.91 out of 5 average rating, 355 reviews

Cabin in Big Bear Lake

Feet Away From Slopes Modern Snow Summit Cabin

4.97 out of 5 average rating, 108 reviews

A spacious pool area is showcased with a clear blue pool reflecting the evening sky. Surrounding the pool are lounge chairs and a dining table with an umbrella for shade. The house features large windows that invite natural light, enhancing the outdoor living experience.

Home in Riverside

Tesla EV Charger, 2 KING BEDs, 3 minute to UCR