Family-friendly holiday rentals in Highland

Adorable Cozy Cottage, base of Beautiful Mountains

This adorable cottage is located at the base of the San Bernardino mountains where you have views of the snow-capped mountains in the colder seasons & views of the beautiful sunsets all year! Close to freeways, malls & hiking trails. Relax poolside as the cottage doors open to the pool & outdoor BBQ & fire pit. It's a great get-away location with all newly remodeled amenities for a comfortable stay. Plenty of parking. NEW onsite DAY SPA services! THIS SPACE IS NOT SUITABLE FOR SMALL CHILDREN

Family · Indoor spaces · Check-in

@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!

Kitchen · Family · Location

Mountain Lake A-Frame | Forest, AC, Auto-Generator

Enchanting A-Frame cabin offers the perfect blend of adventure and tranquility. Explore trails, mountain towns, or unwind in the hammocks. Sits on a double lot, so you have space to yourself. Cutest small mtn town & 30 min to Big Bear 🔸Auto Generator (no worrying @ blackouts, summer or winter, happens often) 🔸NEW AC mini split 🔸 NEW cozy couch 🔸Propane BBQ & Fire Pit (with tanks) 🔸Private acre of forest 🔸 5-minute walk to lake 🔸 Hammocks & swing 🔸 Fireplace 🔸 Washer/Dryer BYOD

Kitchen · Indoor spaces · Barbecue

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!

Indoor spaces · Kitchen · Air conditioning

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!

Indoor spaces · Family · Hospitality

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).

Kitchen · Family · Location

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.

Kitchen · Indoor spaces · Check-in

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.

Indoor spaces · Kitchen · Laundry

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.

Indoor spaces · Family · Accuracy

Quiet Vineyard View 2-bedroom Home Near Oak Glen

This 1700sqft spacious vineyard-view home is nestled on Yucaipa's North Bench in a peaceful, rural cul-de-sac. Close proximity to Oak Glen and Yucaipa's dedicated open space make this home a perfect landing spot for comfort and safety. Beautiful views of the mountain and vineyards. Centrally located to Oak Glen, Big Bear, Palm Springs. Bedroom 1: CalKing Bed Bedroom 2: Queen Bed Additional Beds: (2) Twins and pack-n-play upon request No parties/events are permitted

Family · Indoor spaces · Decor

Clean Modern ADU Close to NOS/ Yaamava/ Big Bear

This beautiful ADU-full-home is perfect for families or groups of up to 6 guests. With a private entrance and free parking, you’ll enjoy the freedom to come and go as you please. This home is minutes from Yaamava, NOS Event Center, Big Bear, or Mount High Ski Resort for summer/winter activities. Great for those going to Coachella, Los Angeles, Anehiem, or Orange County. Smart TV. WiFi. A/C. Washer and Dryer. Kitchen. Self Check-in. Close to freeways.

Indoor spaces · Kitchen · Condition

Dreamy Escape Private Entrance/pool/near Yaamava

Our location is close to dining, hiking, shopping, movie theaters, and popular attractions like the National Orange Show Event Center (NOS), Yaamava Resort & Casino, vibrant nightlife, Redlands University, and Loma Linda University. You'll love our place for its location, inviting ambiance, outdoor space, and friendly neighborhood. It's the perfect spot for couples, solo adventurers, and business travelers looking for a cozy getaway!

Indoor spaces · Family · Air conditioning