Family-friendly vacation rentals in Highland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Highland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

The exterior of a historic home is featured, framed by tall palm trees and greenery. A clear blue sky enhances the inviting atmosphere. The two-story house displays a balcony and multiple windows, while a pathway leads to the entrance, with parked cars visible nearby.

Guest suite in Redlands

4.9 out of 5 average rating, 569 reviews

(1) Cozy Redlands Retreat with Victorian charm

Private room, entrance & restroom. Well decorated, great view of the San Bernardino Mountains. This room has everything you need for a comfortable stay! Room includes television, wifi, mini refrigerator, small table (2), work space (desk & chair), coffee machine & more. Down Town Redlands is 1 mile away. Big Bear Lake/Snow less than an hour away, & L.A about 60 miles away. Conveniently located right off the 10 fwy. Security cameras recording at all times all around the outdoors of the property.

Top guest favorite

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.

Guest suite in San Bernardino

4.99 out of 5 average rating, 138 reviews

All New cozy SUITE in Arrowhead Country Club!

SPACIOUS, BRAND NEW, INDEPENDENT SUITE 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!

Top guest favorite

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

4.99 out of 5 average rating, 310 reviews

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

Guest favorite

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

4.93 out of 5 average rating, 113 reviews

LUX 4BR near NOS & Yaamava w Private Backyard

Nestled on the foothills of the San Bernardino Mountains is our luxurious 4-bed house, boasting a professionally designed interior that will capture your heart the moment you arrive. An effortless 5-minute drive transports you to downtown, while the top destinations of Lake Arrowhead, Disneyland, and Palm Springs are within an hour's journey. On the inside, 2300 sq. ft. of space awaits – complete with a 55” HDTV, a foosball table, ultra-fast 500 MB/s Wi-Fi, and access to a private backyard!

Guest favorite

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.

Guesthouse in San Bernardino

4.84 out of 5 average rating, 237 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

Top guest favorite

A two-story mini home is showcased beside a refreshing swimming pool, surrounded by a neatly landscaped garden filled with various plants. The clear blue sky enhances the peaceful outdoor atmosphere, while a palm tree rises above the structure.

Guesthouse in Fontana

4.96 out of 5 average rating, 206 reviews

The Blue Cabin

Relax at this unique, tranquil, and comfortable mini home in our backyard. Surrounded by a beautiful garden with a wide variety of succulents and a relaxing pool. With a space to enjoy reading or listening to music. Equipped with microwave, Keurig coffee machine, mini refrigerator, toaster, blender, washer/dryer, and tableware. The mini home has air conditioning and heating system for comfort and a smart TV. No parties allowed.(SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

Top guest favorite

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.

Guest suite in Redlands

4.97 out of 5 average rating, 268 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.

Superhost

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.

Home in San Bernardino

4.81 out of 5 average rating, 191 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.

Top guest favorite

A serene exterior view of a white two-story home is presented, with a wide driveway leading toward the entrance. To the left, rows of grapevines are visible, framed by mountainous greenery under a clear blue sky.

Home in Yucaipa

4.96 out of 5 average rating, 130 reviews

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

Guest favorite

A stylish indoor bar area features sleek stools and illuminated counters, creating a modern social space. An outdoor scene reveals palm trees and a beautifully lit pool, creating a serene retreat. A vibrant putting green is visible, along with a red billiard table, showcasing recreational options.

Home in San Bernardino

4.89 out of 5 average rating, 118 reviews

Tropical Oasis Heated Pool & Spa/Firepit/Game Room

Pool HEATER and Jacuzzi HEATER HAVE SEPERATE ADDITIONAL FEES READ UNDER OUR POOL INFORMATION Experience a resort-style retreat nestled against the breathtaking backdrop of mountains and palm trees. Indulge in a rejuvenating stay at our home, designed to provide the perfect blend of relaxation and excitement. Located in the serene north part of San Bernardino, our inviting home is ideal for intimate getaways or gatherings with family and loved ones.

Top guest favorite

A spacious sleeping area features a queen-size bed adorned with blue and white linens. Adjacent, a small dining table with two chairs is positioned near a window dressed with dark curtains. A flat-screen TV is mounted on the ceiling, enhancing the room's comfort.

Guesthouse in Highland

4.93 out of 5 average rating, 156 reviews

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!

Guest favorite

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.

Home in San Bernardino

4.92 out of 5 average rating, 133 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 so you can chill. 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 ◆15 minute drive to Yaamava' Resort & Casino ◆9 minute drive to National Orange Show (NOS) Center