Family-friendly vacation rentals in Highland

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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

A round wooden dining table is surrounded by six upholstered chairs featuring a light fabric design. The table is set with six plates and a centerpiece of natural elements, including a candle. Soft lighting enhances the warm interior with earthy tones.

Home in Fontana

4.94 out of 5 average rating, 353 reviews

DJ's Bed & Bistro

(Insomniac: $800/2 or $900/3 up to 8 guests) Rustic-elegance. New paint. Private front entrance, porch, living/dining room, bedroom w/queen size bed, & full bath. Attached but private & sealed off from the main house. NO KITCHEN and NO RESTAURANT. Self-serve/complementary coffee & tea bar with 1st day breakfast pastry. Snack center for purchases. Microwave, toaster, refrigerator, k-cup coffee, hot-water kettle. Air mattresses with bedding provided by request, with 3 or more paid guests.

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, 139 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!

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, 238 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

Guest favorite

The exterior of a historic two-story house is visible, surrounded by well-kept grass and mature trees. A porch extends across the front, and multiple windows offer glimpses into the interior. The building reflects classic architecture with a subtle, inviting color palette.

Guest suite in Redlands

4.89 out of 5 average rating, 444 reviews

(2) Downtown Redlands Retreat: Cozy Master Suite

This is a nice master bedroom, converted to a guest suite. The room has a private entrance, and private bathroom. Walls were recently torn down & made sound proof so as to not disrupt our guest with noises inside the house. This house has a lot of history, it’s over 120 years old. It’s perfectly situated about a minute away from the freeway is a central locations, in the beautiful & historic city of Redlands. Security cameras recording at all times all around the outdoors of the property.

Guest favorite

A small living area features light-colored sofas adorned with patterned cushions. A coffee table is placed on a textured red rug, with a decorative item at its center. A television is positioned on a stand next to a door leading outside, with natural light filtering through nearby windows.

Apartment in Redlands

4.9 out of 5 average rating, 137 reviews

2-BDR attached apt in rural Redlands neighborhood.

Our “RURAL REDLANDS” neighborhood is quiet with local wild creatures roaming (coyotes, rabbits and squirrels). Although other hosts welcome pets, we requests no pets for our guests that have extreme allergies. Our RURAL is an older home; not fancy but comfortable. Two bedrooms, kitchenette and living room. Private from us. We are near University of Redlands, Historic Downtown Redlands, restaurants, as well as Oak Glen apple farms. We’re 60 miles from Palm Springs, Casinos, Disneyland

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, 210 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*)

Guest favorite

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

4.89 out of 5 average rating, 103 reviews

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!

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.

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, 132 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

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, 135 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

Guest favorite

The exterior of a guest house is captured, featuring a white facade and a wooden staircase leading to the entrance. Surrounding plants add greenery, and a sandy pathway extends from the driveway. A covered porch is visible, framed by wooden railings.

Guesthouse in Redlands

4.93 out of 5 average rating, 159 reviews

Sunset Bungalow

Welcome to Sunset Bungalow. A beautiful guest house located on historic Sunset Dr in the city of Redlands. Within walking distance to renowned Kimberly Crest Mansion at Prospect Park. Downtown Redlands is just a few short minutes drive away along with University of Redlands, Loma Linda University, Redlands Hospital, Loma Linda Hospital, VA Hospital and ESRI. Sit back and relax in this calm, stylish space.