Holiday houses in Highland

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Top-rated holiday rentals in Highland

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Guest favourite

A modern kitchen and dining area features sleek white cabinetry and stainless steel appliances. A spacious island with seating for four stands at the center. Light wood flooring complements the area, while large windows allow natural light to brighten the space.

Guest suite in San Bernardino

4.94 out of 5 average rating, 51 reviews

3BDModern Unit-NOS/Yaamav/Mtns.

This beautiful 3beds-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 offers easy access to entertainment. This home is minutes from Yaamava and NOS Event Center and about a one-hour drive to Big Bear and Mount High Ski Resort for summer/winter activities. Smart TV. WiFi. AC Experience this Modern home with amenities and spacious accommodations. We can’t wait to welcome you.

Superhost

Guesthouse in San Bernardino

4.7 out of 5 average rating, 27 reviews

Attached back, House

Very Small back House behind the main residence, one bedroom with Window, AC, one bathroom, Full bathroom, with stand up shower. one living room what a sleeper sofa. kitchen with a gas cooktop, microwave, keurig coffee machine, mimi fridge. With a shared backyard and Drive Way. Conveniently located near 215 and 210 Freeway. Just 3 miles away from N.O.S. Center. About 5 miles from Yaamava Casino. Enjoy easy access to everything located near waterman ave, and baseline st not far from, Stater Bros

Top Guest favourite

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, 141 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 favourite

A vibrant yellow vintage car is parked on a gravel driveway, surrounded by colorful flowers and lush greenery. Small, charming container homes are visible in the background, nestled among the trees under a clear blue sky.

Shipping container in San Bernardino

4.92 out of 5 average rating, 305 reviews

#2 Cozy Tinyhouse"Route 66" Container- private

Longterm rental, peaceful, rural neighborhood, if you’re looking to get just outside of the city. No smoking , NO animals due to health conditions. 1.5 hour or less to Santa Monica, Venice Beach, less than 2 hours from San Diego, & 3 hours to Las Vegas. 5 min from the world famous motocross track! Glen Helen amphitheater, Route 66, and hot spot for paragliding is just 5 minutes away! CozyTiny Container home is private, with all comforts. Relax at the foot of the mountains with 1 parking spot.

Guest favourite

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 Arrowhead

4.84 out of 5 average rating, 246 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 favourite

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 Downtown Redlands

4.89 out of 5 average rating, 454 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.

Top Guest favourite

Home in Highland

5 out of 5 average rating, 26 reviews

Retro Retreat | Blackjack+Billiards | Vinyl Vibes

Planning your weekend escape? Retro Retreat is your perfect getaway just minutes from Yaamava Casino, ONT Airport, and Inland Empire hotspots 🔥 🎰 4 min to Yaamava Resort & Casino 🎓 18 min to Loma Linda University ✈️ 27 min to Ontario Airport (ONT) 🍔 13 min to Downtown Redlands 🎡 15 min to NOS Events Center 🌲 35 min to Lake Arrowhead After a fun night out, unwind in the peaceful sunroom with loved ones at the heart of this home. Dates fill fast. Lock in your stay at Retro Retreat!

Guest favourite

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 Amber Hills

4.89 out of 5 average rating, 114 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 favourite

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, 276 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 favourite

A charming guesthouse exterior is presented with a paved patio featuring potted plants. A comfortable seating area is visible, along with glass doors that allow natural light into the space. Lush palm trees surround the area, enhancing the inviting atmosphere.

Guesthouse in Highland

4.96 out of 5 average rating, 267 reviews

Serene Escape Tiny House Living /pool/near Yaamava

We are located close to dining , hiking, shopping, movie theaters, National Orange Show Event Center (NOS Events), Yaamava Resort and Casino, some nightlife, Redlands University and Loma Linda University. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. Our place is good for couples, solo adventurers, and business travelers. Perfect little getaway! I have another listing-click on my photo to view.

Guest favourite

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, 141 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

Superhost

A well-arranged bedroom features a spacious bed with crisp white linens and a navy blue throw blanket. Two bedside lamps illuminate the area beside elegant wall art. Natural light filters in through a window, complemented by soft wall colors and wooden flooring.

Guesthouse in San Bernardino

4.87 out of 5 average rating, 30 reviews

High finished ADU One queen bed and one sofa bed

Newly built ADU 5 MINUTES AWAY from Loma Linda University & Hospital Quiet and peaceful neighborhood The space is includes: - New white bathroom (necessities provided) - New Kitchen equipped with all necessities - Closet space - Laundry room The space is attached to the existing house with separate access from the side of the house. Your space will be 100% private. With digital lock.