Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favourite
Guesthouse in San Bernardino
5 out of 5 average rating, 16 reviews

Adorable studio w/full kitchen' washer&dry & patio

Keep it simple at this peaceful and centrally-located place. Adorable Studio is designed for the traveling professional. Full kitchen, washer and dryer, 50-inch smart tv and storage space. Located in the hills ofVerdemont Heights, one of the best areas in the Inland Empire. Lots of walking trails and close to lots of restaurants. Victoria Gardens, Rialto Renaissance Market place, and Redlands. Also centrally-located to many hospitals. Armc, Kaiser,Loma Linda, SB com, and close to high desert.

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
4.93 out of 5 average rating, 58 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.

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, 146 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 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
4.85 out of 5 average rating, 257 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
Home in Highland
5 out of 5 average rating, 34 reviews

Cozy Fall Retreat | Crackling Firepit & Game Night

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
4.9 out of 5 average rating, 124 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, 283 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.

Guest favourite
The entrance to the condo features a white door with an arched window. A welcoming doormat is placed at the entrance. Potted flowers and a decorative plant are positioned beside the door, while a light fixture is mounted above.
Apartment in Loma Linda
4.9 out of 5 average rating, 20 reviews

Small Condo 5 minutes from LLUH!

Newly built small condo 5 MINUTES AWAY from Loma Linda University & Hospital Quiet and peaceful neighborhood The space is includes: - newly remodeled bathroom (necessities provided) - small kitchenette equipped with all necessities - closet space - laundry room The space is part of the house with separate access from the side of the house. The laundry is shared with another apartment adjacent to this. No access to the main house. Your space will be private.

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, 270 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.

Top guest favourite
The kitchen area features sleek grey cabinetry, modern stainless steel appliances, and a light-colored wooden dining table surrounded by four matching chairs. The layout promotes an open feel, allowing for easy accessibility and movement.
Vacation home in Highland
5 out of 5 average rating, 44 reviews

Modern apartment ready for your enjoyment

Modern one bedroom apartment with all the amenities needed to guarantee a relaxing stay. You will only be 5 minutes from Yaamava ( San Manuel Casino) Costco, 32 miles from Big Bear, and only 25 miles from Lake Arrowhead. Night life is only a 15 minute uber drive away from Downtown Redlands. Ontario international airport is 30 minutes away. The National Oange show event center is less then 15 minutes away and the Glen Helen Amphitheater is a 20 minute drive away.

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
4.88 out of 5 average rating, 51 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.

Guest favourite
A modern guest space features a spacious bed with a neutral-toned comforter and a yellow accent pillow. An open kitchen area with wood cabinetry is visible in the background, along with a cozy sitting area and a large wall-mounted television. Natural light brightens the room.
Guesthouse in Wildwood Park
4.97 out of 5 average rating, 32 reviews

Luxury Private Studio / Near Yaamava & NOS Center!

Welcome to our Luxury Guest house in San Bernardino California! Our Guest house is a new construction and everything is brand new! It can fit up to 4 people if needed but this space is Ideally for 2 people. Our guest house offers a full bathroom and kitchen. This unit is completely separate from the main unit and you will have full privacy. We are 10 minutes away from the NOS Center.

Popular amenities for Highland vacation rentals

When is the best time to visit Highland?

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Avg. price$144 CAD$151 CAD$144 CAD$153 CAD$149 CAD$153 CAD$152 CAD$152 CAD$146 CAD$138 CAD$148 CAD$138 CAD
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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Highland?

    Experience the best of Highland with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Highland?

    Yes! Work meets play with ease at over 30 house rentals in Highland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Highland?

    Make yourself at home in Highland by choosing from our most frequently booked neighborhoods. We have over 260 vacation rentals in Northwest Redlands, over 60 vacation rentals in East Highlands, and over 290 vacation rentals in North Redlands.

  • Do house rentals in Highland have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Highland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Highland have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Highland. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Highland?

    Four-legged friends are welcome in Highland. Choose from more than 10 house rentals for guests traveling with pets.

  • Are there family-friendly house rentals in Highland?

    Highland has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Highland?

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with air conditioning, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Highland

  • Total vacation rentals

    Explore 100 vacation rentals in Highland

  • Nightly prices starting at

    Highland vacation rentals start at $55 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    100 of Highland vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Highland rentals

  • 4.8 Average rating

    Highland stays are highly rated by guests—averaging 4.8 out of 5!