Holiday houses in Highland

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Top-rated holiday rentals in Highland

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 150 reviews

Cozy independent Studio in Arrowhead Country Club!

SPACIOUS, BRAND NEW, INDEPENDENT STUDIO 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 spacious deck features a cozy wooden seating area with a light gray sofa and accent chair, surrounded by lush greenery and mountains in the distance. A small side table holds a decorative plant, adding a touch of nature to the serene outdoor space.
Cabin in Running Springs
4.98 out of 5 average rating, 285 reviews

@wild_olive_den ~ Serene Weekend 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!

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
4.86 out of 5 average rating, 276 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, 37 reviews

Retro Retreat | Game Lounge & 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, 150 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!

Superhost
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 Arrowhead
4.93 out of 5 average rating, 129 reviews

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).

Guest favourite
A bright sleeping area features a spacious bed with stylish linens and decorative pillows. A round mirror hangs above a modern sink in an adjoining area, complemented by floating shelves adorned with towels and greenery. A dining table with sleek chairs occupies the cozy kitchen space.
Home in San Bernardino
4.94 out of 5 average rating, 102 reviews

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.

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 Loma Linda
4.97 out of 5 average rating, 295 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
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
4.91 out of 5 average rating, 155 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 ig arbnbproperties

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.
Holiday home in Highland
5 out of 5 average rating, 47 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
Guest suite in Downtown Redlands
4.88 out of 5 average rating, 610 reviews

Private Cozy Suite & Bath | Self Check-In

Private-entry guest suite with keypad access, private attached bathroom, Wi-Fi, workspace, TV with streaming, mini fridge, and microwave. Cozy and ideal for 1–2 guests. Located in a historic 1895 home—updated with a few quirks: toilet paper goes in trash (older pipes), shower is simple and functional (not luxury). Climate control is via a portable AC unit and small heater (not central), which comfortably does the job. Quiet space, no parties.

Top Guest favourite
Guesthouse in Highland
4.93 out of 5 average rating, 165 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!

Popular amenities for Highland holiday rentals

When is the best time to visit Highland?

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Avg. price$179 NZD$188 NZD$179 NZD$191 NZD$186 NZD$191 NZD$190 NZD$190 NZD$183 NZD$195 NZD$179 NZD$181 NZD
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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 40 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 290 vacation rentals in North Redlands, over 270 vacation rentals in Northwest Redlands, and over 60 vacation rentals in East Highlands.

  • 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.

  • Are there pet-friendly house rentals in Highland?

    Four-legged friends are welcome in Highland. Choose from more than 20 house rentals for guests traveling with pets.

  • Are there Highland vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Highland, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Highland have air conditioning?

    Absolutely! We offer over 70 house rentals with air conditioning in Highland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Highland have wifi?

    Absolutely! We offer over 70 house rentals with wifi in Highland. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Highland

  • Total holiday rentals

    Explore 100 holiday rentals in Highland

  • Nightly prices starting at

    Highland holiday rentals start at $68 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Highland holiday rentals include Wi-Fi 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!