Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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

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Top guest favorite
A comfortable seating area features a large leather chair and ottoman, positioned in front of a modern gas fireplace, which is glowing warmly. Floor-to-ceiling windows reveal scenic views of the outdoors, and subtle lighting from above creates a cozy ambiance.
Chalet in Crestline
4.98 out of 5 average rating, 471 reviews

Magical Mid-Century Cabin Epic Views & Fireplace

Nestled just a short distance from LA, embrace the idyllic landscape of picture-perfect sunsets from the balconies and awe-inspiring views from the house. Discover the orchestra of ravens and crows while savoring your morning coffee, or get lost in a book by the fireplace. Featured in Fodor’s Travel “Best Airbnbs and cabins of the year”! A 4-minute drive to Lake Gregory, 12 minutes to Lake Arrowhead, & 45 minutes to Big Bear. So much to explore or stay cozy inside, you will enjoy your time here.

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, 150 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
The outdoor patio features a rustic fire pit surrounded by several Adirondack chairs, inviting relaxation. A wooden deck leads to the entrance of the cabin, set against lush greenery and shade provided by tall trees. The cabin's stone chimney adds character to the setting.
Cabin in Crestline
4.95 out of 5 average rating, 174 reviews

Designer Cabin at LAKE Gregory- walk to town

A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

Guest favorite
A spacious living room features high cathedral ceilings and large windows allowing natural light to enter. Modern blue sofas are arranged around a glass coffee table, complemented by stylish accent chairs. A lush indoor plant adds a touch of greenery, enhancing the warm atmosphere.
Villa in Redlands
4.92 out of 5 average rating, 154 reviews

Peaceful Private Retreat In The Heart Of Town

Meticulously designer-renovated modern home “The Nest “is surrounded by mature tree and nestled beneath the mountains in South Redlands. Whether you’re looking to spend time with loved ones, vacationing or work remotely in a peaceful environment, this is the place to do it all. Relax by the fireplace while light pours in from the wall of windows, with pleasant sparkling pool, grill and chill on the backyard, and explore nature right outside your front door. Conveniently located in Redlands!

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 Arrowhead
4.85 out of 5 average rating, 273 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 person sits at a table with a small vase of flowers, enjoying a scenic view of rolling green mountains and a clear blue sky. The lush landscape extends into the distance, with varying shades of green and hills melting into the horizon.
Guest suite in Crestline
4.99 out of 5 average rating, 254 reviews

100-Mile View | Romantic Mountain Hideaway

Holly Hill Chalet is curated for romantic interludes and peaceful retreats. While the interior is stylish and cozy, the true star of the show is the view: an ever-changing masterpiece that transitions from golden sunrises to cinematic sunsets. From our expansive patios and park-like garden, you have a front-row seat to the awe-inspiring expanse below. As twilight descends, the horizon transforms into a sea of twinkling city lights, igniting the atmosphere with a touch of mountain magic.❤️

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
4.95 out of 5 average rating, 241 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 Amber Hills
4.89 out of 5 average rating, 144 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!

Guest favorite
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 Wildwood Park
4.81 out of 5 average rating, 215 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.

Superhost
Guest suite in Downtown Redlands
4.88 out of 5 average rating, 608 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 favorite
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!

Guest favorite
The living area features a blue sofa and a gray armchair, arranged around a low coffee table. Natural light fills the space through a large window with horizontal blinds. A bright yellow door adds a pop of color, enhancing the modern kitchen view in the background.
Home in Redlands
4.95 out of 5 average rating, 154 reviews

Entire home near campus - private yard

Entire house with private yard and parking 1/4 mile from the U of Redlands. Built in 2022, this home with no shared walls offers two bedrooms, 1.5 bathrooms + a hot/cold outdoor shower, a fully equipped kitchen, and a washer/dryer. 50 AMP outlet for EV charging onsite. The home is 2 miles from downtown Redlands, 1.2 miles from Casey Orchards and The Grove, and 2 miles from Hanger 24 Craft Brewery.

Popular amenities for Highland places to stay

When is the best time to visit Highland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,742 ZARR1,825 ZARR1,742 ZARR1,858 ZARR1,808 ZARR1,858 ZARR1,841 ZARR1,841 ZARR1,775 ZARR1,891 ZARR1,742 ZARR1,759 ZAR
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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 vacation rentals in Highland

  • Total vacation rentals

    Explore 100 vacation rentals in Highland

  • Nightly prices starting at

    Highland vacation rentals start at R664 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 4,050 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & 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

  • Wi-Fi availability

    100 of Highland vacation 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!