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
Cottage in San Bernardino
4.94 out of 5 average rating, 338 reviews

Adorable Cozy Cottage, base of Beautiful Mountains

This adorable cottage is located at the base of the San Bernardino mountains where you have views of the snow-capped mountains in the colder seasons & views of the beautiful sunsets all year! Close to freeways, malls & hiking trails. Relax poolside as the cottage doors open to the pool & outdoor BBQ & fire pit. It's a great get-away location with all newly remodeled amenities for a comfortable stay. Plenty of parking. NEW onsite DAY SPA services! THIS SPACE IS NOT SUITABLE FOR SMALL CHILDREN

Top guest favorite
An A-frame cabin stands amidst lush trees, illuminated by evening lights. A cedar hot tub, surrounded by natural boulders, emits steam, inviting relaxation. The exterior features large windows that bring the outdoors in, while a seating area is positioned nearby for enjoying the serene atmosphere.
Cabin in Running Springs
5 out of 5 average rating, 223 reviews

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Hiking

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings and high-end linens ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds No pets permitted

Top guest favorite
The spacious living area features a vibrant orange sectional sofa, complemented by wooden cathedral ceilings and a large window overlooking the outdoors. Decorative elements include mounted deer heads and a selection of records on a wooden shelf, creating a cozy atmosphere.
Cabin in Rimforest
4.95 out of 5 average rating, 498 reviews

Fort Black Bear w/ Hot Tub - Lake Arrowhead

Our chic mountain retreat is everything you'd want in your Lake Arrowhead getaway. Beautiful wood cathedral ceilings accent the views of trees, boulders and peeks of the city lights far below. The expansive great room is anchored by a stone fireplace, wrap around sectional and large inviting dining area. A fully outfitted cook's kitchen, roman tub with picture window, king size bed and large dining table make this the ultimate retreat. Enjoy the cedar clad hot tub set next to massive boulders!

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, 154 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!

Top 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, 188 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.

Top guest favorite
An antique suitcase is featured with a weathered exterior, showcasing faded travel stickers and a vintage design. Its metal clasps and handle exhibit signs of wear, highlighting its history and charm. The suitcase rests on a textured surface, adding to its nostalgic appeal.
Guesthouse in Yucaipa
4.98 out of 5 average rating, 184 reviews

Yucaipa's Cottage on a Hill

Welcome to our quiet country cottage located on top of a hill overlooking the canyon and City of Yucaipa. With all the amenities you'll need during your stay, you will feel right at home. Less than five minutes to the freeway, your home away from home will be the perfect place to rest your head at the end of the day. The Cottage is the central location to LA, the beaches, Disneyland, Palm Springs, San Diego and the mountains. And if you don't want to leave, there's plenty to do right here!

Top guest favorite
Cabin in Green Valley Lake
4.94 out of 5 average rating, 165 reviews

The Best Views and Vintage Cozy Cabin!

The most stunning sunset you have ever experienced with a scenic view of Lake Arrowhead in the distance! This rustic cabin sits on the edge of the San Bernardino Mountains, and has everything you need to get away. Green Valley Lake is located at 7200 feet making it the highest village, meaning more snow in winter and cooler temps in the summer. There is a swimming beach w/ lifeguards, boats to rent, and a well-stocked fishing lake 5 minutes away. We’re close to the ski slopes and hikes too.

Superhost
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
4.86 out of 5 average rating, 155 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
Guest suite in Downtown Redlands
4.88 out of 5 average rating, 493 reviews

Private King Suite & Bath | Self Check-In

Spacious private-entry guest suite converted from the home’s master bedroom. Fully separate from the main house with keypad access, private attached bathroom, Wi-Fi, large TV, mini fridge, microwave, and seating area. Sleeps up to 3 with a king-size bed and optional full bed. Located in a historic 1895 home—updated but with a few quirks: toilet paper goes in the trash (older pipes). Quiet space, no parties. I live on-site, respect your privacy, and am always available if needed.

Guest favorite
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
4.92 out of 5 average rating, 107 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 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, 144 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
Cabin in Running Springs
4.99 out of 5 average rating, 306 reviews

Mid-Century Perfect Romantic Getaway Hot Tub|Sauna

This Black A-Frame cabin sits high among the pines in Running Springs, offering peaceful treetop views from decks on all three levels. With warm mid-century modern design, it’s the perfect romantic escape. Snuggle in the cozy loft, enjoy vinyl or a movie in the secret cinema room, and unwind together in the new barrel sauna. Perfect for couples celebrating anniversaries, honeymoons, special getaways, or simply enjoying quiet, meaningful time together in the forest.

Popular amenities for Highland places to stay

When is the best time to visit Highland?

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Avg. priceR1,743 ZARR1,826 ZARR1,743 ZARR1,859 ZARR1,809 ZARR1,859 ZARR1,843 ZARR1,843 ZARR1,776 ZARR1,892 ZARR1,743 ZARR1,760 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 vacation rentals with a dedicated workspace in Highland?

    Yes! Work meets play with ease at over 40 vacation 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 300 vacation rentals in North Redlands, over 280 vacation rentals in Northwest Redlands, and over 50 vacation rentals in East Highlands.

  • Are there family-friendly vacation rentals in Highland?

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

  • Are there pet-friendly vacation rentals in Highland?

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

  • Are there Highland house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals 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 60 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 90 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 4,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 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!