Vacation rentals in Highland

Find and book unique accommodations on Airbnb

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 ﺩ.ﺇ 147 per night before taxes and fees

  • Verified guest reviews

    Over 4,650 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!

Top-rated vacation rentals in Highland

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

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Guest favorite
A spacious bedroom features a large bed framed by two lamps on nightstands. A cozy seating area with a light gray couch and decorative pillows is present. Sliding glass doors allow natural light, leading to the outdoors. A round wall decor adds a tasteful touch to the wall.
Home in Highland
4.95 out of 5 average rating, 61 reviews

Cactus Casino- w/game room-next to Yaamava Casino!

Relax and enjoy your stay in this modern chic newly renovated home. Have fun with family and friends in the garage turned game room and a small golf area in the fully fenced backyard! Enjoy cooking a meal in the fully stocked kitchen or BBQing outside on the grill. You will have 3 separate areas you can enjoy your meals, outside in the backyard or either of the 2 dinner tables inside.This home is STEPS away from Yaamava (San Manuel) Casino and just minutes away from restaurants and grocery store

Guest favorite
Home in San Bernardino
5 out of 5 average rating, 16 reviews

Hidden Elmwood- 3 bedroom - 1 queen bed / 2 full

Enjoy the sunrise from the second floor balcony as you sip on that first morning cup of Joe. Absorb the warm and inviting embrace from the San Bernadino Mountains in the background and when you are ready, head over to nearby favorites like the Yaamava Casino, NOS Event Center , The San Bernadino County Museum or The Fiesta Village Family Fun Park- all located just a few minutes away. In the mood to explore? Disneyland and Knottsberry Farm Amusement parks, Big Bear Lake and the beach -1 hr away!,

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, 164 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
Home in Highland
5 out of 5 average rating, 50 reviews

Perfect Weekend Retreat | Hot Tub+Firepit+Games

🌄 From warm natural lighting blending indoor and outdoor spaces, to thoughtfully curated modern decor, Retro Retreat was designed as an immersive getaway from the moment guests arrive. 🌴 Visiting Southern California? Checkout what’s nearby: 🎰 4 min to Yaamava Resort & Casino 🎓 18 min to Loma Linda University 🍔 13 min to Downtown Redlands 🎡 15 min to NOS Events Center ✈️ 30 min to Ontario Airport 🌲 60 min to Big Bear Lake 🏰 75 min to Disneyland Resort 🏖️ 90 min to Laguna Beach

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 Highland
4.88 out of 5 average rating, 171 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
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
4.91 out of 5 average rating, 124 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 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, 283 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 favorite
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, 62 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.

Guest favorite
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, 93 reviews

Clean Modern ADU Close to NOS/Yaamava/FIFA/BigBear

This beautiful ADU-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 is minutes from Yaamava, NOS Event Center, Big Bear, or Mount High Ski Resort for summer/winter activities. Great for those going to Coachella, Los Angeles, Anehiem, or Orange County. Smart TV. WiFi. A/C. Washer and Dryer. Kitchen. Self Check-in. Close to freeways.

Superhost
Guest suite in San Bernardino
4.88 out of 5 average rating, 26 reviews

LuxuryKing Suite•Private Entry/Bath+HotTub+Balcony

Spacious private king suite on the second floor with its own entrance, offering comfort and privacy. Features a king bed, mini living room, and fully filtered water throughout. Enjoy a private balcony with seating—perfect for relaxing. Includes a hot tub, stand-up shower, and two walk-in closets. Enjoy the beautiful sunset. Guests have access to their suite and the pool only (SHARED POOL). No access to the main house or back unit.

Superhost
Apartment in San Bernardino
4.84 out of 5 average rating, 44 reviews

Luxury CalKing master bedroom Apartment

Luxury 600 sq. ft. Apartment Near Loma Linda Just 10 minutes from Loma Linda Hospital and 5 minutes from San Bernardino Airport, this quiet, peaceful apartment offers: • Private entry & dedicated parking • 1 bedroom, full kitchen, and modern bathroom • Living room with fireplace • Laundry room, AC, and high-speed Wi-Fi Fully equipped with 5-star hotel amenities for maximum comfort.

Superhost
Home in Redlands
5 out of 5 average rating, 7 reviews

Modern 3-Bedroom Furnished Home

This spot is in a quiet residential area near the University of Redlands and local parks. You'll find grocery stores, coffee shops, and casual restaurants just a short drive away. The neighborhood has a suburban vibe, with well-kept homes and sidewalks for leisurely walks. Quick access to the 10 freeway simplifies commuting or getting around town.

Popular amenities for Highland places to stay

When is the best time to visit Highland?

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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.

  • 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 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 guesthouse rentals in Highland have air conditioning?

    Absolutely! We offer over 10 guesthouse 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.

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

    Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.