Holiday rentals 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, 147 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!

Top guest favourite
The living area features a plush sectional sofa adorned with colorful pillows, creating a vibrant focal point. A wall-mounted Smart TV is positioned for easy viewing. An open kitchen with modern appliances is visible in the background, alongside a dining area with bright chairs.
Home in Redlands
4.91 out of 5 average rating, 108 reviews

Bright Vibes Home|Sleeps 8|1Blk to Univ|Pacman+BBQ

Step into our inviting Redlands home full of bright vibes and fun! Centrally located near the University, this lively gem features an indoor gym, playful outdoor spaces with Tic-Tac-Toe, fire pit + BBQ, and a lively atmosphere. Whip up culinary delights in the fully equipped kitchen, unwind in cozy bedrooms, and enjoy modern amenities. Explore downtown's lively scene, indulge in local attractions, and create unforgettable memories at our spirited Redlands retreat! 30+ day/ insurance stays okay.

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, 128 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, 287 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.

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.
Guest house 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.
Holiday home in Highland
5 out of 5 average rating, 45 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
Flat in San Bernardino
5 out of 5 average rating, 3 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
A welcoming living area features a leather sofa and two green armchairs arranged around a wooden coffee table. A fireplace is set into a stone wall, accompanied by decorative elements. Natural light enters through multiple windows framed with wooden blinds, enhancing the warm wooden ceiling.
Cabin in Running Springs
4.8 out of 5 average rating, 121 reviews

Pet-Friendly Cabin | Trails Nearby | Private Deck

Escape to Double Diamond Cabin—your cozy, pet-friendly mountain retreat! Just a 5-min walk to trails or a short drive to Green Valley Lake. Relax by the fire or stargaze from the deck. With fast Wi-Fi, a fenced yard, and the comforts of home, it’s perfect for couples, families, and remote workers. A $300 refundable pet deposit is required. Well-behaved pets welcome!

Guest favourite
The exterior of Sunset Cottage is shown, featuring a welcoming porch with a railing and an umbrella providing shade. The white building displays a tiled roof and a wooden door, surrounded by a grassy area, under a partly cloudy sky.
Guest house in Redlands
4.89 out of 5 average rating, 357 reviews

Sunset Cottage

Welcome to Sunset Cottage. A newly renovated home located on historic Sunset Dr in the city of Redlands. Within walking distance to renowned Kimberly Crest Mansion at Prospect Park. Downtown Redlands is just a few short minutes drive away along with University of Redlands, Loma Linda University, Redlands Hospital, Loma Linda Hospital, VA Hospital and ESRI.

Superhost
A remodeled kitchen area features a wooden ceiling with exposed beams. A central island with bar stools provides seating. Appliances, including a refrigerator and washing machine, are present. Patterns on the backsplash add visual interest, and natural light enters through a window.
Cabin in Crestline
4.9 out of 5 average rating, 354 reviews

The Cozy Cabin

Get away from the hustle and bustle of the city and have yourself a peaceful and relaxing stay at this remodeled cabin in the mountains. Enjoy the large deck with some coffee in the morning, mediate and do yoga while Blue Jays fly by, or just simply enjoy nature Explore nearby hikes, great restaurants, and of course Lake Gregory!

Top guest favourite
A living room area features a neutral-toned couch complemented by decorative pillows. A round ottoman sits in the center atop a patterned area rug. A large mirror and wall art add visual interest, while plants bring a touch of greenery to the space.
Guest house in Redlands
4.96 out of 5 average rating, 483 reviews

The Porch

The Porch is located in a new and calm neighborhood. It is an attached, but separate unit from the main home. It has a private entrance, walk way, and is self check in. In our place, you will never have to worry about cleaning at the end of you trip, we take care of it all.

Top guest favourite
A private entrance is depicted, showcasing a solid, dark door framed by light-colored trim. Windows with white shutters are positioned on either side, allowing natural light to accentuate the neutral-colored exterior wall, complemented by stone detailing near the base.
Flat in Redlands
4.97 out of 5 average rating, 39 reviews

Safe & Quiet ADU in Redlands, CA

ADU with the following: Private One Bedroom, Bath, Living Room, and In-unit washer/dryer, Private Entrance, and free designated parking. In a quiet and safe modern neighborhood.

Popular amenities for Highland holiday rentals

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 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 290 vacation rentals in North Redlands, over 270 vacation rentals in Northwest Redlands, and over 60 vacation rentals in East Highlands.

  • 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 holiday rentals in Highland

  • Total holiday rentals

    Explore 100 holiday rentals in Highland

  • Nightly prices starting at

    Highland holiday rentals start at € 34 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    100 of Highland holiday 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!