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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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Superhost
A small living area features light-colored sofas adorned with patterned cushions. A coffee table is placed on a textured red rug, with a decorative item at its center. A television is positioned on a stand next to a door leading outside, with natural light filtering through nearby windows.
Apartment in Redlands
4.9 out of 5 average rating, 139 reviews

2-BDR attached apt in rural Redlands neighborhood.

“RURAL REDLANDS” has a quiet neighborhood with a few creatures (coyotes, rabbits and squirrels). Although other hosts welcome pets, we request “no pets” (returning guests with allergies). Older 60’s home; not fancy but comfortable. Two bedrooms, kitchenette and living room. Private entrance; we share a living room wall and A/C. We are near U of Redlands, Downtown Redlands, restaurants, Oak Glen apple farms. . We’re 60-70 miles from Palm Springs, Casinos, BigBear Mtns, Disneyland, & beaches

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, 141 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
A vibrant yellow vintage car is parked on a gravel driveway, surrounded by colorful flowers and lush greenery. Small, charming container homes are visible in the background, nestled among the trees under a clear blue sky.
Shipping container in San Bernardino
4.92 out of 5 average rating, 305 reviews

#2 Cozy Tinyhouse"Route 66" Container- private

Longterm rental, peaceful, rural neighborhood, if you’re looking to get just outside of the city. No smoking , NO animals due to health conditions. 1.5 hour or less to Santa Monica, Venice Beach, less than 2 hours from San Diego, & 3 hours to Las Vegas. 5 min from the world famous motocross track! Glen Helen amphitheater, Route 66, and hot spot for paragliding is just 5 minutes away! CozyTiny Container home is private, with all comforts. Relax at the foot of the mountains with 1 parking spot.

Top guest favorite
The outdoor space features a sparkling swimming pool surrounded by a landscaped patio. The cottage is seen in the background with large glass doors, inviting natural light. Beautiful plants and greenery enhance the serene atmosphere, providing a pleasant space for relaxation.
Guesthouse in Redlands
4.99 out of 5 average rating, 319 reviews

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

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
4.84 out of 5 average rating, 246 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
The exterior of a historic two-story house is visible, surrounded by well-kept grass and mature trees. A porch extends across the front, and multiple windows offer glimpses into the interior. The building reflects classic architecture with a subtle, inviting color palette.
Guest suite in Downtown Redlands
4.89 out of 5 average rating, 454 reviews

(2) Downtown Redlands Retreat: Cozy Master Suite

This is a nice master bedroom, converted to a guest suite. The room has a private entrance, and private bathroom. Walls were recently torn down & made sound proof so as to not disrupt our guest with noises inside the house. This house has a lot of history, it’s over 120 years old. It’s perfectly situated about a minute away from the freeway is a central locations, in the beautiful & historic city of Redlands. Security cameras recording at all times all around the outdoors of the property.

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, 114 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 favorite
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, 276 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 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, 138 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
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, 267 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.

Guest favorite
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
4.92 out of 5 average rating, 141 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

Guest favorite
The exterior of a guest house is captured, featuring a white facade and a wooden staircase leading to the entrance. Surrounding plants add greenery, and a sandy pathway extends from the driveway. A covered porch is visible, framed by wooden railings.
Guesthouse in Redlands
4.93 out of 5 average rating, 168 reviews

Sunset Bungalow

Welcome to Sunset Bungalow. A beautiful guest house 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. Sit back and relax in this calm, stylish space.

Popular amenities for Highland places to stay

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 $20 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 260 vacation rentals in Northwest Redlands, over 290 vacation rentals in North 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 wifi, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 $40 per night before taxes and fees

  • Verified guest reviews

    Over 3,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 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!

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