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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Guest favorite
A transformed garage space features various leisure activities, including a foosball table, a pool table, and a poker table. Comfortable seating is provided by a gray sofa and a yellow armchair. Bright overhead lights enhance the modern design of the room.
Home in Highland
4.95 out of 5 average rating, 59 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

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, 234 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
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, 158 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!

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, 193 reviews

Cozy Cabin at LAKE Gregory- walk to shops and lake

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
Home in Highland
5 out of 5 average rating, 44 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

Superhost
Home in Highland
4.76 out of 5 average rating, 135 reviews

Spacious 3 bedroom near Yaamava Casino

This spacious 1,800-square-foot, three-bedroom home is a comfortable retreat for families or groups looking to enjoy everything San Bernardino and the surrounding area has to offer. Tucked away on a peaceful street, the home is just minutes from the lively Yaamava’ Resort & Casino and a quick drive to the NOS Events Center and charming Redlands. Whether you're visiting for entertainment, relaxation, or a weekend getaway, this home offers a convenient and comfortable base for your stay.

Superhost
Home in Highland
4.87 out of 5 average rating, 162 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 modern living room features a sleek leather sofa and a cozy ottoman centered on a decorative area rug. A stylish light fixture hangs overhead, while a fireplace with an elegant mantel adds warmth. Large windows invite ample natural light, showcasing outdoor views.
Villa in San Bernardino
4.93 out of 5 average rating, 132 reviews

LUX 4BR near NOS & Yaamava with Private Backyard

Nestled on the foothills of the San Bernardino Mountains is our luxurious 4BR house, boasting a professionally designed interior that will capture your heart immediately! Only 5-minute drive to downtown, while the top destinations of Lake Arrowhead, Disneyland, and Palm Springs are within an hour's journey. 2300 sq. ft. of space awaits – a 55” HDTV, a foosball table, ultra-fast 500 MB/s Wi-Fi, and access to a private backyard with jacuzzi and BBQ (extra fee need to apply).

Guest favorite
Home in San Bernardino
4.92 out of 5 average rating, 116 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 spacious living area is highlighted by an L-shaped sectional sofa, with a cozy throw draped over it. A light-colored rug adds warmth to the wood flooring. The open layout leads to a modern kitchen, equipped with dark cabinetry and stainless-steel appliances. Bright lighting enhances the welcoming vibe.
Home in Yucaipa
4.96 out of 5 average rating, 145 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
Guesthouse in Highland
4.96 out of 5 average rating, 279 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, 54 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.

Popular amenities for Highland places to stay

When is the best time to visit Highland?

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Avg. price€ 93€ 92€ 100€ 96€ 94€ 96€ 95€ 95€ 92€ 98€ 90€ 91
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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 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 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 10 house 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 € 34 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!