Pet-friendly holiday rentals in Highland

House & Barn Historic Beauty •Events & gatherings!

A block from downtown State street. Tall trees line the streets of the historical magic that is Redlands 🍊 ✨I have a sister house! Next door is The Olive Branch. This is perfect for larger parties An inground fire pit is the perfect way to get everyone together & cuddle. Or maybe just night under the stars as the sound from The Redlands Bowl Plays into the yard Spend the day playing poker downstairs in the Carriage house or make your way up the stairs and drift away in to hippie land.

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

Single-Story Cabin with Hot Tub, EV Charger & Yard

Welcome to Little Bearfoot Cabin! A 1925 single-story cabin with modern spa-like amenities and separate A-Frame office with fast wi-fi for digital nomads. Luxurious summer camp vibes. Cozy up by the fire pit making s'mores, enjoy al fresco dinners, and relax in the hot tub nestled under towering evergreens. If not outdoors in the amazing yard, enjoy central AC/heat. Less than a mile to lake, Village, and Lake Arrowhead Brewery. Access to walk the private trails. Dog & kid friendly. EV Charger

A-Frame in the Sky - “Rim of the World” Views!

Breathtakingly Gorgeous Views, like nothing you've seen before. EV charger, SAUNA, spa and Views to the Pacific Ocean and Catalina Island. Golden hour sunsets that fade into the city lights for 100 mile views. AFrame in the Sky, sits up high in the clouds and is backed up to the National Forest. Hiking Trails are out your front door. Snow Valley Ski Resort is 10 minutes away and Lake Arrowhead less than five minutes away. Hot Springs, hiking, shopping, fine dining, skiing, snowboarding

Modern Cabin with Stunning Views, Outdoor Firepit

Lake Pass Included In Your Stay! “Skyridge Cabin” is a modern 3-bedroom, 2-bath A-frame retreat in Lake Arrowhead with stunning mountain and desert views. It features two king bedrooms, and a queen with a trundle, accommodating up to 6 guests. Highlights include a wood-burning fireplace (wood provided), a balcony with Adirondack chairs, a fire pit, new Nest-powered AC/heat, games for kids, Google Home, and a Frame Smart TV in the living room. Perfect for a secluded mountain getaway.

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!

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).

Magical lake house with spectacular views

Gorgeous, tranquil retreat with enriching views of the lake and nature. A storybook bridge with the soothing flow of the stream beside it sets the mood for relaxation, inspiration and/or romance immediately. The home opens to captivating views of the entire lake from the curated, open floor plan. Ideal for cooking, quality dining, working on something creative or simply a peaceful escape from the city. Multiple terraces and balconies to enjoy the crisp air and setting.

Private Designer Cabin | Endless Forest Views

"Truly magical..." Located on the end of a private cul de sac, surrounded by forest and endless nature views, our redesigned 1970s cabin combines the warmth of a classic mountain home with mid-century style and designer touches throughout. An idyllic nature-filled getaway for up to 6 people where new amenities make your stay relaxing and no detail is overlooked. Includes access to Lake Arrowhead lakefront trails w registration. See more on IG @mileendhouse

Glen Oak Rim | Hot Tub · Game Room · Epic Views

Couples, Families, & Mountain Peace Seekers only, please. Located at the base of a steep private drive and overlooking the San Bernardino Basin sits this stunning California family cabin. Originally constructed in 1965, the dwelling's Mid-Century details have been lovingly restored while not forgetting a single modern amenity. Brilliantly designed by SoCalSTR® | IG: @socalstr "Top 1%" local market performer according to AirDNA

Modern Swiss Chalet | Sweeping Views | Hot Tub

Perched on stilts, this modern Swiss chalet is nestled in the mountains of Southern California. Designed with tranquility and comfort in mind, the cabin blends its 1970’s charm while elevating modern luxuries like heated floors, a chef’s kitchen, and wall-to-wall doors. Enjoy all nature has to offer with skiing in the winter, hiking in the summer, and breathtaking views, epic sunsets, and stargazing all year round.

Entire home near campus - private yard

Entire house with private yard and parking 1/4 mile from the U of Redlands. Built in 2022, this home with no shared walls offers two bedrooms, 1.5 bathrooms + a hot/cold outdoor shower, a fully equipped kitchen, and a washer/dryer. 50 AMP outlet for EV charging onsite. The home is 2 miles from downtown Redlands, 1.2 miles from Casey Orchards and The Grove, and 2 miles from Hanger 24 Craft Brewery.