Pet-friendly holiday rentals in Highland

Hilltop Retreat | Heated Pool + Spectacular Views

Welcome to The Vibe Estate 🌴✨ A hilltop retreat designed for meaningful moments with family and friends. Enjoy breathtaking views 🌄, a heated cocktail pool 💧, and a spacious home perfect for meals, games 🎲, and connection. A peaceful escape to unwind, recharge, and create unforgettable memories together 💛. 🆓 Enjoy the Heated Pool and Propane BBQ Grill free of charge. Everything is set up to help families and friends spend quality time together. Please message host with special requests.

Designer cabin at LAKE Gregory- walk to town

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.

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!

Birchwood A-Frame (walk to village/lake/brewery)

You can search far and wide, and not find an A-frame as impeccably designed as this one. It's one-of-a-kind for Lake Arrowhead and we can't wait for you to experience this gem in person. The beauty of nature surrounding the home perfectly complements the natural elements used within the home. You'll love the feeling of complete tranquility from the moment you walk through the door. We invite you to be our guest and come relax in the mountains. We do not allow fires in the blue fireplace.

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 w 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).

Romantic Holiday Escape | Prvt Hot Tub & Fireplace

Welcome to The Den, a 1960s cabin reimagined by LBL Design Co. This moody, romantic retreat blends almond-blasted ceilings, warm wood tones, and modern finishes — complete with a private hot tub under the pines. Perfectly centered in the San Bernardino Mountains, it’s your base for snow days, trail adventures, and slow, cozy nights by the fire. Sip wine on the deck, roast s’mores under the stars, and unwind beside the glowing fireplace on our plush velvet sofa.

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.

Idyllic A-Frame - Lake rights - Hot tub

Relax and get away at this beautiful A-frame that combines the peacefulness of a cozy cabin along with easy access to all that Lake Arrowhead has to offer. Our home has been updated and remodeled while still maintaining the original details that make this A-frame so special. Our home has lake access for registered guests. Please inquire about wristbands if you’d like to use the lake. Featured on Apartment Therapy!

Mtn. Hideaway: Your Relaxing Escape (Sauna & Cozy)

Welcome to Iris & Pine Cottage! Relax among the pines with your drink of choice. Enjoy the local nature, Saturday farmers market, local hikes, and food. Conveniently located: Snow Valley (6 mi), Lake Arrowhead (8.7 mi), Santa's Village (5.7 mi), and Big Bear (12.9 mi). Easy parking, fast WiFi, desk & printer, fireplace, outdoor grill, and deck with string lights. Book now for an unforgettable stay!

Peaceful A-Frame Cabin with Hot Tub Escape

Welcome to the Running Springs Tree House! Nestled in nature, our cozy retreat is the perfect getaway. Ski at Snow Valley—just a 10-minute drive away—or explore trails and seasonal creeks with a short walk to the San Bernardino National Forest. Visit Santa’s Village at Sky Park nearby. After a day of adventure, unwind in the hot tub or cook a meal in our fully equipped kitchen. Relax and rejuvenate!

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.