Vacation 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.

Value · Location · Air conditioning

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

Value · Family · Air conditioning

Log Cabin w/Gorgeous Views, Hot Tub+King Beds

Charming Authentic Log Cabin with Mountain Views+Hot Tub This cozy 2br/1ba authentic log cabin offers ultimate relaxation with 2 king beds, plush blankets and cozy spaces to unwind. Enjoy beautiful mountain views from a 4-seater hot tub under the trees or from the private small deck below. The family room has a 65" 4K TV hanging over the log-burning fireplace (firewood sold nearby). Backing straight up to the SB national forest, this cozy retreat promises peace, comfort, and unforgettable views

Value · Family · Comfort

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 Huntington Beach

Value · Location · Layout

Scenic views pool/spa/bbq/karaoke/games No Parties

Escape to this ultimate spacious retreat featuring stunning panoramic views, a sparkling pool and spa with optional heating for year-round enjoyment. Perfect for groups, accommodates up to 15 guests and offers endless entertainment with a game room, board games, and karaoke. Cook in the fully equipped kitchen or relax by the BBQ. Located just 2.9 miles from Yaamava’ Resort, 24 miles from Lake Arrowhead, and 33 miles from Big Bear, with shops and groceries nearby, it’s your dream getaway!

Location · Value · Backyard

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!

Location · Value · Amenities

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.

Family · Value · Long stay

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.

Family · Value · Amenities

Dreamy Escape Private Entrance/pool/near Yaamava

Our location is close to dining, hiking, shopping, movie theaters, and popular attractions like the National Orange Show Event Center (NOS), Yaamava Resort & Casino, vibrant nightlife, Redlands University, and Loma Linda University. You'll love our place for its location, inviting ambiance, outdoor space, and friendly neighborhood. It's the perfect spot for couples, solo adventurers, and business travelers looking for a cozy getaway!

Location · Family · Long stay

LuxuryKing Suite•Private Entry/Bath+HotTub+Balcony

Spacious private king suite on the second floor with its own entrance, offering comfort and privacy. Features a king bed, mini living room, and fully filtered water throughout. Enjoy a private balcony with seating—perfect for relaxing. Includes a hot tub, stand-up shower, and two walk-in closets. Enjoy the beautiful sunset. Guests have access to their suite and the pool only (SHARED POOL). No access to the main house or back unit.

Family · Value · Check-in

Mountaintop Pool Paradise | Mins to NOS Center

🏔️🏝️Welcome to Your Private Oasis!🏝️🏔️ Nestled in a serene gated community, this 2,300 sq. ft. 3-bedroom, 2.5-bath home offers the ultimate retreat. Relax by the pool or enjoy quality time in the cozy, open living spaces. Conveniently located, you’re just 10 minutes from SB Raceway, 15 minutes from San Manuel Casino, 20 minutes from the scenic Cajon Pass, close to NOS Center, Cabazon Outlets and under an hour from Disneyland.

Location · Value · Quiet

Apogee A Frame Cabin Cliffside Swing and Hot Tub

Designer A-frame retreat perched among boulders and pines in Lake Arrowhead. Featuring vaulted ceilings, floor-to-ceiling windows, and a statement fireplace, this home blends modern design with cozy cabin vibes. Enjoy a private hot tub with mountain views, cliffside swing, firepit, and multiple outdoor lounge spaces. Minutes to the lake, village, and trails—perfect for a romantic escape or relaxing getaway.

Location · Value · Hospitality