Holiday rentals in Oak Glen

Vineyard Retreat, Pool & Amazing Views!

Experience luxury in this 6-bedroom vineyard estate with a grand pool, hot tub, and breathtaking views. Perfect for family gatherings or quiet retreats, our home offers a wheelchair accessible King suite, a music room with a grand piano, a dining area and billiards. Minutes from Serendipity Garden and historic Yucaipa Uptown, this property also features a full kitchen, outdoor BBQ and a full living room with 80" TV. Event chairs and tables available—ideal for celebrations or serene getaways!

Cozy Suite w/ Kitchen 8 min to Casino & 10-Freeway

Welcome to our stunning studio retreat in the heart of Banning! Immerse yourself in relaxation and luxury in this cozy one-bedroom. The studio features a well-designed layout, with a kitchen, dining table, and its own bathroom. All supplies needed to cook, with spices, pans, cups, plates and more. Near the city of Banning you'll find: 10-Freeway 5 min Cabazon Outlet 8 min Morongo Casino 11 min Palm Springs 31 min Joshua Tree Park 56 min Agua Caliente Casino 31 min Riley’s Farm 23 min

Cozy Master Studio w/ Private Entrance

Cozy and comfortable master suite with private entrance. New french doors open into a private bedroom with a newly remodeled bathroom, small kitchenette, 2 large closets, and a quaint outdoor area that extends the living area. Smart television mounted to the wall and a ceiling fan to keep guests cool. Property located in Upper Yucaipa only 5 minutes from downtown Yucaipa, YPAC, restaurants, the regional park and 10 minutes from Oak Glen Preserve, 15 minutes from Historic Redlands.

Hill View Apartment in Oak Glen

Hill View Apartment is nestled in the San Bernardino Mountains in beautiful Oak Glen. The Oak Hollow property is walking distance to Oak Glen Steak House, or a short drive to Los Rios Rancho, Oak Tree Mountain, and Riley's Farm! Minutes from Serendipity and the Homestead wedding venues, we provide the perfect spot to enjoy all Oak Glen has to offer! Whether it is apple season, Wedding time, Farm to Table dinners, or sledding, Hill View can be your home away from home.

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

Forest Falls Creek side hot tub & vintage Cabin

This location is phenomenal located right on a freshwater creek. The sound of the water from creek and the views of the water below the deck are amazing. 1939 rustic original Vintage Cabin with stone fireplace. Deck with hot tub overlooking creek. Very simple camp stove, rustic feel. TV only plays DVD’s. Verizon cell service phone for you use w/wifi hotspot. Another cabin across the road to rent for added space: airbnb.com/h/vintage-mountain-cabin-with-hot-tub

Eagles Nest

Are you up for an adventure in this forest treehouse-like cabin on a cliff. Known locally as the "Eagles Nest." This is a thousand square foot 2 bedroom 2 bath cabin that was built by locally well-known artisan/builder Paul Fourgues. While it is nestled in the canopy of the Northwest-facing slopes of forest falls, it is also high on a massive boulder, giving the feel of being suspended over the canyon. It is a romantic hide-away.

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.

"The Olive Branch"

"The Olive Branch" is located in upper Yucaipa. Minutes away from beautiful Oak Glen, Forest Falls, and Historic Uptown Yucaipa. "The Olive Branch" is a stylish one bedroom, one bath, living area and kitchenette casita, attached to the main home with its own private entrance. "The Olive Branch" is in a great location for attending weddings in beautiful Oak Glen. No children, pets, or smoking permitted.