Holiday rentals in Calimesa

Secluded & Quiet Guest House-Cherry Valley-Morongo

Enjoy the lovely setting of this romantic spot in nature. Secluded and located in a farm area overlooking the San Gorgonio/San Bernardino National Forest/Big Bear mountains and yet just two miles away from the freeway 10. You will love the darkness and tranquility of rural life at night. Close to Oak Glen, Yucaipa, Redlands, Beumont, Banning, San Jacinto wedding venues and outdoor activities. No more CA blackouts with our Tesla battery back up. Free 2-220v level-2 EV charging at your convenience

Backyard pickleball with a modern twist!

Make memories at this family-friendly backyard retreat. Enjoy plenty of outdoor patio seating while the family plays basketball, pickleball, cornhole or darts. Gather around the fire pit. Inside, gather by the kitchen island or play ping pong. There’s plenty to do inside and out. Covered patios allow for rain or shine relaxation. Special events here can be arranged. Oak Glen is a 5 minute drive. Several hiking/bike trails are nearby. We’re happy to help find activities that suit your interest.

Yucaipa's Cottage on a Hill

Welcome to our quiet country cottage located on top of a hill overlooking the canyon and City of Yucaipa. With all the amenities you'll need during your stay, you will feel right at home. Less than five minutes to the freeway, your home away from home will be the perfect place to rest your head at the end of the day. The Cottage is the central location to LA, the beaches, Disneyland, Palm Springs, San Diego and the mountains. And if you don't want to leave, there's plenty to do right here!

Private Studio w/Secure parking & Private Entrance

If you are a non smoker with no pets we are offering our Studio near East Redlands area. The studio is setup for travel working professionals.. Currently only 1 guest is allowed. This unit is 100% self contained. Kitchenette is fully equipped. Private bath w/shower. Everything in the studio is cleaned sanitized and then cleaned again. Wash/Fold Laundry is included along with Secure parking for 1 vehicle. This unit is attached but sealed from the main home, not ideal for day sleepers.

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!

2-BDR attached apt in rural Redlands neighborhood.

Our “RURAL REDLANDS” neighborhood is quiet with local wild creatures roaming (coyotes, rabbits and squirrels). Although other hosts welcome pets, we requests no pets for our guests that have extreme allergies. Our RURAL is an older home; not fancy but comfortable. Two bedrooms, kitchenette and living room. Private from us. We are near University of Redlands, Historic Downtown Redlands, restaurants, as well as Oak Glen apple farms. We’re 60 miles from Palm Springs, Casinos, Disneyland

Guesthouse - Downtown Redlands - Private Entrance

Modern and fully equipped private guest suite in Redlands with its own entrance, full kitchen, dining nook,TV, and queen bed. The futon in the living room converts into Queen bed. Enjoy a private bathroom, large closet, A/C, and stylish decor throughout. Located minutes from downtown shops, the Redlands Bowl, restaurants, and parks. Ideal for solo travelers, couples, or work stays. Clean, cozy, and designed for comfort—whether you're here for a weekend escape or an extended visit.

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

Quiet and cozy guest suite

Our private suite is clean & welcoming with a private studio-like floor plan with its own entrance. My wife and I are working professionals who love to host and meet new people. Our home is located within one hour of 36 hospitals & one hour to several universities including Riverside, Redlands, and CBU. Cabazon shopping outlets are 15 minutes away. Lovely Palm Springs about 38 minutes. Golfing, shopping, desert, mountains, food and more is at your fingertips!