Holiday houses in Calimesa

4.92 out of 5 average rating, 63 reviews

Guesthouse in Yucaipa

Amazing Mexican Casita, Resort Pool,Spa,Fire,WIFI

This brand New Mexican style casita has all the handcrafted features your looking for. As soon you open the 100 year old wood door you will immediately walk onto the authentic Saltillo tile. You will enjoy the spacious 17 foot vaulted ceiling with a wrought iron vintage chandelier. Dark walnut live edge counters with handcrafted talavera tile backsplash in kitchen and bathroom.Full kitchen. Special loft that easily sleeps 4. Two amazing comfortable bedrooms Separate temp control in each room.

4.91 out of 5 average rating, 112 reviews

Home in Nuevo

Mountain Views Near Lake - Spacious Rural Retreat

15 miles to over 40 wineries in Temecula, just minutes to lakes, casinos, apple farms, skydiving, water park, mountain charms of Oak Glen, Idyllwild and more. Our spacious property provides the atmosphere to unwind, rejuvenate and enjoy a peaceful stay in our rural setting. Our space features a classic and timeless aesthetic with elements such as a gambrel roof, extra-large picture windows, 180 degrees of clear mountain views & sunsets on the deck which overlooks the entirety of the property.

4.76 out of 5 average rating, 25 reviews

Home in Yucaipa

The Logan | Sleeps up to 20

This large property sleeps up to 20 guests, perfect for family reunions or friend getaways. Enjoy a bright living room, a fully equipped kitchen, and a spacious dining area for memorable meals together. Outside, a beautifully landscaped yard offers space for barbecues and relaxation. Family-friendly amenities ensure comfort for all ages. Located near local attractions and outdoor activities, this retreat is your ideal base for exploring Southern California. Book your unforgettable stay today!

4.89 out of 5 average rating, 95 reviews

Home in Yucaipa

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!

4.96 out of 5 average rating, 55 reviews

Guest suite in Yucaipa

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.

4.97 out of 5 average rating, 263 reviews

Guest suite in Redlands

Amazing Large 1 Bedroom, No Chores Home

Bring the whole family to this wonderful place in the heart of Loma Linda. The bedroom has its own retreat with a sleeper sofa for the kids or friends. Within a couple of miles you have Loma Linda University and Loma Linda VA. A couple miles East and you are in Downtown Redlands where you have entertainment, plentiful restaurants, and nightlife. Or enjoy the peaceful citrus trails this beautiful neighborhood offers which lead you to large parks where you can enjoy a picnic.

4.86 out of 5 average rating, 108 reviews

Loft in Banning

Apartment w/ Kitchen 8 min to Casino & 10-Freeway

A beautiful apartment with a cozy one-bedroom and bathroom. Enjoy a relaxing and exclusive vacation in this apartment with a kitchen, kitchen appliances (stove, microwave, fridge), dining table, and living room. One loveseat that converts to a bed. Also a washer/dryer at no extra cost! In the city of Banning, a perfect area near, Cabazon Outlet is 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

4.96 out of 5 average rating, 126 reviews

Home in Yucaipa

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

4.93 out of 5 average rating, 145 reviews

Guesthouse in Redlands

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.

4.91 out of 5 average rating, 131 reviews

Apartment in Redlands

2-BDR attached apt in rural Redlands neighborhood.

Our “rural Redlands” is quiet and has local wild creatures roaming (coyotes, rabbits and squirrels). It’s an older home and not fancy. The pictures are what you get. 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, and Big Bear.

5 out of 5 average rating, 59 reviews

Guesthouse in Yucaipa

"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.

4.95 out of 5 average rating, 119 reviews

Home in Redlands

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.

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Other great holiday rentals in Calimesa

4.88 out of 5 average rating, 84 reviews

Guest suite in Redlands

Cozy Retreat Apartment

ChristinaRating, 5 stars1 month ago

Michelle’s home was so cozy with a beautiful backyard! Her husband came out to greet us upon arrival. It’s in a great location next to the freeway, a few recognizable food chains, and a short driving distance from a couple of shopping centers. Checking in and out was easy and home instructions were clear. There were dishes, a cooktop, mini fridge, and cookware to use. There was also a TV, ac/heat controls, and wash cloths. The neighborhood was very peaceful and quiet! I would definitely stay again when in the area!

Private room in Loma Linda

4.97 out of 5 average rating, 196 reviews

Large Private Room/Bath+Keyless 100% Private Entry

FayRating, 5 stars3 weeks ago

BEST View of the San Bernardino Mountains and night lights. BEST view watching hummingbirds and other birds outside the window frolicking, which made a VERY relaxing stay. BEST amenities and well stocked with everything so I didn’t need to ask for any thing. Queen bed VERY comfortable. This is my MOST FAVORITE PLACE to stay in the valley. Second time here. You will love it here!!!

4.9 out of 5 average rating, 10 reviews

Private room in Beaumont

Private 1Bed Shared 1 Bath in Beaumont (Room #2)

Ana PaulaRating, 5 stars1 month ago

The place was perfect for my work week in Beaumont. Great communication from host. The place was clean, tidy, and quiet. We played music chairs with parking the cars 😂, but it all worked out great! I would be definitely be back.

4.92 out of 5 average rating, 24 reviews

Private room in Beaumont

Cozy Red Room in Beaumont

OrlandoRating, 5 stars2 weeks ago

Cyndi is really nice and the place is very clean and quiet.

Private room in Running Springs

4.88 out of 5 average rating, 199 reviews

Quiet, valley view, relaxing,

MiguelRating, 5 stars1 month ago

The room was very nice and with a view. Beautifully decorated and confortable. It was so peaceful and birds were singing softly in the morning. David and Sharon were so nice and generous about my needs. The coffee was great. I enjoyed my stay.

Private room in Moreno Valley

5 out of 5 average rating, 3 reviews

Moreno Valley Private Room

BillRating, 5 stars5 months ago

the place can accommodate many people as there are 6 bedrooms that all have locks. the bedrooms all have mini-splits in them. the main part of the house the was set below 60 and it was cold to shower. but other than that it was a great place with a nice kitchen area. and a good location with many good places to eat local cuisine nearby.

4.89 out of 5 average rating, 123 reviews

Private room in Hemet

Desert Oasis Retreat

MarleeRating, 5 stars1 month ago

Jim is such an exquisite host! I appreciate all the hard work & great efforts he puts into going above & beyond for each & every one of his guests! 💯🙂