Holiday houses in Calimesa

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Top-rated holiday rentals in Calimesa

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Guest favourite
A small living area features light-colored sofas adorned with patterned cushions. A coffee table is placed on a textured red rug, with a decorative item at its center. A television is positioned on a stand next to a door leading outside, with natural light filtering through nearby windows.
Apartment in Redlands
4.9 out of 5 average rating, 149 reviews

2-BDR attached apt in rural Redlands neighborhood.

“RURAL REDLANDS” has a quiet neighborhood with a few creatures (coyotes, rabbits and squirrels). Although other hosts welcome pets, we request “no pets” (returning guests with allergies). Older 60’s home; not fancy but comfortable. Two bedrooms, kitchenette and living room. Private entrance; we share a living room wall and A/C. We are near U of Redlands, Downtown Redlands, restaurants, Oak Glen apple farms. . We’re 60-70 miles from Palm Springs, Casinos, BigBear Mtns, Disneyland, & beaches

Top Guest favourite
Home in Running Springs
4.96 out of 5 average rating, 24 reviews

Contemporary Cabin, flat entry for 3 cars!

This gorgeous two level mountain home has been fully remodeled from top to bottom offering 3 bedrooms, 2 full bathrooms, with laundry, gorgeous furniture & finishes over 2000 ft.² of brand new decking overlooking the tree lines, multiple areas to enjoy peace or to entertain with hammocks, swing chairs, barbecue grill, and fire pit! There is vaulted beam ceilings throughout central heat, and central air as well as two wood-burning fireplaces! Truly a one-of-a-kind property in the mountains!

Top Guest favourite
A cozy living area is characterized by wooden walls and flooring. A dark brown leather sofa faces a coffee table, while a single recliner chair is positioned nearby. Natural light enters through two windows adorned with blinds, complementing a wall-mounted electric fireplace.
Cabin in Big Bear
4.94 out of 5 average rating, 646 reviews

Serenity in the Tree Tops

This studio is nestled in the mountains of Big Bear with a view of varied pines & forestry. Perfect place for R&R and getting in touch with nature. Surround yourself with fresh air & sounds of the forest. 4.5 miles to Big Bear Lake, 4 miles to Snow Summit and 5 miles to Bear Mountain Ski Resort; 5.5 miles to The Village (shopping, dining, coffee, ice cream); 5 miles to Golf Course and Big Bear Alpine Zoo; 1.9 miles to Big Bear Speedway and Snow Play; half a mile from Community Market.

Top Guest favourite
A spacious bedroom is highlighted by a comfortable queen-sized bed, adorned with soft linens and pillows. Two large windows with sheer curtains invite natural light, and a modern ceiling fan is positioned above. A small dining table with chairs is neatly arranged by the entrance.
Guest suite in Yucaipa
4.96 out of 5 average rating, 78 reviews

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.

Guest favourite
Guest suite in Downtown Redlands
4.88 out of 5 average rating, 482 reviews

Private King Suite & Bath | Self Check-In

Spacious private-entry guest suite converted from the home’s master bedroom. Fully separate from the main house with keypad access, private attached bathroom, Wi-Fi, large TV, mini fridge, microwave, and seating area. Sleeps up to 3 with a king-size bed and optional full bed. Located in a historic 1895 home—updated but with a few quirks: toilet paper goes in the trash (older pipes). Quiet space, no parties. I live on-site, respect your privacy, and am always available if needed.

Top Guest favourite
The exterior of a two-story home is presented, featuring a blend of neutral tones. A well-maintained landscape of low shrubs and decorative stones surrounds the property, enhancing the curb appeal. A driveway leads to a single-car garage, contributing to a welcoming street view.
Guest suite in Redlands
4.97 out of 5 average rating, 292 reviews

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.

Guest favourite
A spacious bedroom features a large bed with light bedding and a soft pink throw. Framed artwork decorates the wall above the bed. A bedside table is visible next to the bed, while a full-length mirror reflects the room. A doorway leads to an en suite bathroom.
Guest suite in Beaumont
4.94 out of 5 average rating, 31 reviews

The Beau Cottage | Beautiful and Private Stay

Welcome to The Beau Cottage – a peaceful, private retreat in Beaumont, perfect for working, relaxing, or visiting loved ones. This cozy home features its own entrance, full kitchen, spacious bedroom, living room, and private bathroom. Cook your favorite meals with the stove, oven, microwave, toaster oven, and coffee maker. Conveniently located about an hour from many SoCal destinations. Other guests may be on-site in separate units, but your space is fully private.

Top Guest favourite
An open layout private suite is depicted, featuring a spacious bed with a light blanket and a small kitchenette area. A countertop, microwave, and refrigerator are visible. Ceiling fans provide airflow to the light-filled room, enhancing comfort with warm wooden flooring throughout.
Guest suite in Beaumont
4.97 out of 5 average rating, 117 reviews

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!

Top Guest favourite
Guesthouse in Highland
4.93 out of 5 average rating, 165 reviews

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!

Guest favourite
A stylish studio space features a spacious bed covered with a white quilt. A black dresser and a kitchenette area with a sink and mini-fridge are visible. Modern decor elements include patterned wallpaper, a wall-mounted TV, and a gold accent table, complemented by natural light from window shutters.
Apartment in Yucaipa
4.94 out of 5 average rating, 18 reviews

Luxury Studio in Uptown Yucaipa

Luxury Studio Welcome to our new fully remodelled Studio in uptown Yucaipa!! Located only a couple of minutes walk to restaurants , breweries, wine bars, performing arts center and the Yucaipa summer outdoor music concerts and much more. Driving: Yucaipa Regional park 3 Minutes Oak glen 10 Minutes Golf course 10 Minutes Forest Falls 15 Minutes Palm Springs 35 minutes Ontario airport 35minutes Big Bear 50 minutes

Top Guest favourite
The exterior of a guest house is captured, featuring a white facade and a wooden staircase leading to the entrance. Surrounding plants add greenery, and a sandy pathway extends from the driveway. A covered porch is visible, framed by wooden railings.
Guesthouse in Redlands
4.94 out of 5 average rating, 197 reviews

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.

Top Guest favourite
A charming outdoor seating area features two rattan chairs alongside a small round table. An umbrella provides shade, while stone walls and a wooden pergola add texture to the inviting entrance. Lush greenery enhances the space, contributing to a serene atmosphere.
Guesthouse in Yucaipa
5 out of 5 average rating, 72 reviews

"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.

Popular amenities for Calimesa holiday rentals

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