Holiday rentals in Calimesa

Guest house in Cherry Valley

An outdoor gazebo is illuminated by soft blue lights, featuring a dining set and comfortable seating area. The space is surrounded by a well-kept patio, providing an inviting atmosphere for evening gatherings under the night sky.

4.97 out of 5 average rating, 118 reviews

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

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4.96 out of 5 average rating, 23 reviews

A vibrant outdoor pickleball court is displayed under a clear blue sky, with a basketball hoop positioned nearby. Accessories, including a decorative tote bag labeled 'Pickleball,' basketball, soccer ball, and a set of paddles, are arranged neatly beside the court's net.

Home in Yucaipa

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.

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4.98 out of 5 average rating, 197 reviews

An antique suitcase is featured with a weathered exterior, showcasing faded travel stickers and a vintage design. Its metal clasps and handle exhibit signs of wear, highlighting its history and charm. The suitcase rests on a textured surface, adding to its nostalgic appeal.

Guest house in Yucaipa

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!

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An outdoor living space is presented, featuring an oversized sectional with bright blue cushions, complemented by a patterned area rug. A glass coffee table sits in the center. The heated pool is visible in the background, surrounded by lounging chairs under umbrellas.

4.98 out of 5 average rating, 82 reviews

SoCal’s Pet Friendly Luxury Family Pool spa Resort

You deserve this. This luxury home sits perched atop rolling hills that lead to Joshua Tree, Los Angeles, San Diego and Palm Springs. A warm French country style permeates this amenity-brimming home. Heated pool, spa, game room, pet run, fully equipped kitchen, and much more, make your stay a unique and family fun experience. Make time to explore Southern California's best from this centrally located gem. Relax, revive. Escape. Experience yourselves again! Home has a back up generator!

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A welcoming entrance is framed by lush green ivy climbing over a covered porch. The dark front door is adorned with a seasonal wreath. Rocking chairs and potted plants create an inviting atmosphere, while a small doormat adds a pop of color near the entrance.

4.95 out of 5 average rating, 106 reviews

Downtown Redlands Historic Wonderland

Downtown Redlands 2 Min Walk From State St. Food, Bars, Fun. Peace & Yoga I own a studio & teach private classes in the back studio- I am very quiet, you are always welcomed to join & I love helping Great for a couple/Travel Nurse & Medical/ Student or World Travelers 🧳 LAX Ontario & San Bernardino Airports within 20 minutes. Located near LLU, SB County, Káiser, Redlands Hospital & The University of Redlands, SBCU, LLUMC Valley & Crafton & of course Coachella & Bicycle Classics.

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4.89 out of 5 average rating, 91 reviews

Guest house in Yucaipa

Authentic Mexican Casita, Pool, Spa, Fire, WIFI

This Amazing Authentic Mexican style guest house has all the handcrafted features you’re looking for. Greeted by a 100 year old wood door and beautiful Saltillo tile. You will enjoy the spacious 17 foot vaulted ceiling with a wrought iron vintage chandelier out of a castle. Dark walnut live edge counters with handcrafted talavera tile backsplash in kitchen and bathroom.Full kitchen. Loft sleeps 4, 2 bedrooms with queens. This is a guests house located at the back of our property

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4.96 out of 5 average rating, 157 reviews

A serene exterior view of a white two-story home is presented, with a wide driveway leading toward the entrance. To the left, rows of grapevines are visible, framed by mountainous greenery under a clear blue sky.

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

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4.99 out of 5 average rating, 325 reviews

The cabin, set among tall trees, features a gray exterior with warm, glowing windows. A stone pathway leads to the entrance, framed by natural landscaping. The tranquil setting hints at a peaceful atmosphere, ideal for a quiet getaway, especially during evening hours.

Cabin in Forest Falls

Palisades View - Cabin With Spa

This cabin was recently remodeled and modernized with: - Air conditioning (central AC) - Spa/hot tub on the deck with great view - Electric car charging station (L2, fast charger) - High speed internet - Laundry washer and dryer - Smart TV with YouTube TV included. You can log in with your NetFlix, etc. This cabin is located... 1/2 mile from Forest Home. 20 minutes from Oak Glen. 20 minutes from Redlands 15 minutes from Yucaipa 60 minutes from Big Bear

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A comfortable living area features a beige sectional sofa and two armchairs arranged around a coffee table. A flat-screen television is mounted above a modern fireplace. A dining table with four chairs is positioned nearby, with a large area rug beneath them.

4.99 out of 5 average rating, 139 reviews

Spacious 4 bedroom home in the heart of town!

Your entire group will enjoy easy access to everything from this centrally located home. Only one mile to the University of Redlands, and less than a mile to all the great restaurants, bars, and shopping boutiques on State St. Easy access to both on and off-ramps of the 10 freeway. Almost everything inside the house is new! With over 2 years of ALL 5-star reviews, this is hands down the best place to stay in Redlands! Don't hesitate, we book up fast.

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4.96 out of 5 average rating, 25 reviews

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.

Flat in Yucaipa

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

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The living area features a blue sofa and a gray armchair, arranged around a low coffee table. Natural light fills the space through a large window with horizontal blinds. A bright yellow door adds a pop of color, enhancing the modern kitchen view in the background.

4.96 out of 5 average rating, 180 reviews

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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The exterior of a one-story house is displayed, featuring a welcoming yellow front door and a patio area. Spiky green plants are positioned alongside the entrance, while gravel landscaping surrounds the walkways. Tall cypress trees are visible in the background, contributing to the home's appealing facade.