Vacation rentals in Calimesa

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Top-rated vacation rentals in Calimesa

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Top guest favorite

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.

Guesthouse in Cherry Valley

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

4.97 out of 5 average rating, 120 reviews

Top guest favorite

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.

4.96 out of 5 average rating, 23 reviews

Top guest favorite

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.

Guesthouse 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!

4.98 out of 5 average rating, 198 reviews

Guest favorite

Guest suite in Yucaipa

Quiet & Cozy Getaway - Efficiency Retreat

Relax in this charming, peaceful getaway tucked away in a quiet cul-de-sac. This secondary unit features two comfortable bedrooms: one with two full beds and the other with a queen bed, a futon (sofa bed) and a full bathroom (bathroom located in and accessed through this bedroom only) a convenient kitchenette with a burner, coffee maker and toaster. Enjoy your coffee or meals on the private patio. Walking distance from Old Town Yucaipa, 15 minutes from Oak Glen, Riley’s Farm and hiking trails.

4.89 out of 5 average rating, 28 reviews

Guest favorite

An outdoor living space features a large pool surrounded by sun loungers, with a cozy fire pit area nearby. The two-story estate is visible in the background, showcasing a blend of modern and rustic elements against a backdrop of mountainous scenery.

Home in Cherry Valley

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!

4.9 out of 5 average rating, 127 reviews

Guest favorite

A spacious dining area features a large wooden table surrounded by tall, dark chairs. Soft natural light filters through plantation shutters, illuminating the elegant decor. In the background, a pool table adds a recreational element, enhancing the inviting atmosphere of the open floor plan.

Home in Redlands

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!

4.98 out of 5 average rating, 84 reviews

Top guest favorite

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.

Home in Redlands

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.

4.95 out of 5 average rating, 110 reviews

Guest favorite

An open living area features a comfortable sectional sofa and a light-colored area rug. Adjacent dining space includes a table surrounded by chairs. Decorative elements include a wall clock and a welcoming sign. Natural light streams through large windows, illuminating the space.

Home in Loma Linda

Whole Home in Loma Linda on Quiet Cul-de-Sac

Enjoy this family-friendly haven while in the Inland Empire. Situated just minutes from the main Loma Linda Campus as well as walking distance to multiple parks and playgrounds, this quiet home on a cul-de-sac near Lawton and Bryn Mawr is perfect for families wanting a private place. We have a crib set up for you and have set up the area to be child-friendly. We love hosting families. Short drive to Historic Downtown Redlands as well as great hiking trails in the Hulda Crook hills.

4.98 out of 5 average rating, 58 reviews

Top guest favorite

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

4.96 out of 5 average rating, 158 reviews

Guest favorite

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

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

4.96 out of 5 average rating, 25 reviews

Top guest favorite

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.

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.

4.96 out of 5 average rating, 181 reviews

Guest favorite

A spacious home is displayed with a manicured lawn and palm trees in the front. The structure is complemented by stone features and a three-car garage. The backdrop showcases distant mountains and a blue sky dotted with clouds.

Home in Cherry Valley

Luxury 3bd 3b Oak Glen Pool Resort Panoramic Views

Live the luxurious life from high above the city. Unwind on the rooftop sundeck while gazing at the panoramic views or take a dip in the pool. After the sun sets, head inside and enjoy the beautifully decorated spaces and comfy beds. This home is just two miles from Oak Glen apple picking and several wedding venues. Bring the whole family to this amazing home in an ideal location.

4.98 out of 5 average rating, 53 reviews