Holiday houses in Calimesa

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Top-rated holiday rentals in Calimesa

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Guest favourite
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
4.97 out of 5 average rating, 117 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

Top Guest favourite
Guesthouse in Morongo Valley
4.99 out of 5 average rating, 511 reviews

Wilderness Cabin w/ Mini Donkeys & Wood-fired Tub

The Cabin at Painted Canyon Homestead This serene cabin is situated at the mouth of a canyon overlooking Morongo Valley, where the high desert meets the San Gorgonio & San Jacinto Mountains. As the guest house on our property of 5 acres, the cabin is privately located bordering vast public lands. Wander the property, hike the canyon trail, visit our four cheeky mini donkeys, & enjoy the wood-fired hot tub (or use it with fresh cold water!). Perfectly suited for two w/ lots of space to explore!

Top Guest favourite
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
4.96 out of 5 average rating, 23 reviews

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.

Top Guest favourite
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
4.98 out of 5 average rating, 194 reviews

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!

Guest favourite
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 Yucaipa
4.9 out of 5 average rating, 124 reviews

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!

Guest favourite
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.
Home in Redlands
4.97 out of 5 average rating, 79 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!

Top Guest favourite
A circular seating area, framed by large panoramic windows, offers a scenic view of the landscape at sunset. Wooden benches with cushions provide comfort, while a gentle gradient of colors in the sky transitions from soft blues to warm hues, enhancing the natural surroundings.
Cabin in Idyllwild-Pine Cove
5.0 out of 5 average rating, 60 reviews

Goldenview Cabin | Spa | Sauna | "BEST VIEW EVER"

Welcome to Goldenview Cabin, located on the side of a mountain, just several minutes from Idyllwild. With panoramic views, you can see the ocean 100 miles away, five mountain ranges, lakes, and city lights below. Nestled between huge granite boulders and adjacent to national forest land, it’s an amazing setting where you’ll relax and feel connected to nature. When not hypnotized by the view, enjoy the indoor swim spa, a barrel sauna, and new gourmet kitchen, or gather around the fire pit.

Guest favourite
Cabin in Forest Falls
4.9 out of 5 average rating, 123 reviews

Vintage Mountain Cabin with Hot Tub

Located at 6000 feet on a remote dirt road, you will need 4 wheel drive or all wheel drive and chains to get here if there is snow. Great hiking. Step back in time to 1930’s cabin life with the upgrade of a modern hot tub under the stars. Cabin has 2 wood stoves, a beautiful stained glass window, large bedroom, sleeping loft, fun enclosed patio with bar style stools, darts, chess and bbq. There another cabin across the road for added space: airbnb.com/h/forest-falls-1939-vintage-cabin

Top Guest favourite
A modern mountain cabin is showcased amidst towering trees, featuring multiple decks that extend from the structure. Large glass windows reflect the surrounding greenery, while a blend of wood and stone accents highlights its natural setting.
Cabin in Idyllwild-Pine Cove
5.0 out of 5 average rating, 332 reviews

Luxury Cabin - Cedar Tub, Seasonal Creek & Views

Haven is Idyllwild's answer to mountain cabin luxury. Set overlooking a peaceful seasonal creek flowing winter and spring. A custom built inspirational hideaway, nestled in the mountains near LA. Immerse in nature with the creature comforts of a curated modern cabin. This spacious cabin sits in a forested valley overlooking a seasonal stream with a cedar hot tub. Ceiling to floor windows look out at the surrounding mountains & jaw-dropping rock cliffs. An expansive, open cabin feel.

Top Guest favourite
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
4.96 out of 5 average rating, 153 reviews

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

Top Guest favourite
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
4.99 out of 5 average rating, 320 reviews

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

Top Guest favourite
The A-frame chalet showcases large wall-to-wall glass doors, inviting natural light. A spacious deck with comfortable outdoor seating surrounding a bright orange fireplace offers views of the surrounding wooded landscape and boulders.
Cabin in Big Bear Lake
4.97 out of 5 average rating, 249 reviews

Modern Swiss Chalet | Sweeping Views | Hot Tub

Perched on stilts, this modern Swiss chalet is nestled in the mountains of Southern California. Designed with tranquility and comfort in mind, the cabin blends its 1970’s charm while elevating modern luxuries like heated floors, a chef’s kitchen, and wall-to-wall doors. Enjoy all nature has to offer with skiing in the winter, hiking in the summer, and breathtaking views, epic sunsets, and stargazing all year round.

Popular amenities for Calimesa holiday rentals