Vacation rentals in Calimesa

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Top-rated vacation rentals in Calimesa

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Top guest favorite
An A-frame cabin stands amidst lush trees, illuminated by evening lights. A cedar hot tub, surrounded by natural boulders, emits steam, inviting relaxation. The exterior features large windows that bring the outdoors in, while a seating area is positioned nearby for enjoying the serene atmosphere.
Cabin in Running Springs
5 out of 5 average rating, 230 reviews

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Hiking

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings and high-end linens ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds No pets permitted

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
4.96 out of 5 average rating, 110 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 favorite
An open-plan living area features a plush sectional sofa adorned with a striped blanket. A circular dining table sits nearby, illuminated by sunlight streaming through large windows that showcase natural surroundings. A wood-burning stove provides warmth in the corner, enhancing the cozy ambiance.
Cabin in Banning
5 out of 5 average rating, 170 reviews

Boulderland A-frame on 8 acres / 4 miles from Town

Welcome to our cozy A-frame cabin nestled on the outskirts of Idyllwild California. This secluded retreat is the perfect place to escape the hustle & bustle of the city and reconnect with nature. The open-plan living area features a fully equipped kitchen, comfortable seating, and a wood-burning stove, perfect for cozy nights in. Step outside & you'll be greeted by the beautiful natural surroundings. Relax on the spacious deck & take in the views of the surrounding trees, valley & mountains.

Guest favorite
The outdoor patio features a rustic fire pit surrounded by several Adirondack chairs, inviting relaxation. A wooden deck leads to the entrance of the cabin, set against lush greenery and shade provided by tall trees. The cabin's stone chimney adds character to the setting.
Cabin in Crestline
4.95 out of 5 average rating, 192 reviews

Designer Cabin at LAKE Gregory- walk to town!

A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

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
4.98 out of 5 average rating, 184 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 favorite
A charming A-frame log cabin is framed by the glow of a sunset, with wooden decks leading to a cozy fire pit surrounded by Adirondack chairs. The mountain backdrop adds to the serene ambiance of the outdoor space.
Cabin in Whitewater
4.97 out of 5 average rating, 170 reviews

A-Frame Cabin, 360 degree mountain views, hot tub

Just 15 minutes from Palm Springs, you'll find Whitewater Cabin. Seen in Travel & Leisure and on Discovery Plus, this architectural marvel is a magical retreat in the beautiful Whitewater preserve. Massive hand-carved cedar timbers form a bucolic A-frame exterior, while luxurious décor sets an ideal atmosphere for romance…or simply escaping the hustle and bustle. Explore Whitewater Preserve, enjoy a desert hike, plunge into the oasis pool and then settle in for some remarkable stargazing.

Top guest favorite
Home in Morongo Valley
4.97 out of 5 average rating, 206 reviews

Pioneertown | Views | 5 acres | Privacy | JTNP

Treat yourself to a Desert Retreat. This 1 bedroom, 1 bathroom home invites you to hear, see, and feel everything Southern California's high desert offers. Mountain views, Saguaro Cacti, citrus trees, and so much more can all be taken in from the comfort of a lounge chair in this sprawling 5 acres. Private, yet conveniently near Joshua Tree National Park, Morongo Casino, Pioneer Town, shops, and restaurants, you can escape the noise of everyday life without sacrificing any of its comforts

Top guest favorite
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 out of 5 average rating, 323 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 favorite
A modern white structure is framed by a colorful sunset sky, with warm interior lights glowing softly through the expansive glass doors. A heart made of stones is positioned in the foreground, adding a touch of natural art to the desert landscape.
Home in Pioneertown
4.98 out of 5 average rating, 322 reviews

Sol to Soul - Named by Condé Nast: Coolest In Cali

Come experience the otherworldly at Sol to Soul, a 10-acre sanctuary in the privacy of Pipes Canyon in storied Pioneertown, surrounded by a mystical theater of boulders and Joshua Trees in the starkly beautiful Mojave Desert. With dark skies for ultimate Milky Way viewing, you will reclaim your sense of awe and magic and leave more inspired + spellbound by life than when you arrived. Recognized as the Best Airbnb in California (Condé Nast) and a top 10 U.S. accommodation (Delsey).

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
4.96 out of 5 average rating, 144 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 favorite
Cabin in Running Springs
4.99 out of 5 average rating, 309 reviews

Mid-Century Perfect Romantic Getaway Hot Tub|Sauna

This Black A-Frame cabin sits high among the pines in Running Springs, offering peaceful treetop views from decks on all three levels. With warm mid-century modern design, it’s the perfect romantic escape. Snuggle in the cozy loft, enjoy vinyl or a movie in the secret cinema room, and unwind together in the new barrel sauna. Perfect for couples celebrating anniversaries, honeymoons, special getaways, or simply enjoying quiet, meaningful time together in the forest.

Top guest favorite
The exterior of the modern A-Frame is surrounded by tall trees, showcasing a blend of rustic charm and contemporary design. The warm glow from the windows highlights inviting spaces inside. A wrap-around deck is visible, creating a welcoming atmosphere for relaxation amidst nature.
Cabin in Big Bear
4.97 out of 5 average rating, 114 reviews

Cozy A-Frame Vibes w Lake & Ski views, AC

Welcome to your elevated A-frame escape—guests love the stunning lake & ski slope views, stylish design, and luxurious comfort throughout. A perfect blend of modern and rustic for a memorable getaway. Sleeps 5 | 2 bedrooms | 5 beds | 1 baths Panoramic lake & ski slope views Iconic A-frame w/ mid-century modern style Luxury bedding & new mattresses Fully stocked kitchen for easy meals Bright, design-forward living space Ideal for year-round stays & relaxation

Popular amenities for Calimesa vacation rentals

  1. Airbnb
  2. United States
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  4. Riverside County
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