
Holiday houses in Calimesa
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Calimesa
Guests agree: these stays are highly rated for location, cleanliness and more.

Peaceful & Private w Stunning Mountain View’s
Our private, separate and detached guesthouse is located in a rural country setting with mountain views all around for those seeking a relaxing and peaceful atmosphere to unwind, relax, rest and rejuvenate, 15 miles to over 40 wineries in Temecula, just minutes to lakes, casinos, apple farms, skydiving, water park, mountain charms of Oak Glen, Idyllwild and more. Our space features a modern contemporary aesthetic inside w stunning mountain views & sunsets on the deck to stargaze and unwind.

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Skiing
❤️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

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

Treetop Terrace - View, level entry, rec room, A/C
Perched high on Idyllwild’s North Ridge, Treetop Terrace sits in a canopy of oak trees and offers amazing views from its expansive upper deck. Enjoy the charm of its mid-century architecture and vintage-inspired furnishings. Features include floor-to-ceiling windows, an open-concept layout, a recreation room, and wheelchair accessibility. Conveniently located 3-minutes from the village, it is easy to enjoy the charms of Idyllwild and the beautiful San Jacinto mountains from the Treetop Terrace.

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.

Midnight Chalet A-Frame w/ Spa ~ Fireplace ~ BBQ
Welcome to Midnight Chalet, a modern A-Frame located in Big Bear Lake. This 2 bedroom 1 bath cabin is near The Village and Lake. The home includes an upgraded kitchen and bath and amazing deck with a firepit and Bbq! Beautiful views of the trees and mountains in the background from our second story will have you never wanting to leave. Hang outside and Bbq while relaxing by the firepit or spend the day lounging on the large deck immersed in nature. This is truly an all season getaway!

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.

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).

Romantic Hilltop Retreat | Views, HotTub, Pool, AC
Touch the stars and sleep in the clouds at this unique, tranquil getaway designed for ageless, timeless magic. Fully remodeled brick cabin built into your own mountain. Welcome the sunrise & the sunset as you revive your creative romantic. This hilltop hideaway is a serene landing for a divine, high-desert retreat. Where the elements conspire to deliver your daydreams, soak in the spaciousness. - 25min to Joshua Tree National Park - 25min Palm Springs - 20min to Pioneertown

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.

Wooded Bliss @ Maple Mid century Lake open May 10
Welcome! We're excited to have you stay in our 1,042 sq ft 1960's cabin! Hiking trails to explore and skiing, snow tubing; 15 min to SNOW VALLEY Complimentary Smores & whiskey. Cabin is 3 min walk to Lake. You can fish for trout, swim at beach and boat. Lake open May 10 to October 31 2025 for boats. Complimentary use of snowplay sleds and snowball maker. We will snowplow the driveway for your arrival. Check weather conditions and roads as chains or 4WD may be required.

The Roadhouse Follow us at @roadhousewinecountry
The RoadHouse! A cozy, stylish spot smack dab in the middle of wine country. You can walk to many wineries from our location, really! Or stay on site and enjoy the private jacuzzi spa (always hot!), have a round of mini golf or just relax on the deck. Located on a fully fenced property The Roadhouse has everything you need for a fantastic wine country getaway. Don’t forget to get up early and check out the hot air balloons. They land outside our fence most days!
Popular amenities for Calimesa holiday rentals
Other great holiday rentals in Calimesa

Backyard pickleball with a modern twist!

Luxury Private Suite Mountain & Orange Grove Views

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

Rustic Farmhouse Retreat

Stairway to Haven - Lake Views (hot tub+fire pit)

The Reserve: Heated Pool • Spa • Fire Pit • Views

Cottage Ranch Retreat Oak Glen & 123 Lavender Farm

Charming & Peaceful Verdemont Ranch Casita Retreat
Destinations to explore
- Southern California Holiday rentals
- Los Angeles Holiday rentals
- Stanton Holiday rentals
- Las Vegas Holiday rentals
- Channel Islands of California Holiday rentals
- San Diego Holiday rentals
- Phoenix Holiday rentals
- Central California Holiday rentals
- Palm Springs Holiday rentals
- Scottsdale Holiday rentals
- San Fernando Valley Holiday rentals
- Henderson Holiday rentals
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Snow Summit
- Palm Springs Convention Center
- Pechanga Resort Casino
- Mountain High
- Honda Center
- National Orange Show Events Center
- Angel Stadium of Anaheim
- Palm Springs Aerial Tramway
- Monterey Country Club
- Desert Falls Country Club
- Rancho Las Palmas Country Club
- Indian Canyons
- Alpine Slide at Magic Mountain
- Indian Wells Golf Resort
- Desert Willow Golf Resort
- Tahquitz Creek Golf Resort
- Palm Desert Country Club
- Snow Valley Mountain Resort
- Chino Hills State Park
- Glen Ivy Hot Springs Spa
- Big Bear Alpine Zoo
- Mt. Baldy Resort




