Vacation rentals in Calimesa

Magical Mid-Century Cabin Epic Views & Fireplace

Nestled just a short distance from LA, embrace the idyllic landscape of picture-perfect sunsets from the balconies and awe-inspiring views from the house. Discover the orchestra of ravens and crows while savoring your morning coffee, or get lost in a book by the fireplace. Featured in Fodor’s Travel “Best Airbnbs and cabins of the year”! A 4-minute drive to Lake Gregory, 12 minutes to Lake Arrowhead, & 45 minutes to Big Bear. So much to explore or stay cozy inside, you will enjoy your time here.

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

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.

Balsam Bungalow - Lake View 1 min to ski - Hot Tub

Balsam Bungalow is a Mid-century bungalow, nestled on a piney hillside, with state forest and Lake views, in the exclusive & charming Moonridge neighborhood. Walk/drive to Big Bear slopes located .3 miles away. Snow Summit 9 min drive. State Forest Hiking trails 2 blocks away. Snuggle by the masonry fireplace & take in the picturesque view w/ ceiling to floor windows. Enjoy the wooded yard with wrap around deck, fire pit, BBQ, eating area & scenic hot tub- that is serviced after each guest.

@wild_olive_den • Serene Mountain Getaway Cabin

★ Featured in Condé Nast Traveler ★ Experience a designer escape at the Wild Olive Den. Perched above Running Springs with panoramic views, our cabin features a relaxing hot tub, EV charger, and 3 scenic decks. Perfect for families or a romantic getaway: 🏔 15min to Lake Arrowhead & Snow Valley Ski 🎡 7min to SkyPark / Santa’s Village 💻 Fast 370 Mbps Wi-Fi 🧸 Fully kid-equipped (Pack & Play/High chair) + Central A/C & Backup Generator! Relax by the fire or spin vinyl on the record player!

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!

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!

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.

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

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.

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

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.