Vacation rentals in San Simon

The Scale House

Take it easy at this unique and tranquil getaway. The Scale House is located in the heart of wine country. It is across the road from a beautiful Vineyard and within 3 miles of six more vineyards. The night sky is perfect for stargazing. If you are a bike rider, you are in the perfect area. It is located next to an elevator that was used for 50 years before farming changed in the valley. The scales were removed and the house has been remodeled making it feel new and comfortable for a night away.

Cowboy Hideaway

Our little place is surrounded with all the nature and wildlife one needs. The peace and quiet with endless starry nights are relaxing and rejuvenating for the soul. Bring your family and enjoy our newly renovated 3 bedroom 2 bath home. It offers plenty of space with a fenced back yard and firepit for those beautiful nights. It also boasts a 7 stall barn for your horses so no one is left home alone. With just a short drive you can be at endless trails, historic towns, vineyards and family farms.

Cochise Stronghold Canyon House

Take it easy at this unique and tranquil getaway. Walk out the front door and into the mountains for an adventure or relax under the peaceful oaks and simply recharge. This classic adobe brick home captures simple luxury. Listen to the creek babble, run or roar when the rains come. Observe the lifeblood of the desert from the private bridge that crosses it. Bring your horses or pack goat and set them to roam in the paddock. Soak the stillness and take in the starry nights far from city lights.

Studio Cabin: Glamping with Mountain Views

3:10 to Dragoon studio cabin is only 1 hr east of Tucson and 3 miles off the I-10 in the tiny town of Dragoon. Our property borders trust land w/unobstructed mountain views. We are near the Willcox Wine Trail, Cochise Stronghold, and Chiricahua Nat'l Monument. The cozy cabin is equipped with an outdoor hot shower, cassette toilet, heat/ac, kitchenette and double bed. This is glamping at its finest in Cochise country! (At 4600' elevation, we are 10-15 degrees cooler than Tucson or Phoenix!)

Log House. Rodeo NM/Portal AZ

Historical Rodeo, NM Cienega Ranch homesteaded by our family in 1878. Visit nearby Cave creek in Portal Az , (18 Miles) a famous destination for birders and naturalists alike. 130 species of birds observed on our private pond and mature tree covered site .Astronomers will find an excellent Bortle 1 dark sky site and views for miles, a secluded and Private farm/ranch with all amenities. 5 yr old home and fully stocked kitchen, dedicated remote work space, high speed fiber internet 100/7 mg

Indian Ridge Casita

The Casita (large studio type) sits up above Sulphur Springs Valley at 4400', much cooler temps, over looking Cochise Stronghold and the Dragoon Mountains. Secluded, and views galore. Chirachua National Monument, Whitewater Preserve, Fort Bowie, Willcox, good food, wineries, old western town. If you have horses, we have accommodations on our other property for them . Only two pets are allowed. Must have approval from host if more are requested. Pets MUST be listed in booking details.

Observatory Cabin Near Rodeo, NM & Portal, AZ

Escape to a peaceful high-desert retreat in southern New Mexico, just: • 15 miles from Portal, Arizona • 17 miles from Cave Creek Canyon • 8.6 miles from the Chiricahua Desert Museum Valley Vista Getaway is an award-winning tiny home with panoramic desert and mountain views, located under true Bortle 1 dark skies. Spend your days exploring the incredible birding, hiking, and wildlife of the Portal–Chiricahua region, then return each night to quiet desert skies filled with stars.

Quail Run Hideaway

Quiet country setting one mile from Willcox. Well behaved pets welcome, doggy door fenced in area. Sit quietly on the back deck to see birds including quail come to feed. Bird seed is provided. Sit on the front deck in the evenings and enjoy the hoot of our resident Great Horned Owl. The Sandhill cranes fly over in the morning and early evening, this happens in the late fall thru the middle of March. Several wine tasting rooms are available in Willcox and the surrounding area.

Cowboy Cabin at Myrtle Kraft Cottages

Relax with the whole family at this peaceful place. Rustic setting in lovely Portal, AZ, and an easy walk to the Portal Store/Cafe. Cave Creek fronts the property; stunning granite canyons a short drive; view birds and other wildlife from your private porch or drive short distances to multiple great birding sites in and around the legendary Chiricahua Mountains. And a fabulous night sky! Full kitchen, spacious bedroom, fold-out bed in living room. TV and Wi-Fi. And pets welcome!

Four Bar Cottages: The Hacienda – Cozy with Birds

Relax in rustic comfort at The Hacienda Cottage, nestled on a historic horse ranch at the base of the Chiricahua Mountains. This cozy one-room stay sleeps up to 4 with a queen bed and two twins. Includes a mini-fridge, microwave, toaster, coffee maker, full bath, A/C, and satellite TV. Enjoy a peaceful back porch with bird feeders and access to our private wildlife pond. No pets, no same-day bookings, and a 2-night minimum in March–May. A quiet desert escape awaits!

Cochise Casita | Unique Straw-Bale Desert Retreat

Welcome to the Cochise Casita! Escape to the High Desert. Experience a true open-concept sanctuary designed to showcase the rugged beauty of the Cochise Stronghold. Built with unique straw-bale construction, this home provides natural insulation and a peaceful, grounded atmosphere you won't find in a standard rental. High ceilings and expansive windows create a seamless connection with the 20-acre landscape, making the desert the centerpiece of your stay.

Historic Wine Country Adobe | Near Chiricahuas

Escape to a historic adobe home in the heart of Willcox wine country. This charming 1BR retreat on 3+ private acres offers stunning mountain views, a full kitchen, and a serene setting. Perfect for exploring local vineyards, tasting rooms, and the breathtaking Chiricahua National Monument. A true rural Arizona getaway. Ideal for up to 4 guests, the master bedroom boasts a comfortable king bed, complemented by a queen sleeper sofa in the living room.