Holiday rentals in San Simon

Majestic Getaway in Southwest

Newer construction desert home with beautiful views of Chiricahua Mountains. 2 master bedrooms with king size beds, 2 1/2 baths, fully equipped kitchen. Den has pullout couch. Amenities: Cable, internet, washer/dryer, AC. Home is located on 4 acres in Arizona Sky Village, Portal, AZ. Minutes from Coronado National Forest. Birders Welcome! This area is one of the top birding sites in North America. Cave Creek Canyon is located nearby. For astronomers, this area has the darkest skies in the United States.

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.

Sky Islands Retreat in Rodeo w/ Mountain Views!

Escape the hustle and bustle of life and retreat to this biodiverse area bordering Rodeo, NM and Portal, AZ. This 3-bed, 2-bath vacation rental sits on 20 acres, featuring a cozy living area, a full kitchen, and on-site walking trails. Enjoy local birdwatching, take an Eco-tour, hike the Second Switchbacks Silver Peak Trail, explore Cave Creek Canyon, or tour The Chiricahua Desert Museum! At day's end, relish the stunning sunsets and stargaze into the darkest skies in America. It's up to you!

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!)

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.

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.

The Hollywood Cowboy

Ultra-eclectic bunkhouse inspired by Hollywood’s depiction of the Wild-West! Authentic decor abound in the space, from the framed B movie posters to antique whisky jugs and local art to the original travel maps and promotions that bought adventure-seekers to the West on Route 66 during the golden years of America travel - one could spend the day just enjoying all there is to look at in this fun space but we guarantee the town is even better!!

Cienega Ranch Guesthouse SouthWest Working Ranch

Historical Rodeo, NM Cienega Ranch homesteaded by our family in 1878. Walk the paths of Geronimo, Billy the Kid and Cochise the Apache. Geronimo ate his last meal as a free man on our ranch. ( see books Portal to Paradise and Bad Company and Burnt Powder, ) 130 species observed on the ranch acerage. Visit nearby Portal Az , (18 Miles) famous destination for birders and naturalists alike. PETS UPON APPROVAL ONLY $80 per stay per animal )