Some info has been automatically translated. Show original language

Holiday rentals in San Simon

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in San Simon

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top guest favourite
A silhouette of storage silos against a dramatic sunset, showcasing shades of orange and purple in the sky. The horizon features distant mountains, and open fields are visible in the foreground, contributing to the rural charm of the landscape.
Farm stay in Willcox
4.96 out of 5 average rating, 161 reviews

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.

Guest favourite
A cozy living room is filled with comfortable seating, including brown leather couches and an armchair. A wooden coffee table sits in the center, adorned with magazines and a plant. Natural light enters through a window, complemented by warm, earthy decor elements.
Ranch in Willcox
4.87 out of 5 average rating, 113 reviews

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.

Top guest favourite
The exterior of the cabin is viewed from the patio, featuring a covered seating area with two chairs and a small table. A door leads into the cabin, with a privacy curtain partially drawn. An outdoor shower and a separate utility area are also visible.
Tiny home in Dragoon
4.98 out of 5 average rating, 257 reviews

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!)

Top guest favourite
Home in Cochise County
4.95 out of 5 average rating, 367 reviews

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.

Top guest favourite
Tiny home in Animas
5 out of 5 average rating, 55 reviews

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.

Top guest favourite
The kitchen features a central island with seating for three, complemented by wooden bar stools. White cabinetry and a gray refrigerator create a modern atmosphere. Pendant lights hang over the island, illuminating the workspace, while large windows provide natural light.
Home in Willcox
4.99 out of 5 average rating, 223 reviews

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.

Guest favourite
A panoramic view of a mountainous landscape is captured from a wooden porch. The scene includes dry trees and a small rustic structure, framed by wooden beams. The sky is partly cloudy, and the mountains in the distance display a rugged terrain.
Cabin in Portal Rd
4.95 out of 5 average rating, 82 reviews

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!

Top guest favourite
The entrance to the Hacienda Cottage is highlighted, featuring a wooden door with a sign and surrounded by neatly trimmed shrubs. A planter with vibrant flowers adds a touch of color, while a pathway leads to the door under dappled sunlight.
Cottage in Portal
4.95 out of 5 average rating, 182 reviews

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!

Top guest favourite
A historic adobe structure is seen surrounded by open land. The exterior features a simple, unadorned design with a metal roof and multiple windows. A green gate leads into the yard, while a few white chairs are positioned nearby, inviting a relaxed outdoor atmosphere.
Home in Willcox
4.92 out of 5 average rating, 63 reviews

Stage house in Dos Cabesas

A unique historic stage house located in quiet ghost town Dos Cabesas. Built in 1860 in the former mining town, originally made of adobe, cool in the summer and warm in the winter. Located next to the sky island wilderness, full of various animals and bird species. Experience unplugged lifestyle in rural Arizona. Close to Chiricahua mountains and Cochise stronghold, a home to ancient Apache tribe. Hot water and heat. No Wi-Fi. Bedding and kitchen supplies.

Top guest favourite
A spacious bedroom features a wooden bed adorned with a patterned blanket. Natural light streams in through a window with sheer curtains, illuminating the turquoise walls. A wooden dresser and mirror complement the decor, while a textured rug adds warmth to the floor.
Farm stay in Rodeo
4.96 out of 5 average rating, 178 reviews

Geronimo Bunkhouse

Step back into history, to the time of Geronimo and the Wild West. This original bunkhouse has been lovingly restored by a local artist . Geronimo had his last meal as a free man in the Cienega Ranch bunkhouse. The Cienega Ranch was homesteaded by our great great grandfather Augustus Chenowth. Experience the working ranch and the flavor of days gone by. Explore the family graveyard where Uncle Bob's arm is buried along with family and assorted outlaws.

Top guest favourite
A scenic view of rugged mountains is framed by lush greenery and blooming flowers. The foreground features a soft-colored adobe wall with wooden railing, enhancing the connection to the surrounding natural landscape.
Guest house in Portal
5 out of 5 average rating, 173 reviews

Canyon View Cottage near Portal, AZ

This is a cozy one-room cottage with bath (shower) that comfortably sleeps two on a queen-sized bed. A small refrigerator, toaster, coffeemaker (coffee/tea pods, creamer and sugar supplied), dinnerware and microwave allow you to prepare simple meals and picnic lunches for your excursions into the canyon and national forest. The wisteria covered front porch offers a place to kick back/relax with views of the surrounding mountains.

Top guest favourite
A single-story home is framed by lush desert vegetation, situated against a backdrop of rugged mountains. The structure features a metal roof, blending into the natural landscape. The surrounding area showcases diverse greenery under a clear blue sky.
Home in Portal
4.96 out of 5 average rating, 291 reviews

Green Witch House at the Arizona Sky Village

Our house is a well-equipped home decorated in south western style. It has been rented by visitors from many parts of the world since 2005, some of whom have returned many times. It is situated at the mouth of Cave Creek Canyon in the beautiful Chiricahua Mountains which are noted for their abundance of wildlife and walking trails. The pristine night skies is evidenced by the number of private observatories.

Popular amenities for San Simon holiday rentals

  1. Airbnb
  2. United States
  3. Arizona
  4. Cochise County
  5. San Simon