Holiday houses in San Simon

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Top-rated holiday rentals in San Simon

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Top Guest favourite
The exterior of a newer construction desert home is displayed, featuring a light-colored stucco facade and a covered porch with wooden beams. A gravel driveway leads to the entrance, surrounded by sparse desert vegetation and views of the mountains in the background.
Home in Portal
4.92 out of 5 average rating, 183 reviews

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.

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, 131 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.

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.
Guesthouse in Portal
5 out of 5 average rating, 163 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. We are fully vaccinated and encourage our guests to be the same.

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, 236 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!)

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
4.92 out of 5 average rating, 52 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!

Guest favourite
The front exterior of the cottage is shown, featuring a covered porch supported by wooden beams. A door with a window is framed by two equally sized windows on either side. Green grass stretches in the foreground, complemented by trees that provide shade.
Cottage in Portal
4.92 out of 5 average rating, 105 reviews

Four Bar Cottages: The Apache – A Birding Escape

Escape to Apache Cottage, a cozy two-room retreat at the base of the Chiricahua Mountains on a historic ranch. Perfect for birders, hikers, and stargazers, it sleeps 4 with a queen bed and two twins. Enjoy a kitchenette, full bath, satellite TV, wraparound porch, private patio, and bird feeders right outside your window. Located on 80 peaceful acres near Cave Creek Canyon. No pets, no same-day bookings, and a 2-night minimum stay in March–May. A perfect nature getaway awaits!

Top Guest favourite
The exterior of the guest house is shown under a vibrant blue sky adorned with white clouds. The structure features a green metal roof, white walls, and large windows. A tree and pebbled ground surround the building, enhancing its tranquil setting.
Apartment in Willcox
5 out of 5 average rating, 185 reviews

High Desert Dreams Guest House

The Guest House is a fully contained separate building. It is located 30 miles SE of Willcox, AZ near the Chiricahua Mountain Range. The Guest House is newly remodeled and has approximately 750 sq ft of living space. The interior is decorated in Cowboy/Mexican/Indian decor. The scenery boasts mountains, open pasture and blue skies! The Chiricahua National Monument is a short 4 miles from our place. If you are looking for a quiet and peaceful place to stay, this is it!

Top Guest favourite
The exterior of the casita is showcased, featuring stucco walls and a flat roof. Native plants, including palm trees and desert shrubs, frame the entrance. A gravel path leads towards the door, with a clear blue sky above highlighting the serene landscape.
Home in Cochise County
4.95 out of 5 average rating, 315 reviews

Indian Ridge Casita

The Casita sits up above Sulphur 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. All pets MUST be listed in booking details.

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
4.95 out of 5 average rating, 162 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 vibrant red bird is perched on a railing, showcasing its distinct coloring. The background features soft greenery, suggesting a natural environment. The bird is positioned clearly, allowing for appreciation of its details against the blurred foliage.
Home in Willcox
4.92 out of 5 average rating, 155 reviews

"Birdsong Hideaway"

Just off interstate 10, a peaceful, comfortable country setting. The surrounding trees are home to many species of birds. Very close to all the amenities that historical Willcox AZ has to offer. Centrally located near wineries and tasting rooms. Numerous restaurants and museums very close. Sit on the front porch and view the beautiful Dos Cabezas Mountains. House is equipped with handicap ramp and bathroom hand bars.

Top Guest favourite
A view of the exterior of The West-End Hideaway showcases a charming wooden building with a sloped roof. A stone pathway leads to the entrance, enhanced by two seating areas with colorful chairs. The foreground features a gravel landscape, while a dramatic sunset fills the sky, casting warm hues.
Guesthouse in Tombstone
4.99 out of 5 average rating, 191 reviews

Cozy, Private, Sunset View

Located on historic Allen Street. Within eight minutes walking and two minutes driving time to the Tombstone Historic District. Private entrance and lighted covered parking. The property is fenced and secured for child and pet safety. Queen Bed & Queen Sofa Sleeper. Refrigerator W/ice maker & water, microwave, coffee pot, toaster oven. Has all modern comforts with a true Old West ambience. Fantastic Sunset View!

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, 270 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