Vacation rentals in San Simon

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Top-rated vacation rentals in San Simon

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Top guest favorite
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
4.93 out of 5 average rating, 203 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 favorite
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, 162 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 favorite
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, 117 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 favorite
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, 261 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 favorite
Home in Cochise County
4.95 out of 5 average rating, 372 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 favorite
Tiny home in Animas
5 out of 5 average rating, 56 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.

Guest favorite
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, 83 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 favorite
Home in Cochise
4.9 out of 5 average rating, 83 reviews

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.

Guest favorite
Home in Willcox
4.9 out of 5 average rating, 71 reviews

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.

Top guest favorite
A single-story ranch house with a red roof is surrounded by desert land and evergreen trees. Mountain ranges are visible in the background under a clear sky, providing a serene and open atmosphere.
Home in Rodeo
4.98 out of 5 average rating, 212 reviews

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 )

Top guest favorite
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, 177 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 favorite
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
4.94 out of 5 average rating, 192 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.

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