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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
4.92 out of 5 average rating, 197 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, 157 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 comfortable living area features a plush couch adorned with decorative pillows. A coffee table sits in the center, with a decorative basket placed atop. The background reveals an open kitchen with wooden cabinetry and modern appliances, enhancing the inviting and functional space.
Home in Benson
4.91 out of 5 average rating, 220 reviews

Bright & relaxing 2 bedroom close to everything!

Relax with the whole family at this peaceful place to rest. Plenty of parking for semi-truck and trailers. Fans, WiFi, large seating area, large flat screen tv. Private, outdoor gazebo and seating with lawn and plenty of space for your furry family member to run and kids to play. Easy freeway access, gas station just down the street, bar/restaurant 1 mile away, 30 mins to Tucson, 10 mins to Benson, 30 mins to Tombstone, 30 mins to Sierra Vista, 30 mins to Fort Huachuca, 1.5 hrs to Douglas.I

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
4.86 out of 5 average rating, 111 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
A green adobe home is nestled among tall trees, surrounded by natural grass and desert plants. The structure’s rounded features and large windows reflect a harmonious connection to the landscape, while the sky above exhibits a soft overcast hue.
Home in Cochise
4.93 out of 5 average rating, 137 reviews

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.

Top guest favorite
A private guesthouse is set against a backdrop of high desert terrain. Earthy tones and adobe architecture characterize the exterior, while large windows reflect the openness of the space. A hot tub is positioned nearby, surrounded by minimal desert vegetation.
Cottage in Gila
4.99 out of 5 average rating, 327 reviews

Guesthouse Las Palomas, Gila, New Mexico.

We are in Gila, NM! This is high desert, 83 ranch acres on Bear Creek, beside the Gila Wilderness, a private guesthouse w/private hot tub, amazing wildlife, beautiful views, dark night skies, reasonably fast Wifi (20+mbps), Internet TV, Tempurpedic Queen + Queen with Tempurpedic top, ORGANIC breakfast fixin's to start you off in a well appointed kitchen. Propane BBQ Grill. Dog friendly (only with all vaccinations and never left alone in house), eco-friendly. This is a vacation destination.

Top guest favorite
Home in Cochise County
4.95 out of 5 average rating, 362 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
Cabin in Tombstone
4.95 out of 5 average rating, 444 reviews

Authentic 1880s Miner's Cabin by Tombstone Brewery

Our original to the town adobe style miner's cabin, built in the 1880s, will take you back in time with its scenic mountain views and breathtaking night sky. The interior of the cabin has been carefully restored using a historic color palate, craftsman-style furniture, antiques and decor. Situated just a block away from Tombstone Brewery and only two blocks from historic Allen Street - walk to the best Tombstone shopping, saloons and attractions, then kick back on our porch and relax.

Top guest favorite
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, 218 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.

Top guest favorite
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
4.96 out of 5 average rating, 180 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 favorite
A friendly donkey interacts at the window of a rustic kitchen. On the wooden countertop, a plate holds a slice of cake, accompanied by a knife. A woman, holding a glass, enjoys the moment against a backdrop of desert scenery.
Ranch in Benson
4.97 out of 5 average rating, 182 reviews

Ranchito Paraiso: Rustic Elegance Farm Stay

Just a quick 3/4 zip off I-10, Kasita Morada is the perfect desert oasis after a long drive or ideal as a weekend getaway or artist’s retreat: a rustic, elegant, artsy casita in a ranch setting, Enjoy afternoon happy hour or your morning beverage with free-roaming donkeys and sweet piggies, surrounded by phenomenal views in a peaceful setting. Kasita has an exotic "Portugal meets Old Mexico" vibe. Come here to work, create, and/or relax.

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, 209 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 )

Popular amenities for San Simon vacation rentals

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