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, 195 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, 156 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
4.86 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, 136 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
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, 256 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, 360 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, 442 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, 214 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
Apartment in Willcox
5 out of 5 average rating, 192 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!

Guest favorite
The exterior of a single-story house is shown, featuring a light-colored facade with a pitched roof. Surrounding terrain is open with greenery, including shrubs and grassy areas. The sky is partly cloudy, adding depth to the backdrop of the house.
Home in Willcox
4.87 out of 5 average rating, 179 reviews

"Gila Hacienda"

Easy access off I-10. Close to town but quiet and private. Wineries are close and Playa for birdwatching. Horse trailer friendly, with 4 horse pens available, 2 are covered. There is dry camping if needed. Near Quail Park Rodeo Arena. Beautiful hiking in the Chiricahua Mountains, Cochise Stronghold or Dragoons. Short travel distance to Indie Motorsports. Very centrally located. A relaxing home to return to after a trip to the Mountains, Inde Motorsports or Tombstone!

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 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, 208 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