Holiday rentals in San Simon

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Top-rated holiday rentals in San Simon

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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, 130 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
The exterior view showcases a porch with railing, overlooking a landscape of gently rolling hills under a clear blue sky. Sparse vegetation is present, with gravel underfoot and a distant mountain serving as a backdrop.
Home in Cochise County
4.96 out of 5 average rating, 135 reviews

Deer Haven Hideaway

Relax with the whole family at this peaceful place to stay. Cooler temps, low traffic (almost) zero! We have a pond that birds, javelinas and the deer love! Two pastures with shade shelters if you are traveling with horses. Historic town of Willcox food, wineries, museum, and a theater. Chihuahua National monument, Cochise Stronghold, Turkey Creek, Fort Bowie, Bisbee, Tombstone, Douglas, are within an hour drive. Much cooler temps here as the elevation is 4400'. Please check out my Guidebook.

Top guest favourite
A cozy living area is highlighted by a comfortable sectional sofa adorned with decorative pillows. A small coffee table sits in front, accompanied by a patterned area rug. Soft light filters through a large window, complemented by a welcoming entry door featuring a friendly greeting.
Guest house in Cochise County
4.99 out of 5 average rating, 218 reviews

Cochise Stronghold Airb&b

Sandy and I invite you to enjoy a secluded hide away from the hustle and bustle of city life. We are located 4 miles from the Cochise Stronghold Mountains, The Chiricahua National Monument to the East is 45 minutes away. Our small town of Sunsites host the Iron Skillet which serves breakfast and lunch ,while TJ's bar and grill serves meals all day. Wonderful BBQ! Lots of History with Tombstone just an hour away. Kartchner Caverns State Park is 45 minutues away. Don't forget our wines!

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, 162 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!)

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
4.98 out of 5 average rating, 168 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 cozy living area features a light-colored sofa with a decorative pillow, situated beside a small table draped with a lace cloth. Wooden cabinets line one wall, complemented by a kitchenette with modern appliances and a welcoming entry door. Natural light flows in through a large window.
Guest house in Saint David
4.88 out of 5 average rating, 154 reviews

"Tree of Life" 1 BR guest house with laundry rm.

This is a cute guest house in the heart of Cochise county. We are near Tombstone, Bisbee, Sierra Vista, Benson and Kartchner caverns. The house is neat and clean. It contains all of the amenities needed for your enjoyment. Saint David is generally 5 to 10 degrees cooler than Tucson and Phoenix. We have two A/C - Heater units to keep the temperature inside at your comfort level. We now have a laundry room available. Golf clubs available to use at nearby golf courses.

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.
Flat 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!

Guest favourite
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, 167 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 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, 168 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 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, 200 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 )

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