Holiday rentals 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, 135 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 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, 220 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, 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, 237 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
An inviting living space features terracotta tiled flooring and a large window that frames outdoor views. A round fireplace sits against a warm-colored wall, and a chandelier hangs from the wooden ceiling beams. Two lamps illuminate a small table near a patterned area rug.
Home in Cochise County
4.95 out of 5 average rating, 321 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 favourite
The yurt is located on an elevated platform, surrounded by sparse trees and natural landscape. Its circular design features a warm-colored exterior, and a deck extends around the yurt, offering outdoor seating. Outbuildings are visible in the background, enhancing the rural setting.
Yurt in Bisbee
4.88 out of 5 average rating, 464 reviews

Yurt at the Top of the Mountain

Spacious yurt. Located in the high desert mule mountains with amazing views of fantastic starry skies, sunsets and sunrises. Close to hiking, the center of town, shopping, restaurants and main roads. Giving you the luxury of the open outdoors, the feeling of privacy with out being secluded. Easily accessible and comfortable. The space is intimate. Note: Dogs welcome, no other pets please. Resident dogs close by behind their own fenced yard space. Thanks we hope you enjoy yurtself here!

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, 177 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 favourite
The kitchen features modern white cabinetry and stainless steel appliances, including a refrigerator and a gas stove. A spacious countertop provides ample preparation area, with a sink centrally situated. A small dining table is positioned nearby, creating a functional and inviting cooking space.
Guest suite in Sierra Vista
5 out of 5 average rating, 109 reviews

White Brick Suite Sierra Vista

Attached all new remodeled Luxury Guest suite in Sierra Vista AZ. Private entrance and private living quarters with a full kitchen that is stocked with all the needed dish/cookware. You have control of your A/C and heat in the studio suite. This includes your own private bathroom, king size bed, living/dining room, and your own washer dryer. Located in a quiet neighborhood in central Sierra Vista, a short distance from various trails, hikes, bird watching, and Ft. Huachuca.

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, 106 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.
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!

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, 164 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.

Popular amenities for San Simon holiday rentals

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