Vacation rentals in San Simon

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Top-rated vacation rentals in San Simon

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Guest favorite

A rocky terrain is depicted with rugged formations under a partly cloudy sky. The scene showcases rolling hills in the background, characterized by gentle slopes and varied textures of brown and green vegetation, reflecting the natural features of the surrounding Chiricahua Mountains.

Home in Portal

4.92 out of 5 average rating, 179 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.

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, 120 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 favorite

A welcoming entrance features a gently sloped pathway made of stone and tiles, leading to the front door. The exterior wall is painted in warm earth tones, complemented by a small overhang. Scenic mountain views are visible in the background, enhancing the natural surroundings.

Guesthouse in Cochise County

4.99 out of 5 average rating, 212 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 favorite

A cozy cottage is seen surrounded by a blanket of fresh snow, showcasing southwestern architecture with a warm color palette. Majestic mountains rise in the background, shrouded in mist, while desert flora, including yucca plants, adds texture to the winter landscape.

Guesthouse in Portal

5 out of 5 average rating, 154 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.

Guest favorite

A covered porch provides a spacious area for relaxation, featuring a wooden table surrounded by chairs. A patterned rug adds warmth to the space, with green and white lawn chairs positioned for comfortable seating. The view extends to a grassy field bordered by horse pens.

Home in Willcox

4.87 out of 5 average rating, 156 reviews

"Gila Hacienda"

Just off Interstate 10. Horse trailer friendly, with 4 horse pens available for use, 2 are covered. There is dry camping and an RV hook up. Quiet and secluded from the traffic and close to Quail Park Rodeo Arena. Wineries close and the Playa for bird watching. Beautiful hiking in the Chiricahua Mountains, Cochise Stronghold or Dragoons. Great places to eat in the area, BBQ, Mexican Food or Steak! Very centrally located. A relaxing and quiet place to come back to, from a visit in Tombstone!

Guest favorite

Home in Cochise

4.94 out of 5 average rating, 113 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 image captures a serene desert landscape at sunset, featuring gentle mountains bathed in warm, golden light. The foreground includes sparse vegetation and dry grass, with a fenced area visible. A peaceful atmosphere is suggested by the expansive sky and fading daylight.

Tiny home in Dragoon

4.98 out of 5 average rating, 228 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

A vibrant sunset is captured, featuring a blend of deep oranges and purples in the sky. Dark silhouettes of trees and foliage frame the bottom, contrasting with the colorful atmosphere above.

Cabin in Portal

4.95 out of 5 average rating, 155 reviews

Four Bar Cottages - The Hacienda

A quaint cottage located at the base of the Chiricahua Mountains. Perfect for birders, astronomers, or families, located on a historic family-owned horse ranch. During our high season of March, April and May there is a TWO NIGHT MINIMUM STAY that is strictly enforced. We do NOT allow dogs or cats. We are self check-in: the door to the cottage will be unlocked and the key on the table. Check-in time is 3:00 pm or later and check-out time is 10:00 am. WE DO NOT ACCEPT SAME-DAY BOOKINGS.

Top guest favorite

Home in Willcox

4.98 out of 5 average rating, 153 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

A large, leafy tree stands prominently in an open field with rolling hills in the background. The tree's broad canopy provides a contrast to the blue sky filled with fluffy white clouds. The surrounding landscape features sparse vegetation and distant mountains.

Apartment in Willcox

5 out of 5 average rating, 182 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

A stunning sunset paints the sky in vibrant hues of orange and pink, reflected in a calm body of water. Silhouetted mountains serve as a backdrop, while flocks of birds gather peacefully at the water's edge, creating a serene natural scene.

Home in Cochise County

4.94 out of 5 average rating, 301 reviews

Indian Ridge Casita

The Casita sits up above Sulphur 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. All pets MUST be listed in booking details.

Guest favorite

A quiet street in Tombstone, lined with trees, features the charming architecture of historical buildings. Soft evening light highlights the façades, while a gravel path runs through the center, inviting exploration of the local shops and attractions.

Bungalow in Tombstone

4.89 out of 5 average rating, 385 reviews

The Hollywood Cowboy

Ultra-eclectic bunkhouse inspired by Hollywood’s depiction of the Wild-West! Authentic decor abound in the space, from the framed B movie posters to antique whisky jugs and local art to the original travel maps and promotions that bought adventure-seekers to the West on Route 66 during the golden years of America travel - one could spend the day just enjoying all there is to look at in this fun space but we guarantee the town is even better!!

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Popular amenities for San Simon vacation rentals

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Other great vacation rentals in San Simon

Top guest favorite

A rustic barn with a weathered metal exterior is visible in the background, surrounded by a grassy landscape. Fencing lines the foreground, with wooden posts spaced evenly along the property. A horse can be seen grazing nearby, with trees in varying autumn colors framing the scene.

Cottage in Cochise County

5 out of 5 average rating, 60 reviews

Sunglow Retreat

DrewRating, 5 stars3 months ago

Sunflower Retreat was one of the most fantastic places we have ever stayed! The house and land is of great beauty. The nourishment we got from the experience was profound! Sharon and Rob are excellent hosts and we can’t wait to return again soon.

Top guest favorite

A spacious living area is shown with light-toned hardwood flooring and a large sectional sofa arranged around a central area rug. A recliner is positioned nearby, and shelves line the walls, creating a cozy yet open atmosphere. Natural light fills the space from multiple windows.

Home in Safford

5 out of 5 average rating, 32 reviews

Where friends & family meet!

WendyRating, 5 stars1 week ago

What a lovely but comfortable home! I was there with colleagues, and each one of us was more than pleased. We had everything we could possibly need—and more! We had plenty of options if we wanted to gather: the kitchen, library, and family room. If we needed privacy, the spacious bedrooms gave us that and included a television, rocking recliner, and bathroom (only two rooms had a shared bathroom which worked for our group). I especially enjoyed the gorgeous back yard; I felt like I was in the countryside as I watched the birds each morning, including a sweet cardinal. Rebecca was more than responsive; she was generous, kind, and accommodating. We hope to rebook this home next year when we return for the conference.

Guest favorite

Home in Animas

5 out of 5 average rating, 9 reviews

Sky Islands Retreat in Rodeo w/ Mountain Views!

GaryRating, 5 stars5 months ago

We spent several days at Rhonda and Mark's place over the New Year holiday. The house offers spacious living quarters, a large kitchen with plenty of work space, and great vistas in all directions. The night sky is stunning and the house maintains night-sky friendly outdoor lighting. The house is very clean and we really appreciated the pet-free policy. Rhonda was very responsive.

Superhost

Clouds stretch across the sky, illuminated by soft rays of sunlight. The silhouette of mountains is visible in the background, surrounded by open land. The scene captures a serene blend of light and shadow, emphasizing the natural beauty of the landscape.

Cabin in Rodeo

4.81 out of 5 average rating, 53 reviews

The Cowboy Room with a great western theme.

SueRating, 5 stars2 months ago

The Cowboy Cabin is a beautiful, quiet place. It's so cutely decorated and very well maintained. The landscaping is beautiful, with a variety of birds and a dark sky. We had everything we needed for a great stay on our bike ride. Though bikes are not allowed in the rooms, Dan showed us where to park the bike for the night and it was very convenient. We would definitely book with Dan again in the future.

A gray fox stands atop a wooden table in the outdoor space, showcasing its bushy tail and sleek fur. The background features scattered rocks and foliage, adding to the natural setting. The image captures a moment of wildlife observation at the property.

Home in Portal

4.69 out of 5 average rating, 16 reviews

Gloria’s Roost

AnneRating, 5 stars2 weeks ago

It is a cute and nice little place. It is not too difficult to find and very convenient — just a short drive to hiking trails and restaurants. Portal Lodge is close by and Sky Islands Grill is 10-minute drive away and very good. We particularly enjoyed watching birds from the big one-sided window. There are also many books and magazines to browse at. Overall, it is a peaceful place to stay. Everything is as expected for its location and size.

Top guest favorite

A spacious covered patio features a seating area with dark wicker furniture and cushions. Potted plants surround the area, and the backdrop includes lush greenery and distant mountainous terrain. The patio is designed for relaxation and enjoyment of the surrounding natural scenery.

Apartment in Portal

5 out of 5 average rating, 15 reviews

Querencia #2 - Cave Creek Home

DebraRating, 5 stars2 weeks ago

Unit was perfect for a quick birding trip from Tucson. Priced well, kitchen had everything we needed. This was one of the only units available for a one night stay. Many of the units in this area require 2 nights or more which was just too much time for us. Bed was comfortable, there are bird feeders and a shared patio facing the beautiful mountains. Very peaceful and serene.

An inviting entrance to a museum is visible, featuring a prominent sign displaying the name 'Desert Museum.' The surrounding landscape includes desert plants and cacti, contributing to the natural beauty of the area. A clear blue sky at dusk adds to the serene environment.

Guesthouse in San Simon

4.8 out of 5 average rating, 83 reviews

Silver Peak Casita - Portal , AZ

MarilynRating, 5 stars1 month ago

This was a really nicely laid out condo with all we could need to cook,clean and rest. The area is gorgeous. The restaurant ha excellent food and service. Out hikes and climbs went well. Please consider Dominic to this remote part of the world where wildlife and scenery as beautiful

Ancient rock art is displayed on a rugged stone surface, featuring red ochre designs, including a circular shape and abstract figures. The texture of the stone is visible, with natural variations in color and depth, under soft natural lighting that highlights the historic markings.

Campsite in Animas

5 out of 5 average rating, 11 reviews

Full Hook-up Mtn-View RV Sites under the Stars

EvelynRating, 5 stars18 months ago

Gene was so nice to greet us out at the entrance on his ATV. Gorgeous drive from I-10 - but don't be like us and trust online Maps with the address. Instead, take a screenshot of Lynn's directions on the confirmation page (scroll down on a phone). Then the place is easy to find!

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Vacation rentals in San Simon

Top-rated vacation rentals in San Simon

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