
Vacation rentals in San Simon
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in San Simon
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

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.

Watch the sunset from a private hot tub!
Experience the tranquility and remoteness of desert living in this private studio suite with a kitchen, hot tub, and mature vegetation that wraps the entire porch. Use this as a base for your adventures in the area. Whether rock climbing the granite domes, strolling along abundant hiking trails in both the Dragoons and Chiricauhua mountains, exploring old mines, sipping wine at a local vineyard, or searching for local flora/fauna: relaxing after in this sanctuary is the perfect end to the day.

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.

Pecan Country Retreat sleeps 13
The Pecan Country Retreat is a private cozy 2-story getaway perfect for creating lasting memories with loved ones. From couples to large families, this home can sleep up to 13 people comfortably. It is furnished with 4 bedrooms and 2.5 baths and includes a fully-equipped kitchen and laundry room. There are an abundance of tourist attractions all within an hour. Built on 2 acres with gorgeous pecan trees and amazing sunset views, this newly renovated home will feel like a tucked away paradise.

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.

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.

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!

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!!

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 )

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.
Popular amenities for San Simon vacation rentals
Other great vacation rentals in San Simon

Sunglow Retreat

3 Bed Home on Historic 80 near Benson & Tombstone

Wine Country Adobe | Summer Retreat in Willcox

Silver Peak Casita

Mid-centry RV with Retro Decor In Tombstone

The Big Mesquite Lodge!

Mesquite Retreat

Sky Island Retreat • Mtn Views • Nature • Quiet
Destinations to explore
- Phoenix Vacation rentals
- Salt River Vacation rentals
- Scottsdale Vacation rentals
- Sedona Vacation rentals
- Tucson Vacation rentals
- El Paso Vacation rentals
- Albuquerque Vacation rentals
- Puerto Penasco Vacation rentals
- Flagstaff Vacation rentals
- Ciudad Juárez Vacation rentals
- Ruidoso Vacation rentals
- Verde River Vacation rentals





