Vacation rentals in San Simon

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Top-rated vacation rentals in San Simon

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Guest favorite

Home in Portal

4.91 out of 5 average rating, 154 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.

Jan 31 – Feb 7

G$23,847 GYD per night

Guest favorite

Home in Rodeo

4.97 out of 5 average rating, 157 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 $60 per stay per animal / possible Extra cleaning fees 60-100 depending on animal(s)

Aug 1 – 8

G$22,848 GYD per night

Guest favorite

Apartment in Portal

4.98 out of 5 average rating, 162 reviews

Querencia #1

Cozy 500' 1 BR duplex. 1.5 miles from Portal. Hi-speed WiFi & Basic DishTV. Fully equipped kitchen inc. oven & furnished coffee/tea bar. Spacious covered patio w/grill perfect for enjoying dinner with hummingbirds & gorgeous AZ sunsets/sunrises. Huge fenced yard with remote gate. Back Up Generator. Owner/Mgr always physically avail.able. Walk out back gate into Coronado Forest for multiple hiking trails. Now renting both sides of duplex. Patio is shared. "New" 1bd/bath great value check site!!!

Feb 14 – 21

G$20,480 GYD per night

Guest favorite

Guesthouse in Portal

5.0 out of 5 average rating, 132 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.

Oct 20 – 27

G$27,424 GYD per night

Guest favorite

Home in Willcox

4.86 out of 5 average rating, 112 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!

Oct 19 – 26

G$34,716 GYD per night

Guest favorite

Cabin in Portal

4.94 out of 5 average rating, 126 reviews

Four Bar Cottages - The Hacienda

A quaint cottage located at the base of the Chiricahua Mountains, a naturalist's paradise. Perfect for birders, astronomers, mountain bikers or historians, located on a historic family-owned horse ranch. Please note that 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. Check-in time is 3:00 pm or later, and check-out time is 10:00 am. WE DO NOT ACCEPT SAME-DAY BOOKINGS. Thank you for understanding.

Aug 25 – Sep 1

G$24,646 GYD per night

Guest favorite

Tiny home in Dragoon

4.98 out of 5 average rating, 172 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!)

Oct 29 – Nov 5

G$14,413 GYD per night

Guest favorite

Guesthouse in Cochise County

4.99 out of 5 average rating, 178 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 Talking Irons Coffee shop with wonderful pastries and all sorts of coffee, teas and breakfast items . The Local Grub serves breakfast, lunch and pizzas while TJ's bar and grill serves meals all day. Wonderful BBQ! Lots of History.

Sep 29 – Oct 6

G$20,389 GYD per night

Guest favorite

Guesthouse in Elfrida

4.98 out of 5 average rating, 147 reviews

Clean & quiet with stunning views.

Stunning mountain views! Room to breath and abundant wild life. 40 acres of open range, our little vineyard, and our gardens are all available for you to relax among. A Bird Watches Paradise. Close to Chiricahua National Monument, Turkey Creek, Coronado Nation Forest, Ft. Bowie, White Water Draw WildlifeArea, were the Sand Hill Cranes winter, Cochise Strong hold, Tombstone, Bisbee & Sierra Vista. Conveniently located near a restaurant, store and fuel station. And 420 friendly!

Oct 20 – 27

G$23,321 GYD per night

Guest favorite

Guesthouse in Saint David

4.86 out of 5 average rating, 133 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.

Feb 17 – 24

G$12,583 GYD per night

Guest favorite

Apartment in Willcox

5.0 out of 5 average rating, 151 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!

Jul 17 – 24

G$33,491 GYD per night

Guest favorite

Bungalow in Tombstone

4.89 out of 5 average rating, 321 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!!

Jul 12 – 19

G$18,630 GYD per night