Pet-friendly holiday rentals in San Simeon

Romantic Vineyard Guesthouse - 2 min from wineries

Top 1% of all listing with 900+ 5-star reviews. Enjoy a romantic stay in our amenity rich Guesthouse with covered parking on our vineyard estate. You'll love the quiet and stargazing in this amazing location. We are just minutes from Paso Robles' best wineries and a quick 5 minute drive to quaint downtown Paso Robles - where you can enjoy shopping, parks, and restaurants. Within San Luis Obispo county you are 45 minutes from wineries, festivals, farmers markets, CalPoly, and of course the beach.

Cute Cambria Cottage~Ocean Views and Dog Friendly!

Charming 1100 sq. ft. Cape Cod, 2 story quest cottage. Large, open studio living/dining/kitchen area plus 3/4 bathroom. Quaint beachy/casual decor. Queen bed is downstairs, full and sidaybed upstairs. Cable tv/ dvd combo and Roku for streaming, electric fireplace and WiFi. Our stand alone cottage is separated from main home by a great enclosed deck with ocean views. Private walkway to cottage without stairs and wheelchair accessible, ample off street parking in large driveway and dog friendly.

Back Bay Getaway - Dog Friendly - Home in Los Osos

Our peaceful home is located a short walk from the back bay of Los Osos. Its new design makes for a restful getaway with its luxurious bedroom, hot tub, and soothing bath. Our home is close to many local favorite hiking, biking, kayaking, surfing, and paddle boarding locations such as Montana de Oro and Morro Bay. The outdoor patio is the perfect setting for a family bbq with a lawn for your pets to play. A short distance away is delicious cuisine, coffee shops, golfing, and local art studios.

Vintage Ranch Cottage, Paso Robles, California

Nestled on 66 acres in the heart of Paso Robles wine country and featured on Netflix's hit show, Stays Here, is Vintage Ranch Cottage. Surrounded by mature vineyards and rolling hills, the cottage leaves nothing to be desired of the Paso Robles wine country experience. Centrally located 10 minutes to downtown, 5 minutes to the Adelaida wine trail, 15 minutes to Lake Nacimiento and 35 minutes to the coast! Come enjoy gorgeous Paso Robles and "stay here" at Vintage Ranch! @vintageranch on IG

Welcome to The Hidden Cottage Downtown Morro Bay

The Hidden Cottage is an adorable vintage cottage in downtown Morro Bay. Our cozy cottage is truly a hidden gem featuring 2 bedrooms 1 bath that was built in early 1920s and retains most of its sweet charm. Right downtown and a quick walk to the Embarcadero and beach. Perfect location to walk to restaurants, bars, music, shopping, movies, coffee and more! Morro Bay is short drive to Wine Country, SLO, Pismo Beach, Cambria. Bring your pets we love all animals! Fun and walkable location!

Baywood Cottage #3 | Walk to Bay | Dog Friendly

DESCRIPTION This amazing property is located in the heart of Baywood, Los Osos. This 360 square foot cottage accommodates three guests comfortably. This cottage is walking distance of the Bay where you can find endless trails and places to explore water activities, restaurants, bars and local brew houses. The outside patio is located to the left of the front door and is perfect for enjoying the beautiful weather the Central Coast has to offer. There's even an EV Charger on-site!

Renovated Private Hippy Beach Shack With Full Bath

Enjoy all that Morro Bay has to offer from this recently renovated eco-friendly live/work space featuring everything needed for a quiet retreat by the beach. Enjoy the cool, foggy mornings listening to the seagulls and foghorn with a cup of Coffee in the private courtyard, or cozy up with a book in bed and listen to the ocean waves at night. Find peace to complete your work from the decked-out office area. Whatever your Morro experience is, enjoy it at The Shack! License #16312467

Blue Bonnet Ridge

Spring flowers paint the hills of the Central Coast. Warm days and crisp nights make spring a great time to enjoy the beauty of the wildflowers and wild life of the the back canyons. Enjoy the peace and solitude of the Central Coast back country in this 10ft x 12ft furnished wall tent. Enjoy the magnificent sunset over the vibrant greens, pinks and yellows of springtime in the back canyons. Temperatures average mid 60s/70s in the daytime and upper 40s/low 50s at night.

Casita Oliva

Romantic, freestanding casita with private courtyard, set upon the hillside of a working olive farm in Paso Robles, California. Vintage Moroccan and Spanish light fixtures, built-in Moroccan queen-sized bed, refrigerator, coffee maker and basic utensils make this a perfect home-away-from-home or private retreat. The en suite bathroom features a porcelain tub/shower and stone sink. An outdoor fireplace and gorgeous views to the surrounding hillside complete the setting.

440 Acre log cabin, Lake Nacimiento

Ever dream of escaping to an authentic cabin in the woods with no neighbors, no “people” noise, no boundaries, simply the sounds of undisturbed nature? Bee Rock’s “El Rancho Cantina”, it’s storybook cabin & sprawling 440 acres on a seasonal arm of Lake Nacimiento offers its serene ambiance & panoramic setting to those seeking a space away from it all. Visitors can enjoy recreating at both Lake Nacimiento & Lake San Antonio. Both Marinas are a short 10-15-minute drive.

Historic 1919 carriage house

The J Birdsall Banker property was developed from 1917 to 1919. The carriage house was constructed in 1919 and converted into housing during the housing shortage of World War 11 We have always referred to it as the honey moon suite because so many couples have lived there over the last 65 years. Couples still sometimes still stop to look and share old memories The carriage house was recently upgraded with all new interiors and is comfortably furnished

Peaceful Suite by the Bay

Unwind in our peaceful private suite on a quiet acre by the bay. Enjoy ocean sounds, eucalyptus trees, birdlife, and bay views from your suite, covered deck, and giant fenced front yard. Easy walk down to the bay for walking trails/kayaking/paddleboarding. Just 5 minutes from Montana de Oro state park epic beaches and hiking/biking trails. Close to great food, wine, and coffee - plus friendly visits with our donkey (Ozzie), horse (Nina), and chickens!