Holiday rentals in San Simeon Bay

The Los Osos Valley Guest House

Settle into authentic 'SLO CAL' in our cozy and casual Surf Ranchita - The Los Osos Valley Guest House is a rustic hideaway nestled between quaint rural farmlands, laid back Los Osos and the rugged natural coastline. It's a perfect base stay with it's casual rustic vibe, unique character and renovated modern conveniences. Enjoy a fully stocked 3 bedroom house with hot tub, infrared sauna, outdoor shower, 4 TVs private WiFi, heated marble floors, BBQ patio and outdoor seating with amazing views.

Lavender Farm Retreat with Hot Tub

Paso Robles Lavender Co. is nestled amidst the picturesque wine country, our lavender farm offers a unique short-term rental experience that combines the tranquility of nature with the luxury world class wineries at your fingertips. The home accommodations are thoughtfully designed to provide you with a cozy and inviting space to unwind and rejuvenate, while acting as a "home base" for your adventures. We are off Vineyard Drive and Hwy 46 West, in a country setting, 20 minutes to the coast.

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 daybed 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.

Magnolia Vineyard Winemakers Cottage

Located on a hill near well-known wineries is Magnolia Vineyard Wine Makers Cottage. There are expansive views from the deck overlooking our Vineyard, oak-studded hillside, and city lights beyond. This remodeled barn offers complete privacy yet is only eight minutes from downtown Paso Robles. This charming 3 bedroom, 2 bath outfitted with fine linens, and all the essentials. On the large deck one can sip on a glass of wine watching the sunset or sip on a cup of coffee to watch the sunrise.

Vintage Cottage - on vineyard + feat. on Netflix

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!

Lake Views Hilltop Ranch - 160 Acre Escape

Secluded private hilltop cabin just 5 minutes from the marina, between Lake Nacimiento and Lake San Antonio. Set on 160 lake-view acres—bring your boats! Horses and longhorn cattle graze nearby (and no flies!). This artfully designed 3BR, 2BA ranch home offers sweeping lake, valley, and mountain views. Located on the Wildflower Triathlon route—perfect for cycling, scenic drives to wineries and missions, and epic stargazing. Wildlife sightings possible!

Coastal Breezes -10 Minutes from Hearst Castle

Coastal Breezes & 10 minute drive to Hearst Castle.| Escape the hustle in this peaceful, light-filled haven. Featuring massive sliding glass doors that blur the line between the cozy living room and the Pacific Ocean, our home invites the outdoors in. After a day of exploring Hearst Castle (just 10 minutes away!) or walking the Moonstone Beach boardwalk, come home to sink into plush bedding and watch the sunset from your private ocean-view deck.

Enchanting Cambria home ocean view: 2blocks2ocean

Welcome to our comfortable and clean 3-bedroom ocean view home. Feel the ocean breeze, listen to the waves and relish the view as you savor your morning coffee on one of the two decks. This marine terrace Cambria home boasts a great location in a quiet neighborhood on the Marine Terrace. It is an easy 2-block stroll to the ocean and a 5-minute walk to the start of the Bluff Trail of the 400 acre oceanside Fiscalini Ranch preserve.

Modern Cayucos Bungalow - Ocean Views and Hot Tub

Welcome to our modern and chic Cayucos surf shack! Perched upon the hillsides of southern Cayucos, enjoy sweeping ocean views of Estero Bay, from the front balcony while sitting next to the outdoor gas fire pit, or from the secluded back patio while soaking in your very own private hot tub! This cottage includes a spacious backyard for your pup to roam that backs up to hundreds of acres of nature and open space.

Ranch living w/ incredible views

Enjoy ranch style living located only 5 mins from downtown Cambria. We’re located right outside the coastal fog belt, so when it’s foggy in town we usually have perfect temps and sunshine! Even though it’s considered a “tiny home” it is very spacious with full amenities including full-size refrigerator, a nice gas BBQ grill, free level 2 charging, and a full size washer and dryer.

Olive House - tranquil retreat on an olive farm

Escape to Olive House, a private hillside retreat in Paso Robles with 360-degree vineyard views. This 2-bed, 2-bath home comfortably fits 4 guests. Features include a full kitchen, multiple fireplaces, and a stunning courtyard. Enjoy rustic charm and modern comforts, just a short drive from historic downtown. Perfect for a romantic getaway or a peaceful wine country adventure.

The Owl Box

Private, quiet above garage apartment with beautiful forest views. Access to forest trailhead that leads to ocean. Newly remodeled unit with handmade Cambria Pines counter tops. Cozy gas fireplace, three quarter bath with custom shower and cal king bed. Kitchen nook with small fridge, microwave, sink, coffee maker and hot water pot. Wifi available. Two night minimum.