Holiday rentals in San Simeon

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.

Bayview Retreat – King Beds, Rock View, EV Charger

Need more space? Book the downstairs 1 bed/1 bath unit too! Welcome to one of the newest vacation rental on the Embarcadero—fully renovated with brand new everything! Wake up to stunning views of Morro Rock from the master bedroom and catch glimpses of the ocean from the cozy living room. Stroll to Morro Rock and unwind on the nearby sandy beach. Sleep soundly on ultra-soft luxury linens, plush pillows, and a comfy hybrid mattress that makes every night feel like a getaway.

Charming Cambria Retreat, 3BD 2BA HotTub, FirePit

Welcome to Whispering Pines, your serene retreat in Cambria! Nestled in the majestic pines, this beautifully remodeled 3BD (3 beds, 1 sofa bed) , 2BA home offers peaceful forest views and daily visits from local wildlife. Enjoy cozy evenings by the fireplace, unwind in the brand-new hot tub, and enjoy the outdoor fire pits under the stars. With vaulted ceilings, outdoor seating areas, & a fully stocked kitchen, this home is perfect for families & friends - pets welcome too!

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.

Pet Friendly 2 Bdrm- Awesome East Village location

Pet Friendly low key two bedroom apartment is your cozy home base, in the heart of Cambria's sunny historic East Village, with splendid hikes in every direction, a blooming shared front garden, organic market and fantastic restaurants at a stone’s throw, and 2 miles to Moonstone beach. Who needs to drive! This listing has a queen bedroom and a small single bedroom - so it's suitable for folks wanting 2 separate beds, for up to 3 people.

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.

Oceanside, Restored, Vintage, Retreat in Cambria

Escape to our charming beach house with unparalleled ocean views. This cozy retreat features a fireplace in the living rooms, an open-concept design, a fully equipped kitchen, and three comfortable bedrooms. Spend your days unwinding on the expansive deck, perfect for lounging and barbecues. Explore the nearby town's attractions and immerse yourself in the coastal beauty of Cambria. Your dream beach vacation awaits.

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.