Cottage holiday rentals in San Simeon

Big Sur Blue Cottage with Ocean view

Located on South Coast Big Sur, this Off-the-grid house sits atop a hill with expansive ocean views. Perfect for a digital detox. NOTE: "The cottage is currently only accessible via south Hwy 1 from Cambria due to a landslide closing the northern route. Attractions in North Big Sur, including Julia Pfeiffer State Park,McWay Falls, are unreachable. Detours add 4 hours; plan accordingly. We're not liable for itinerary changes." NOTE: 4WD/AWD VEHICLE AN ABSOLUTE MUST TO GET TO THE HOUSE. NO TESLA

Cutest in Cayucos! - 2 bed Casita steps from beach

Stylish, simple all-newly renovated cottage 2-min walk from the sand in idyllic California beach town. Two-unit property a short 3-blocks to restaurants and iconic pier. Perfect for surfing, beachcombing, wine tasting, hiking, sightseeing, fishing. The ideal mid-state stop, it is near Morro Bay, Cambria, Paso Robles vineyards, Hearst Castle and PCH/Big Sur. Front yard with gas firepit and shared beautiful backyard. Guest house on property too. CondeNast selected Best AirBnbs in California 2024

The Cottage at Old Morro

After a little time off Airbnb, The Cottage is back and better than ever Spring 2025! The perfect stop for your Central Coast adventure! Tastefully appointed and well stocked, the cottage is perfect for a getaway to Paso Robles wine country, the beach, San Luis Obispo, hiking trips or the famous HWY 1! The cottage is set in a beautiful spot at the lower end of our property under a mature and majestic grove of oak trees adjacent to a beautiful white barn with overhead twinkling bistro lights.

Peaceful Cottage in an Olive Grove

Come relax in this cozy cottage removed from the frantic world but so close you can easily go back at any time. Whether you choose to unwind in the serenity that surrounds our olive farm or venture out to experience all that SLO County has to offer, you'll be in the perfect spot for either or both. We're on a road less traveled with neighbors few and far between but located just 10 minutes from wine tasting, beaches, downtown SLO, the Village of Arroyo Grande, hiking trails and so much more.

Vintage Ranch Cottage, Paso Robles

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

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.

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!

Ocean View Cottage: Hot Tub - 2 King beds - Solar

-This is the LOWER LEVEL 950 sq ft unit of the DUPLEX. -PLEASE reconsider booking if you have difficulties taking the MANY steps from the street to your cottage. -ONLY for the BOOKED # of guests, NOT for their "visitors". -The solar powered cottage is tucked up in a very quiet neighborhood on the hills of Morro Bay. -You'll have access to the entire cottage with its own entrance, an adjacent deck, as well as to all 6 new decks, kids' slide, bridge to "Crow's nest", the new hot tub

Beautiful Ocean Front Cottage, Cayucos California

Welcome to our beautiful ocean front cottage by the sea. The front garden welcomes you and the view out the back will calm and restore your soul. Walk down the private steps to the beach. Hot water outside shower, gas fire pit, ocean viewing deck - it is all there to complete your ocean front vacation experience. Fully stocked kitchen and all linens provided. You will love it! Due to severe allergies of some of our guests we cannot accommodate service animals at this time.

1929 Spanish colonial home walkable to everywhere!

This cute 2 bedroom/1 bath historical home with two king beds and convertible twin chair offers everything you'll need: outdoor patio, indoor dining, full kitchen, fast WiFi, Roku TV w/ streaming channels, ceiling fans, comfy linens, parking w/ EV charger, and more! Walking distance to everything in downtown MB and the waterfront, even our famous Morro Rock. Please ask any questions before booking, and thanks for considering little Morro Bay for your next vacation!

Historic Little Red Cottage in Harmony

Our Rustic Little Cottage in the heart of the picturesque Town of Harmony, population 18 (if you count the cows) is the perfect artist or couples retreat looking for inspiration and a place to unplug and unwind, hence no wifi or television. The town is in the country surrounded by open pasture lands. Lots of wildlife and critters such as field mice, oppossums, raccoons abound. Harmony is right off scenic Highway 1 between Cayucos and Cambria.

J & T Beach Cottage, Ocean Views & Walk to Beach

Permit #STR25-075 Cute and clean beach cottage, 3 short blocks to Atascadero State Beach/Morro Strand, rooftop patio with panoramic views of Morro Rock and the beach. 2 bedrooms, each with their own fully renovated bathroom. Simple, fully equipped kitchen, sat TV, wifi, and washer/dryer. Plenty of off-street parking. Great for beach getaways. Close to Cayucos, Cambria and the West Paso Robles wineries.