
House holiday rentals in San Simeon
Find and book unique houses on Airbnb
Top-rated house rentals in San Simeon
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in San Simeon
House rentals with a pool

Paso Panorama-Swimming Pool, Hot Tub, & Views

4bd w/ Pool/Hot Tub. Quiet and relaxing. Pets ok!

Luxury Mountain View Retreat Pool/jacuzzi

Modern Poolside Paradise+Wineries+Pool+Hot Tub

Getaway at the Oaks +Heated pool+hot tub

OCEAN VIEW! 1 Block to the Sea~ 2 KINGs & 2 Queens

Our Place Inn

Spacious Family Oasis w/ Pool & Hot Tub Retreat
Weekly house rentals

Mid-century home in the heart of Arroyo Grande.

Wine Country Hilltop Retreat

Bayview Getaway

Pelletiere Estate Winery’s Modern Farmhouse

Hilltop Retreat. Spacious house on alpaca ranch.

Baywood Park Garden Cottage

The Beach House - On Cayucos Beach

Baywood Cottage #3 | Walk to Bay | Dog Friendly
Private house rentals

Old Vine House - 360 degree vineyard views!

Winery Row | Pickleball Court | Peaceful Hamlet

4.5 Acre Farmhouse in Wine Country w/Hot Tub

Close to Dtown! Gorgeous MidCentury w/fire pit

Wine Country Oasis ♡ Central to SLO, Paso, Beaches

Wine cellar House

Cayucos Sunsets and Spectacular Views

Beach House ON Pismo Beach
Destinations to explore
- Central California Holiday rentals
- San Francisco Peninsula Holiday rentals
- San Francisco Holiday rentals
- San Francisco Bay Area Holiday rentals
- Channel Islands of California Holiday rentals
- San Fernando Valley Holiday rentals
- Santa Monica Holiday rentals
- Los Angeles Holiday rentals
- Gold Country Holiday rentals
- Northern California Holiday rentals
- Stanton Holiday rentals
- Southern California Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Cayucos Beach
- Cayucos State Beach
- Montaña de Oro State Park
- Pfeiffer Big Sur State Park
- Morro Strand State Beach
- Sand Dollar Beach
- Natalie's Cove
- Dairy Creek Golf Course
- B & E Vineyard & Winery
- Pismo State Beach
- Moonstone Beach
- Hearst San Simeon State Park
- Morro Bay Golf Course
- Allegretto Wines
- Mission San Luis Obispo de Tolosa
- Pirates Cove Beach
- Jade Cove
- Spooner's Cove
- McWay Beach
- Arroyo Laguna Beach
- Morro Rock Beach
- Baywood Park Beach
- Bovino Vineyards
- Bianchi Winery