Book Holiday Homes in San Simeon

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Featured Holiday Homes in San Simeon

46W/Winery close, Bocce! Perfect for 1 couple, multi-adult, family! Dog Friendly

46W/Winery close, Bocce! Perfect for 1 couple, multi-adult, family! Dog Friendly

Templeton
Located in Paso Robles, this vacation home is in a rural location, within a 5-minute drive of Twin Cities Community Hospital and Castoro Cellars Winery.
46W/Winery close, Bocce! Perfect for 1 couple, multi-adult, family! Dog Friendly
Fully Renovated, Charming Craftsman Home in Downtown Paso Robles Wine Country

Fully Renovated, Charming Craftsman Home in Downtown Paso Robles Wine Country

Paso Robles
With a stay at this vacation home, you'll be centrally located in Paso Robles, within a 10-minute drive of Sensorio and Carnegie Library.
Fully Renovated, Charming Craftsman Home in Downtown Paso Robles Wine Country
Oceanfront Cayucos Cottage on the sand

Oceanfront Cayucos Cottage on the sand

Cayucos
When you a stay at this vacation home in Cayucos, you'll be on the beach, just steps from Morro Strand State Beach and Estero Bay.
Oceanfront Cayucos Cottage on the sand
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Colorful Artist's Bungalow Walk Downtown Paso

Colorful Artist's Bungalow Walk Downtown Paso

Paso Robles
With a stay at this vacation home, you'll be centrally located in Paso Robles, within a 10-minute drive of Sensorio and Anglim Winery.
Colorful Artist's Bungalow Walk Downtown Paso
Wine Country Retreat

Wine Country Retreat

Templeton
With a stay at this vacation home in Templeton, you'll be within a 15-minute drive of Sensorio and Twin Cities Community Hospital.
Wine Country Retreat
Gathering Place overlooking beach, pier, and downtown Cayucos

Gathering Place overlooking beach, pier, and downtown Cayucos

Cayucos
A stay at this vacation home places you in the heart of Cayucos, within a 5-minute walk of Cayucos State Beach and Cayucos Pier.
Gathering Place overlooking beach, pier, and downtown Cayucos
UNDER THE OAKS-Hot Tub & Walk Downtown

UNDER THE OAKS-Hot Tub & Walk Downtown

Paso Robles
The price is AU$601 per night from 8 Dec to 9 Dec
AU$601
includes taxes & fees
8 Dec - 9 Dec
With a stay at this vacation home, you'll be centrally located in Paso Robles, within a 10-minute drive of Sensorio and Anglim Winery.
UNDER THE OAKS-Hot Tub & Walk Downtown

Coach House Cottage in heart of wine region with vineyard views

Coach House Cottage in heart of wine region with vineyard views

Templeton
The price is AU$493 per night from 1 Dec to 2 Dec
AU$493
includes taxes & fees
1 Dec - 2 Dec
Located in Templeton, this vacation home is in a rural location, within a 15-minute walk of Hunt Cellars and Four Lanterns Winery.
Coach House Cottage in heart of wine region with vineyard views
MARVELOUS MIDCENTURY-Hot Tub & 5 Blocks to Town Center

MARVELOUS MIDCENTURY-Hot Tub & 5 Blocks to Town Center

Paso Robles
With a stay at this vacation home, you'll be centrally located in Paso Robles, within a 10-minute drive of Sensorio and Anglim Winery.
MARVELOUS MIDCENTURY-Hot Tub & 5 Blocks to Town Center
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

San Simeon Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our San Simeon vacation homes are the perfect way for you to wing it.

Holiday houses in San Simeon let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of San Simeon in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local San Simeon adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in San Simeon with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of San Simeon vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

San Simeon Holiday Homes essential information

Accommodation
541 Holiday Homes
Lowest Price
AU$103
Highest Price
AU$601
Popular accommodation
46W/Winery close, Bocce! Perfect for 1 couple, multi-adult, family! Dog Friendly, Fully Renovated, Charming Craftsman Home in Downtown Paso Robles Wine Country, Oceanfront Cayucos Cottage on the sand, Colorful Artist's Bungalow Walk Downtown Paso, Wine Country Retreat, Gathering Place overlooking beach, pier, and downtown Cayucos, UNDER THE OAKS-Hot Tub & Walk Downtown, Coach House Cottage in heart of wine region with vineyard views, MARVELOUS MIDCENTURY-Hot Tub & 5 Blocks to Town Center

Top trending hotels in San Simeon

Cavalier Oceanfront Resort

Cavalier Oceanfront Resort

3.5 out of 5
9415 Hearst Drive, San Simeon, CA
Fully refundableReserve now, pay when you stay
The price is AU$249 per night from 8 Dec to 9 Dec
AU$249
includes taxes & fees
8 Dec - 9 Dec
With a stay at Cavalier Oceanfront Resort in San Simeon, you'll be on the beach, just a 2-minute walk from Cambria State Marine Park and 8 minutes by foot from ...
Cavalier Oceanfront Resort
The Morgan Hotel San Simeon

The Morgan Hotel San Simeon

3.5 out of 5
9135 Hearst Drive, San Simeon, CA
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 1 Dec to 2 Dec
AU$154
includes taxes & fees
1 Dec - 2 Dec
Located in San Simeon, The Morgan Hotel San Simeon is by the ocean, just a 3-minute walk from San Simeon State Park and a 5-minute drive from Moonstone Beach ...
The Morgan Hotel San Simeon
Silver Surf Motel

Silver Surf Motel

2 out of 5
9390 Castillo Dr, San Simeon, CA
Fully refundableReserve now, pay when you stay
The price is AU$103 per night from 19 Dec to 20 Dec
AU$103
includes taxes & fees
19 Dec - 20 Dec
When you stay at Silver Surf Motel in San Simeon, you'll be near the beach, within a 10-minute walk of San Simeon State Park and Cambria State Marine Park.
Silver Surf Motel
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Ragged Point Inn and Resort

Ragged Point Inn and Resort

3 out of 5
19019 Highway 1, Ragged Point, San Simeon, CA
Fully refundableReserve now, pay when you stay
The price is AU$258 per night from 27 Nov to 28 Nov
AU$258
includes taxes & fees
27 Nov - 28 Nov
With a stay at Ragged Point Inn and Resort in San Simeon, you'll be 3.8 mi (6.1 km) from Salmon Creek Falls Trail and 15 mi (24.2 km) from San Simeon Pier.
Ragged Point Inn and Resort
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.