Book Holiday Homes in San Luis Obispo Wine Country

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Featured Holiday Homes in San Luis Obispo Wine Country

Dog-friendly condo with amazing views & beach access - snowbirds welcome

Dog-friendly condo with amazing views & beach access - snowbirds welcome

Pismo Beach
Located in Pismo Beach (Downtown Pismo Beach), this vacation home is within a 5-minute walk of Pismo Beach Pier and Pismo State Beach.
Dog-friendly condo with amazing views & beach access - snowbirds welcome
BEACHFRONT with Spa

BEACHFRONT with Spa

Oceano,
With a stay at this vacation home in Oceano, you'll be on the beach, within a 10-minute drive of Pismo Beach Pier and Pismo State Beach.
BEACHFRONT with Spa
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
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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
Wine Country Retreat

Wine Country Retreat

Templeton
The price is AU$559 per night from 18 Nov to 19 Nov
AU$559
includes taxes & fees
18 Nov - 19 Nov
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
WALK to Beach, Pier and Downtown - Parking - BBQ - View

WALK to Beach, Pier and Downtown - Parking - BBQ - View

Pismo Beach
With a stay at this vacation home, you'll be centrally located in Pismo Beach, a 2-minute drive from Pismo Beach Pier and 15 minutes from California Polytechnic ...
WALK to Beach, Pier and Downtown - Parking - BBQ - View
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
2-Story Gem | Downtown Access | Private Backyard

2-Story Gem | Downtown Access | Private Backyard

San Luis Obispo
With a stay at this vacation home in San Luis Obispo, you'll be within a 15-minute drive of California Polytechnic State University, San Luis Obispo and Pismo ...
2-Story Gem | Downtown Access | Private Backyard
The Casita at Rancho Dos Hijas Estate

The Casita at Rancho Dos Hijas Estate

San Luis Obispo
With a stay at this vacation home in San Luis Obispo, you'll be within a 10-minute drive of Wolff Vineyards and Chamisal Vineyards.
The Casita at Rancho Dos Hijas Estate
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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 Luis Obispo Wine Country 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 Luis Obispo Wine Country vacation homes are the perfect way for you to wing it.

Holiday houses in San Luis Obispo Wine Country 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 Luis Obispo Wine Country 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 Luis Obispo Wine Country adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in San Luis Obispo Wine Country 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 Luis Obispo Wine Country 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 Luis Obispo Wine Country Holiday Homes essential information

Accommodation
604 Holiday Homes
Lowest Price
AU$184
Highest Price
AU$559
Popular accommodation
Dog-friendly condo with amazing views & beach access - snowbirds welcome, BEACHFRONT with Spa , 46W/Winery close, Bocce! Perfect for 1 couple, multi-adult, family! Dog Friendly, Oceanfront Cayucos Cottage on the sand, Wine Country Retreat, WALK to Beach, Pier and Downtown - Parking - BBQ - View, Gathering Place overlooking beach, pier, and downtown Cayucos, 2-Story Gem | Downtown Access | Private Backyard, The Casita at Rancho Dos Hijas Estate

Top trending hotels in San Luis Obispo Wine Country

Quality Suites Downtown San Luis Obispo

Quality Suites Downtown San Luis Obispo

3 out of 5
1631 Monterey St, San Luis Obispo, CA
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 1 Dec to 2 Dec
AU$198
includes taxes & fees
1 Dec - 2 Dec
With a stay at Quality Suites Downtown San Luis Obispo in San Luis Obispo, you'll be within a 15-minute walk of California Polytechnic State University, San ...
Quality Suites Downtown San Luis Obispo
Madonna Inn

Madonna Inn

3.5 out of 5
100 Madonna Road, San Luis Obispo, CA
Fully refundableReserve now, pay when you stay
The price is AU$236 per night from 19 Nov to 20 Nov
AU$236
includes taxes & fees
19 Nov - 20 Nov
With a stay at Madonna Inn in San Luis Obispo (Laguna), you'll be within a 15-minute drive of California Polytechnic State University, San Luis Obispo and Pismo ...
Madonna Inn
Spyglass Inn

Spyglass Inn

3 out of 5
2705 Spyglass Dr, Pismo Beach, CA
Fully refundableReserve now, pay when you stay
The price is AU$277 per night from 1 Dec to 2 Dec
AU$277
includes taxes & fees
1 Dec - 2 Dec
When you stay at Spyglass Inn in Pismo Beach, you'll be on the waterfront, within a 15-minute drive of Pismo Beach Pier and California Polytechnic State University, ...
Spyglass Inn
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La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown

La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown

3 out of 5
1845 Monterey St., San Luis Obispo, CA
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 1 Dec to 2 Dec
AU$184
includes taxes & fees
1 Dec - 2 Dec
With a stay at La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown, you'll be centrally located in San Luis Obispo, within a 5-minute drive of California ...
La Quinta Inn & Suites by Wyndham San Luis Obispo Downtown
Don't see what you're looking for?
See all available properties in San Luis Obispo Wine Country
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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.