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San Luis Obispo County Holiday Rentals with Pools

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    Travellers to San Luis Obispo County are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    28 Matching Rentals in San Luis Obispo CountyView all 375 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Beautiful and Spacious Country Home 1 Mile from Downtown1 / 36
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Farmhouse Splendor With All the Amenities!1 / 25
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    High Ridge Manor1 / 19
    (1)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Satellite TV
    • Washer
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    • Grill
    • Hot Tub
    • Mountain Views
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The most beautiful B and B I have ever been to. We had the best time. We were on a girl's trip and were greeted with a tour and the most amazing spinach dip appetizer. Then warm...
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    About this property
    House, 7 Bedrooms, 6.5 Baths (Sleeps 16), Can be rented as whole house or split. A luxury retreat nestled in the charming country lanes of beautiful Paso Robles sits The High Ridge Manor & it's seemingly unending acres of rolling hills, breathtaking views & unbelievable vibrant sunsets. The...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Important Please Note Holiday Season: reservations that block both Xmas and New Years may not be accepted, unless they are 10 days or longer. These policies may be relaxed within 30-60 days of arrival. Please contact us with any questions. Please Note: Because of the age of this home, the stairs to...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
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    About this property
    Stunning 360 degree views greet you upon arrival at Peak at Paso. This secluded, hilltop hideaway, just minutes from wineries and downtown Paso Robles, is the perfect destination for your family gathering, or wine-tasting adventure. From the first glimpse, the patio living and pool, with incredible...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    High atop the hills of Paso Robles, in the Estrella AVA District of the Central Coast wine region, lays The Gables at the Rockin’ K. The Rockin’ K welcomes you in with such luxurious attention to detail you may never want to leave! The flow-through floor plan creates space for entertaining both...
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    San Miguel, San Luis Obispo County 93451
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • DVD Player
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With ocean views in prestigious Park Hill, this 3BR/2.5BA Cambria house (sleeps 6) is just 2 blocks from the beach. Inside, find a game room, a dog- and kid-friendly yard (Yes, your furry friend is welcome!) This beach house is located between world-famous Moonstone Beach & Fiscalini Ranch...
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    Cambria, San Luis Obispo County 93428
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Children's Pool
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    You can vacation in Avila Beach at San Luis Bay Inn! 7 Nights/Sleeps 4-6(specify) Available: August 25-September 1, 2016 (amazing weather) AND June 16-23, 2017 Check-In: 4:30 PM Check-Out: 10:00 AM Spacious One Bedroom/1 Bath - A/C, King Bed, A couch and chair with pull out beds, Full Kitchen...
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    Avila Beach, San Luis Obispo County 93424
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Blacklake Golf Condos - Many Happy Returnees!1 / 11
    (39)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Blacklake Golf Resort vacation rental condo is located overlooking the ninth fairway of the Lakes course. There is a nice patio with afternoon sun for watching the golfers go by but the condo is set above the course for privacy. Please see the reviews by our previous guests below detailing...
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    Nipomo, San Luis Obispo County CA
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Hidden Hills Olives and Oaks is located amid glorious rolling hills and majestic oaks in the countryside of the California Central Coast. Enjoy staying in a home away from home, just moments away from wine tasting and everything the area has to offer. Relax on the porches with morning coffee,...
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    Templeton, San Luis Obispo County 93465
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    6 Bedrooms, 3 Bathrooms, Sleeps 22 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Wi-Fi
    • Balcony
    • DVD Player
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    • Satellite TV
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    Pet friendly
    Kid friendly
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    About this property
    6 Bedroom Home Sleeps 16+, OCTOBER SPECIAL!! Call for Details--Walk to AWARD WINNING WINERIES • Great for Weddings - Workshops, Non-profit & Corporate Retreats, Family Reunions • Country House: 6 bedrooms, sleeps 16+, large kitchen with 2 refrigerators, and large dining area • Great Room (500 sq...
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    Templeton, San Luis Obispo County 93465
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 22
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    Central California Avila Beach - 2 Bedroom Lockoff Unit July 20171 / 6
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Sauna
    • Ocean Views
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We had a wonderful 5-night stay in our 2-bedroom ocean view unit! The unit was perfect - it was quiet, large, clean, with a well-equipped full kitchen and balcony with an...
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    About this property
    The perfect 'base camp' for your Central California Coast vacation expedition! Stay at the OCEAN VIEW San Luis Bay Inn in beautiful Avila Beach, California. <BR><BR>Located 15 minutes south of San Luis Obispo; 1 hour south of Hearst Castle, and 20 minutes from the Edna Valley Wine Country....
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    Avila Beach, San Luis Obispo County 93424
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Hot Tub
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this your hidden, quiet gem nestled at the start of Peachy Canyon Rd in downtown Paso Robles. Gateway to wineries such as Stacked Stone, Calcareous and all the Far Out west side Wineries. Explore all day and return to this large Spanish-tiled California hacienda home complete with a...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests rave about this 3BR/2.5BA condo located right on hole 9 of the Lakes Course in the Blacklake Golf Resort. If perfecting your swing isn’t your thing, cool down in the community pool or take a 10-minute drive to Oceano Beach. Santa Barbara wine country is only 35 minutes away. When you’re...
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    Nipomo, San Luis Obispo County 93444
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Washer
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    • Private Outdoor Pool (Unheated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The villa in Denia has 4 bedrooms and has capacity for 6 people. The villa is comfortable, is ample, and has 150 m². It has views to the sea and to the mountain. The house is situated in a quiet neighborhood in a mountainous zone. The accommodation is equipped with the following things: garden,...
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    Creston, San Luis Obispo County 93432
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly listed stunning property is located on 8-acres on a private lot in the esteemed West Ridge private community. Upon entrance on to the property you will park your vehicles under the carport to the right of the garage. Walk through the gardens where you will see your guest house on the...
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    Location Information
    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This oceanfront resort is a 2-minute walk from the Avila Beach trolley, 0.3 miles from the Central Coast Aquarium and 11 miles from Mission San Luis Obispo de Tolosa. The airy, polished studio suites have balconies with sea views, free Wi-Fi and flat-screen TVs with premium channels, plus...
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    Avila Beach, San Luis Obispo County 93424
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet neighborhood street across from almond orchards and just minutes from downtown Paso Robles, this vacation rental is a great house for couples, or families planning to share swim fun, good meals, and spacious living. The private yard houses both pool and hot tub for relaxing fun in the...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
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    • Private Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ours is a very cute 1 bedroom cottage apartment on a wooded property adjacent to an attractive main house. The apartment is completely furnished, with a private, secure entrance, private bath (shower), king bed, queen futon in the living area, Wi-Fi, Direc tv and Netflix (we now have a flat...
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    Cambria, San Luis Obispo County 93428
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Unheated)
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Candlewood Creek, a charming home nestled at the end of a quiet cul-de-sac just two miles from old town Paso Robles. It’s close to shopping, 46 West wineries and the route to the coast, as well as the Paso Robles Golf Club. After a lovely time of vineyard tours, wine tasting, olive oil...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cottontail Creek Ranch/8bd/6baths/Pool/ Cayucos/P1 / 25
    (26)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Satellite TV
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    • DVD Player
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    • Mountain Views
    • Washer
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
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    Reviewed 31 May 2016
    I just spent a long weekend at Cottontail Creek Ranch with my large family to celebrate my birthday and what an incredible experience at Cottontail Creek Ranch. There are so...
    Reviewed 3 September 2014
    It is hard to express what a wonderful place Cottontail Creek Ranch is. The kitchen was roomy enough for multiple cooks and was well stocked. Upon arrival the dining table was...
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    About this property
    The coastal lodge of Cottontail Creek Ranch is a Destination in itself. The luxury 5000 sq. ft home has 5 ensuite bedrooms with king and queen beds with private baths and 3 additional sleeping areas. Included on the ranch is a 20 yd Lap pool with spa and kids step and a tennis court. The...
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    Cayucos, San Luis Obispo County 93430
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing Paso Robles 4-bedroom, 4-bath estate retreat, on a large 2.5 acre lot, is the ideal destination to get away from the crowds and enjoy peaceful tranquility. Take advantage of bike route maps for rides from 7 to 40 miles, prepared by your host with knowledge of the local area. Lounge by...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step right off of Blacklake Golf Course and into your 3BR/2.5BA condo in peaceful Nipomo. Sleeps 6. Located on the 9th hole, it’s only a 10-minute drive to the beach and the Central Coast. Need more space? Unit #1407 is right next door and great add-on for larger groups. Link to area attractions:...
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    Nipomo, San Luis Obispo County 93444
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Hot Tub
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At the gateway to the California Central Coast is this beautiful serene retreat. Sorry No Pets and No Smoking allowed anywhere on the premises. However, any time of the year you can enjoy cycling, hiking, golfing, sport fishing nearby and of course micro brew tasting and wineries. You can visit...
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    Atascadero, San Luis Obispo County 93422
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Satellite TV
    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Siena Suite is one of three Suites at our B&B "Villa San Giovanni". The others are the "Corigliano" and "Borolo" Suites. Each of the suites are reserved separately at $275/night/suite. It is tastefully furnished and styled after accommodations you might find were you in Italy itself. The room...
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    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3BR, 3BA Nipomo Condo with Golf Course Views, Close to Wine Country1 / 25
    (1)Terrible
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get the best of both worlds at this 3BR, 3BA (sleeps 6) Nipomo Condo located on the 9th hole of the Blacklake Golf Course. The quiet community with a swimming pool offers quiet and privacy nearby Santa Barbara wine country and several beaches. Link: https://youtu.be/2yojYO6CEKw Inside the Rental...
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    Location Information
    Nipomo, San Luis Obispo County 93444
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Corigliano Suite is one of 3 suites at our B&B "Villa San Giovanni". The other suites are the "Siena" and "Borolo" suites Each of the suites are reserved separately at $275/night/suite.The room is spacious with a sitting and working area, television, King bed and private bath and offers...
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    Location Information
    Paso Robles, San Luis Obispo County 93446
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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