Holiday rentals with a pool in San Luis Obispo

Poolside Paradise+Views+Wineries+Spa+Game Room

Ultra-modern luxury retreat situated on a secluded oak studded acre in upscale west-side Templeton. This freshly remodeled high-end residence features an open concept floor plan designed for effortless entertaining. Unique artwork & ornate vintage pottery add to the chic design of the home. Enjoy the secluded surroundings, including a substantial swimming pool, hot tub, game room, BBQ, outdoor dining area & firepit conversation set all overlooking the rolling hills. A true 5-star experience!

Value · Family · Hot tub

Private Villa with Pool, Views & Close to Town

Welcome to “Hacienda Damas y Vaqueros” (Ladies and Cowboys) we are excited to show you the best of what Paso Robles has to offer (shhh…the secret is getting out….). Our Spanish “hacienda” style home sleeps 12 comfortably all on one level, perfect for your multi-family getaway, girls or boys weekend, or simply escaping to wine country with a few friends. Highlights: 5 Bedrooms; sleeps 12 4 bathrooms Pool and Spa Chef's kitchen Private studio Big Outdoor Space Peace & quite with views!

Location · Value · Condition

Last Wknd Sum. 20%Off • Pool•Kitch. Slps 6•4 Beds

Where Comfort Meets Care With 850+ reviews (4.78 stars) and 12 years as a Superhost, our focus is on creating a stay that feels truly cared for. Guests arrive to wine, cheese, fresh pastries, and a fridge stocked with breakfast favorites. Daily pool upkeep, and thoughtful touches throughout make it easy to relax—and hard to leave. With private entrance to the warm seasonal pool and relaxing patio, you’ll love the spacious bathroom with full amenities. Sleeps 5+ with 3 queen beds & futon.

Location · Value · TV

Spacious SLO CAL Home w/ Pool, Spa. Pet Friendly!

Relax and recharge at this pet-friendly retreat in Arroyo Grande, perfect for families, couples, and special occasions! Enjoy your own heated pool (seasonally heated Apr-Oct), year-round heated spa, and spacious yard in a peaceful neighborhood. Just minutes from iconic spots like Pismo Beach, Avila Beach, and Cal Poly, it’s ideal for exploring wineries, hiking, and the stunning Central Coast. Whether you’re celebrating or relaxing, this home offers everything for an unforgettable stay.

Location · Family · Parking

Campover Ranch in Paso Robles - Saltwater Pool

Welcome to Campover Ranch. A 10 acre wine country retreat in Paso Robles, California that comfortably fits 6 adults + 4 kids. Thoughtfully designed with all the comforts for a relaxing and easy stay. Swim in the custom pool, relax in the well designed home, play in the treehouse, cook s'mores over the outdoor fire pit or follow the country road to some of the best wine tasting in the area. *Each bedroom has a queen bed + sleeping nook ideal for kids. Read room descriptions for details.

Family · Value · Cleanliness

Lux Château, Hot Tub, OutdoorMovies, Game Rm, Pool

Chateau Vigne, a French country-inspired retreat perfect for families & friends—Soak in the hot tub under the stars, watch an outdoor movie + relax at the fire pit under a vine covered gazebo ⚜ On 1.35 acres tucked in majestic oaks, just 3 min. off Hwy 101. ⚜ Sleeps 10 (12 w/ kids) w/ spacious, stylish interiors & abundant amenities. ⚜ Hot tub, plunge pool, fire pit, Outdoor movies & game room. ⚜ Gorgeous grounds & plenty of room to gather, relax, play. ⚜ No guest fees, book your esc

Value · Family · Beach

Luxury Mountain View Retreat Pool/jacuzzi

Private Luxury Retreat with Panoramic Mountain Views. Centrally located just 15 minutes from Cal Poly or downtown San Luis Obispo 15 minutes from Paso Robles Wine Country, less than 5 minutes to the quaint little town of Santa Margarita. Location is centrally to all the area has to offer including beaches. Pool can be heated to 82 degrees for a fee, please inquire for pricing which varies per season. Please read guest access description for important info about the property.

Location · Family · Amenities

Gorgeous Hilltop Oasis with Pool and Expansive Views

Feel cares slip away in the serene saltwater pool set among ancient oaks and endless vistas. Enjoy one of Atascadero's most beautiful neighborhoods, sitting atop the Hills of the Central Coast. Morning strolls are a literal walk in the clouds with stunning canyon views and deer roaming nearby. It's hard to believe this property is only 8 minutes from the freeway. This comfortable tri-level four bedroom home is perfectly practical for family or group entertaining.

Location · Family · Cleanliness

Pool+Hot Tub+Outdoor Living

Message me now to see how you can earn extra discounts! Perched atop a secluded hill in Wine Country, your soon-to-be vacation home offers a stunning retreat just a stone's throw away from the vibrant downtown square. You will LOVE the tranquil nights with the covered patio complete with a BBQ grill and a cozy fire pit. Indulge in a friendly game of cornhole or giant jenga. Unwind from the day by swimming or with a soothing soak in the hot tub.

Value · Family · Pool

Atascadero Guesthouse Central Coast Wine Country

This light and airy hideaway was designed and built by the host incorporating her own handiwork in art and furnishings. Initially a granny flat, it's been transformed into a comfortable and spacious hang out. Its central location makes it ideal to explore the area. The twin beds can be easily configured to a king bed. Price includes a 13% local tax. We are on gated 3 acres. The pool sits between the guest house and our house.

Family · Location · Hospitality

Estate Vineyard Views, Pool, Hot Tub, & Tennis

Stunning house on 35 acre hilltop estate with 4 bedrooms, master King, two guest Queens, 2 single trundle beds for two adults or 4 kids. Full kitchen, two full sized refrigerators, freezers, Viking range, dishwasher, BBQ, oven, high speed internet, smart TVs. Pool with hottub, pergola views, pool table, games, tennis court, horseshoes, firepit, hiking, incredible sunset views. Linens, towels, basic kitchen supplies provided.

Location · Family · Heating

Private Vineyard Resort: slide, waterfalls, cabana

Unwind in style at this stunning 4-bedroom villa with a 5-star resort-like pool, complete with a slide, waterfalls, outdoor kitchen and poolside bar. Enjoy endless fun playing ping pong, shuffleboard, and billiards; or gather around the fire pit with a local wine for an unforgettable evening. Just down the road from Paso Robles’ top wineries in the prestigious Adelaida District.

Value · Location · Layout