Vacation rentals with a pool in San Benito County

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Top-rated rentals with a pool in San Benito County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Home in Hollister
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The Vine Estate Spanish Hacienda Pool Hot Tub

Welcome to The Vine Estate, a Spanish-style retreat along scenic Lone Tree Road. This 4-bed, 3-bath home features a pool, spa, private steam room, chef’s kitchen, spacious living areas, and a brick courtyard with mature arbor—ideal for quiet mornings and peaceful evenings. Minutes from downtown Hollister and local wineries. Private 5-acre property with multiple dwellings. Guests may access the main house and designated areas only. No parties, events, or unregistered guests. Quiet hours enforced.

Top guest favorite
A tranquil nighttime scene featuring a well-lit pool and hot tub surrounded by lush landscaping. A tall palm tree stands prominently beside the pool, with ambient lighting illuminating the area. The moonlight casts a serene glow over the water, enhancing the inviting atmosphere.
Home in Hollister
4.98 out of 5 average rating, 44 reviews

California Tropical Refuge- Pool & Hot Tub

We invite you to R house designed for (Reunions, Recreation, Rest, Recovery, Refreshment and Rejuvenation) in a spacious stylish environment, together with your family and friends. Relax beside a beautiful pool and hot tub nestled among lush landscaping and tropical palm trees. A perfect home for a long vacation or weekend reuniting with extended family and friends at nearby wedding venues. Leal (.09 m) Visit Pinnacles National Park (25m) or the California Coast (35-37m) to Carmel or Santa Cruz

Top guest favorite
A gated entrance leads guests along a well-paved driveway lined with mature trees and lush vineyards. Rolling hills serve as a backdrop, complementing the serene landscape under a clear blue sky.
Guesthouse in Hollister
4.97 out of 5 average rating, 87 reviews

Luna Llena

Welcome to our spacious studio nestled on the second floor of a detached unit within this picturesque estate. With an enchanting backdrop of Diablo Range mountains, while the surrounding vineyard provides a delightful ambiance to relish. You can wake up to the occasional misty mornings that add a touch of mystery and charm. prepare to be captivated by the most gorgeous sunsets that paint the sky with hues of enchanting colors. Welcome to your oasis of tranquility and natural beauty!

Guest favorite
A serene pool area features clear water reflecting surrounding trees and décor. The space is illuminated by warm lights, highlighting the lush greenery along the perimeter. A peaceful atmosphere is created as the sun begins to set, suggesting a tranquil evening ahead.
Guest suite in Greenfield
4.89 out of 5 average rating, 98 reviews

Piney Creek Retreat

When you are ready to take a break from it all, escape to the mountains and relax in your 400 sq ft attached but private studio. Lounge by the pool during the day, and unwind in the hot tub with your favorite glass of wine from one of the many nearby wineries. When you are ready to mingle again, Carmel Valley Village is 45 min away, with Carmel by the Sea and Monterey being another 15 min. For the adventurous, Arroyo Seco campground is less than 10 min; and Pinnacles NP is 45 min.

Guest favorite
An inviting pool area is framed by a spacious deck and lush landscaping, complemented by a covered outdoor kitchen and seating area. Natural light highlights the vibrant red of the home's exterior against a backdrop of rolling hills and greenery.
Home in Carmel Valley
4.86 out of 5 average rating, 66 reviews

Serene Vineyard Chateau with Pool, Hot Tub, BBQ

Disconnect from city life in the heart of Carmel Valley wine country. The Vineyard Chateau sits on 5 creek-front acres with a working Merlot vineyard and countless amenities. Explore 25+ wine tasting rooms in Carmel Valley Village, a scenic hike in nearby Ventana Wilderness, or chill & grill by the seasonal saltwater pool (May-Oct). Add a personalized on-site wine experience, massage, or private chef for an even more unforgettable getaway. Perfect for a family or two couples.

A queen-size bed is arranged with various pillows in soft shades of gray and white. A decorative pillow with the word 'Cozy' is placed at the front, complemented by a plush green round pillow. Soft lighting is provided by mounted lamps above the bed.
Place to stay in Hollister
4.82 out of 5 average rating, 105 reviews

AirBnb Farm Charm

We are using other platforms at this time due to the participation of AirBNB's CEO in the current administration. Check back when the world is sane. Want to get away? This is the perfect getaway in the country. We have a unique space for you to enjoy all of those things in comfort. Our unit has a queen size bed that inclines for watching TV or reading. The bathroom is split, allowing for guests to shower while others are using the toilet and sink area.

A two-story house features a welcoming entryway with a decorative front door under a broad arch. Soft pink hues reflect on the exterior walls. A well-maintained lawn and flowerbeds with blooming plants are visible in the front yard, complemented by a garage with a white door.
Home in Salinas
4.71 out of 5 average rating, 7 reviews

Home near Pebble Beach, Carmel, Monterey

Bring the whole family to this great place with lots of room for fun. Enjoy our heated pool, ping pong table, and more!

Popular amenities for San Benito County rentals with a pool