Vacation rentals with a pool in San Benito County

Find and book unique homes with a pool on Airbnb

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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Guest favorite

Home in Hollister

5 out of 5 average rating, 24 reviews

California Tropical Refuge

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

Home in Carmel Valley

New place to stay

Tuscan Retreat

You will feel like you are immersed in the Italian countryside when visiting this stunning vineyard home overlooking hills of grapevines with views of the surrounding countryside. Take a dip in the pool, relax in the jacuzzi, unwind while playing bocce ball, horseshoes or taking long walks. A wrap around porch runs along three sides of the house providing shade on hot days and five sets of French doors invite the outside in. This home provides the perfect get away for friends and family.

Top guest favorite

Guesthouse in Hollister

4.96 out of 5 average rating, 67 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

Guest suite in Greenfield

4.93 out of 5 average rating, 75 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

Home in Carmel Valley

4.85 out of 5 average rating, 55 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.

Camper/RV in Aromas

New place to stay

Vintage Airstream + Sauna Glamping Retreat

Welcome to Saunastream. With a vintage 1965 Airstream Safari, Finnish sauna, sunset views, and a pool, this glamping escape is anything but ordinary. The restored Airstream includes a queen bed, a sitting area, and a fridge. Pour water over hot stones in the cedar-lined sauna and sit in silence as the heat rises. The pool and fire pit lounging area offers views towards Monterey Bay. Relaxing, quiet hilltop location, 30 minutes from Monterey and Santa Cruz.

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.

Tiny home in Firebaugh

5 out of 5 average rating, 4 reviews

Tiny House with an outdoor Hot Tub - Very private!

Mercey hot springs is an off grid natural hot springs oasis located in the Diablo range of Central California, 13 miles west of I-5. With 20 individual outdoor tubs, stunning natural surroundings, Mercey is a magical place for you to unwind, relax, heal and enjoy nature. You can hike and mountain bike in our quiet 144 acre property or just chill, observe the wildlife and birds that call Mercey home. Experience Tranquility at its best!

Top guest favorite

Farm stay in Paicines

4.96 out of 5 average rating, 55 reviews

Ranch Luxury near Pinnacles with Private Pool

Set on a private hilltop overlooking our ranch, surrounding mountains and valleys, the Bar SZ Ranch House boasts 4,500 square feet of living space plus a detached apartment/bridal suite and private pool and pool house. With a wrap-around porch, 6 bedrooms, lush yard, indoor and outdoor fireplaces, and much more, the Ranch House is the perfect, peaceful escape from city life.

Superhost

Home in Salinas

4.88 out of 5 average rating, 8 reviews

Salinas Valley Ranch II

Welcome to “Little Ranch” in Salinas, California. Move off the beaten path and nourish your soul at this little home on a 20-acre stretch of healthy farmland. “Little Ranch” is a place for those who prefer to live an uncomplicated life. It is a 600-square foot dwelling offering one (1) bedroom, one (1) bathroom, a laundry room, and a private patio.