Pinnacles National Park which includes wild flowers

San Benito County rentals with pool

We found 6 rentals with pool — enter your dates for availability

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November 2025

December 2025

Explore San Benito County rentals with pools

Showing deals for: 14 Feb - 17 Feb

Premier Host

Stunning wine country estate with pool, vineyard, expansive vistas & more

Sleeps 20 · 8 bedrooms · 6 bathrooms

for 3 nights, 1 home

AU$3,102 per night

includes taxes & fees

Premier Host

Fantastic Vacation Retreat, Family Reunions , and Private Pool!

Sleeps 20 · 6 bedrooms · 6 bathrooms

for 3 nights, 1 home

AU$2,459 per night

includes taxes & fees

Relax on the veranda with evening lights, vineyard views and unmatched comfort

Premier Host

Welcome to the Grand Fitz Place Wine Country 6BR Retreat • Pool, Hot Tub & Views

Sleeps 15 · 6 bedrooms · 5 bathrooms

for 3 nights, 1 home

AU$1,966 per night

includes taxes & fees

Premier Host

Private Villa W/ Pool/spa, GameBarn, 4300 sq ft- Perfect for families and large groups

Sleeps 45 · 9 bedrooms · 4 bathrooms

for 3 nights, 1 villa

AU$5,135 per night

includes taxes & fees

60ft grapevine pergola with 2 14 ft wine barrel tables offering plenty of shade

Tuscan villa nestled in the vineyard - Villa Riposo

Sleeps 10 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 villa

AU$3,609 per night

includes taxes & fees

Premier Host

A quiet, relaxing, country getaway with a creek, pool and private hot tub.

Sleeps 4 · 1 bathroom

for 3 nights, 1 apartment

AU$451 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Explore San Benito County rentals with pools

Stunning wine country estate with pool, vineyard, expansive vistas & more

Fantastic Vacation Retreat, Family Reunions , and Private Pool!

Welcome to the Grand Fitz Place Wine Country 6BR Retreat • Pool, Hot Tub & Views

Private Villa W/ Pool/spa, GameBarn, 4300 sq ft- Perfect for families and large groups

Tuscan villa nestled in the vineyard - Villa Riposo

A quiet, relaxing, country getaway with a creek, pool and private hot tub.

Find spaces that suit your style

Rentals with Pool in San Benito County

Holiday Rental options in San Benito County