Vacation rentals with a pool in San Jose

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Jose

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

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Superhost

Guest suite in San Jose

4.88 out of 5 average rating, 644 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

Our home is on 1/2 acre hilltop lot, in a secluded, very quite cul-de-sac, with easy access to major freeways, minutes from SJC airport, downtown, SAP, SJSU, convention center. This listing is for an entire separate unit, attached to main house. It features 2 rooms with private yard and pool to yourself. You are free to relax in the back yard with view, surrounded by mature trees, hummingbirds, butterflies while surf the net, or swim in our solar thermal heated pool when weather permitted.

Jul 18 – 25

G$26,534 GYD per night

Guest favorite

Guest suite in Scotts Valley

4.96 out of 5 average rating, 629 reviews

Snug and Cozy between the Skyline and the Sea

Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

Sep 18 – 25

G$15,832 GYD per night

Superhost

Tiny home in Aptos

4.78 out of 5 average rating, 315 reviews

Bamboo Cottage in Aptos Mountain Retreat & Spa

Om Oasis is a beautiful and lush retreat center on several acres of a remote and peaceful 15 acre mountain top property. We host guests who wish to connect with the beauty of nature and experience peace. We are 10-15 minutes up the mountain and partially off-grid with little to no cell reception but with a great WiFi connection. There are a total of 7 guest accommodations (including this one) spread out over our developed 3 acres, making it always a very private experience and easy to distance.

Jun 3 – 10

G$25,341 GYD per night

Guest favorite

Home in San Jose

4.92 out of 5 average rating, 154 reviews

Splash Pad

4 BD/3.5 baths 2900 SQFT. 4 blocks from Downtown Willow Glen and Starbucks on*The Avenue* UPSTAIRS: Master*en suite*King bed and a Graco-Tot-Yard. Two Guest Bedrooms*2 queen beds. DOWNSTAIRS: Fourth Guest Bedroom*Triple Twin Adult Size Bunks*Gourmet Kitchen*LivingRoom*Formal DiningRoom*FamilyRoom*Pool Table*WIFI* SmarTVs* Detached Garage*Man Cave*Cabana*Private Toilet*Sink*ChangingRoom*Pool* Spa*Outdoor Gas Firepit*Outdoor Gas Fireplace*Entire home is for guests’ use. It is a Single Family Home.

Jan 19 – 26

G$227,471 GYD per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Jul 9 – 16

G$70,114 GYD per night

Guest favorite

Home in Mountain View

4.88 out of 5 average rating, 112 reviews

Little Poolside House near Downtown Mountain View!

Absolutely the best location in Mountain View, steps from Downtown! Situated near all the entertainment, nightlife & attractions this vibrant city has to offer. This beautifully furnished little poolside house is just minutes from the Caltrain & light rail, Shoreline Lake, Stanford, Menlo Park, NASA Ames Center & more! Step outside for a stroll and explore local and international cuisine, wonderful farmers market and shopping! Perfect for family or friends, you will love this Bay Area getaway!

Jun 30 – Jul 7

G$37,842 GYD per night

Guest favorite

Guest suite in San Jose

4.94 out of 5 average rating, 108 reviews

Private Queen Suite-Private Entry, Pool & Hot Tub

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Campbell and Willow Glen. We follow all cleaning guidelines to protect the health of all guests. We have a professional cleaning crew, so just relax and enjoy. Check-out like a hotel, no starting laundry!You will enjoy a well designed private room with queen bed, private entrance and connected private bathroom in our serene and safe neighborhood. Very high speed internet is included.

Oct 11 – 18

G$30,590 GYD per night

Superhost

Guest suite in Los Altos Hills

4.8 out of 5 average rating, 148 reviews

A private hillside suite nestled among oaks

Better than the Four Seasons or the Rosewood! Beautiful, compact, private in-law suite in the walk out basement of our modern home. Enter via outdoor stairs from parking area to suite. Serene bay views and lush greenery below grand oaks. Your suite has a very comfortable King bed, Japanese washlet, closet space, TV, wi-fi, private washer/dryer, fully equipped kitchen with gas stove, microwave, fridge/freezer & dishwasher. Ceiling fan, radiant in-floor cooling/heating. Private parking. 280 SF.

Jul 13 – 20

G$31,646 GYD per night

Guest favorite

Guesthouse in Monte Sereno

4.97 out of 5 average rating, 387 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Sep 22 – 29

G$31,759 GYD per night

Guest favorite

Apartment in San Jose

4.98 out of 5 average rating, 223 reviews

Apartment above the valley.

This 2 bedroom apartment. It has outside stairs that lead up to a large private deck (with with spectacular view of Silicon Valley). The entrance is via sliding door from the deck. There are two bedrooms, one bathroom and a combined full kitchen/living room. The ground level pool and patio are shared space with owners. Living room has couch, TV, and Roku streaming. Apartment has good WiFi. Sit on the private deck and you may see wild turkeys, deer, and even a cow!

Nov 22 – 29

G$38,697 GYD per night

Guest favorite

Bungalow in San Martin

4.99 out of 5 average rating, 105 reviews

Moose Mountain Vineyards Bungalow

Relax in an elegant 2 bed bungalow sitting atop Moose Mountain Vineyards. Enjoy the panoramic view of San Martin as well as the 13,000 grape vines growing on property. Relax in the hot tub or infinity pool, or sip estate wine on one of our four decks as the sunset takes your breath away. Enjoy a complimentary whole food plant-based breakfast with ingredients sourced onsite. This stay offers many opportunities to explore the inner workings of Moose Mountain Vineyards.

Nov 15 – 22

G$91,624 GYD per night

Guest favorite

Guesthouse in Los Gatos

4.97 out of 5 average rating, 860 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Jul 16 – 23

G$46,762 GYD per night