Vacation rentals with a pool in Evergreen, San Jose

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Top-rated rentals with a pool in Evergreen, San Jose

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

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Top guest favorite

A serene swimming pool reflects the clear blue sky, surrounded by lush landscaping. Natural stone steps lead to the house, flanked by vibrant foliage and small waterfalls, creating a tranquil retreat.

Home in Portola Valley

4.93 out of 5 average rating, 157 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

Top guest favorite

A spacious living area is equipped with a flat-screen TV mounted on the wall and an ornate cabinet. A comfortable grey chair and a glass coffee table are positioned on a soft carpet. Natural light is welcomed through a nearby window, enhancing the cozy atmosphere.

Home in Mountain View

4.9 out of 5 average rating, 162 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!

Guest favorite

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

4.93 out of 5 average rating, 369 reviews

Your Silicon Valley Luxury I Sauna, Hot Tub, Pool

Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Top guest favorite

A spacious outdoor area features a glimmering pool set against lush greenery. A patio with comfortable seating and a covered area is visible in the background, providing a place for relaxation. Trees and shrubs frame the scene, adding to the tranquil atmosphere.

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 428 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.

Guest favorite

A large in-ground pool is set in a landscaped garden, surrounded by a mix of greenery and fencing for safety. The smooth pool surface reflects the blue sky, while a covered area with red seating is visible in the background.

Home in Willow Glen

4.8 out of 5 average rating, 211 reviews

Beautiful Large 4BR Home with POOL

Need a vacation or a great place to stay in the Bay area in San Jose? Look no further as you'll love this "Resort" style, very spacious 4 BR home with large in-ground pool- beautifully remodeled and furnished with plush furniture, art deco, comfy beds, upgraded modern amenities and beautiful landscaped garden. Family and business friendly. Conveniently located minutes to downtown San Jose, Trains, Malls, SAP & Levi's Stadium, SCU, SJSU and SJC. Highways 87-280-101. Book your escape today!

Top guest favorite

The image features a clear pool surrounded by a stone edge, with vibrant orange and purple flowers in bloom along the perimeter. Lush green palm trees and other landscaping elements provide a natural backdrop, creating a serene outdoor setting.

Guest suite in Cambrian

4.96 out of 5 average rating, 158 reviews

Private Queen Suite-Pool & Hot Tub, private entry

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, Campbell and Willow Glen. Great for Mountain Winery Concerts, 49ers/Levi's Stadium and SJC. 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. Hot tub and Pool are a perfect way to relax and end the evening.

Guest favorite

A well-maintained garden pathway leads to a pool area surrounded by lush greenery. Tropical plants and vibrant flowers add color to the landscape, while a variety of trees provide shade. The tranquil setting invites relaxation with the pool visible in the background.

Guest suite in Woodside

4.89 out of 5 average rating, 452 reviews

Separate entry room near Stanford

This separate entry room opens to a beautiful one-acre garden with a pool, jacuzzi, cable TV/wireless, and parking. We are just off 280 and Woodside Rd., 4 miles from Stanford. It is peaceful and quiet and we are hands-off hosts. There is no access to the house and the room does not have a frig, microwave or dishes. We are set up for independent guests who want to come and go on their own and enjoy local restaurants in Woodside, Palo Alto or RWC. Please note the very short entry door.

Superhost

A scenic pool area is framed by tall pine trees, with a vibrant sunset reflecting in the calm water. The landscape features gentle hills in the background, enhancing the serene environment.

Home in Ben Lomond

4.96 out of 5 average rating, 113 reviews

The Hacienda- Santa Cruz Mountain Ridgetop Retreat

"Welcome to the Hacienda", a modest mid-century retreat located in the beautiful Santa Cruz Mountains. The Hacienda is located just 5 minutes from Ben Lomond town, 10 minutes from Henry Cowell State Park and only a 20 minute drive from Santa Cruz beaches. Our unique private home includes a pool & hot tub which sits on the ridgetop overlooking the gorgeous San Lorenzo Valley. If you're looking for peace & tranquility or simply need to relax and recharge, the Hacienda awaits your arrival.

Guest favorite

The outdoor swimming pool is surrounded by a fenced area, featuring a textured patio and lounge space. Sunlight reflects off the clear water, with rolling hills providing a scenic backdrop in the distance. Lush greenery lines the pool area, enhancing the tranquil environment.

Bus in San Jose

4.96 out of 5 average rating, 135 reviews

Cozy BUS on Farm Animal Rescue with CITY VIEW

Stay on a farm animal rescue in a 38’ yellow school bus conversion. If you are interested we also host an Airbnb Experience called Life With Farm Animals At Rancho Roben Rescues where you get a 90-120 minute up close encounter with all of the animals - taking time to learn about each of the unique creatures that lives here and the opportunity to interact with them directly. Pet a chicken, groom a pony, feed a goat, take a walk patrolling the fields with our livestock guardian dogs.

Superhost

A serene private pool is surrounded by a spacious patio area, featuring a gazebo and a shaded seating space with lounge chairs. Lush greenery surrounds the property, creating a calm atmosphere, while the water shimmers under soft lighting, inviting relaxation.

Guest suite in San Jose

4.86 out of 5 average rating, 733 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

Our home is on 1/2 acre hilltop lot, in a secluded, very quiet 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 private pool when weather permitted.

Superhost

A serene pool area is surrounded by lush greenery and colorful potted plants. Loungers are arranged along the poolside, and warm sunlight reflects off the water's surface. String lights are visible above, adding a cozy touch to the outdoor space.

Home in San Jose

4.81 out of 5 average rating, 326 reviews

Bay Area getaway w/ Pool + Heated Spa + EV charger

Spacious Victorian with POOL and EV Charger. 1/2 mile from downtown San Jose and close to airport. 4 bed/ 3 bath home with incredible backyard, equipped with 1/4 basketball court and gas firepit. Whole Foods, Coffee Shops and Breweries in walking distance! We have a movie style projector with Apple TV, Netflix and more! Full laundry room with washer and dryer. Our house is pet friendly, supplied with dog leash, pet bowls and several parks in walking distance.

Top guest favorite

The outdoor pool is framed by a spacious deck, featuring a stone cabana with large glass doors. Surrounding greenery adds a natural touch, while clear blue skies create a serene atmosphere. Sun loungers are positioned nearby, inviting relaxation by the refreshing water.

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 978 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!