Vacation rentals with a pool in Downtown San Jose

4.92 out of 5 average rating, 174 reviews

A serene outdoor space features a swimming pool surrounded by lush vegetation and a gently sloping waterfall. Steps lead from the house to the pool area, with a slide positioned nearby. A vineyard is visible in the background, enhancing the tranquil setting.

Home in Portola Valley

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.

4.94 out of 5 average rating, 350 reviews

A bright bedroom is equipped with a spacious bed and two bedside tables, each featuring a lamp. Colorful botanical wall art adds detail to the decor. A full-length mirror stands against the wall, with light filtering in through a window fitted with vertical blinds.

Condo in Santa Clara

La Casa de Alpaca

Welcome to La Casa de Alpaca. Our home is located in the beautiful Rivermark community of Santa Clara. The space consists of 2 bed / 2 bath located on the top floor, with access to a pool, hot tub, gym, and yoga room. Local Destinations: Santa Clara Convention Center Great America Theme Park Downtown San Jose Levi's Stadium SAP Center Oracle Rivermark shopping area: restaurants and groceries AMC Mercado 20 Plaza: restaurants and movies We are business traveler ready with high-speed Internet.

Guesthouse in Monte Sereno

The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.

4.98 out of 5 average rating, 461 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.

Apartment in East San Jose

A refreshing pool glistens under the sun, surrounded by well-manicured green lawns. A white picket fence encloses the area, enhancing the garden's appeal. The charming two-story structure features a sloped roof and multiple balconies, providing a welcoming atmosphere in a serene outdoor setting.

4.98 out of 5 average rating, 289 reviews

Apartment above Levi Stadium.

18 miles from Levi Stadium! Your Superbowl HQ Take tram to stadium and avoid traffic JAM and parking nightmare! This 2 bedroom apartment. With with spectacular view of Silicon Valley and Levi Stadium). There are two bedrooms, one bathroom and a combined full kitchen/living room. 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! The Rental fee includes the Santa Clara Short Term Rental Tax!

4.8 out of 5 average rating, 233 reviews

A spacious living area features a striking stone wall, complemented by a large flat-screen TV mounted above an elegant dark cabinet. Plush seating options, including a brown leather sofa and chairs, invite relaxation, while a decorative chandelier adds a refined touch to the room.

Home in Willow Glen

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!

4.94 out of 5 average rating, 441 reviews

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

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

4.94 out of 5 average rating, 154 reviews

The interior of the converted school bus features rustic wooden cabinetry and appliances. A spacious teak countertop extends over the cooking area, complemented by a red refrigerator. Sunlight illuminates the living area, showcasing a cozy seating arrangement and large windows with views of the surrounding nature.

Bus in East San Jose

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.

Guest suite in Willow Glen

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.

4.95 out of 5 average rating, 192 reviews

Private Queen Suite-Pool & Hot Tub, private entry

This is your Getaway and World Cup spot! Enjoy your private suite, bathroom and large smart TV with all the action. Located within 3 miles of downtown Los Gatos and Campbell great food options. Levi's Stadium 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center/NCAA/Sharks 4.6 miles. We have professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.

4.93 out of 5 average rating, 175 reviews

An aerial view captures the expansive outdoor area of the Anton Menlo Apartments. A resort-style pool is centrally located, surrounded by lounge chairs and shaded seating areas. Lush landscaping and modern architecture define the space, with additional amenities visible, including a community lounge.

Apartment in Menlo Park

Beautiful Spacious Living w/Resort Like Feel

Welcome to our lovely spacious studio apartment located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a fully furnished living area, queen comfortable bed, and a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals. Bedroom does not have a door, as this is a studio.

4.97 out of 5 average rating, 1,022 reviews

An outdoor area features a serene pool surrounded by blooming flowers and lush greenery. The distant horizon showcases a sparkling view of the city lights below, under a clear evening sky transitioning from dusk to night.

Guesthouse in Los Gatos

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!

Apartment in Downtown San Jose

A landscaped pool area features a clear blue pool surrounded by lounge chairs. Palm trees and greenery enhance the serene environment. Adjacent buildings are visible, providing a modern backdrop to the outdoor space.

5 out of 5 average rating, 24 reviews

Luxe Apartment Downtown San Jose w/ Gym, Pool

Experience San Jose in a modern luxe apartment with great vibes and amenities → Lightning Fast Wi-Fi → Comfortable Queen Bed → Dedicated Office Workspace → Fully Stocked Kitchen → 55" Smart TV → Washer+Dryer → Private Parking Amenities: → Clubhouse+Lounge → Dedicated Corporate Office Workplace → Rooftop Courtyard with BBQ → Pool+Hot Tub → Full-Size Gym Ideal for business travelers, travel nurses & corporate clients looking to experience San Jose in style.

Guesthouse in Willow Glen

A tranquil Watsu pool is surrounded by lush greenery and vibrant plants. A fabric shade cover is suspended overhead, providing protection from the sun. Natural stone flooring complements the pool's serene ambiance, creating a peaceful retreat atmosphere.

4.97 out of 5 average rating, 637 reviews

Cabana with Warm Watsu Pool

Our guests best describe it as: ‘Like luxury hotel meets Zen retreat meets Day Spa meets Bali rain forest meets mom and pop warm hospitality’. A private cabana close to shops and restaurants in downtown Willow Glen. You’ll love our place because of the tranquil setting, warm watsu pool, Finlandia sauna, hot plunge, and beautiful gardens. Our place is good for couples, solo adventurers, and business travelers.

Popular amenities for Downtown San Jose rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 118 reviews

A two-story home is surrounded by well-maintained grass and trees. The front features a welcoming porch with two green chairs, a brick chimney, and large windows showcasing the indoor space. A pathway leads to the entrance, framed by manicured landscaping.

Home in Palo Alto

Large Home in Palo Alto, 5 bedrooms, Pool

4.72 out of 5 average rating, 78 reviews

An outdoor area features a tranquil pool surrounded by lush landscaping and stone pathways. Two lounge chairs are positioned by the poolside, inviting relaxation. A spacious home with multiple levels stands in the background, showcasing large windows and a deck that overlooks the serene setting.

Home in East San Jose

Stunning Group Retreat w/Pool!

4.92 out of 5 average rating, 97 reviews

A spacious living area is designed with a large L-shaped sectional sofa adorned with colorful throw pillows. A dark coffee table is centrally placed on a vibrant area rug, while natural light filters through large windows, enhancing the overall brightness of the room.

Home in Santa Clara

Silicon Valley Executive home in Santa Clara

4.86 out of 5 average rating, 58 reviews

A single-story home features a beige exterior with a welcoming front yard. Lush greenery surrounds the entrance, including a variety of shrubs and plants. The driveway leads to a white garage door, while light clouds float overhead in a blue sky.

Home in San Jose

Perfect home with pool for family vacations!

4.85 out of 5 average rating, 48 reviews

A community pool area is surrounded by palm trees, creating a relaxed atmosphere. The pool features a light blue surface, with lounge chairs positioned along the deck. Nearby, a play area is visible, enhancing the communal space for residents.

Home in Santa Clara

Modern Retreat in the Heart of Silicon Valley

4.96 out of 5 average rating, 102 reviews

The solar-heated pool is illuminated at night, showcasing a serene blue hue. Three water features flow gracefully into the pool, highlighting the tranquil setting. The surrounding area is dimly lit, enhancing the peaceful ambiance of the outdoor space.

Home in Campbell

Luxury 4-Suite Carbon-Neutral Home With Pool

4.97 out of 5 average rating, 73 reviews

A serene backyard showcases a solar-heated pool surrounded by a spacious patio. Lush greenery and trees line the perimeter, creating a peaceful ambiance. Soft lighting illuminates the area, with a cozy seating arrangement visible in the background, enhancing the outdoor gathering space.

Home in Evergreen

Casa Feliz | Pool | Sauna | Family Fun

4.75 out of 5 average rating, 72 reviews

A spacious backyard features a shimmering pool surrounded by a sun deck. Lounge chairs and an umbrella provide shaded seating, while potted plants and a wooden planter add greenery. A colorful float rests in the water, contrasting with the clear blue sky overhead.

Home in San Jose

Starbird Oasis: Pet Friendly with Private Pool!

Condo rentals with a pool

A spacious living area features a plush navy sectional sofa adorned with yellow accent pillows. A glass coffee table is positioned in front of the sofa. A small decorative Christmas tree is set in the corner, alongside an acoustic guitar and a stylish lamp.

Condo in San Jose

Spacious 2BR/2BA w/ Patio + Hot Tub Access

Condo in Downtown San Jose

5 out of 5 average rating, 4 reviews

Modern 2‑bed, 2‑bath top‑floor apartment.

4.83 out of 5 average rating, 6 reviews

The exterior of the townhouse features a landscaped front yard with low-maintenance greenery, including shrubs and small trees. A concrete pathway leads to the blue front door, framed by an adjacent wooden fence. The two-story structure presents a modern design with a neutral color palette.

Condo in San Jose

Charming 1 bedroom, 1 bath, 2 Story Condo.

5 out of 5 average rating, 7 reviews

A decorative tray is placed on a glass table, featuring a floral arrangement in a vase, a small teacup, and a cream-colored container. Natural light filters through the partially opened blinds, creating a bright and inviting space.

Condo in Berryessa

San Jose Charming Home in the Heart of Bay Area

A cozy living room features a plush grey sofa and a modern coffee table, situated beneath an elegant ceiling design. A large flat-screen TV displays vibrant imagery against a stylish wall, complemented by decorative shelves with accent lighting and tasteful ornaments.

Condo in Willow Glen

4.83 out of 5 average rating, 24 reviews

Luxury Condo Minutes to Levi’s Stadium & World Cup

4.75 out of 5 average rating, 32 reviews

Condo in Mountain View

Modern 1B1B condo + quiet patio | Downtown Mt View

A welcoming living area features a light-colored sofa and a striped armchair, complemented by a glass coffee table. A round mirror hangs above the sofa, reflecting ambient lighting from a table lamp. A small workspace is visible with a desk and chair.

Condo in Palo Alto

4.83 out of 5 average rating, 12 reviews

Contemporary 2BR - Blocks from Stanford Campus

Condo in Menlo Park

4.75 out of 5 average rating, 4 reviews

Pool Access! Base to See Stanford & Int’l Soccer

Other vacation rentals with a pool

Guesthouse in Monte Sereno

A charming cottage is framed by lush greenery and a mature tree, providing shade to a cozy seating area with comfortable outdoor furniture. The inviting entrance of the cottage features large windows that enhance the connection to the surrounding nature.

4.96 out of 5 average rating, 79 reviews

Private cottage in orchard and vineyard setting

4.86 out of 5 average rating, 58 reviews

A sunroom features large windows that provide views of the garden and pool area. A round dining table is surrounded by four upholstered chairs. A ceiling fan hangs above, contributing to a bright and airy ambiance, while greenery is visible outside.

Apartment in San Jose

Relaxing 3‑Room with yard Pool • Near Santana Row

Guest suite in Willow Glen

4.97 out of 5 average rating, 32 reviews

Cozy Suite+Pool by Santana Row, Silicon Valley Gem

5 out of 5 average rating, 34 reviews

A bright living space features a modern sofa adorned with neutral-toned cushions, complemented by a round black coffee table. Large sliding doors provide access to a balcony and allow natural light to fill the room. A small potted plant adds a touch of greenery.

Apartment in Santa Clara

Chic-Roomy 2Br 2Ba/Pool • Near Levis, Apple, Nvdia

5 out of 5 average rating, 44 reviews

A spacious lawn area is bordered by natural stone features and shaded by trees. Sunlight casts long shadows across the grass, creating a calming ambiance. A wooden chair is positioned on gravel nearby, providing a relaxing spot for guests to enjoy the outdoor space.

Villa in Monte Sereno

Los Gatos Villa: hot tub, sauna, pool, huge yard

Guesthouse in Monte Sereno

A vibrant garden area is filled with various potted plants in colorful containers, featuring blooming flowers in shades of pink and white. A stone staircase leads to an inviting cottage entrance, surrounded by lush greenery and decorative items that enhance the serene environment.

4.99 out of 5 average rating, 75 reviews

D’s Garden Cottage

Guesthouse in Willow Glen

A cozy sleeping area features a wooden bed frame with a soft gray and yellow bedding set. A decorative throw blanket is draped over the foot of the bed. A bedside table holds a lamp, providing gentle lighting, beside sheer curtains that frame a nearby window.

4.87 out of 5 average rating, 15 reviews

The Willow Glen Get-A-Way with hot tub & pool