Holiday rentals with a pool in Cupertino

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.

Apartment in Rivermark of Santa Clara

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.

4.94 out of 5 average rating, 344 reviews

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.

Guest house in Almaden Valley

The spacious interior features rustic wooden walls and exposed beams. A cozy bed with plush bedding is highlighted by warm lighting. A comfortable seating area is nearby, along with a large round mirror and a modern flat-screen TV on the wall.

4.99 out of 5 average rating, 598 reviews

Sanctuary in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, steampunk original art, state-of-the-art technology with a unique spa experience, providing the perfect private retreat. Surrounded by numerous hiking trails, many friendly animals, and vast wild forest all around us to explore to your liking, along with this exclusive unit serves to provide a refreshing, rejuvenating space to reconnect with your loved one, yourself and of course Mother Nature!

4.88 out of 5 average rating, 187 reviews

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

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 house 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, 453 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.

4.98 out of 5 average rating, 281 reviews

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.

Flat in San Jose

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, 227 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, 150 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 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.

4.96 out of 5 average rating, 183 reviews

Private Queen Suite-Pool & Hot Tub, private entry

This is your NCAA Basketball & 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 awesome food. 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.

4.9 out of 5 average rating, 105 reviews

An aerial view showcases a resort-style pool surrounded by lounge chairs and shaded cabanas, set within lush landscaping. Nearby, a patio area with seating is visible, while the modern apartment buildings create a backdrop for this inviting outdoor space.

Flat in Friendly Acres

Luxury 2BR Apt near Tech Companies and Stanford

Welcome to our Luxurious 2 bedroom 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 spacious and fully furnished living area, two comfortable bedrooms both with queen size bed, a pair of modern bathrooms, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.

Guest house 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, 624 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.

A bright living area features a spacious sectional sofa adorned with neutral cushions. A modern coffee table sits in the center, complemented by a decorative bowl. Natural light streams through multiple windows, illuminating the light wooden floor and the cozy fireplace with a stone surround.

4.91 out of 5 average rating, 128 reviews

Private Oasis with Pool and Fire Pit

Escape to our private oasis where every detail is designed for your ultimate comfort. Indulge in a refreshing swim in our pool. Unwind and relax in our outdoor lounge area complete with a cozy firepit, perfect for savoring a glass of wine with your loved ones. Whether it’s a family retreat, a couples getaway or a work gathering, your ideal stay begins here! ** We do not offer pool heating **

Popular amenities for Cupertino rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 17 reviews

Home in Rose Garden

The Rose Garden Retreat: Premier Luxury Experience

4.91 out of 5 average rating, 111 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

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.

4.74 out of 5 average rating, 72 reviews

Stunning Group Retreat w/Pool!

4.9 out of 5 average rating, 60 reviews

A serene outdoor area showcases a sparkling saltwater pool surrounded by lush tropical landscaping. Sun loungers are positioned nearby, offering a relaxing spot for guests. A pool house can be seen in the background, framed by vibrant greenery under a clear blue sky.

Home in The Willows

Mission style, w. Pool, Hot tub, walk to downtown

Home in Rivermark of Santa Clara

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.

4.93 out of 5 average rating, 94 reviews

Silicon Valley Executive home in Santa Clara

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.

4.86 out of 5 average rating, 56 reviews

Perfect home with pool for family vacations!

5 out of 5 average rating, 20 reviews

Retromodern | Pool | Games | 2LV

5 out of 5 average rating, 8 reviews

Home in Los Gatos

Modern Family Stay |Steps to Parks + DT Los Gatos

Apartment rentals with a pool

Apartment in San Jose

New place to stay

Sweet home near Apple 2 bedrooms, 1 queen, 1 twin

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.

Apartment in Willow Glen

4.95 out of 5 average rating, 20 reviews

Luxury 2BR Condo Near Levi’s Stadium

Apartment in Mountain View

4.72 out of 5 average rating, 29 reviews

Modern 1B1B condo + quiet patio | Downtown Mt View

5 out of 5 average rating, 5 reviews

A spacious living area features a light-colored sectional sofa with decorative cushions. A wooden coffee table rests in front of it, and a modern floor lamp is positioned nearby. Sliding glass doors lead to a balcony, allowing natural light to fill the room.

Apartment in Lynhaven

1BR/1BA Near Santana Row | Work-Friendly + Parking

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.

Apartment in Palo Alto

4.83 out of 5 average rating, 12 reviews

Contemporary 2BR - Blocks from Stanford Campus

Apartment in Menlo Park

New place to stay

Pool Access! Base to Visit Stanford, See World Cup

5 out of 5 average rating, 3 reviews

Apartment in Palo Alto

Large two-bedroom two bath condo in Palo Alto

4.88 out of 5 average rating, 26 reviews

This two-story condo is set within landscaped grounds, featuring a mix of grassy areas and walkways. The exterior is highlighted by a combination of neutral-colored walls and wood accents. A small patio area can be seen at the side, accompanied by trees and shrubbery.

Apartment in San Jose

Charming 2 bedroom 2 story condo - No smoking

Other holiday rentals with a pool

Flat in Rivermark of Santa Clara

A modern living space features a dining area with a round table and patterned chairs. A cozy seating area includes a sofa decorated with cushions, complemented by a colorful area rug. Large glass doors lead to a terrace, offering a view of greenery.

4.75 out of 5 average rating, 8 reviews

Cozy 1BR Apt in the heart of Silicon Valley

4.61 out of 5 average rating, 28 reviews

A covered entryway features a bright red door framed by a small window beside it. A modest brick wall creates a raised garden bed with a small plant, adding a touch of greenery. The surrounding area has natural light streaming in.

Flat in Santa Clara

Deluxe Studio near Kaiser SC:Traveler/Tesla intern

Guest suite in Boulder Creek

A serene outdoor area features a solar-heated pool surrounded by lush greenery. Comfortable lounge chairs are positioned under a wooden pergola, offering a space for relaxation. The backdrop consists of rolling hills and trees, creating a peaceful natural setting.

4.92 out of 5 average rating, 78 reviews

Huckleberry Woods Sanctuary: Pool and Spa

Home in Rivermark of Santa Clara

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.

4.85 out of 5 average rating, 47 reviews

Modern Retreat in the Heart of Silicon Valley

Guest house in Emerald Hills

A serene outdoor pool area is surrounded by lush hills under a partially cloudy sky. The pool features calm waters reflecting the evening light, while a hot tub is positioned at one end. Distant hills offer a scenic backdrop to the setting.

5 out of 5 average rating, 20 reviews

Casita Luna- Pool house 19 mins to Stanford

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.

4.8 out of 5 average rating, 351 reviews

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

A serene garden area is depicted, featuring neatly trimmed shrubs and ornamental trees under a clear blue sky. Vibrant rose bushes add color to the landscape, while a simple bench is positioned on a gravel path, creating a peaceful outdoor space.

Guest suite in San Jose

4.86 out of 5 average rating, 768 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool