Holiday rentals with a pool in Atherton

4.93 out of 5 average rating, 173 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, 339 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.

4.96 out of 5 average rating, 287 reviews

Guest house in Oakland

Pool, Jacuzzi, Sauna, Huge Views, gated, ADU

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated May 31st to October 30th. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

4.99 out of 5 average rating, 352 reviews

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

Guest house in Woodside

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.

4.88 out of 5 average rating, 185 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!

4.96 out of 5 average rating, 179 reviews

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

Private Queen Suite-Pool & Hot Tub, private entry

World Cup spot! Enjoy your private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, Campbell and Willow Glen. Great forLevi's Stadium, Mountain Winery Concerts, 15 minutes-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 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, 450 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.

4.97 out of 5 average rating, 182 reviews

A serene outdoor space showcases a clear lap pool surrounded by lush greenery and palm trees. A shaded seating area under a canopy is visible, along with vibrant plants reflecting in the water, creating an inviting atmosphere for relaxation.

Guest suite in Sunnyvale

Lux Serenity • Garden Retreat • Biz Travel Ready

💼 Great for Business & Solo Travelers – Prime Silicon Valley location near major tech companies – Easy access to 85, 280, 101, and 237 – Walk or ride to Caltrain, buses, Starbucks, gyms, groceries, and restaurants – Private entrance with self check-in/out – Safe & quiet neighborhood with free 24/7 parking – High-speed WiFi & workspace for working remotely – Kitchenette, Nespresso, microwave & essentials – Spa-style bath with rain shower & aromatherapy – Access to shared saltwater lap pool

4.88 out of 5 average rating, 467 reviews

A spacious bed with an intricate patterned cover is positioned in a well-lit room. Towels are neatly arranged on the bed. A colorful piece of wall art adds a touch of character, while natural light filters through a nearby window.

Guest suite in Woodside

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.

4.91 out of 5 average rating, 108 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

This large 5 bedroom and 3 bath home in Palo Alto has plenty of room for big groups and families. The home features 1 king bed, 3 Queen beds, 2 twin beds and a Queen pull-out sofa sleeper. The kitchen is beautiful and well equipped and this large home has plenty of room for everyone to relax. Enjoy the manicured backyard with large deck, BBQ and sparkling pool (w/child safety fence; pool/hot tub not heated). Close to Levi's Stadium, Stanford and downtown Palo Alto.

Guest house in Almaden Valley

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.

4.97 out of 5 average rating, 1,007 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!

4.88 out of 5 average rating, 271 reviews

A cozy cottage is surrounded by lush greenery and a variety of shrubs. Stairs made of bricks lead up to a welcoming entrance with multiple windows that allow natural light to fill the interior. The setting is serene, with trees enhancing the tranquil atmosphere.

Guest house in Belmont

Private Garden Cottage in Belmont Hills

A fully accessorized cottage in a private and quiet setting at the heart of the San Francisco Bay Area. Newly renovated backyard with always blooming flowers, fruit trees, hot tub, and pool. Regular visits from deer, and professional night illumination make this place feel like a magical forest getaway, quiet and secluded from the surrounding city. Enjoy the multitude of patios for reading and relaxation. We even have a tree house for the kids.

Popular amenities for Atherton rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 225 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

4.94 out of 5 average rating, 48 reviews

An aerial view of a spacious property showcases a two-story house, surrounded by verdant trees and open fields. A sparkling private pool is visible on the rooftop, with ample outdoor space and a well-maintained driveway leading to the entrance.

Home in Castro Valley

Trailside Home, Panoramic Views

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

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

4.94 out of 5 average rating, 17 reviews

A private outdoor area is highlighted by a sparkling pool surrounded by lounge chairs with orange cushions. Tall trees provide shade, while a parasol stands nearby. A scenic backdrop features views of the valley, ensuring a serene atmosphere for relaxation.

Home in Pleasanton

Country Club Living on Golf Course & amazing views

4.9 out of 5 average rating, 118 reviews

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.

Home in San Jose

Private Oasis with Pool and Fire Pit

4.9 out of 5 average rating, 31 reviews

A modern heated pool, surrounded by landscaped gardens and stone seating, reflects the evening sky. The elegant home features large windows and a wooden deck that provides outdoor relaxation spaces. A cozy storage unit sits nearby, harmonizing with the tranquil outdoor setting.

Home in Castro Valley

The Cool Pool House

4.67 out of 5 average rating, 9 reviews

Home in San Jose

Spacious 4BR house | Beautiful Yard + Pool | A/C

Apartment rentals with a pool

Apartment in Civic Center

A modern living space presents a deep-seated couch paired with a stylish coffee table, set against a backdrop of vibrant artwork. Natural light filters in through a window, while a door leads to the outside. A dining area is visible in the corner.

4.9 out of 5 average rating, 313 reviews

Lakeside Retreat (w/ private parking)

Apartment in Redwood Shores

A spacious living area features a high ceiling with a chandelier and large windows that allow natural light to fill the room. A plush sectional sofa is complemented by a coffee table and two cozy chairs. A flat-screen TV is mounted on the wall, adding to the modern decor.

5 out of 5 average rating, 18 reviews

Charming Luxury 2BR w/ Monitor and Adjustable desk

4.75 out of 5 average rating, 4 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.

Apartment in San Jose

Charming 1 bedroom, 1 bath, 2 Story Condo.

An ultra-modern building is depicted at twilight, showcasing a large outdoor pool surrounded by lounge chairs. The landscape includes well-maintained greenery and lit areas, enhancing the resort-style atmosphere. Large windows reveal activity inside, while the sky transitions from deep blue to night.

Apartment in Menlo Park

4.87 out of 5 average rating, 15 reviews

KING BED | Fully Furnished Luxury Condo Gym & Pool

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 Pool, & Gym | Near Levi’s Stadium

A spacious living area features a large sectional couch adorned with decorative pillows. A wooden coffee table sits in the center of the room, complementing the light-colored area rug. Natural light enters through the windows, and a large TV is positioned neatly against the wall.

Apartment in Foster City

4.62 out of 5 average rating, 39 reviews

Entire 1BR Apt•Bright, Clean, Spacious & All Yours

4.76 out of 5 average rating, 68 reviews

An open-concept living area features a spacious sectional sofa and a coffee table, complemented by a dining area with tall, modern stools. Natural light enters through sliding glass doors leading to the patio, while a well-equipped kitchen with wooden cabinetry is visible in the background.

Apartment in Oakland

Waterfront Condo! Great for Month rentals!

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

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.

5 out of 5 average rating, 7 reviews

Cozy 1BR Apt in the heart of Silicon Valley

4.83 out of 5 average rating, 47 reviews

A living area is showcased with a neutral-toned sectional sofa and a black coffee table, positioned on a textured area rug. A brick fireplace frames a large television mounted on the wall. Light from windows illuminates the open layout leading to a dining space.

Villa in Castro Valley

By The Bay Retreat

Guest house 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, 74 reviews

Private cottage in orchard and vineyard setting

Flat 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, 20 reviews

Luxe Apartment Downtown San Jose w/ Gym, Pool

5 out of 5 average rating, 15 reviews

A spacious living area is highlighted by a large grey sofa adorned with yellow and white cushions. Floor-to-ceiling windows provide ample natural light, while a variety of indoor plants create a refreshing ambiance. A circular coffee table is centered on a patterned area rug.

Flat in Oakland

Artsy 2BD Loft, Pool & H/tub

5 out of 5 average rating, 3 reviews

Flat in San Francisco

Entire 1BR Steps from Moscone Center

5 out of 5 average rating, 3 reviews

A sunlit villa displays a charming white exterior with terracotta roof tiles. Two distinct chimneys rise above, while a balcony adds character. Surrounding oak trees provide a natural backdrop, contributing to a serene atmosphere, with gentle hills visible in the distance.

Villa in Woodside

Camellia Cottage with Pool View (Long Term+)