Vacation rentals with a pool in Milpitas

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.

Condo 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, 342 reviews

The Alpaca House

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.

4.88 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!

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, 451 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.

4.99 out of 5 average rating, 110 reviews

An open living space features a modern kitchen with stainless steel appliances, including a refrigerator and microwave. A dining table is set for four. A comfortable sofa sits adjacent to a large television, with a workspace that includes a desk and ergonomic chair. A decorative Christmas tree adds a festive touch.

Loft in San Jose

Quiet Santana Row LUXE with Mt View

Quiet, luxurious loft on Santana Row. Recently remodeled. New LG WashTower. Sleep Number Bed. Full Kitchen w/ Nespresso, smart kettle, Vitamix Blender. Lululemon MIRROR. Theragun Mini. Best upscale dining & shops downstairs. Valley Fair Mall across the street. Underground parking. Security 24/7. 70 in TV. Electronic standing desk w/ Herman Miller Aeron Chair. Ideal for business/leisure. EXCLUSIVE select dining & shopping discounts Tesla Level 2 charging + Supercharging @ Winchester Garage

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, 182 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.

4.86 out of 5 average rating, 767 reviews

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

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.

Apartment in Friendly Acres

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.

4.93 out of 5 average rating, 168 reviews

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.

Guesthouse 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, 1,009 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!

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, 623 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 Milpitas rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 8 reviews

Home in Santa Clara

Retreat @ Oasis Pool/Hot Tub/Billiards/Game SF Bay

4.91 out of 5 average rating, 110 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.

4.73 out of 5 average rating, 70 reviews

Stunning Group Retreat w/Pool!

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

5 out of 5 average rating, 18 reviews

Retromodern | Pool | Games | 2LV

The exterior of the home is showcased with a warm color scheme and a distinctive tile roof. Lush greenery and manicured landscaping frame the property, while a spacious driveway leads to an attached garage. Surrounding hills and an open field are visible in the background.

4.81 out of 5 average rating, 26 reviews

Large Modern Home in Evergreen

4.94 out of 5 average rating, 18 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

4.73 out of 5 average rating, 11 reviews

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

Condo rentals with a pool

Condo 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.

Condo in Willow Glen

4.95 out of 5 average rating, 20 reviews

Luxury 2BR Condo 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.

Condo in Foster City

4.63 out of 5 average rating, 41 reviews

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

4.72 out of 5 average rating, 29 reviews

Condo in Mountain View

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.

Condo 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.

Condo in Palo Alto

4.83 out of 5 average rating, 12 reviews

Contemporary 2BR - Blocks from Stanford Campus

4.85 out of 5 average rating, 39 reviews

Condo in San Jose

Luxe 2Bed/2Bath w/ Parking, Fast WiFi, Pool & Gym

Condo in Menlo Park

New place to stay

Easy Access to Stanford! Walkable Condo

Other vacation rentals with a pool

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.

Apartment in San Jose

Apartment above Levi Stadium.

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, 77 reviews

Huckleberry Woods Sanctuary: Pool and Spa

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!

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

4.77 out of 5 average rating, 74 reviews

The spacious living area features a modern sectional sofa and a glass coffee table, complemented by colorful artwork on the walls. Bright lighting from hanging fixtures enhances the open layout that connects to the kitchen area with stainless steel appliances.

Apartment in San Jose

2 BR/2 full bath Modern Santana Row Condo sleeps 6

5 out of 5 average rating, 43 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, and huge yard

Cabin in Woodside Heights

A private entrance is highlighted by a covered porch with two comfortable chairs and a small table. A large planter stands next to the door, while lush greenery surrounds the area, creating a serene outdoor setting.

4.96 out of 5 average rating, 23 reviews

Guesthouse in woodside -