Vacation rentals with a pool in Los Gatos

Guest suite in Willow Glen

Private Queen Suite-Pool & Hot Tub, private entry

This is your Getaway spot! Enjoy your private suite, bathroom and large smart TV, pool and hot tub outside your door. Located within 3 miles of downtown Los Gatos and Campbell with great food options. Levi's Stadium/49ers 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.

4.95 out of 5 average rating, 212 reviews

Guest suite in Scotts Valley

A private entrance is visible, leading into the unit. Lush greenery hangs over the door, while a wooden deck offers space for relaxation. Potted plants surround the area, and BBQ grills are positioned near the poolside, enhancing the outdoor ambiance.

Snug and Cozy between the Skyline and the Sea

Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

4.96 out of 5 average rating, 850 reviews

4.93 out of 5 average rating, 179 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.

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.

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, 464 reviews

4.8 out of 5 average rating, 237 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!

4.95 out of 5 average rating, 125 reviews

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

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.

4.93 out of 5 average rating, 153 reviews

A spacious outdoor pool lined with a brick border shimmers under the clear sky. Comfortable lounge chairs are positioned beside the pool. Lush green trees and a fenced area provide a serene backdrop to this inviting space.

Villa in Santa Cruz

Luxury garden villa w/ hot tub and game room

Welcome to our Luxury Villa in the Santa Cruz mountains, a paradise where you can relax and make unforgettable memories. Our villa boasts a spacious patio where you can enjoy your meals surrounded by enchanting gardens. Unwind in our pool, relax in the hot tub, or challenge your friends to a game of pool on professional sized pool table, in our brand-new recreation room. The room features a beautiful handmade walnut bar, complete with a commercial ice maker, sink, and fridge.

4.97 out of 5 average rating, 254 reviews

A private swimming pool is surrounded by lounge chairs under shade umbrellas. The pool, featuring a gentle curve, has clear blue water and an entry step. Lush greenery and a fence provide privacy, while distant views of a serene landscape can be seen in the background.

Home in Aptos

Private Pool Villa for family getaways

Looking for a comfy space to spend time with friends and family? Beach or great outdoors more your thing? 10 minutes from Seacliff State Beach and 12 minutes to Nisene Marks, this sunny locale is your comfortable home base for your next adventure. Why not just hang out by the pool? The water typically stays comfortable for swimming from April-September. Enjoy dining for 8 inside or on the patio. So close to the sea, but above the foggier lower elevations. Family friendly!

4.99 out of 5 average rating, 620 reviews

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.

Guesthouse in Los Gatos

Sanctuary in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, original art and spa amenities, 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!

4.94 out of 5 average rating, 452 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 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.

Place to stay in Los Gatos

An aerial view displays the serene property nestled among towering redwoods. A sparkling pool is surrounded by lush greenery, with a patio and seating area visible in the background. The landscape features diverse plants, enhancing the tranquil atmosphere of this private retreat.

Stay Alpha Home • Modern Redwood Retreat with Pool

Permit 231266 - Nestled in the Santa Cruz mountains is this serene oasis, rustic with modern touches and a stunning pool (the upper pool and main pool are not heated). Embrace yourself with the lush tropical setting and gorgeous redwood groves in this mesmerizing, unique villa. With distance between you and the closest neighbor, it’s perfect for families and nature enthusiasts seeking a rejuvenating retreat. Your redwood getaway awaits!

4.78 out of 5 average rating, 114 reviews

4.92 out of 5 average rating, 100 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

Great location in the center of Silicon Valley tech. companies, Levis Stadium, Santa Clara golf and tennis center and Santa Clara convention center. This location is walking distance to hiking, biking trail, and Safeway. It is also walking distance from Cisco, Samsung, Oracle, Hynix, Intel (Altera), Santa Clara convention center and many others. We have recently upgraded the house with brand new carpet on the 2nd floor and stairs!

Popular amenities for Los Gatos rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.78 out of 5 average rating, 131 reviews

A welcoming exterior view of the family house is showcased, surrounded by a spacious front yard. A large pine tree offers shade while a decorative pot with greenery adds a touch of nature. The driveway leads to a double garage with a clean facade.

Home in San Jose

Modern Rustic Home With Private Pool

4.96 out of 5 average rating, 180 reviews

A spacious deck is showcased with comfortable seating arrangements, complemented by a dining table. Lush greenery in planters is visible, along with panoramic ocean views under a clear blue sky. A cozy rug anchors the seating area, inviting relaxation.

Home in Aptos

Relax + Unwind in Brand New 2BD Modern Bch Retreat

4.96 out of 5 average rating, 133 reviews

The entrance to the Amesti School features a deep red wooden facade with large windows. A pair of inviting chairs are positioned on the covered porch, complemented by a simple light fixture. The front door is framed by an elegant trim, welcoming guests.

Home in Watsonville

Old Amesti Schoolhouse mid-bay amidst farmland

4.92 out of 5 average rating, 123 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

4.85 out of 5 average rating, 147 reviews

The spacious living room features light wooden flooring and white ceiling beams. Comfortable gray sofas surround a white coffee table on a patterned rug. Large windows allow natural light to fill the room, illuminating the fireplace and inviting atmosphere.

Home in Mountain View

Modern 4bd/3ba w/ pool In Downtown MV

4.9 out of 5 average rating, 147 reviews

A serene outdoor area features a sparkling pool and spa surrounded by lush greenery. Comfortable lounge chairs are positioned nearby, while a gazebo provides shade. The blue water reflects the sky, enhancing the peacefulness of this private retreat.

Home in Santa Cruz

Santa Cruz Beach House with Pool & Spa

4.96 out of 5 average rating, 27 reviews

Home in Campbell

Luxe 3BR Retreat with Pool & Hot Tub

5.0 out of 5 average rating, 9 reviews

Home in Willow Glen

San Jose Home with Pool, Hot Tub, + Game Room

Condo rentals with a pool

A view captures a multi-story building positioned near the shore, with cars parked along the street. The ocean stretches beyond, featuring calm blue waters and a clear sky above. The beach is visible in the distance, enhancing the coastal atmosphere.

4.88 out of 5 average rating, 105 reviews

Walk to the beach, panoramic ocean view, and pool!

4.98 out of 5 average rating, 113 reviews

Beautiful Ocean View 2 BR-Seascape-Miles of Beach

4.94 out of 5 average rating, 355 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

A vibrant landscape features blooming flowers in shades of pink and white in the foreground, while the serene ocean stretches into the distance. The scene is framed by tall trees, creating a harmonious blend of nature with the beach visible under a clear blue sky.

4.86 out of 5 average rating, 199 reviews

Beach Front Villa at Seascape Resort

4.78 out of 5 average rating, 595 reviews

Aptos Condo with Spectacular Ocean Views

A sunny balcony is seen with two chairs and a small table, surrounded by decorative plants. The ocean can be viewed in the background, with clear skies and sunlight reflecting on the water. A vibrant rug covers the balcony floor.

5.0 out of 5 average rating, 131 reviews

Oceanview Villa w/ 2 Decks, ONE Pool & Fireplace

A two-story condo with a contemporary exterior features vertical wooden siding in soft blue tones. A wide staircase leads to the entrance, which is sheltered by a canopy. Large windows allow natural light to enter, surrounded by greenery and a small shrub at the front.

4.81 out of 5 average rating, 297 reviews

Sandpiper by the Sea

An open living area features a comfortable grey sofa facing large windows that showcase ocean views. A round dining table with four chairs is positioned near the kitchen, enhancing the spacious layout. Soft lighting is provided by a ceiling fixture.

4.93 out of 5 average rating, 137 reviews

OCEAN Views and Steps from the BEACH, New & Modern

Other vacation rentals with a pool

4.94 out of 5 average rating, 158 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

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.

Apartment above Levi Stadium.

4.98 out of 5 average rating, 303 reviews

4.84 out of 5 average rating, 746 reviews

An expansive view of the ocean dominates the scene, showcasing the beach coastline and a pier extending into the water. The horizon features a clear blue sky, while a railing is visible in the foreground, providing a sense of elevation.

Apartment in Aptos

Modern Ocean View 2 BD w Parking.

4.78 out of 5 average rating, 454 reviews

A modern living area features soft grey furniture arranged around a gas fireplace. A dining table with plush chairs sits nearby, reflecting natural light from the sliding glass doors leading to a patio. Decorative elements include a round mirror and coastal artwork.

Apartment in Aptos

*Official Resort Listing* Partial View 2 BDR Villa

4.93 out of 5 average rating, 172 reviews

Cottage in Ben Lomond

Central Coast; Meadow, Hot Tub, Polite Pets Welcom

4.83 out of 5 average rating, 29 reviews

Cabin in Los Gatos

Los Gatos Mountain Retreat | Heated Pool & BBQ

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.

D’s Garden Cottage

4.99 out of 5 average rating, 88 reviews