Holiday rentals with a pool in Los Gatos

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.

4.96 out of 5 average rating, 797 reviews

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!

4.99 out of 5 average rating, 351 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.

Guesthouse 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.

A scenic view captures the tranquil coastline, where soft waves meet the sandy beach. Lush greenery frames the foreground, enhancing the natural beauty leading to the ocean. The distant resort building is visible, complementing the serene landscape under a partly cloudy sky.

4.96 out of 5 average rating, 134 reviews

Royal Villa - Ocean View - Heated Pool - Seascape

If you're looking for the best, you've found it. There's not a larger or better 1 bedroom condo in the main building at Seascape. It is the only 864 sq ft end unit with ocean view balcony and lots of windows to let the light in! Oh, and has a actual kitchen with a full size fridge and dishwasher. No matter what special occasion brings you to town, this is the condo you will want stay in! Seascape Beach Resort has amazing sunsets, a soft sandy beach, top notch restaurants, and so many amenities.

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, 178 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.

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, 449 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, 105 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

Superhost

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

4.8 out of 5 average rating, 225 reviews

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, 347 reviews

A balcony features two chairs and a small table, overlooking a bright blue pool and the ocean beyond. Sunlight illuminates the space, enhancing the view of the nearby beach and the landscape of the surrounding resort.

Townhouse in Aptos

2bed OceanFront condo w/Pools+HotTub

Enjoy the comforts of a beach condo with the features of a luxury resort style retreat. This 2 bedroom 2.5 bathroom Villa has two balconies with incredible Ocean Views. Modern kitchen, and beach themed decor make this condo a vacation retreat you cannot miss. Plus 3 pools, heated year round! Located on 17-miles of secluded beachfront in Aptos California, south of Santa Cruz. Treat yourself to exquisite fine dining at the Sanderlings Restaurant, beach pathways and more!

A welcome sign for Rio Del Mar Beach is prominently displayed amid colorful flowering plants. The backdrop features a vibrant sunset, casting warm hues over the surrounding area, while palm trees frame the scene, creating a coastal atmosphere. Nearby, a parking area is visible.

4.98 out of 5 average rating, 205 reviews

Stunning Views @ RDM BCH w/Attached Garage

Escape to the sunny north shore of the Monterey Bay, to our landmark spacious beach condo with panoramic Pacific Ocean views in the coastal village of Rio Del Mar. Built in 1970, pride and respect for friends and neighbors is the hallmark of this overlook. Come breathe in the sea air, pour a glass of wine and watch the sea come to life with a toast to a lovely sunset. Wrap up your evening stargazing on the deck and awake to sound of waves crashing on the shore.

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, 1,006 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, 621 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 Los Gatos rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 42 reviews

Spacious living area features large glass doors that provide stunning views of the ocean and natural light. A cozy sectional sofa with blue and white accents is complemented by a wooden coffee table. The open kitchen is visible, showcasing light cabinetry and modern appliances.

Home in Aptos

2 bedroom Rio Del Mar Apt - Stunning Ocean Views

Superhost

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

4.91 out of 5 average rating, 106 reviews

Large Home in Palo Alto, close to Levi's Stadium

4.9 out of 5 average rating, 145 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

5 out of 5 average rating, 18 reviews

Home in San Jose

Retromodern | Pool | Games | 2LV

4.96 out of 5 average rating, 99 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

4.98 out of 5 average rating, 109 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

4.93 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

4.95 out of 5 average rating, 118 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

Condo rentals with a pool

A winding concrete path leads through a well-maintained green lawn bordered by flowering plants. Tall trees stand in the background, framing the entrance to the beach, where a glimpse of the ocean can be seen in the distance.

4.98 out of 5 average rating, 108 reviews

Luxury Garden View - Relax and Unwind - Seascape

5 out of 5 average rating, 133 reviews

Spectacular Ocean View- Heated Pool & Spa Seascape

A private balcony with a wooden railing features a small round table and two chairs. Ocean views are visible beyond the resort's pool area and neighboring buildings, showcasing the bright blue sky above.

4.9 out of 5 average rating, 104 reviews

2 BD Ocean Views at Seascape Resort North Bluff!

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.

4.94 out of 5 average rating, 124 reviews

OCEAN Views and Steps from the BEACH, New & Modern

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 out of 5 average rating, 108 reviews

Oceanview Villa w/ 2 Decks, ONE Pool & Fireplace

A private balcony features a table and two chairs, overlooking the ocean and beach. The setting sun casts warm colors across the horizon, enhancing the view of the serene landscape and distant shoreline.

4.91 out of 5 average rating, 171 reviews

Seascape Oceanf 1 bdr suite hottub Aptos SantaCruz

4.77 out of 5 average rating, 557 reviews

Aptos Condo with Spectacular Ocean Views

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, 281 reviews

Sandpiper by the Sea

Other holiday rentals with a pool

4.95 out of 5 average rating, 22 reviews

A spacious bed is positioned centrally in the room, adorned with a patterned throw. Two pillows are placed at the head of the bed, complemented by bedside tables with softly glowing lamps. A framed piece of art hangs above, featuring a colorful abstract design.

Apartment in Palo Alto

Beautiful Palo Alto -15 mins to Stanford(1090-104)

5 out of 5 average rating, 43 reviews

The living area features a spacious leather sofa paired with a sculptural coffee table. A large window allows natural light to fill the space, showcasing a cozy, modern aesthetic with a plant adding a touch of greenery. The dining area is visible in the background.

Apartment in Menlo Park

Menlo Park 2bd @ Sandhill near Stanford - Pool, Gym

Apartment in Rivermark of Santa Clara

A welcoming living area features a sleek black television stand and a cozy armchair with a bold pattern. Two round wooden coffee tables display decorative items, while a shelf filled with books and art adds character to the space. Natural light filters through sheer curtains.

5 out of 5 average rating, 21 reviews

Cozy 3BR Near SJC

4.9 out of 5 average rating, 10 reviews

A spacious communal area features modern furnishings with a mix of light and dark tones. A circular dining table with soft, upholstered chairs centers the room, while a large television is mounted on a textured wall. Greenery adds a refreshing touch to the elegant design.

Apartment in Menlo Park

Zen Japan-inspired Suite - Resort hot tub/pool/gym

Superhost

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.

Apartment in Santa Clara

4.61 out of 5 average rating, 28 reviews

Deluxe Studio near Kaiser SC:Traveler/Tesla intern

4.84 out of 5 average rating, 49 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

Guesthouse 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