Vacation rentals with a pool in San Mateo

4.99 out of 5 average rating, 326 reviews

A tranquil pool area is surrounded by lush greenery and rustic wooden structures. The clear water reflects the trees and sunlight above. A wooden deck offers space for relaxation, while adjacent seating arrangements and a grill provide options for outdoor enjoyment.

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.

Guesthouse in Monte Sereno

A spacious outdoor area features a glimmering pool set against lush greenery. A patio with comfortable seating and a covered area is visible in the background, providing a place for relaxation. Trees and shrubs frame the scene, adding to the tranquil atmosphere.

4.98 out of 5 average rating, 426 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, 243 reviews

Guesthouse in Oakland

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer 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 82F May 1st-Oct. 31st. 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)

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.

4.95 out of 5 average rating, 147 reviews

Private Queen Suite-Pool & Hot Tub, private entry

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, Campbell and Willow Glen. Great for Mountain Winery Concerts, 49ers/Levi's Stadium and 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.

4.89 out of 5 average rating, 447 reviews

A well-maintained garden pathway leads to a pool area surrounded by lush greenery. Tropical plants and vibrant flowers add color to the landscape, while a variety of trees provide shade. The tranquil setting invites relaxation with the pool visible in the background.

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.

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 576 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cozy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland, 50 mile from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mile from Walnut Creek BART station and 1 mile from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big and is good for couples, solo and business travelers.

Guest suite in Walnut Creek

A tranquil swimming pool is surrounded by lounge chairs, nestled among lush greenery and tropical plants. The two-story house features large windows, allowing natural light to brighten the space, while a path leads to the garden area.

4.99 out of 5 average rating, 587 reviews

Garden Oasis Suite with Spa and Pool, Walnut Creek

How about a rejuvenating get-away with a pool and spa? Bask in the late afternoon sun on a patio lounger overlooking a serene pool and tropical garden. Enjoy an evening snack while watching a movie or enjoy a good read. Luxuriate in a deluxe spa before falling into a comfy bed. Keep your work area separate from the bedroom. Split AC/heater. Deep cleaning. Two Airbnb units off same foyer. 27 steps. Neighborhood annexed to Lafayette. $25/person for additional guests or early check-in.

4.96 out of 5 average rating, 155 reviews

Guesthouse in San Rafael

Hillside Oasis Btwn SF, Napa w/ Big Views + Pool!

Welcome to your retreat! Drive through the gate to a peaceful setting. Sunset from your private deck in the hills above San Rafael. It's like a treehouse but with no stairs! Stay home all day (guests love the bed!) or visit the adorable towns and famous hikes of Marin. 45 mins to Napa/Sonoma or 15 min to San Francisco - experience the best of the Bay from here. Happy to help you plan. Separate building from main house. TV: Netflix, Hulu, Disney+ & more! Pool heated May - August.

Guesthouse in Walnut Creek

A swimming pool is surrounded by a concrete deck, featuring several colorful floatation devices. Two wicker chairs and a small table are positioned near the edge, providing a space to relax amidst green trees in the background under a clear blue sky.

4.95 out of 5 average rating, 105 reviews

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

4.94 out of 5 average rating, 154 reviews

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.

Apartment in Menlo Park

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

The outdoor pool is framed by a spacious deck, featuring a stone cabana with large glass doors. Surrounding greenery adds a natural touch, while clear blue skies create a serene atmosphere. Sun loungers are positioned nearby, inviting relaxation by the refreshing water.

4.97 out of 5 average rating, 967 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!

4.97 out of 5 average rating, 352 reviews

The salt-water pool offers a serene atmosphere, featuring a natural stone waterfall that cascades into the shimmering water. Surrounding oak trees create a calming environment, while the clear, inviting pool reflects dappled sunlight.

Home in Lafayette

Bay Area Refuge- Waterfall/Cave Spa, Amazing Views

Relax and rejuvenate your spirit in this uniquely designed home, situated under a canopy of sprawling oaks and with incredible panoramic views of Mt. Diablo and the valley, and multiple areas to relax. Hang out on the deck with a glass of wine, take a dip in the refreshing salt-water pool, or just melt away in our therapeutic cave spa. Centrally located in the East Bay just minutes from Lafayette, Walnut Creek, Berkeley and ~35 minutes from San Fran.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for San Mateo 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, 102 reviews

A cozy outdoor space is illuminated by string lights, creating a warm ambiance. A small round table sits in the center, surrounded by chairs. Nearby, a garden cottage and trees provide a natural backdrop, enhancing the serene atmosphere of the backyard.

Home in Oakland

Summer-house/OASIS on quiet street in ROCKRIDGE!

DanielRating, 5 stars1 month ago

A house with a personal touch with decorations of the owner’s many travels. The backyard is beautiful in spring, even fragrant, when flowers are in bloom. They are integrated into the home via some nice French doors into the kitchen.

4.78 out of 5 average rating, 59 reviews

A private pool is nestled in a spacious backyard surrounded by lush greenery and trees, offering a view of the hills in the distance. Poolside loungers are positioned on one side, while well-kept gardens and a patio area enhance the inviting outdoor space.

Home in Clayton

A Travelers Dream Come Stay with us!

JulietRating, 5 stars3 weeks ago

We enjoyed our stay in Clayton while our home was for sale. The location is wonderful with an easy walk to downtown Clayton and all its wonderful restaurants. We took advantage of the easy access to many walking trails which our pups r joyed as much as we did!

4.8 out of 5 average rating, 206 reviews

A large in-ground pool is set in a landscaped garden, surrounded by a mix of greenery and fencing for safety. The smooth pool surface reflects the blue sky, while a covered area with red seating is visible in the background.

Home in Willow Glen

Beautiful Large 4BR Home with POOL

MoniqueRating, 5 stars1 day ago

Gwen’s place was great!! Spacious with a very nice backyard with a pool. I wish we had more time to enjoy it!!

4.92 out of 5 average rating, 206 reviews

An outdoor area features a turquoise umbrella shading a round dining table with five chairs, positioned near a swimming pool. A gas grill is visible beside the table. Colorful pool floats are arranged in the clear water, while a tree offers additional shade in the background.

Home in Concord

Pool, Hot tub, Napa, SFO Clean

LizRating, 5 stars1 month ago

Great central spot in Concord. Georgie is a fantastic host and the house is extremely well supplied. Our stay was wonderful.

4.8 out of 5 average rating, 5 reviews

An overhead view of the living space shows a foosball table beside a light-colored sectional sofa. A chandelier hangs from the ceiling, illuminating the room. An entertainment unit and decorative artwork provide a welcoming touch to the open layout.

Home in Santa Clara

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

SharynRating, 5 stars2 months ago

I booked this home for my colleagues from overseas, and they had a fantastic stay. The host was highly professional and responsive, promptly addressing all requests and ensuring everyone’s comfort throughout their visit. Their attentiveness made the experience seamless and enjoyable. Highly recommended!

4.85 out of 5 average rating, 47 reviews

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.

Home in San Jose

Perfect home with pool for family vacations!

TraciRating, 5 stars1 week ago

We had a great stay. The home was very comfortable and stocked with everything we needed. Good pillows and towels. We enjoyed the pool and hot tub as well as the park down the road. Thanks so much.

4.92 out of 5 average rating, 93 reviews

The exterior view captures a spacious waterfront home with a private dock featuring a floating pool. Palm trees line the property, and outdoor seating areas are visible. A covered section houses a boat, enhancing the serene waterfront setting.

Home in Discovery Bay

Waterfront home w/ private dock and pool

CarinRating, 5 stars3 weeks ago

Kim's place perfectly fit are needs! Lots of room to spread out., we hosted a small group of family to organize for a celebration of life from the mother. Everything was very serein and peaceful. Kitchen was extremely well equipped!! Outdoor space magical!! We would love to book again.

4.89 out of 5 average rating, 27 reviews

A serene swimming pool is surrounded by a wooden deck, featuring a lounge chair and an umbrella. Sunlight reflects off the water's surface, while lush greenery provides a natural backdrop. A clear blue sky enhances the tranquil outdoor setting.

Home in Oakland

Oakland Hills home with Pool!

Maureen NoraRating, 5 stars1 month ago

This house is incredibly spacious and looks exactly like the photos. All of the linens are well organized and the kitchen had tons of counter space. The fireplace was dreamy in the kitchen and we loved the absolutely enormous television! Very, very soft beds as well.

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Condo rentals with a pool

Condo in Downtown Oakland

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.

4.92 out of 5 average rating, 291 reviews

Lakeside Retreat (w/ private parking)

BenRating, 5 stars2 weeks ago

Great stay, the parking was a huge plus. Didn’t use the laundry but also great to have. Would certainly stay again!

4.67 out of 5 average rating, 3 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.

Condo in San Jose

Charming 1 bedroom, 1 bath, 2 Story Condo.

TomRating, 5 stars11 months ago

Everything was great! The unit had everything you could possibly need for a trip (stocked bathroom, stocked kitchen, tons of extra towels and blankets). The neighborhood was also very quiet, which was great because we're light sleepers. I would definitely recommend this spot and would stay again.

4.87 out of 5 average rating, 31 reviews

An outdoor swimming pool surrounded by landscaped grounds is presented, featuring sun loungers and shaded seating areas. The water is clear and inviting under sunlight, and the view of the nearby buildings and trees adds to the serene environment.

Condo in Emeryville

Furnished 1 bedroom Apartment, Pool, Gym - Monthly

PatriciaRating, 5 stars1 month ago

My husband & I stayed at Henricks condo for 6 weeks as we were helping to watch our grandchildren who live in same condo complex. Henrick was in touch with us often & was willing to come by and help with whatever we might need. He actually did come over as soon as we had a problem with the TV/Internet and he gladly fixed the problem by heading out to the store. The bed & linens were very comfortable and everything was neat & clean. We felt very safe here with 24 hr security & also knowing that the fire & police station were across the street. The condo complex is well-maintained and the residents are very welcoming. We took many walks on the boardwalk in the complex which abuts the SF Bay. We often treated ourselves to a soak in the hot tub or a dip in the resort style pool! Henrick was kind to reach out on our last days there, wishing us a safe trip back. He was very receptive to any suggestions & thoughts we had about the condo for future guests including ourselves!!

4.93 out of 5 average rating, 29 reviews

A spacious living room is highlighted by a cozy gray sofa and a circular coffee table placed on a light area rug. A ceiling fan is positioned above, and a decorative piece is displayed on the wall. Natural light filters in from large windows, and a fireplace is present.

Condo in Walnut Creek

Downtown Modern Living Condo!

SherryRating, 5 stars1 month ago

Anis was an excellent host and the place was as described. Clean and quiet.

4.91 out of 5 average rating, 11 reviews

A modern living space is visible, featuring a black leather seating area with a large cushion. The dining area is furnished with a wooden table and chairs. A doorway leads to a bright kitchen, while the walls are painted in a light color, giving an airy feel.

Condo in San Rafael

Modern, bright 2 bedroom/1 bath 2nd story

CharlesRating, 5 stars5 months ago

We had a great stay at Tanya's place! The condo was clean and comfortable. It’s perfectly located for exploring the North Bay with easy access to 101 and 580. Tanya was very attentive, making sure everything was satisfactory. She also gave local recommendations for groceries and dining. We would definitely recommend this listing to anyone visiting the San Rafael area and would stay here again.

4.92 out of 5 average rating, 13 reviews

A spacious living area is visible, featuring a large black leather couch and a wooden coffee table. A soft rug lies under the seating area. A dining table can be seen in the adjacent room, complemented by warm wood flooring and ample natural light from nearby windows.

Condo in Menlo Park

Willow Place

MaximeRating, 5 stars2 weeks ago

Perfect Airbnb experience. The location, the apartment, the pool, Ryan's helpfulness -- everything was way above expectations.

4.67 out of 5 average rating, 12 reviews

The lake view features multiple sailboats gliding across the water, with a backdrop of tall buildings and a clear sky. Below, a vibrant market scene displays food stalls under palm trees, with a retro sign indicating a nearby venue offering breakfast and lunch.

Condo in Grand Lake

Cozy condo by the lake

GaryRating, 5 stars2 weeks ago

The accommodations were nice and the area was quiet. It was a short walk to shops, restaurants, a movie theater and a 5 minute drive to a supermarket. It was a short walk to the lake which had a circumferential walking path. We particularly liked the locked parking garage. We will definitely come back.