Vacation rentals with a pool in San Mateo

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Mateo

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene swimming pool reflects the clear blue sky, surrounded by lush landscaping. Natural stone steps lead to the house, flanked by vibrant foliage and small waterfalls, creating a tranquil retreat.

Home in Portola Valley

4.93 out of 5 average rating, 155 reviews

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.

Top guest favorite

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

4.99 out of 5 average rating, 330 reviews

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.

Top guest favorite

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

4.89 out of 5 average rating, 161 reviews

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!

Top guest favorite

Guesthouse in Oakland

4.97 out of 5 average rating, 248 reviews

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)

Top guest favorite

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 Willow Glen

4.95 out of 5 average rating, 153 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.

Guest favorite

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

4.89 out of 5 average rating, 451 reviews

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.

Guest favorite

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 581 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.

Top guest favorite

Guesthouse in San Rafael

4.96 out of 5 average rating, 162 reviews

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.

Guest favorite

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.

Guesthouse in Walnut Creek

4.95 out of 5 average rating, 108 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

Top guest favorite

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.

Guest suite in Walnut Creek

4.99 out of 5 average rating, 589 reviews

Garden Oasis Suite with Spa and Pool, Walnut Creek

How about a rejuvenating get-away with pool and hot tub? Relax on a patio lounger overlooking a tropical garden. Enjoy an evening snack while watching a movie. Super comfy bed and separate living room. Deep cleaned. 2 separate units off same foyer; but no shared walls. Private locked unit door. Shared access to spa/pool (9am-11pm) for overnight guests only. 27 stairs to reach house. Host lives upstairs. Complimentary beverage for 3+ nights. After 10 stays, $100 credit.

Top guest favorite

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.

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 974 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!

Top guest favorite

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

4.97 out of 5 average rating, 355 reviews

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

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Cottages

Quaint homes, peaceful surroundings

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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

Guest favorite

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

4.81 out of 5 average rating, 104 reviews

Summer-house/OASIS on quiet street in ROCKRIDGE!

MartinRating, 5 stars3 weeks ago

Very homey and welcoming. Family enjoyed celebrating time together in all spaces of the house, especially the back patio where our young child made believe on the well-designed pirate ship. Friendly, kind host. We walked to adorable Rockridge and BART many times. Highly recommended.

Guest favorite

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

4.92 out of 5 average rating, 207 reviews

Pool, Hot tub, Napa, SFO Clean

DonRating, 5 stars6 days ago

The place was clean and beautiful. We needed a home away from home while construction was going on at our place. And found it here.

Guest favorite

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

4.8 out of 5 average rating, 210 reviews

Beautiful Large 4BR Home with POOL

NatashaRating, 5 starstoday

Immaculately maintained, spacious property. Very relaxing. Close to all the necessary shops. Well equipped for families.

Guest favorite

An inviting outdoor space features a saltwater pool surrounded by lush greenery and lounge seating. A covered area displays comfortable seating and decorative hats, with towels neatly arranged in baskets nearby. The bright sky enhances the serene atmosphere of the garden retreat.

Home in Menlo Park

4.89 out of 5 average rating, 54 reviews

Mission style, w. Pool, Hot tub, walk to downtown

SolinRating, 5 stars10 months ago

We stayed at Sara's while visiting family nearby, but her home felt like a vacation in itself. The backyard is magical - we spent a fair amount of time there, swimming, grilling/dining, reading/napping. The backyard (and its myriad diversions) even lured our tech-obsessed teenagers away from their devices for extended periods. Everything was well maintained, no detail overlooked. We also enjoyed the access to a peloton bike and workout equipment. The interior was clean, organized, stylish but comfortable. The sunroom and small courtyard off of the bedrooms were great for yoga or stealing a quiet moment with a cup of coffee or book. Sara was responsive and attentive. Instruction booklet was clear and helpful. The stay exceeded our expectations. We hope to be back.

Top guest favorite

An outdoor space is adorned with colorful lanterns and a vibrant flag, creating a lively atmosphere. A hot tub is visible alongside a small pool featuring an illuminated ring. Comfortable seating areas are surrounded by tropical plants, enhancing the welcoming environment for guests.

Home in Oakland

5 out of 5 average rating, 72 reviews

Cactus House & Suite: 4 bedroom 3 bathroom

AlbertRating, 5 stars9 months ago

Had an excellent stay with our family. Will is one of the best airbnb hosts we have ever had and would stay again at this home or any other home he hosts without hesitation. The cactus home is luxurious and has amazing amenities like heated bathroom floors, great outdoor space with pool and hot tub, and a well equipped kitchen.

Top guest favorite

An outdoor space features a swimming pool surrounded by lounge chairs and a wooden dining table with umbrellas for shade. Lush greenery and hills are visible in the background, providing a serene atmosphere. The patio has large tiles to create a spacious walkway.

Home in San Anselmo

5 out of 5 average rating, 31 reviews

Hill Top Spa Retreat

SreejitRating, 5 stars2 weeks ago

Job’s place is a true gem. The pictures dont do the place justice. Its beautfully decorated with excellent amenites both in and outside the house. The view is unbeatable and the locaion is so peaceful. The pool house was one of the top highlights. Job was a very helpful host and super responsive to our requests. I would definitely come back here. Thank you Job for sharing your place with us

Guest favorite

A sparkling, heated pool occupies the backyard, surrounded by lush greenery and palm trees. Brick edging outlines the pool, enhancing the outdoor space, while a privacy fence adds to the tranquil setting. Sunlight reflects off the water, creating an inviting atmosphere.

Home in San Jose

4.86 out of 5 average rating, 125 reviews

Beautiful 3BD Home w/ Heated Pool and Fire Pit

BaharehRating, 5 stars15 months ago

The house was great for our family stay. Lots of space, all on one level, and beautiful outdoor space. We travelled with our kids and they had a great time in the pool :) Note there is extra cost if you want the pool to be heated. Thanks for a great stay!

Guest favorite

A refreshing swimming pool is framed by lush greenery and bordered by a clean patio area. Two lounge chairs are positioned nearby, inviting relaxation. Sunlight reflects off the water, creating a calming atmosphere suitable for unwinding or enjoying time with family.

Home in Hayward

4.83 out of 5 average rating, 63 reviews

The Happy Hideaway - Pool, enjoyable backyard!

JoseRating, 5 stars4 weeks ago

We loved the place, it had everything needed for a comfortable stay. Mei was very attentive and quick to respond to any question we had. I highly recommend it.

Show all

Condo rentals with a pool

Superhost

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.

Condo in Downtown Oakland

4.92 out of 5 average rating, 293 reviews

Lakeside Retreat (w/ private parking)

DennisRating, 5 stars3 weeks ago

Very responsive and helpful host… would definitely go back and stay there when visiting the Bay Area again

Superhost

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

4.75 out of 5 average rating, 4 reviews

Charming 1 bedroom, 1 bath, 2 Story Condo.

TomRating, 5 stars12 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.

Guest favorite

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

4.94 out of 5 average rating, 31 reviews

Downtown Modern Living Condo!

ColleenRating, 5 stars1 day ago

It was a quiet complex and the house was a great option for us for a couple nights. Would stay again.

Guest favorite

A cozy living area features a deep blue sofa and a round coffee table atop a soft area rug. Natural light filters through multiple windows, illuminating various plants that enhance the inviting space. A small accent chair and a decorative stool add to the inviting arrangement.

Condo in Mission District

4.96 out of 5 average rating, 23 reviews

Art Deco Mission Flat

ShawnRating, 5 stars3 months ago

Lyssette’s lovely flat was exactly as described & very comfortable. It is in the heart of the mission district with so many restaurants & neat shops nearby. Highly recommended!

Superhost

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

4.67 out of 5 average rating, 12 reviews

Cozy condo by the lake

GaryRating, 5 stars1 month 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.

Guest favorite

Condo in Mountain View

4.95 out of 5 average rating, 134 reviews

Spacious Top Floor Condo Retreat

KarenaRating, 5 stars1 week ago

During my stay at Joann’s place, I felt safe and very comfortable. The whole home is bright and spotlessly clean, with greenery visible outside the windows. Parking was very convenient, and communication with her was smooth throughout. The kitchen was fully equipped, allowing me to cook and enjoy a good glass of red wine. The sofa was cozy and the bed was spacious. I was pleasantly surprised to find such a wonderful place—thank you!

Guest favorite

A spacious outdoor pool is featured in front of a modern two-story building, showcasing large windows and a tan stucco exterior. Lounge chairs are arranged around the pool area, with palm trees and vibrant landscaping visible in the background.

Condo in Santa Clara

4.94 out of 5 average rating, 314 reviews

The Alpaca House

CarrieRating, 5 stars2 weeks ago

Great apartment that is close to the airport and easy to find. Was given great step by step instructions on how to access the apartment. It was actually bigger than I anticipated and quite quiet.

Guest favorite