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Vacation rentals with a pool in San Mateo County

Find and book unique homes with a pool on Airbnb

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Popular amenities for San Mateo County rentals with a pool

House rentals with a pool

Superhost
A small round table is positioned between two high-backed chairs, providing a cozy seating area. Above the table, a flat-screen television displays an image of the Golden Gate Bridge, complemented by a decorative vase on the table.
Home in San Mateo
4.73 out of 5 average rating, 26 reviews

Charming English Oasis

IgorRating, 5 stars3 months ago
I really enjoyed my two-week stay at Will's place! The apartment was clean and cozy, and the building appeared modern and new. I noticed a few reviews mentioning minor issues, but honestly, I had a great experience. The location is good – you can easily walk to a bakery, supermarket, and restaurants. Will was a great host, always available, friendly, and helpful with any questions. I recommend Will's place to anyone visiting the city – it's a great choice!
Guest favorite
A secure child safety fence encloses a refreshing pool area. The pool features a light blue surface and is surrounded by a concrete patio, framed by lush greenery and well-maintained landscaping. The fence's gate is visible, providing access to the pool.
Home in Palo Alto
4.93 out of 5 average rating, 87 reviews

Large Home in Palo Alto w/Pool

AnilRating, 5 stars1 week ago
Very professional, courteous and excellent communication. The location and the accommodation excellent. The hosts also allowed us to check in very late and send us lots of good information around the areas.
Guest favorite
A spacious living area is highlighted by large windows that allow natural light to fill the room. Comfortable seating options, including a sectional sofa and accent chairs, are arranged around a central coffee table, with decorative artworks and a media unit enhancing the decor.
Home in Los Altos Hills
5 out of 5 average rating, 10 reviews

Fab Family Home in the Hills

VickyRating, 5 stars3 weeks ago
We had a peaceful and restorative stay in Maureen's house. The house and grounds are spacious, private and beautiful. We rented two bedrooms/1 bath (the main floor of the house), perfect for 3 of us. Our son was recovering from jaw surgery so the recliner in the family room was much appreciated, and the kitchen/dining areas huge and super functional. The hosts are very communicative and helpful, as well as easy-going. This was the perfect home for our purposes!
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, 55 reviews

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

MorganRating, 5 stars6 months ago
Sara and Nic were gracious and very responsive hosts. Their home is spacious, clean, comfortable, and suited our needs perfectly. The outdoor space also looked wonderful but we didn't use it much because our visit was during winter.
A well-maintained garden path leads to the entrance of a contemporary split-level home. The pathway, lined with lush greenery and potted plants, features textured stone steps that invite guests toward the spacious porch. Large windows allow for natural light to illuminate the facade.
Home in San Mateo
4.94 out of 5 average rating, 16 reviews

Life Home

BenRating, 5 stars98 months ago
The Life House is an amazing property. Our small team came into town for a few conferences and Life House was a perfect place to lay our heads each night. Highly recommend it to anyone seeking a fun, open, inspiring space. Marky was a great host. He made sure everything was ready and quickly responded to any questions we had.
Guest favorite
A spacious backyard features a large swimming pool surrounded by lounge chairs and umbrellas. Palm trees and vibrant landscaping enhance the tranquil atmosphere. A hot tub is positioned nearby, and the area is enclosed by wooden fencing for added privacy.
Home in Felton
4.9 out of 5 average rating, 31 reviews

Tropical Felton Oasis

NicoleRating, 5 stars6 days ago
We love staying here. It’s so peaceful and beautiful, I cry when it’s time to go home! Jessica is very responsive. We had an issue with the hot tub and her handyman fixed it that very night. This is our second stay, and we will be back. Highly recommended.
Guest favorite
An aerial view showcases the serene landscape of Foster City, featuring winding waterways and lush green spaces. The neighborhood is characterized by neatly arranged homes, with the Bay Area hills visible in the distance and expansive blue skies above.
Home in Foster City
4.91 out of 5 average rating, 35 reviews

McAlvarez Cottage

LynnetteRating, 5 stars11 months ago
Absolutely loved our stay and would not hesitate to book again. It had everything we could need and more, just what we needed after a busy day exploring. Colleen was very responsive to any messages we sent. Would 100% recommend.
Guest favorite
A spacious living room features a striking wooden ceiling with exposed beams. A central stone fireplace is flanked by comfortable seating arrangements. Elegant chandeliers add ambient lighting. Natural wood floors complement the warm tones of the decor, creating a welcoming focal area for relaxation.
Home in Boulder Creek
4.94 out of 5 average rating, 18 reviews

Nuby's Bed & Breakfast (SCC Permit #251085)

LaurenRating, 5 stars3 days ago
Our stay at Alex and Nuby’s place was such a nice family getaway. The beautiful pool, hot tub, and campfire area among the redwoods made it feel outdoorsy without actually having to tent camp. The kitchen is spacious and fun to cook in. Very modern appliances and large windows to make it feel airy as we prepped. A nice BBQ and outside deck to dine on as well. The entire place is spacious, clean, and cozy.

Condo rentals with a pool

A spacious living area features a high ceiling with a chandelier and large windows that allow natural light to fill the room. A plush sectional sofa is complemented by a coffee table and two cozy chairs. A flat-screen TV is mounted on the wall, adding to the modern decor.
Condo in Redwood City
5 out of 5 average rating, 18 reviews

Charming Luxury 2BR w/ Monitor and Adjustable desk

RachelRating, 5 stars3 months ago
The place is as described. It has everything you need. Communication with the host was great and very accommodating. I would definitely return and stay again!
An outdoor swimming pool and hot tub are surrounded by several lounge chairs and umbrellas. A garden area with greenery encircles the pool. The building's exterior, with light-colored walls and terracotta roof tiles, is visible in the background.
Condo in Palo Alto
4.83 out of 5 average rating, 12 reviews

Contemporary 2BR - Blocks from Stanford Campus

AndreaRating, 5 stars81 months ago
The apartment is placed in a perfect position. You can find everything you need in a walking distance like a supermarket, good places to grab something to eat and gyms. the check-in was easy and perfectly matched the description Dee provided me before the arrival. The house is very spacious and the kitchen fully equipped. I recommend this place for a comfy stay in Palo Alto.
A modern sectional sofa with light upholstery is positioned in the foreground, featuring a spacious chaise lounge. The room is bright, with high ceilings and a circular pendant light hanging above. A staircase with a black railing leads to the loft area in the background.
Condo in San Mateo
5 out of 5 average rating, 3 reviews

Luxury loft by the water

SondraRating, 5 stars1 month ago
As a solo female traveler in town for business, this place was great. Short distance to the office but had everything you needed for working remote. Loved the kitchen set up and had everything I needed to make breakfast and dinner. The bed was so comfortable, I didn’t want to leave! My rav4 fit well in the garage. The walking path outside was great for either starting your day or winding down.
A resort-style pool area is surrounded by modern apartment buildings. Sun loungers line the poolside, with vibrant umbrellas providing shade. At one end of the pool, a fireplace offers a cozy ambiance, while palm trees add greenery to the setting. Clear skies enhance the inviting atmosphere.
Condo in Menlo Park
4.4 out of 5 average rating, 5 reviews

Discover Luxury at Elan Menlo Park

VikRating, 5 stars13 months ago
Stayed there with family of 4. Apt was nicely furnished , family friendly + complementary crib was provided. All very high quality and very clean. Only small negative was the location but we spent most our time at the apt or somewhere else. Didn’t bother us. Quick access to the rest of Bay Area
A modern living area is presented with a comfortable sectional sofa and stylish coffee table. A large window offers views of the outdoors, while plants and decorative elements enhance the inviting ambiance. Soft lighting illuminates the space, creating a serene environment.
Condo in East Palo Alto
5 out of 5 average rating, 5 reviews

Modern 2BR Condo | Business & Long-Term Stays

AmreshRating, 5 stars1 month ago
This was one of the best Airbnb stays I’ve had. Tucked in a quiet, green neighborhood just minutes from downtown Palo Alto, the location was perfect. Peaceful & residential, yet incredibly convenient. Having an organic grocery store within walking distance was a big plus. The home itself is beautifully done, spotless, thoughtfully designed, & filled with everything you might need for a comfortable and relaxed stay. The kitchen was well-equipped, the bed was cozy, and the entire space had a calm, welcoming vibe that instantly put me at ease. But what truly elevated the experience was Johana. She is one of the kindest and most considerate hosts I’ve ever met, warm, responsive, and genuinely invested in making sure everything was perfect. Whether it was a quick question or a small request, she was always just a message away and incredibly thoughtful in her responses. You can tell she really cares. I would stay here again in a heartbeat & I am looking forward to it.
A resort-inspired pool is framed by lounge chairs, with umbrellas providing shade. Modern apartment buildings are visible in the background, showcasing a sleek design. A communal area with a fire feature is positioned at the far end, creating a welcoming atmosphere for relaxation.
Condo in Menlo Park

Menlo Park's Creative Retreat

An outdoor entertainment space features a modern fire pit beneath a mounted TV. Comfortable seating is arranged around the area, showcasing plush cushions in neutral and pastel tones. Lush greenery borders the space, enhancing the tranquil atmosphere.
Condo in Menlo Park

Spacious 2BR Bliss at Elan Menlo Park

The resort-inspired pool is surrounded by lounge chairs and umbrellas, creating a relaxing atmosphere. Two modern apartment buildings frame the space, with a fire pit visible in the background. Clear blue skies reflect on the water's surface, enhancing the inviting setting.
Condo in Menlo Park

Unwind at Elan Menlo Park

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