
Holiday rentals with a pool in San Mateo
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in San Mateo

Total holiday rentals
Explore 100 holiday rentals in San Mateo

Nightly prices starting at
San Mateo holiday rentals start at $88 NZD per night before taxes and fees

Verified guest reviews
Over 870 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
90 of San Mateo holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across San Mateo rentals

4.7 Average rating
San Mateo stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in San Mateo
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

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.

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 mi from Berkeley/Oakland, 50 mi from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mi from Walnut Creek BART station and 1 mi from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big, has rustic charm and is good for couples, solo and business travelers.

Heated Pool, Jacuzzi, Sauna, Huge Views, Chic ADU!
Tucked between pine, oak, & redwood trees is a 4 year old, high end cottage nestled with amazing views of the mountains. Peaceful, upscale gated, property. 1 mile to large regional parks for hiking, mountain biking & horse stables. Nature at its best! Pool heated to 82F 4/1-10-31. 16 miles to San Francisco, 5-10 minutes to many restaurants. Jacuzzi & barrel sauna, grill. Large patio, pool /new deck (6500 sq foot outdoor oasis shared with main house small family of 4). Own spot in driveway.

Garden Oasis Studio with Spa and Pool Walnut Creek
Former Plus-rated Studio. How about a rejuvenating get-away with pool and hot tub? Picture window overlooking a garden. Sunbathe poolside. Watch TV from a comfy bed before falling into a restful sleep. 27 stairs to house, 3 stairs inside unit. Complimentary beverage for 3+ nights/return stay. After 10 stays, $100 credit. Deep cleaned. 2 separate units off same foyer; no shared walls. Private locked unit door. Shared access to spa/pool (9am-10pm) for overnight guests only. Host lives upstairs.

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.

Luxury Silicon Valley Wellness and Work Oasis
Ideal for guests attending matches at Levi’s Stadium, 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.

Cozy BUS on Farm Animal Rescue with CITY VIEW
Stay on a farm animal rescue in a 38’ yellow school bus conversion. If you are interested we also host an Airbnb Experience called Life With Farm Animals At Rancho Roben Rescues where you get a 90-120 minute up close encounter with all of the animals - taking time to learn about each of the unique creatures that lives here and the opportunity to interact with them directly. Pet a chicken, groom a pony, feed a goat, take a walk patrolling the fields with our livestock guardian dogs.

Private Queen Suite-Pool & Hot Tub, private entry
This is your Getaway and World Cup spot! Enjoy your private suite, bathroom and large smart TV with all the action. Located within 3 miles of downtown Los Gatos and Campbell great food options. Levi's Stadium 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.

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

Views for Miles | Hot Tub | Gated Hilltop Home
Retreat above the city in this one-of-a-kind home and gaze at the sweeping view of Silicon Valley. Rancho Ruby is a revived 1950s ranch designed with a modern California style. Every amenity and detail has been thoughtfully considered for the tech-savvy travelers. The home is open, peaceful, and cool. It sits on a hilltop, situated on a secluded & gated third acre lot to allow tranquility for guests but is only a 15 minutes drive to the city center.

Charming 2BR Apartment near tech Giants & Stanford
Welcome to our Luxurious 2 bedroom 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 spacious and fully furnished living area, two comfortable bedrooms, a pair of modern bathrooms, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.
Popular amenities for San Mateo rentals with a pool
House rentals with a pool

Beautiful Large 4BR Home with POOL

Cozy 2BR w/ Patios, Prime Mountain View Location

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

Sunol Chalet | 80 Acres • Pool • Gym • Game Room

Resort Style Retreat -Private Pool, Hot Tub & View

The Happy Hideaway - Pool, enjoyable backyard!

Private Oasis with Pool and Fire Pit

$1.8M Luxe MeiCasa | 5min Levi | EV | Massage Beds
Condo rentals with a pool

Modern 2‑bed, 2‑bath top‑floor apartment.

Charming 1 bedroom, 1 bath, 2 Story Condo.

Quiet & Comfortable Entire Furnished Apartment

KING BED | Fully Furnished Luxury Condo Gym & Pool

Waterfront Condo! Great for Month rentals!

Modern 1B1B condo + quiet patio | Downtown Mt View

Waterfront Retreat in Bay Area, near San Francisco

Large two-bedroom two bath condo in Palo Alto
Other holiday rentals with a pool

Guest House w/ Pickleball & Pool

Apartment above Levi Stadium.

Chic-Roomy 2Br 2Ba/Pool • Near Levis, Apple, Nvdia

Quiet Foothills Escape with Pool, Patio & BBQ

Timeless Luxury Retreat in a Historic Estate

Guesthouse in woodside -

King bed Silicon Valley haven w/ pool and parking!

Peaceful Family Friendly Entire 2BR/2BA Apt Unit
When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $352 NZD | $416 NZD | $352 NZD | $294 NZD | $483 NZD | $264 NZD | $264 NZD | $393 NZD | $314 NZD | $352 NZD | $337 NZD | $352 NZD |
| Avg. temp | 11°C | 12°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 19°C | 17°C | 14°C | 11°C |
Destinations to explore
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- Rentals with a hot tub San Mateo
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- Rentals with pools San Mateo County
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- Rentals with pools United States
- Stanford University
- Golden Gate Park
- Santa Cruz Beach
- Muir Woods National Monument
- Capitola Beach
- Santa Cruz Beach Boardwalk
- Golden Gate Bridge
- Oracle Park
- Moscone Center
- University of California-Berkeley
- SAP Center
- Henry Cowell Redwoods State Park
- Rio Del Mar Beach
- Mission Dolores Park
- Levi's Stadium
- Pier 39
- Six Flags Discovery Kingdom
- Chase Center
- University of California San Francisco
- Seacliff State Beach
- California’S Great America
- Palace of Fine Arts
- Rodeo Beach
- Montara Beach





