
Holiday 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.

Lux Water View with Balcony Minutes -San Francisco
Luxury Waterfront Retreat | Breathtaking Panoramic Views Wake up to stunning, panoramic water views from every room and balcony in this spa-like, resort-style haven! Whether you're seeking a romantic getaway, executive retreat, or a peaceful stay for remote work or travel nursing, this luxurious space offers the perfect escape. Free onsite parking, 24/7 security patrol for your peace of mind Trader Joe's, restaurants, San Francisco, UC Berkeley, Emeryville Marina & access to Silicon Valley

Pool, Jacuzzi, Sauna, Huge Views, gated, 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 May 31st to October 30th. 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)

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.

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.

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

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.

Private Garden Cottage in Belmont Hills
A fully accessorized cottage in a private and quiet setting at the heart of the San Francisco Bay Area. Newly renovated backyard with always blooming flowers, fruit trees, hot tub, and pool. Regular visits from deer, and professional night illumination make this place feel like a magical forest getaway, quiet and secluded from the surrounding city. Enjoy the multitude of patios for reading and relaxation. We even have a tree house for the kids.

Spacious & Luxurious 1 BR w/Pool & Free Parking
Welcome to our Luxurious 1 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, comfortable Queen size bed, with a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.

Private Oasis Btwn SF, Napa. Big Views + Pool!
Enjoy sunsets from your private deck in the hills above San Rafael — a peaceful retreat that feels like a treehouse (with no stairs!). Just 15 mins to San Francisco and 45 mins to Napa or Sonoma, it’s the perfect base for exploring Marin’s towns and trails or simply relaxing (guests love the bed!). Separate building, heated pool (May–Sept), and streaming TV. I’m happy to help you plan your Bay Area adventure!

Gated 3 BR Home. Heated Pool. Top Location.
Fully remodeled gated home on exclusive private lane in the heart of Walnut Creek. 2000" ft, single story. Pool heated 365 days. Fully landscaped 1/2 acre Yard. Walk to shops, restaurants, parks, hiking and biking trails. Minutes from downtown Walnut Creek, freeways and train (BART) stations to SF and Bay Area. No Guest Cleaning Tasks for check out. *NO PARTIES OR EVENTS * STRICTLY ENFORCED *

Private Oasis with Pool and Fire Pit
Escape to our private oasis where every detail is designed for your ultimate comfort. Indulge in a refreshing swim in our pool. Unwind and relax in our outdoor lounge area complete with a cozy firepit, perfect for savoring a glass of wine with your loved ones. Whether it’s a family retreat, a couples getaway or a work gathering, your ideal stay begins here! ** We do not offer pool heating **
Popular amenities for San Mateo rentals with a pool
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!

Pool, Hot tub, Napa, SFO Clean

Beautiful Large 4BR Home with POOL

Large Home in Palo Alto w/Pool

Little Poolside House near Downtown Mountain View!

Spacious 4BR Home w/Pool, A/C & Multiple KingBed

Chic & Fun Mid-Century Modern sleeps 8 (pool)

3 BR Home on Vineyard nr Palo Alto & Stanford
Apartment rentals with a pool

Charming Luxury 2BR w/ Monitor and Adjustable desk

KING BED | Fully Furnished Luxury Condo Gym & Pool

Furnished 1 bedroom Apartment, Pool, Gym - Monthly

Downtown Modern Living Condo!

Entire 1BR Apt•Bright, Clean, Spacious & All Yours

Waterfront Condo! Great for Month rentals!

Lovely 1B1B condo with patio near downtown MTV

Modern, bright 2 bedroom/1 bath 2nd story
Other holiday rentals with a pool

Lux Apartment-Pool/Parking/Spa

Cozy 1BR Apt in the heart of Silicon Valley

Private cottage in orchard and vineyard setting

Cozy 3BR Near SJC

Charming Studio Guest House in Alamo

Beautiful Nob Hill Studio Apt

Modern-Roomy 2BR/2BA/Pool • Near Levis, Tech & SCU

Country Club Living on Golf Course & amazing views
When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £140 | £112 | £149 | £125 | £205 | £112 | £112 | £166 | £133 | £138 | £141 | £112 |
| 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 |
Quick stats about holiday rentals with a pool in San Mateo

Total holiday rentals
Explore 110 holiday rentals in San Mateo

Nightly prices starting at
San Mateo holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
100 of San Mateo holiday rentals include wifi 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
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