
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.

Spacious Top Floor Condo Retreat
Listen to the calming sounds of all the water features throughout the property from the secluded balcony. Inside, relax in 1000 square feet of upscale surroundings that include wood floors and high quality Tempur-Pedic king mattress. Later, head for the ground-floor pools and hot tub. 1000 sq ft of space on the top floor. Queen size adjustable firmness air mattress with clean beddings available upon request to be set up in the living room. You will be able to access the entire unit, 2 Swimming pools, and the hot tub. I will be available by text, phone or email throughout the stay. The quiet and beautiful setting is surrounded by trees. Within walking distance to CalTrain station, San Antonio shopping center, and Whole Foods, Trader Joe, movie theater plus numerous boutiques. Major tech companies located nearby include G00gle and Faceb00k. Stanford University is within a 10 minute drive. A short 5-10 minute walk to the Cal Train stop but the unit is not impacted by any train noise. The bus stop is conveniently around the corner to take you to Downtown Castro Street or Stanford University and beyond.

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.

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.

Pool, Hot tub, Sauna I Your Silicon Valley Luxury
Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

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-11pm) 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.

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.

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

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.

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

Summer-house/OASIS on quiet street in ROCKRIDGE!

Beautiful Large 4BR Home with POOL

Pool, Hot tub, Napa, SFO Clean

Little Poolside House near Downtown Mountain View!

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

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

Beautiful 3BD Home w/ Heated Pool and Fire Pit

Relax and Rejuvenate. Cave Spa, Incredible Views
Condo rentals with a pool

Lakeside Retreat (w/ private parking)

Gated 1BR Condo: AC, Parking, W/D near Santana Row

Furnished 1 bedroom Apartment, Pool, Gym - Monthly

Downtown Modern Living Condo!

Waterfront Condo! Great for Month rentals!

Lovely 1B1B condo with patio near downtown MTV

1BR/1BA Near Santana Row | Work-Friendly + Parking

Luxe 2Bed/2Bath w/ Parking, Fast WiFi, Pool & Gym
Other holiday rentals with a pool

Suite Studio with Kitchen

Wake up to Breathtaking Bay Views in Tiburon

Beautiful Palo Alto -15 mins to Stanford(1090-104)

Cozy 3BR Near SJC

Unreal Beachfront Marin Getaway!

Spacious Luxury Apartment in Heart of Bay Area

Guesthouse in woodside -

D’s Garden Cottage
When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $289 AUD | $230 AUD | $307 AUD | $257 AUD | $421 AUD | $230 AUD | $230 AUD | $343 AUD | $273 AUD | $284 AUD | $290 AUD | $230 AUD |
| 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 $15 AUD per night before taxes and fees

Verified guest reviews
Over 880 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
40 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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