
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.

The Alpaca House
Welcome to La Casa de Alpaca. Our home is located in the beautiful Rivermark community of Santa Clara. The space consists of 2 bed / 2 bath located on the top floor, with access to a pool, hot tub, gym, and yoga room. Local Destinations: Santa Clara Convention Center Great America Theme Park Downtown San Jose Levi's Stadium SAP Center Oracle Rivermark shopping area: restaurants and groceries AMC Mercado 20 Plaza: restaurants and movies We are business traveler ready with high-speed Internet.

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.

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.

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.

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.

Luxury Silicon Valley Wellness and Work Oasis
Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Luxurious Ritz Suite w fireplace, Business retreat
All natural limestone allergen-free retreat, lush greenery, indoor/outdoor living. Very quiet, safe location, walk to conveniences, parks. Easy parking * Separate french door entrance * Self check-in & check-out with lockbox * Spacious suite with high ceilings * Gas fireplace * Kitchenette * Walk-in closet * Spa bathroom * Upgraded high speed WiFi * Aroma & sound therapy * Portable grill available
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

Large Home in Palo Alto, close to Levi's Stadium

Trailside Home, Panoramic Views

Little Poolside House near Downtown Mountain View!

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

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

Private Oasis with Pool and Fire Pit
Condo rentals with a pool

Charming Luxury 2BR w/ Monitor and Adjustable desk

Charming 1 bedroom, 1 bath, 2 Story Condo.

Furnished 1 bedroom Apartment, Pool, Gym - Monthly

Luxury 2BR Condo Pool, & Gym | Near Levi’s Stadium

Downtown Modern Living Condo!

Entire Condo - comfy and central

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

Waterfront Condo! Great for Month rentals!
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

By The Bay Retreat

Cozy 3BR Near SJC

Charming Studio Guest House in Alamo

Luxe Apartment Downtown San Jose w/ Gym, Pool

KeyLuxe, Jacuzzi—Pool—Gym—Tennis, Walnut Creek
When is the best time to visit San Mateo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $265 AUD | $212 AUD | $282 AUD | $236 AUD | $387 AUD | $212 AUD | $212 AUD | $315 AUD | $251 AUD | $282 AUD | $270 AUD | $282 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 $14 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
30 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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- Castro Street
- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Levi's Stadium
- Capitola Beach
- Muir Woods National Monument
- Oracle Park
- Golden Gate Bridge
- Rio Del Mar Beach
- Seacliff State Beach
- Baker Beach
- Twin Peaks
- SAP Center
- Santa Cruz Beach Boardwalk
- Mission Dolores Park
- Henry Cowell Redwoods State Park
- Pier 39
- Las Palmas Park
- University of California-Berkeley
- Montara Beach
- Six Flags Discovery Kingdom
- Palace of Fine Arts




