
Holiday rentals with a pool in Woodside
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Woodside
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.

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.

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.

Sanctuary in Sierra Azul Open Space Preserve
Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, steampunk original art, state-of-the-art technology with a unique spa experience, providing the perfect private retreat. Surrounded by numerous hiking trails, many friendly animals, and vast wild forest all around us to explore to your liking, along with this exclusive unit serves to provide a refreshing, rejuvenating space to reconnect with your loved one, yourself and of course Mother Nature!

Private Queen Suite-Pool & Hot Tub, private entry
World Cup spot! Enjoy your private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, Campbell and Willow Glen. Great forLevi's Stadium, Mountain Winery Concerts, 15 minutes-SJC. We have a professional cleaning crew, so just relax and enjoy. Check-out like a hotel, no starting laundry! You will enjoy a well designed private room with queen bed, private entrance and connected private bathroom. Hot tub and Pool are a perfect way to relax and end the evening.

Quiet Poolside Cottage for Solitude
New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

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.

Hillside Retreat Private 2-Room Guest Unit & Pool
Our home is on 1/2 acre hilltop lot, in a secluded, very quiet cul-de-sac, with easy access to major freeways, minutes from SJC airport, downtown, SAP, SJSU, convention center. This listing is for an entire separate unit, attached to main house. It features 2 rooms with private yard and pool to yourself. You are free to relax in the back yard with view, surrounded by mature trees, hummingbirds, butterflies while surf the net, or swim in our private pool when weather permitted.

Large Home in Palo Alto, 5 bedrooms, Pool
This large 5 bedroom and 3 bath home in Palo Alto has plenty of room for big groups and families. The home features 1 king bed, 3 Queen beds, 2 twin beds and a Queen pull-out sofa sleeper. The kitchen is beautiful and well equipped and this large home has plenty of room for everyone to relax. Enjoy the manicured backyard with large deck, BBQ and sparkling pool (w/child safety fence; pool/hot tub not heated). Close to Levi's Stadium, Stanford and downtown Palo Alto.

Beautiful Spacious Living w/Resort Like Feel
Welcome to our lovely spacious studio apartment 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 fully furnished living area, queen comfortable bed, and a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals. Bedroom does not have a door, as this is a studio.

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.
Popular amenities for Woodside rentals with a pool
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!

Beautiful Large 4BR Home with POOL

Trailside Home, Panoramic Views

Little Poolside House near Downtown Mountain View!

Retromodern | Pool | Games | 2LV

Luxury 4-Suite Carbon-Neutral Home With Pool

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

Country Club Living on Golf Course & amazing views
Apartment rentals with a pool

Lakeside Retreat (w/ private parking)

Charming Luxury 2BR w/ Monitor and Adjustable desk

KING BED | Fully Furnished Luxury Condo Gym & Pool

Furnished 1 bedroom Apartment, Pool, Gym - Monthly

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

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

Waterfront Condo! Great for Month rentals!

Willow Place
Other holiday rentals with a pool

Lux Apartment-Pool/Parking/Spa

Private cottage in orchard and vineyard setting

Livermore Cottage, Pets ok.

Artsy 2BD Loft, Pool & H/tub

Los Gatos Villa: hot tub, sauna, pool, and huge yard

The Cool Pool House

Spacious 4BR house | Beautiful Yard + Pool | A/C

Livermore Villa | Pool • Resort-Style • Serene
Quick stats about holiday rentals with a pool in Woodside

Total holiday rentals
Explore 20 holiday rentals in Woodside

Nightly prices starting at
Woodside holiday rentals start at £60 per night before taxes and fees

Verified guest reviews
Over 1,120 verified reviews to help you choose

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Woodside holiday rentals include wifi access

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

4.9 Average rating
Woodside stays are highly rated by guests – averaging 4.9 out of 5!
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- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Capitola Beach
- Muir Woods National Monument
- Oracle Park
- Golden Gate Bridge
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- SAP Center
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- Pier 39
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- University of California-Berkeley
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