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

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.

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.

The Hacienda- Santa Cruz Mountain Ridgetop Retreat
"Welcome to the Hacienda", a modest mid-century retreat located in the beautiful Santa Cruz Mountains. The Hacienda is located just 5 minutes from Ben Lomond town, 10 minutes from Henry Cowell State Park and only a 20 minute drive from Santa Cruz beaches. Our unique private home includes a pool & hot tub which sits on the ridgetop overlooking the gorgeous San Lorenzo Valley. If you're looking for peace & tranquility or simply need to relax and recharge, the Hacienda awaits your arrival.

Poolside Retreat with Views • Private Guesthouse
Private hillside retreat with sweeping views, heated pool (May–Sep) & a standalone guesthouse all to yourselves. Ideal for couples seeking a peaceful escape - minutes from Marin's trails, charming towns, & easy day trips to San Francisco, Napa, Sonoma. Enjoy a getaway with the confidence of a top 1% local Superhost, personal recommendations, and a curated guidebook to help you experience the very best of the area. Marin's 1st Green Business Certified vacation rental.

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.

Lafayette Treehouse - Relax and Rejuvenate
Relax and rejuvenate your spirit in this uniquely designed home, situated under a canopy of sprawling oaks. It has incredible panoramic views of Mt. Diablo and the surrounding valley, and multiple areas to relax. Hang out on the deck with a glass of wine, take a dip in the refreshing salt-water pool, or just melt away in our therapeutic cave spa. Centrally located in the East Bay just minutes from Lafayette, Walnut Creek, Berkeley and ~35 minutes from San Fran.

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.

Sanctuary in Sierra Azul Open Space Preserve
Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, original art and spa amenities, 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!

Stay Alpha Home • Modern Redwood Retreat with Pool
Permit 231266 - Nestled in the Santa Cruz mountains is this serene oasis, rustic with modern touches and a stunning pool (the upper pool and main pool are not heated). Embrace yourself with the lush tropical setting and gorgeous redwood groves in this mesmerizing, unique villa. With distance between you and the closest neighbor, it’s perfect for families and nature enthusiasts seeking a rejuvenating retreat. Your redwood getaway awaits!
Popular amenities for San Francisco Peninsula rentals with a pool
House rentals with a pool

Beautiful Large 4BR Home with POOL

Pool, Hot tub SFO, Napa, Clean Home

Fully renovated private cul-de-sac home in Marin

Large Home in Palo Alto, 5 bedrooms, Pool

Little Poolside House near Downtown Mountain View!

Waterfront home w/ private dock and pool

Private Oasis with Pool and Fire Pit

Beautiful 4 Bedroom Hillside Retreat
Apartment rentals with a pool

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

Quiet & Comfortable Entire Furnished Apartment

KING BED | Fully Furnished Luxury Condo Gym & Pool

Downtown Modern Living Condo!

Modern 1B1B condo + quiet patio | Downtown Mt View

New listing, AC, spacious condo w mountain view

Large two-bedroom two bath condo in Palo Alto

Willow Place
Other holiday rentals with a pool

Quiet Poolside Cottage for Solitude

Cozy 2BR w/ Patios, Prime Mountain View Location

Garden Oasis 1 BR Suite w Spa & Pool, Walnut Creek

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

Private Queen Suite-Pool & Hot Tub, private entry

Idyllic NatureEstate:Pool,Jacuzi,PuttGreen,Gardens

Cozy BUS on Farm Animal Rescue with CITY VIEW

Tropical Garden Cottage +HOT TUB &POOL by Downtown
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- Muir Woods National Monument
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- Golden Gate Bridge
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- Moscone Center
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- SAP Center
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