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

Beautiful 4 Bedroom Hillside Retreat
Peaceful retreat on top a hill with breathtaking views of Pinole Valley and surrounded by nature. 4 bedroom 2.5 bathroom home comes with huge backyard, swimming pool*, gazebo, private driveway, beautiful panoramic views. circular driveway. View of the sunset every night. May see the turkey and herd of deer during your stay. 30 minutes away from San Francisco, 15 mins away from Berkeley, and 30 mins away from Napa. *Pool is available but NOT HEATD *Jacuzzi available, NOT HEATED and NOT WORKING

Fairfax Studio-style Cottage
Take it easy at this quaint getaway. Our new 240 sq ft studio cottage sits at the front of our property with a fenced in yard and separate entrance gate. Mini-kitchen has an under-counter fridge/freezer, microwave, toaster oven, induction plate, electric kettle and coffee maker. Heat/cool pump heats or cools the space quickly and quietly. Smart TV w/cable. Full sized bed. Ideal for 2 people. Xtra mattress available. Pet friendly. Swimming pool. 10 min walk to downtown Fairfax. New router 4/24.

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.

Wildwood Retreat and Pool
The Wildwood Retreat is located on a wooded 2 acre country property in the hills above Sonoma just minutes from the Historic Downtown Sonoma Plaza. The newly remodeled studio apt is very private on a separate level below the main house conveniently close to the pool. Amenities include a king size bed, kitchenette, private bath,sunny deck,pool access and convenient parking. Great walks are just outside your door. This tranquil retreat is ideally located for enjoying all the Wine Country offers.

Designer Sonoma Getaway with Pool, Hot Tub & Bocce
Thornsberry House is a luxe Wine Country home nestled between the two oldest wineries in California while just 5 minutes from the Sonoma Square. Renovated to accommodate the most discerning traveler, it consists of two separate buildings connected by a breezeway and large deck. Situated on the east side of town, it offers a true escape where one can walk or bike down to Gundlach Bundschu at the end of our street, or soak up the afternoon light from the heated pool, hot tub or a game of bocce.

Farm Cottage With Private Pool
*NOTE: the pool is solar heated and is only open JUNE 1- OCTOBER 31. Private, quiet, peaceful family or couple-friendly rustic farm cottage, wine country retreat with a private pool minutes away from wineries, like Schug, Gloria Ferrar, Viansa, Ram's Gate and Sonoma town square. Solar-heated pool is open June-October. We are locked in by three dead-end roads, so it's very quiet. Large deck, large pool patio, kids' play structure, and more. Horses are our neighbors and life slows down here.

1 BR suite in Rock & Roll History
A gated driveway and private entryway greets you as your arrive at your bucolic getaway. We are located next to a popular Open Space preserve great for hiking or biking. Both San Francisco and the Wine Country are 45 minutes away! Crosby, Stills, Nash & Young lived on this property when they produced their classic "Deja Vu" album in the early 70's. The album cover photo was taken under our special and majestic oak tree and the photo was developed in the dark room that is now the bedroom.

Gma's Ranch House | Nostalgic Charm, Surreal Views
*Spacious Ranch Retreat: 4 bdrm/4 bath home overlooking a working dairy ranch. *Calm Setting: Enjoy a peaceful environment where your only neighbors are cows! *Outdoor Bliss: Relax by the pool with stunning landscape views, private courtyard, and vast deck. *Fun for All: Arcade/game room for endless entertainment. *Modern Comforts: Deluxe amenities, workspaces with high-speed WiFi, and a full kitchen with organic staples. *Professionally cleaned, no checkout chores, and plenty of parking.

MCM Waterfront Pool/Hot Tub between SF and Napa
Mid Century Modern-MCM Time Capsule right on San Francisco Bay! 15 minutes to Golden Gate Bridge, 30 minutes to wineries. All original architectures and features. Stunning property! To make sure our house fits your needs PLEASE click on “Show more below and read our entire listing as well as the "House Rules" and "Safety & property" sections at the very bottom of this page before sending us a booking request. We live in a quiet neighborhood and have strict noise limits after 10pm!!

Petaluma Wine Country relaxing get away w/pool/spa
Your own studio guest house retreat complete w/ Cal king bed, large bathroom w/ walk-in tiled shower, vaulted beam ceilings, wall fireplace, A/C/heater, 2nd bed sleeper sofa for adult/kids,, Wi-Fi, 60 “TV w/swing arm for in bed movies, walk-in closet, , pool, spa, outdoor furniture, refrig, high top table. Walk to downtown, restaurants, theater district. Hiking 2 blocks away. Washer/dryer *during off Summer months outdoor cushions removed due to the weather. Pool/spa hrs 9am-9pm

Eco Luxury Private Sanctuary / The Farmhouse Oasis
**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols
Popular amenities for Tamalpais-Homestead Valley rentals with a pool
House rentals with a pool

Sonoma Ranch, private pool on 7 acres!

Modern wine country stunner with pool & pickleball

Eclectic Hideaway with Backyard Pool & Hot Tub

Spectacular Stone Pool/Spa with Views; Near Plaza

Nice Wine Country Family Home

Luxury home (+ pool house) with views, pool & spa

Happy House Getaway - Pool, Hot Tub & Wine Country

Silverado Napa Remodeled 3 bed 2 bath
Apartment rentals with a pool

Silverado Resort Dual Suite golf course villa

Silverado! Luxe King Suite Mountain View Balcony

Chic 1 BR Condo Par Excellence at Silverado Resort

Casa Vina at Silverado Resort and Spa | Fireplace

Spring Stay at Silverado | King 1BR

Fairways Silverado Golf and Country

1 bed | 1 bath | Silverado Resort Experience

Beautiful Premium Jr Suite, Silverado Resort & Spa
Other holiday rentals with a pool

Farm in the city & sweeping bayview

Lux Apartment-Pool/Parking/Spa

Villa Annadel - Stunning 5 Bedroom with a Pool

Separate entry room near Stanford

Wine Country Oasis w/ Pool, Hot Tub, Orchard, Barn

Wine Country Gem - Sonoma Cottage with Pool Oasis

2bdr/2ba Silverado Resort : Gated + Golf Views

Sunol Chalet | 80 Acres • Pool • Gym • Game Room
Quick stats about holiday rentals with a pool in Tamalpais-Homestead Valley

Total holiday rentals
Explore 20 holiday rentals in Tamalpais-Homestead Valley

Nightly prices starting at
Tamalpais-Homestead Valley holiday rentals start at $127 SGD per night before taxes and fees

Verified guest reviews
Over 360 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Tamalpais-Homestead Valley holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Tamalpais-Homestead Valley rentals

4.8 Average rating
Tamalpais-Homestead Valley stays are highly rated by guests – averaging 4.8 out of 5!
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- Moscone Center
- Stanford University
- Golden Gate Park
- Oracle Park
- Muir Woods National Monument
- Golden Gate Bridge
- Twin Peaks
- Pier 39
- Six Flags Discovery Kingdom
- University of California-Berkeley
- Montara Beach
- Palace of Fine Arts
- Levi’s Stadium
- California’S Great America
- Bolinas Beach
- Painted Ladies
- San Francisco Zoo
- Googleplex
- Rodeo Beach
- Doran Beach
- Duboce Park
- Safari West
- California Academy of Sciences
- Johnson's Beach




