
Vacation rentals with a pool in Tamalpais-Homestead Valley
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Tamalpais-Homestead Valley

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

Nightly prices starting at
Tamalpais-Homestead Valley vacation rentals start at G$2,092 GYD per night before taxes and fees

Verified guest reviews
Over 280 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Tamalpais-Homestead Valley vacation rentals include wi-fi access

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

4.9 Average rating
Tamalpais-Homestead Valley stays are highly rated by guests—averaging 4.9 out of 5!
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.

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
4.98 out of 5 average rating, 120 reviews
Farm in the city & sweeping bayview
Our house is a half mile from downtown San Rafael. It is a 1/2 acre with goats, organic gardens, and a pool. It is a farm and resort all in one! We have a bay and city view from almost every room in the house. Wineries 20 miles away. Don't' worry if you're not interested in the farm, the unit is far enough away that you will not be bothered by it. For those who love a good petting zoo, feel free to visit our friendly animals. If you like to cook, we have a gourmet kitchen, and espresso machine
4.87 out of 5 average rating, 195 reviews
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/Roku streaming box. Full sized bed. Ideal for 2 people. Xtra mattress available. Pet friendly. Swimming pool. 10 min walk to downtown Fairfax.
4.99 out of 5 average rating, 122 reviews
Vineyard-House Escape in Sonoma Wine Country
Property is managed by Inspired in Sonoma. Gather your group and enjoy a stunning wine-country home just 5 minutes from downtown Sonoma. This 3 bedroom ensemble includes a main house + guest cottage, pool, hot tub, fire pit, lightning fast Wi-Fi, Sonos Indoor/Outdoor sound system and gas fireplace — perfect for lively group days and quiet restful nights. Surrounded by vineyards, yet close to dining and town, this distinctive retreat invites you to indulge in togetherness, and rejuvenation
4.99 out of 5 average rating, 215 reviews
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.
4.88 out of 5 average rating, 133 reviews
Wine Country Villa Heated Pool Hot Tub Upper Level
Welcome to Brush Creek, 20-minutes from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers 2 unique bedrooms, including a regal King Master suite and a second King bedroom. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. Heated Pool (fees may apply). No one else in the property during your stay. SVR26-101
4.97 out of 5 average rating, 112 reviews
Private cul-de-sac home in Marin with pool
Fully renovated 2-bedroom, 1.5-bathroom home with 3 beds, central AC, strong wifi, family-friendly amenities, private pool, and putting green in Gerstle Park, San Rafael, CA. Short walk to parks, tennis / pickle ball court, restaurants, bars, and shops. 30-minute drive to San Francisco, Berkeley, or Wine Country. Whether it's sightseeing, wine tasting, or local cuisine you're seeking out, we've got you covered. *Loud music + parties are prohibited **Pool is only accessible Apr - Oct
4.96 out of 5 average rating, 114 reviews
Idyllic NatureEstate:Pool,Jacuzi,PuttGreen,Gardens
Mountaintop gated 1 acre nature estate, serene, private, 2300 sq' home; 2500 sq' expansive decks & patios. Solar heated swimming pool. Sun! Enormous forest views. 4BD,3 BA; (4th BD is large family room w/ exc American Leather queen sofabed, twin bed, pool table). Living room fireplace; high speed wi-fi; 65"tv; prem cable pkg. Jacuzzi ($150 min. charge), WeberBBQ & outdoor sink. Putting green. Huge garden, patios, carpeted child's play area. Parties or events not allowed during Covid.
4.95 out of 5 average rating, 219 reviews
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!!
4.92 out of 5 average rating, 589 reviews
Mountain View Retreat
Exclusive garden level retreat in the peaceful coastal hills of Marin County. Private entry French doors open to expansive decks, magnificent views, large infinity pool, hot tub, & gas barbecue grill. 2 Flat-screen cable TV's, with premium channels, (living room & bedroom). High-speed Wi-Fi internet throughout. Central location for easy access to San Francisco, Sonoma/Napa wine country, Pacific Coast beaches, spectacular Redwood forests, and endless miles of hiking & biking trails.
4.95 out of 5 average rating, 221 reviews
An Italian Villa in the heart of Napa Valley!
Villa RayEl was inspired by the farmhouses and small villas of Italy. This rustic property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub and several outdoor living spaces. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!
4.95 out of 5 average rating, 207 reviews
Hillside Wellness Retreat | Pool, Gym & A/C
Escape to your own private hillside wellness retreat in Marin. Recharge with sweeping views, a heated saltwater pool, fitness studio, air conditioning, and a peaceful standalone guesthouse all to yourselves. Perfect for couples, solo travelers, remote workers, & small families seeking relaxation, outdoor adventure, or a getaway. Minutes drive from San Francisco, Napa, Sonoma, hiking, yoga, spas, and farm-to-table dining. Verified ultra-fast reliable WiFi and desk.
4.98 out of 5 average rating, 253 reviewsPopular amenities for Tamalpais-Homestead Valley rentals with a pool
House rentals with a pool

Zen Meets Pool Retreat!
4.99 out of 5 average rating, 241 reviews
Large Charming Home Surrounded by a Vineyard
4.97 out of 5 average rating, 167 reviews
Modern wine country stunner with pool & pickleball
4.95 out of 5 average rating, 131 reviews
Haven: 5 King Bedrooms, Heated Pool and Hot Tub
4.88 out of 5 average rating, 104 reviews
Sonoma Family Cottage with Pool & Hot Tub
4.95 out of 5 average rating, 104 reviews
Eco Luxury Private Sanctuary / The Farmhouse Oasis
5.0 out of 5 average rating, 726 reviews
Craftman’s Castle
4.88 out of 5 average rating, 120 reviews
Sonoma Valley Vacation Home with Seasonal Pool
4.99 out of 5 average rating, 271 reviewsCondo rentals with a pool

Lux Water View with Balcony Minutes -San Francisco
4.95 out of 5 average rating, 133 reviews
Silverado! Luxe King Suite Mountain View Balcony
4.99 out of 5 average rating, 551 reviews
Fairway Escape | BBQ | Firepit | Golf Course View
4.99 out of 5 average rating, 104 reviews
Silverado Resort Condo with Pool
4.95 out of 5 average rating, 218 reviews
Silverado Resort - Private 3 Bedroom, 2 Bath Condo
4.9 out of 5 average rating, 107 reviews
Modern Napa Escape | 2BR Golf Course View | Pool
4.99 out of 5 average rating, 160 reviews
Fairways Silverado Golf and Country
4.94 out of 5 average rating, 154 reviews
Chic 1 BR Condo Par Excellence at Silverado Resort
4.99 out of 5 average rating, 273 reviewsOther vacation rentals with a pool

Sunny Inverness Cottage
4.85 out of 5 average rating, 791 reviews
The Guest House Bed and Breakfast
4.91 out of 5 average rating, 275 reviews
Heated Pool, Jacuzzi, Sauna, Huge Views, Chic ADU!
4.97 out of 5 average rating, 316 reviews
Idyllic Sonoma Vineyard Farmhouse With Pool
4.98 out of 5 average rating, 160 reviews
Farm Cottage With Private Pool
4.93 out of 5 average rating, 130 reviews
The Willow Cottage
4.94 out of 5 average rating, 145 reviews
Tropical Garden Cottage +HOT TUB &POOL by Downtown
4.91 out of 5 average rating, 661 reviews
Rustic Cabin in the Redwoods
4.99 out of 5 average rating, 379 reviewsDestinations to explore
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