Holiday rentals with a pool in Kentfield

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.

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.

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.

Spectacular Stone Pool/Spa with Views; Near Plaza

A spectacular stone pool and spa with bubbling stream compliments the warm and welcoming Summers House. (Please see notes below regarding pool and spa fees.) The house exudes charm. Sweeping views reach to the San Francisco Bay. Art, antiques and books create an embracing ambiance. Nestled into three, private wooded acres, Summers House is near wineries, and just 10 minutes from Sonoma Plaza restaurants, shops, and events. Well equipped kitchen, great dining spaces, large deck, comfy beds.

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.

Private Oasis Btwn SF, Napa. Big Views + Pool!

April 2026: The pool is open! Enjoy sunsets from your private deck in the hills above San Rafael — a peaceful retreat that feels like a treehouse (with no stairs!). Just 15 mins to San Francisco and 45 mins to Napa or Sonoma, it’s the perfect base for exploring Marin’s towns and trails or simply relaxing (guests love the bed!). Separate building, heated pool (May–Sept), and streaming TV. I’m happy to help you plan your Bay Area adventure! 1st Green Business Certified vacation rental in Marin!

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!!

707 BARREL LOUNGE Cottage

LIVE ALOHA IN SONOMA! Enjoy this tropical Hawaiian Getaway in the Heart of Sonoma Wine Country. Sonoma is a great little town to eat, drink, shop, hike, bike, walk, swim, and relax. There is so much to do here! This cottage will put you in a vacation state of mind as soon as you arrive. Relax around the pool, enjoy a good book, walk into town or hire a car service and visit some of the many amazing wineries in the Sonoma-Napa-Alexander Valleys. COME ENJOY ALOHA IN SONOMA!

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.

Wine Country Gem - Sonoma Cottage with Pool Oasis

Charming Sonoma cottage perfect for a romantic getaway, girls’ trip, or family stay. Explore Sonoma, Glen Ellen & Napa with ease. The private unit has gourmet appliances, a minimalist-country style, and its own deck with dining + lounge seating. The peaceful 1-acre property features vineyards, a large saltwater pool, a veggie + herb garden, and fruit trees. Relax, recharge, and enjoy the best of wine country living. TOT #3140N