Holiday rentals with a pool in Fairfield

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

Value · Location · Nearby

Silverado Napa Remodeled 3 bed 2 bath

Beautiful Silverado Resort & Spa home with 2 bedrooms, 3 beds (one is pullout sofa in living room), & 2 baths in a gated community. One bathroom is ensuite. Home sleeps 6 guests. One of the pools is next to the unit (open seasonally). Remodeled kitchen, dining room and laundry in property. About 10 stairs from carpet to front door. Tennis court access and extensive walking trails. Located on the grounds of Silverado Resort and Country Club. Just minutes to downtown Napa and numerous wineries.

Family · Location · Indoor spaces

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.

Value · Location · Long stay

Sonoma Family Cottage with Pool & Hot Tub

Property is managed by Inspired in Sonoma. Family-friendly 2-bed, 1-bath Sonoma cottage with a heated saltwater pool, heated for $75 a day (November-March) with a two night minimum. six person hot tub, and firepit. Accommodates up to six Guests with sleeper sofa and junior bunk beds. Close to Sonoma Square, wineries, restaurants, and Napa. Perfect for families or small groups seeking a budget-friendly Wine Country retreat. Book now to enjoy unforgettable Sonoma adventures! Permit # ZPE15-0206

Value · Family · Outdoor spaces

Sherrie's Vineyard View Retreat-Pool, Spa, N.Napa

Enjoy our vineyard view and a glass of wine by the firepit! Relax in our ONE BEDROOM SUITE, ON THE LOWER LEVEL OF OUR TRI-LEVEL HOME. Conveniently located in N. Napa, we're near Alston Park for hiking, wineries, places to eat & shop. Enjoy a fresh-baked BREAKFAST, a dip in the pool (heated mid-June to Sept), spa (year-round) & many places for relaxing. Our suite is well appointed with a comfortable bed, fine linens, duvet, robes & slippers. DRIVING SERVICES may be added to enhance your tours.

Value · Family · Hiking

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.

Value · Location · Indoor spaces

Silverado! Luxe King Suite Mountain View Balcony

Apartment with views! Top floor Silverado Resort Premium 1 bedroom Suite. (not studio), Large 1BR 1 BA 676 sq. ft. w/ rare mountain views. Furnished Balcony. Living dining rooms,separate BR Condo pool steps away! *Price incl tax. Walk to market,dining,mansion. Modern appliances.Full kitchen Luxurious fine Italian linens from Frette on King bed. Just like a 5-star hotel. Roku streaming,Directv Hang out or walk in relaxing grounds! La-Z-Boy queen sofabed, Aug 2025. Free EV chargers nearby.

Value · Family · TV

Craftman’s Castle

This upscale three bedroom home sits on a large grassy lot. Featuring a master suite with king bed overlooking the sky blue pool, dine in the fully equipped kitchen, work remote at our comfortable work station, lounge on the spacious patio, warm up at the fireplace or fire pit, barbecue, or walk on nearby canal trail. Ample parking, washer/dryer, large screen T.V. There is an ADU that is rented occasionally. It is next to the detached garage (not part of rental). No windows view backyard.

Value · Family · Biking

Poolside Retreat | Patio | 10 Min to DT

Enjoy a romantic getaway for two in this cozy, stylish condo—perfect for sunny wine-country days. Just steps from the pool and parking, it’s easy to spend afternoons wine tasting in Napa or strolling Yountville, then unwind on the front porch or private patio with a glass of wine. Guests love the fresh décor, spotless space, and attentive host. With access to resort amenities, restaurants, Tesla charging, laundry, and more, this bright retreat is your ideal spring and summer escape.

Family · Location · View

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!

Location · Family · Biking

Garden Oasis Studio with Spa and Pool Walnut Creek

Former Plus-rated Studio. How about a rejuvenating get-away with pool and hot tub? Picture window overlooking a garden. Sunbathe poolside. Watch TV from a comfy queen bed. 27 stairs to house, 3 stairs inside unit. Complimentary beverage for 3+ nights/return stay. After 10 stays, $100 credit. Deep cleaned. 2 separate units off same foyer; no shared walls. Private locked unit door. Shared access to spa/pool not heated (9am-10pm) for overnight guests only. Host lives upstairs.

Location · Value · Laundry

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Location · Value · Checkout