Vacation rentals with a pool in Fairfield

4.96 out of 5 average rating, 275 reviews

A tranquil pool surrounded by a spacious deck features lounge chairs for relaxation. The sun casts a warm glow over the water, highlighting the adjacent charming cottage and lush greenery. Tall trees provide shade, enhancing the serene atmosphere.

Guesthouse in Oakland

Pool, Jacuzzi, Sauna, Huge Views, gated, ADU

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated May 31st to October 30th. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

4.96 out of 5 average rating, 198 reviews

A serene courtyard features a circular firepit surrounded by four wicker chairs, inviting relaxation. Sunlight filters through the trees, creating a warm ambiance. Lush greenery and a vineyard view extend beyond the enclosure, enhancing the tranquil outdoor space.

Guest suite in Napa

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.

The spacious bedroom features a king bed with soft linens, complemented by bedside tables with lamps on either side. Neutral walls create a calming environment, while a decorative throw pillow adds a touch of warmth. A doorway leads to an ensuite bathroom.

4.99 out of 5 average rating, 154 reviews

Charming Condo: King Bed, Pool Access, 2 Patios

Plan an unforgettable and romantic stay for 2 in this comfortable condo conveniently located just off the condominium pool and parking lot. You’ll love having intimate conversations on the front porch and backyard patio. Enjoy access to resort amenities, restaurants, pool, Tesla charging station, laundry, and more. Guests rave about cleanliness, décor, and responsive host. You’ll look forward to returning to your home base after experiencing wine-tastings or exploring downtown Napa/Yountville!

The exterior of a private cottage is displayed, featuring a inviting entrance framed by shrubs and trees. Sunlight filters through the branches, casting a warm glow on the cottage dimensions. A pathway leads to the door, complementing the landscaped surroundings.

4.95 out of 5 average rating, 117 reviews

Casa Vina at Silverado Resort and Spa | Fireplace

Welcome to Casa Vina! Located in one of the best locations at Silverado, close to the HOA pool, Grill and baked goods from the Market, this end unit cottage has golf course and mountain views, a wood burning fireplace and no one upstairs. Updated with mid-century West Elm furniture, 55" TV, enlarged shower, Casper Mattress, stainless steel kitchenette and Keurig coffee maker, this is one of the nicest junior suites at Silverado. Discounted spa day passes available for purchase, when available.

Farm stay in Walnut Creek

The bedroom features a spacious bed with neutral bedding accompanied by vibrant accent pillows. A colorful piece of wall art adds visual interest, while two windows allow natural light to filter in. A small sitting area is present with a plant nearby, enhancing the welcoming feel.

4.99 out of 5 average rating, 579 reviews

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 bed before falling into a restful sleep. 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 (9am-11pm) for overnight guests only. Host lives upstairs.

A modern living space is displayed with a sectional sofa adorned with decorative pillows. A rectangular coffee table is centered on a subtle area rug, while a round mirror adds depth to the room. The open layout connects to a kitchen area featuring sleek cabinetry and bar seating.

5 out of 5 average rating, 120 reviews

Serene 1 BR Condo at Silverado Resort

Calming, relaxing, and stylish, this newly-remodeled 2nd floor condo at Silverado Resort is modern, serene, and peaceful. It’s perfect for a couple's celebration, a special birthday, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

4.87 out of 5 average rating, 179 reviews

A light-filled living area features a cozy fireplace and large windows, offering views of the surroundings. The open floor plan connects the living space to a dining area and a fully equipped kitchen. Modern amenities such as Wi-Fi and cable TV are indicated in the foreground.

Home in Napa

Silverado Napa Breath Taking Remodel 3 bed 2 bath

Beautiful Silverado Resort & Spa luxury remodeled home with 2 bedrooms, 3 beds (one is pullout sofa in living room), 2 bath, and luxury accommodations with gated entry. 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. Tennis courts access and extensive walking trails. Located on the grounds of Silverado Resort and Country Club. Just minutes to downtown Napa and numerous wineries.

4.96 out of 5 average rating, 179 reviews

The exterior of the villa is adorned with lush greenery and shrubs, creating a serene atmosphere. The warm-toned facade features a tiled roof and wooden shutters. A gravel driveway leads to the entrance, framed by neatly arranged garden spaces and decorative pots.

Villa in Napa

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this 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. 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!

Guesthouse in Walnut Creek

A wooden deck is framed by palm trees, featuring a round table and an adjacent chair. The view captures a sparkling pool, surrounded by lush greenery, inviting relaxation in a serene outdoor setting.

4.91 out of 5 average rating, 607 reviews

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 mile from Berkeley/Oakland, 50 mile from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mile from Walnut Creek BART station and 1 mile from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big and is good for couples, solo and business travelers.

Guesthouse in Walnut Creek

An open-concept living space is highlighted by a modern kitchen featuring light cabinetry and stainless steel appliances. Large windows provide natural light and scenic views. A cozy seating area includes a dark sectional sofa facing a television, and a colorful area rug adds warmth to the floor.

4.96 out of 5 average rating, 124 reviews

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

4.97 out of 5 average rating, 193 reviews

Guesthouse in San Rafael

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

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!

4.83 out of 5 average rating, 103 reviews

The entrance to a cave spa is framed by lush blooming plants, with stone walls and a wooden door. A sign announces 'Estate Cave - Spa Terra - Trinitas Tasting Room' above an arched entrance, complemented by a bench and vibrant flowers in the foreground.

Apartment in Napa

Getaway in Napa! Bowling, Spa and More all Open!

Many of the area's most awarded wineries are just a short drive away. Only 10 minutes from downtown, home to Oxbow Public Market and the Napa Valley Wine Train, shopping & world-class dining. • Guest checking in must be 21+ with valid ID & card for $250/night refundable security deposit (credit card only) • Resort fee of $6.32+tax/night paid at check-in • Name on reservation must match photo ID at check-in

Popular amenities for Fairfield rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 113 reviews

A cozy outdoor space is illuminated by string lights, creating a warm ambiance. A small round table sits in the center, surrounded by chairs. Nearby, a garden cottage and trees provide a natural backdrop, enhancing the serene atmosphere of the backyard.

Home in Upper Rockridge

Summer-house/OASIS on quiet street in ROCKRIDGE!

4.91 out of 5 average rating, 218 reviews

A private outdoor area features a modern hot tub alongside a comfortable seating arrangement. Bright turquoise chairs offer a pop of color, while tall trees provide natural shade. The concrete patio is spacious, ensuring ample room for relaxation and enjoyment.

Home in Concord

Pool, Hot tub, Napa, SFO Clean

An outdoor pool area is highlighted, featuring a spacious pool set against a backdrop of lush greenery and distant hills. Comfortable lounge chairs are positioned along the pool's edge, inviting relaxation. A shaded umbrella adds to the leisure space.

4.93 out of 5 average rating, 116 reviews

Sonoma Ranch, private pool on 7 acres!

5 out of 5 average rating, 4 reviews

Home in Glen Ellen

Oak & Vine: Pool | Hot Tub | Fire Table | BBQ

The image showcases a spacious swimming pool surrounded by a manicured lawn and lounge chairs. Two stylish cabanas are positioned beside the pool. Lush trees are visible in the background, complementing the modern design of the home with solar panels on the roof.

4.97 out of 5 average rating, 101 reviews

Modern wine country stunner!

The living room features a muted green accent wall and a large flat-screen TV mounted above a dark wooden sideboard. A gray sofa and two yellow accent chairs are positioned around a wooden coffee table, which is topped with magazines. Natural light filters through plantation shutters.

4.93 out of 5 average rating, 273 reviews

Eclectic Hideaway with Backyard Pool & Hot Tub

4.94 out of 5 average rating, 108 reviews

The exterior view captures a spacious waterfront home with a private dock featuring a floating pool. Palm trees line the property, and outdoor seating areas are visible. A covered section houses a boat, enhancing the serene waterfront setting.

Home in Discovery Bay

Waterfront home w/ private dock and pool

Two white Adirondack chairs are positioned next to a heated swimming pool, surrounded by lush greenery. The clear blue water reflects the bright sky, while lounge chairs are positioned nearby. The serene atmosphere invites relaxation and enjoyment in the outdoor space.

4.88 out of 5 average rating, 313 reviews

*Heated* Swimming Pool Retreat Near Sonoma Square

Condo rentals with a pool

4.91 out of 5 average rating, 304 reviews

A modern living space presents a deep-seated couch paired with a stylish coffee table, set against a backdrop of vibrant artwork. Natural light filters in through a window, while a door leads to the outside. A dining area is visible in the corner.

Condo in Civic Center

Lakeside Retreat (w/ private parking)

A modern living space features a stylish fireplace with a lit fire, beside a coffee table displaying a bottle of wine and two glasses. A large television screen showcases a golf scene, while sliding glass doors provide access to a private balcony with green views.

4.97 out of 5 average rating, 35 reviews

Fairway Getaway

An open concept living and dining area showcases wooden flooring and a spacious dining table surrounded by woven chairs. A comfortable seating space features a large rug and a bright blue accent chair. Large glass doors offer views of the outdoor area with greenery.

4.95 out of 5 average rating, 110 reviews

Wine Country Living at it's best at Silverado CC

4.77 out of 5 average rating, 56 reviews

An open-concept living area features a spacious sectional sofa and a coffee table, complemented by a dining area with tall, modern stools. Natural light enters through sliding glass doors leading to the patio, while a well-equipped kitchen with wooden cabinetry is visible in the background.

Condo in Oakland

Waterfront Condo! Great for Month rentals!

The open-concept kitchen features modern appliances, including a microwave and oven, complemented by a large island with seating. Natural light floods the space, which seamlessly connects to the living area, revealing views of the outdoor patio through oversized windows.

4.93 out of 5 average rating, 135 reviews

Fairways Silverado Golf and Country

A row of charming cottages is lined along a walkable path, featuring varied exterior colors including blue, yellow, and red. Each unit has large windows and decorative gables, surrounded by neatly trimmed hedges and lush green trees, enhancing the inviting neighborhood atmosphere.

4.73 out of 5 average rating, 2,556 reviews

One Bedroom Cottage Along the Napa River

A modern kitchen features light cabinetry and a spacious island with seating for four. Two pendant lights hang over the counter. Stainless steel appliances are strategically placed, with natural light streaming in through a window, highlighting the sleek design.

5 out of 5 average rating, 80 reviews

*Fairway Retreat at Silverado

A light-filled living area showcases a comfortable sofa accompanied by decorative pillows. A round dining table with chairs is positioned nearby, complemented by potted plants. The kitchenette features cabinetry and appliances, while a large window offers a view to the patio.

4.89 out of 5 average rating, 92 reviews

Your wine and wellness retreat at Silverado Resort

Other vacation rentals with a pool

4.93 out of 5 average rating, 72 reviews

A light-filled living area features a comfortable sofa, decorative chairs, and a dining table for four. Large glass doors provide views of the outdoor space. The well-equipped kitchen is visible in the background, accented by cheerful neutral tones and inviting textures.

Apartment in Napa

Silverado Retreat | Dwtn Minutes Away | Sleeps 4

5 out of 5 average rating, 23 reviews

The interior space features a cozy seating area with a green pull-out couch and a small wooden desk. A round mirror hangs on the wall opposite the open doorway, where natural light filters in through a window. A circular rug complements the minimalist decor.

Cabin in San Rafael

Peaceful Writer’s Cabin in Marin

4.97 out of 5 average rating, 36 reviews

A serene pool area with a sparkling blue surface reflects the surrounding greenery and vibrant flowering plants. Comfortable seating is positioned nearby, and an umbrella provides shade on the edge of the pool, inviting relaxation amid tranquil natural scenery.

Guesthouse in Davis

Fairytale retreat Davis Sacramento

5 out of 5 average rating, 49 reviews

A well-equipped kitchen features a large central island with a light-colored countertop, two pendant lights hanging above. The space showcases stainless steel appliances, ample cabinetry, and an open layout that connects to the living area and dining space, with views of the outdoor surroundings.

Apartment in Napa

*Relaxing Condo at Silverado

4.94 out of 5 average rating, 81 reviews

A long lap pool is framed by neatly trimmed hedges and grass, surrounded by mature trees. The clear water reflects the blue sky and nearby foliage, creating a serene atmosphere. Sunlight illuminates the setting, highlighting the lush garden surroundings.

Guesthouse in Davis

Garden Guesthouse near UC Davis, California

4.94 out of 5 average rating, 17 reviews

A modern kitchen features sleek white cabinetry and a spacious countertop. Stainless steel appliances, including an oven, microwave, and refrigerator, are arranged thoughtfully. A double sink is present, along with a coffee maker and a few water bottles on the countertop.

Apartment in Concord

Quiet area in the Four Corners

5 out of 5 average rating, 13 reviews

The image displays a well-maintained outdoor space with a lush green lawn, framed by a small vineyard. A detached casita can be seen in the background, featuring large glass doors that encourage a connection with the outdoors. A putting green and pool area are also present.

Guesthouse in Danville

Stunning Private Retreat awaits