Vacation rentals in Oakville

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Top-rated vacation rentals in Oakville

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Top guest favorite
Condo in Silverado Resort
4.99 out of 5 average rating, 503 reviews

Silverado! Luxe King Suite Mountain View Balcony

Apartment with views! Top floor Silverado Resort true 1 bedroom (not studio), 1ba 676 sq. ft. w/ rare mountain views from balcony, living and dining rooms. Wood burning fireplace. *Price incl tax. Walk to pool, market, dining, lounge at mansion. Modern appliances, ready for your relaxation. 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 L2 EV chargers nearby.

Top guest favorite
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
4.96 out of 5 average rating, 203 reviews

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.

Top guest favorite
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.
Condo in Silverado Resort
4.99 out of 5 average rating, 127 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.

Top guest favorite
The living room features a comfortable gray sofa and two elegant armchairs surrounding a wooden coffee table. Natural light fills the space through large windows. A dining area is visible through an open doorway, with a plush bed and decorative wall art adding to the atmosphere.
Apartment in Napa
4.99 out of 5 average rating, 421 reviews

Mendez on Main #2 / King Bed/1 bath Walk to town

Indulge in Napa's finest restaurants, wine tasting, and nightlife from our beautifully restored and remodeled apartment in our Victorian home, just a 10-minute stroll from downtown. Our apartment is fully equipped with all the amenities you'd expect, (*No stove) creating a comfortable space for your stay. For the peace and relaxation of all guests, please note that we do not allow pets or children under 12. You can book with confidence knowing that we have a Use Permit from the City of Napa.

Top guest favorite
A cozy living area is furnished with a light-colored sectional sofa adorned with colorful accent pillows. A wooden coffee table holds snacks and glasses, while a lamp illuminates the space. Natural light enters through shutters, creating a warm ambiance.
Cottage in Kenwood
4.99 out of 5 average rating, 269 reviews

Spring getaway in beautiful Sonoma Valley!

Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

Guest favorite
A spacious living area features tall vaulted ceilings and a large flat-screen television mounted on a neutral wall. Natural light is brought in through a skylight and glass sliding doors, while a decorative plant and a wooden coffee table add warmth to the setting.
Home in Napa
4.91 out of 5 average rating, 65 reviews

Charming Napa Browns Valley Home

An exceptionally renovated mid-century home that is tucked away in Napa's highly desirable Browns Valley neighborhood. This home has it all for a luxury trip to Napa. Special features include a great room floor plan with a vaulted ceiling and skylights for lots of natural light, a chef's kitchen, and a lovely backyard complete with a pergola covered with mature wisteria with a charming view. 10 mins to Napa downtown and famous wineries. Freshly brewed coffee and filtered water are included.

Top guest favorite
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
4.96 out of 5 average rating, 186 reviews

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!

Guest favorite
A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.
Treehouse in Bodega Bay
4.95 out of 5 average rating, 197 reviews

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

Top guest favorite
A vibrant hot air balloon floats above a vineyard, showcasing a striking yellow and black pattern. The landscape features well-manicured lawns and shrubs, with a chain-link fence partially enhancing the view of the mountains in the distance.
Home in Napa
4.98 out of 5 average rating, 404 reviews

Vineyard House In The Heart Of Napa Valley

La Casita Megandina will create a memorable vacation experience for you and your family. Our house is centrally located in the heart of the Napa Valley only minutes from wineries and world famous restaurants. Our slogan is “Come Experience the Napa Valley Lifestyle at its Finest”. The house borders on a vineyard which give you an amazing view in a quiet neighborhood. Guests from around the world have enjoyed staying with us and we would like to share our house with you.

Top guest favorite
A private patio features a swinging egg chair, capable of seating at least two people, surrounded by lush bamboo and a grassy area. Outdoor lights can be seen, complementing the serene atmosphere, while a pyramid heater provides warmth for cooler evenings.
Condo in Napa
4.99 out of 5 average rating, 108 reviews

Spacious&PeacefulOasis!Beautiful!PerfectlyLocated!

✨✨ Welcome to Your Modern Napa Stay! ✨✨ Discover the perfect blend of luxury and comfort in our stunning 2 bed, 2 bath spacious space. This contemporary retreat features stylish decor, an open-concept living space, ideal for relaxing after a day of exploring the beautiful wineries and vibrant culinary scene. Whether you're here for a romantic getaway, a trip with friends, or a family vacay, our modern Napa retreat offers everything you need for a memorable stay!

Top guest favorite
A cozy living area features a comfortable gray sofa adorned with patterned cushions. A light marble coffee table sits in front of the sofa, while two modern lamps provide illumination. A piece of abstract wall art adds a touch of color above the seating area.
Apartment in Napa Abajo
4.98 out of 5 average rating, 355 reviews

Downtown Napa Unit C - Walk to Everything

Napa City Certified Vacation Rental Permit #VR16-0058, Napa Business License #26075 - Villa Murialdo in the Heart of Charming Napa, directly across from the the entrance to the Napa River Walk! Choosing the right accommodation in the heart of Napa means you are close to absolutely everything you want to experience during your stay. Villa Murialdo is within walking distance of world famous restaurants and a short drive from the renowned wineries.

Superhost
Home in Napa
4.88 out of 5 average rating, 161 reviews

Charming Napa Retreat | Mins to Downtown

Unique tri-level home near Downtown Napa and Oxbow Market, perfect for one or two couples. Located less than a mile from downtown, the home offers exceptional privacy with two distinct living areas, each with its own kitchen, living room, and deck. Guests enjoy two upstairs bedrooms and baths, a spacious living room with fireplace, dining area, full kitchen, and private deck. 2-night minimum stay. City of Napa Certified Vacation Rental VR16-0006.

Popular amenities for Oakville vacation rentals

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