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 modern living room features a sleek gray sofa paired with a glass coffee table on a light area rug. Subtle wall accents and a cozy fireplace enhance the space, while large windows allow natural light to fill the room.
Condo in Silverado Resort
4.99 out of 5 average rating, 254 reviews

Chic 1 BR Condo Par Excellence at Silverado Resort

Distinctly modern and exquisitely curated, this newly-remodeled 2nd floor condo at Silverado Resort is sleek, subdued, and moody. It’s perfect for a couple's retreat, a girls' getaway, 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.

Guest favorite
An open-plan living and dining area is illuminated by natural light from large glass doors. A comfortable sofa and armchair are arranged around a decorative coffee table. A dining table for four is set with dishware, while a modern artwork adds color to the wall.
Condo in Silverado Resort
4.96 out of 5 average rating, 218 reviews

Gorgeous condo at Silverado Country Club

This beautiful condo at Silverado Country Club is your dream Wine Country Escape. Surrounded by beautiful trees, it's the perfect location for a relaxing stay. The condo features an open plan living room and dining area, a kitchen and two large bedroom suites, one with a king and the second with a queen size bed. Each bedroom has a fully remodeled bathroom with walk in shower. The spacious deck offers a BBQ grill and a picturesque view of the golf course, nestled among beautiful oak trees.

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.

Guest favorite
A solar-heated pool is set within a spacious patio of brick pavers. Two white lounge chairs sit beside the pool, accompanied by large umbrellas providing shade. Lush greenery and a wooden fence are visible in the background, enhancing the serene atmosphere.
Cottage in Sonoma
4.93 out of 5 average rating, 122 reviews

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.

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
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, 107 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
The exterior of a charming single-story home is featured, with a covered porch framed by white columns. A well-maintained garden surrounds the house, showcasing colorful flowers and neatly arranged stepping stones leading to the entrance.
Home in Kenwood
4.94 out of 5 average rating, 114 reviews

Modern Luxury in Sonoma's Valley of the Moon

Come for an amazing visit in this luxury vacation rental with hardwood floors, custom high end furnishings, stone counters and much more. Ideally suited for the sophisticated traveler who desires high quality modern accommodations. Relax in the private backyard overlooking a vineyard and seasonal creek. Enjoy dinner on the 650 square foot deck. Take a stroll through the Zinfandel & Petite Syrah vineyard and end the evening lounging by the warmth of the firepit.

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.

Popular amenities for Oakville vacation rentals

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