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Holiday rentals in Oakville

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Top-rated holiday rentals in Oakville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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, 224 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 favourite
Home in Napa
4.88 out of 5 average rating, 187 reviews

The Harvard House: Napa, Hot Tub + Detached Studio

Kick back and relax in this calm, stylish space! While this home is perfectly situated in a peaceful residential neighborhood, close to wineries and parks... The real highlight is the property itself -- it will definitely give you satisfaction if your goal is to unwind and recharge! This cozy unit suits the new normal work-at-home setup with its fast internet and detached office, which also serves as a Yoga space. Moreover, you will truly feel pampered while soaking in its relaxing hot tub!

Top guest favourite
Apartment in Napa
4.99 out of 5 average rating, 550 reviews

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.

Top guest favourite
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.
Flat in Napa
4.99 out of 5 average rating, 452 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 favourite
A bright and open living area is presented, featuring large windows that offer views of the exterior greenery. Soft, modern furniture is arranged around a central rug, creating a cozy atmosphere. Natural light streams in, accentuating the neutral color palette and elegant decor.
Home in Sonoma
4.99 out of 5 average rating, 133 reviews

Stylish Sonoma Oasis + Hot Tub - Near Wineries

Enjoy a stylish stay in wine country at this centrally located 3 bedroom retreat only 5 mins from Sonoma Plaza. Nestled on the desirable east side of town and surrounded by world-class wineries, including Gundlach Bundschu (the oldest family-owned winery in California) at the end of our tranquil street. Step outside to your private bucolic oasis with wraparound deck, seasonal creek and hot tub where you can unwind sipping local wine while dining al fresco underneath olive & citrus trees.

Guest favourite
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, 78 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.

Guest favourite
A two-story light green house is set amidst lush landscaping, featuring well-maintained lawns and flowering bushes. A covered porch is visible on the upper floor, and trees provide shade around the property. The clear blue sky adds to the inviting outdoor ambiance.
Home in Napa
4.94 out of 5 average rating, 169 reviews

Come and Visit the Valley Sleeps 4 to 8 Guests

Great place for friends and family to gather. Come and see what the valley has to offer. Many wineries, fine dining and great shopping. This home is a beautifully remodeled 4 bedroom 3 bath home (2 of the bedrooms are mater suits). Includes eat in chefs kitchen, sun room / private office, living room, laundry room. Backyard landscaped to feel like a park setting. Large outdoor patio with dining table and seating for 8, Gazebo with outdoor lighting and BBQ Permit #VR17-0060

Top guest favourite
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, 425 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 favourite
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.
Apartment in Napa
4.99 out of 5 average rating, 139 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 favourite
A light-filled living area features a cozy sofa adorned with decorative cushions and a glass coffee table. Soft curtains frame the sliding doors, which lead to an outdoor space. Minimalist decor and wooden furnishings complement the inviting atmosphere.
Flat in Napa
4.97 out of 5 average rating, 321 reviews

Downtown Napa Unit B - 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.

Guest favourite
Flat in Napa
4.88 out of 5 average rating, 323 reviews

2bdr/2ba Silverado Resort : Gated + Golf Views

Escape to a newly renovated Silverado Resort condo tucked beneath oak trees, offering serene golf course views and a true Napa Valley retreat. Bright, spacious, and thoughtfully updated, it’s perfect for relaxing after wine tasting, exploring local wineries, or enjoying scenic mornings with coffee overlooking the greens. Guests may enjoy a complimentary wine tasting at Amizetta Winery (based on availability). Contact host after booking.

Top guest favourite
The spacious bathroom features a modern dual-sink vanity with a large circular mirror above. A freestanding bathtub is positioned beside a natural light-filled window, with greenery adding a touch of nature. A glass shower enclosure is visible, complemented by stylish overhead lighting.
Flat in Napa
4.97 out of 5 average rating, 607 reviews

A Private Guesthouse Studio – The Otter

the Otter studio - a peaceful standalone studio in the heart of Napa Valley wine country. The Otter Studio is less than one mile from Downtown Napa but far enough away from the hustle and bustle to provide a tranquil retreat while retaining every thoughtful amenity. Enjoy our cozy living space. We are legally permitted to rent to Napa Valley visitors. Ask about our other Napa listings if the dates here are booked.

Popular amenities for Oakville holiday rentals