Holiday houses 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
Condo in Napa
4.99 out of 5 average rating, 530 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.

Guest favourite
Home in Napa
4.97 out of 5 average rating, 69 reviews

Rosé All Day | Napa Retreat | Fire Pit & Hot Tub

✨ Rosé All Day 💫 🌹Welcome to Rosé All Day, a Napa Valley retreat ideal for wine tasting weekends or relaxed getaways. This 3 BR/ 2BA residence sleeps up to 8 and features a generous private outdoor space for evenings sipping by the fire pit, or soaking in the hot tub under the stars. Centrally located near downtown Napa, top wineries, renown restaurants and scenic trails, this refined home offers an ideal setting where days unfold slowly and evenings are meant to be enjoyed with loved ones.

Guest favourite
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 Napa
4.96 out of 5 average rating, 231 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 favourite
A spacious living room features large windows allowing natural light to fill the space. Comfortable seating is arranged around a circular coffee table, which holds magazines. A gas-powered fireplace adds warmth, complemented by greenery from nearby plants.
Apartment in Napa
4.99 out of 5 average rating, 425 reviews

Mendez On Main #1 King Bed/10min walk to downtown

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
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, 196 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 favourite
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, 213 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 favourite
Home in Glen Ellen
5 out of 5 average rating, 43 reviews

Napa Sonoma Airstream with Pool (New)

Airstream Cloud in the heart of Napa/Sonoma wine country with pool and hot tub. On 27 private acres just 10 mins from Glen Ellen and 15 mins Yountville; overlooking vineyards and the Sonoma Valley. Well equipped Airstream with all the comforts of a modern home. Breathtaking views of the Sonoma Valley sunsets to the ocean. Sip your coffee near the fire pit or your wine poolside in the loungers. Perfect getaway for 2 in wine country! There is no residence on this private property.

Top Guest favourite
A bright bedroom features a spacious bed adorned with a patterned duvet and decorative pillows. A bedside table holds a small lamp and flowers, while a cozy chair and desk are positioned nearby. Natural light filters through the window, illuminating the soft carpeted floor.
Guest suite in Napa
4.97 out of 5 average rating, 405 reviews

Perfect Location w/ Charm

Permitted by the city of Napa: #VR16-0008 Our guest suite with private entrance in our charming Napa cottage style home provides you with a comfortable home away from home. Your room and bathroom are completely private and there are no shared spaces in the house.The room is part of the house and although private, it is not completely soundproof. The backyard is shared with us. It's bright and sunny, and you are perfectly located for walking downtown or exploring the valley.

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.
Condo in Napa
4.99 out of 5 average rating, 123 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!

Guest favourite
Home in Napa
4.9 out of 5 average rating, 10 reviews

Modern Napa Escape | ZEN Oasis Near Top Wineries

Welcome to our modern Napa Retreat, just 8 minutes from downtown Napa. As locals, we’ve thoughtfully designed this clean, contemporary home to be both stylish and comfortable. Relax in a peaceful setting while staying close to world-renowned wineries, dining, and tastings. Whether you’re here for a weekend getaway with friends to enjoy wine or a family trip, this home is perfect. We’d love to host you and help you experience the best of Napa Valley.

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.
Apartment in Napa
4.97 out of 5 average rating, 578 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.

Guest favourite
Villa in Glen Ellen
5 out of 5 average rating, 28 reviews

When in Glen | Views | Pool & Hot Tub

Welcome to your peaceful dream retreat in Glen Ellen! This hidden gem features breathtaking views and stunning sunsets. Located in the heart of wine country, just minutes away from world-class vineyards, charming boutiques, and top-rated restaurants. Relax by the pool or in the hot tub with a view. This thoughtfully designed home offers brand-new appliances and quality furnishings. No pets.

Popular amenities for Oakville holiday rentals

  1. Airbnb
  2. United States
  3. California
  4. Napa County
  5. Oakville