Oakville holiday rentals

We found 2,270 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Oakville to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, such as air conditioning and a TV. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Oakville

Showing deals for:1 Jan - 8 Jan

Bedroom 6 with queen bed and private bathroom- Dolcetto
Outdoor dining
Living area
Pool
Exceptional
(151 reviews)

Casa Bella Estate in Wine Country w/ New Pool!

Kenwood

8% off
AU$24,168
for 7 nights, 1 home
AU$3,453 per night
includes taxes & fees
Casa Bella Estate in Wine Country w/ New Pool!
Another view of the Great Room.
The Inn is completely surrounded by vineyards
Property grounds
Banquet hall
Exceptional
(67 reviews)

Historic Estate surrounded by vineyards adjacent to Napa. Popular wedding venue

Fairfield

13% off
AU$19,378
for 7 nights, 1 home
AU$2,768 per night
includes taxes & fees
Historic Estate surrounded by vineyards adjacent to Napa. Popular wedding venue
Pool
Property grounds
Property grounds
Exterior detail
Exceptional
(28 reviews)

Luxury Vineyard Creek Ranch Sonoma

Sonoma

8% off
AU$18,255
for 7 nights, 1 home
AU$2,608 per night
includes taxes & fees
Luxury Vineyard Creek Ranch Sonoma
Dinning Room with table sitting for 12-14 adults
Sunset from the pool.
Master Bedroom (CAL King Bed!)
Dinning Room with table sitting for 12-14 adults
Exceptional
(138 reviews)

Gorgeous Vineyard Views, Large private home w/heated Pool & Hot Tub included!

Glen Ellen

16% off
AU$15,321
for 7 nights, 1 home
AU$2,189 per night
includes taxes & fees
Gorgeous Vineyard Views, Large private home w/heated Pool & Hot Tub included!
Bedroom with Vanity Table
Stroll the beautiful gardens and take in the views.
Living Room
Private patio outside kitchen door
Exceptional
(90 reviews)

Sonoma Rosso: Poolside Luxury for 2

Santa Rosa

8% off
AU$3,576
for 7 nights, 1 cottage
AU$511 per night
includes taxes & fees
Sonoma Rosso: Poolside Luxury for 2
Exterior detail
Exterior
Terrace/patio
Interior
Exceptional
(31 reviews)

Napa Valley Retreat 8 bedroom villa

St. Helena

8% off
AU$28,534
for 7 nights, 1 villa
AU$4,076 per night
includes taxes & fees
Napa Valley Retreat 8 bedroom villa
Living area
Exterior
Private kitchen
Bar (on property)
Exceptional
(12 reviews)

Stunning Private Estate in Wine Country - Carneros

Sonoma

8% off
AU$45,604
for 7 nights, 1 home
AU$6,515 per night
includes taxes & fees
Stunning Private Estate in Wine Country - Carneros
Spiral staircase leads to downstairs bedroom & bathroom
Outdoor dining
Living area
Outdoor spa tub
Exceptional
(276 reviews)

Italian Villa with Infinity Pool & Panoramic Views

Glen Ellen

8% off
AU$11,117
for 7 nights, 1 villa
AU$1,588 per night
includes taxes & fees
Italian Villa with Infinity Pool & Panoramic Views
Interior
Fire Table Sitting Area
Kitchen Counter
Dining Room to Outside Area - Two Leaves will Extend the Table
Exceptional
(118 reviews)

Vineyard Views, Pool Hot Tub - Sleeps 8-12 - 4+ Bedrooms/3+ Bathrooms

Sonoma

8% off
AU$9,379
for 7 nights, 1 home
AU$1,340 per night
includes taxes & fees
Vineyard Views, Pool Hot Tub - Sleeps 8-12 - 4+ Bedrooms/3+ Bathrooms
Pool
Interior
Living area
Exterior
Exceptional
(37 reviews)

Luxury Napa Valley Estate Surrounded by Vineyards

Calistoga

9% off
AU$61,540
for 7 nights, 1 home
AU$8,791 per night
includes taxes & fees
Luxury Napa Valley Estate Surrounded by Vineyards
50' Pool
Outdoor dining for lunches and long summer evening for 12 people
Living area
The lavender in July is spectacular.
Exceptional
(260 reviews)

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Kenwood

8% off
AU$17,629
for 7 nights, 1 home
AU$2,518 per night
includes taxes & fees
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Sky Suite with king bed
Sunset over the pool and firepit
Guest house living room opening onto covered porch
Firepit at dusk
Exceptional
(102 reviews)

As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley

Glen Ellen

7% off
AU$14,088
for 7 nights, 1 home
AU$2,013 per night
includes taxes & fees
As featured on CBS's Staycation! Luxury Retreat Overlooking Sonoma Valley
Terrace/patio
Living area
Living area
Private kitchen
Excellent
(6 reviews)

Vineyard Villa: Pool/Spa | Pickleball/Tennis | Dog

Santa Rosa

9% off
AU$12,364
for 7 nights, 1 villa
AU$1,766 per night
includes taxes & fees
Vineyard Villa: Pool/Spa | Pickleball/Tennis | Dog
Interior
Dining
Interior
Dining
Exceptional
(97 reviews)

Private Sonoma Vineyard Estate: Modern Villa + Pool 10 Acre Winery Property

Sonoma

8% off
AU$21,434
for 7 nights, 1 home
AU$3,062 per night
includes taxes & fees
Private Sonoma Vineyard Estate: Modern Villa + Pool 10 Acre Winery Property
Open plan kitchen with large island and 3  bar seats adjacent to dining area
Open plan living room with sightlines to kitchen and all back yard amenities
Chat with the hot-tubers while preparing a gourmet meal
Large island with farmhouse double sink, bar seating and dining room
Exceptional
(162 reviews)

Lovely Home & Cottage with Pool, Bocce and Game Room Near Sonoma Square

Sonoma

8% off
AU$13,871
for 7 nights, 1 home
AU$1,982 per night
includes taxes & fees
Lovely Home & Cottage with Pool, Bocce and Game Room Near Sonoma Square
Livingroom
So close to Sonoma, yet you feel in the middle of country
Property grounds
Living area
Exceptional
(91 reviews)

Single Story Ranch w/ Pool - 2.5 Acres close to Sonoma Square and Sonoma Raceway

Sonoma

8% off
AU$9,626
for 7 nights, 1 home
AU$1,375 per night
includes taxes & fees
Single Story Ranch w/ Pool - 2.5 Acres close to Sonoma Square and Sonoma Raceway
Al fresco dining on the back deck
Living room with XL masonry fireplace
Family Room
Lounge chairs by pool
Exceptional
(129 reviews)

1-acre Private Backyard with Large Pool - 20% off October Stays

Glen Ellen

22% off
AU$7,811
for 7 nights, 1 home
AU$1,116 per night
includes taxes & fees
1-acre Private Backyard with Large Pool - 20% off October Stays
Dining
Property grounds
Backyard and Bocce Court!
Great Room and Kitchen
Exceptional
(256 reviews)

Luxury Home for Family and Friends Near Downtown Napa - 5BDRs

Napa

8% off
AU$14,589
for 7 nights, 1 home
AU$2,084 per night
includes taxes & fees
Luxury Home for Family and Friends Near Downtown Napa - 5BDRs
Private kitchen
Room
Dining
Living area
Exceptional
(120 reviews)

Sonoma Wine Country Madison Escape TOT #2380N

Sonoma

7% off
AU$4,775
for 7 nights, 1 home
AU$682 per night
includes taxes & fees
Sonoma Wine Country Madison Escape TOT #2380N
Kitchen
Dining room
Private kitchen
Property grounds
Exceptional
(264 reviews)

Peaceful, Sonoma oasis - heated pool, fire pit, outdoor dining - close to Plaza

Sonoma

12% off
AU$4,579
for 7 nights, 1 cottage
AU$654 per night
includes taxes & fees
Peaceful, Sonoma oasis - heated pool, fire pit, outdoor dining - close to Plaza
Chef's Kitchen with new dishwasher and new refrigerator.
Relax on main deck overlooking creek - direct access to living room & kitchen.
Wine table that fits 8 people with views into both kitchen and living room.
Evening shot of front of house.  Motion sensor to light pathway to house.
Exceptional
(156 reviews)

Sonoma Valley, Glen Ellen Secluded Wine Country Sophistication

Glen Ellen

8% off
AU$8,821
for 7 nights, 1 home
AU$1,260 per night
includes taxes & fees
Sonoma Valley, Glen Ellen Secluded Wine Country Sophistication
Living area
View from loft/greatroom window of Chardonnay block, pool/spa area and mountains
Pool
View of pool area from adjacent flower garden
Exceptional
(69 reviews)

Carneros Winemaker Estate bw Sonoma & Napa: Sleeps 4, Vineyard, Pool, Spa, Bikes

Sonoma

8% off
AU$8,063
for 7 nights, 1 home
AU$1,152 per night
includes taxes & fees
Carneros Winemaker Estate bw Sonoma & Napa: Sleeps 4, Vineyard, Pool, Spa, Bikes
Exterior
Front Porch
Kitchen
Dining Room
Exceptional
(259 reviews)

Blackberry Cottage located next to Wineberry Lodge

Sebastopol

8% off
AU$3,462
for 7 nights, 1 home
AU$495 per night
includes taxes & fees
Blackberry Cottage located next to Wineberry Lodge
Flat above storage/garage, at the Cork Oak
Sun filled flat with high speed fiber optic internet accessed via wifi, flat screen TV, laundry, and private patio
Relaxing view from Kitchen
Room
Exceptional
(6 reviews)

Flat at the Cork Oak · Sunny, central, quiet flat + yard

Petaluma

12% off
AU$2,189
for 7 nights, 1 room
AU$313 per night
includes taxes & fees
Flat at the Cork Oak · Sunny, central, quiet flat + yard
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Take in the natural beauty of Oakville

Enjoy the area's wineries, architecture and monuments with a rental holiday home in Oakville. This city's restaurants, local tours and mountain views draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Oakville

Do you want to find top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that makes Oakville a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Napa Valley Wine Train (11.3 mi / 18.2 km)
  • Opus One Winery (0.3 mi / 0.5 km)
  • Robert Mondavi Winery (0.5 mi / 0.8 km)
  • Far Niente Winery (0.9 mi / 1.4 km)
  • Silver Oak Napa Valley Winery (1.1 mi / 1.8 km)
  • Mumm Napa (3 mi / 4.8 km)

Exploring the natural features in Oakville

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Oakville. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Yountville Park (2.7 mi / 4.4 km)
  • Jack London State Historic Park (9.4 mi / 15.2 km)
  • Napa River (11.5 mi / 18.5 km)
  • Spring Lake Park (13.6 mi / 21.9 km)
  • Lake Berryessa (14.4 mi / 23.1 km)
  • Skyline Wilderness Park (14.8 mi / 23.8 km)

How to get to and around Oakville

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 22.4 mi (36 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Oakland, CA (OAK-Oakland Intl.), which is 51.1 mi (82.2 km) away.

Frequently asked questions

What is the best area to stay in Oakville when booking a holiday rental?
When considering a holiday rental in Oakville, California, the most appealing area to stay in is the picturesque Napa Valley. This region is renowned for its stunning vineyards and rolling hills, making it a great backdrop for a relaxing getaway. While Oakville itself is a small community, the surrounding neighbourhoods are home to a variety of charming properties, ranging from quaint cottages to luxurious estates, offering a great experience for every traveller.Nearby, the famed Robert Mondavi Winery is a must-visit, where you can enjoy guided tours and tastings that showcase the area's exceptional wines. Additionally, the Culinary Institute of America in Greystone is just a short drive away and offers excellent dining options and cooking classes, making it a delightful spot for food enthusiasts.
When is the best time to visit Oakville for a holiday rental?
The peak season for visiting Oakville runs from May to July, with July being the most popular month. This vibrant period attracts travellers eager to explore the region's renowned wineries and indulge in al fresco dining experiences amid the beautiful Californian landscape. The warm summer weather, with average temperatures ranging from 15 to 30 degrees Celsius, creates the ideal setting for outdoor activities such as vineyard tours, tastings, and leisurely strolls through the charming town.For those looking for a more budget-friendly option, November presents a wonderful opportunity to experience Oakville without the crowds. This quieter month allows visitors to enjoy the stunning autumn foliage and participate in seasonal events, all while benefiting from lower rental rates and a more relaxed atmosphere.
What are the top attractions in Oakville?
In Oakville, California, visitors can explore a range of attractions that highlight the region's rich viticultural heritage. The area is renowned for its picturesque vineyards and wineries, with many offering tastings and tours. Notable wineries, such as those along the famed Highway 29, provide opportunities to sample exquisite Napa Valley wines while enjoying stunning views of the surrounding landscape.The serene atmosphere of Oakville is great for those looking to relax and unwind, with various outdoor activities available, including hiking trails that meander through the beautiful countryside. Additionally, the nearby town of Yountville, known for its Michelin-starred restaurants and charming boutiques, is just a short drive away and adds to the area's appeal.For culinary enthusiasts, Oakville is close to the vibrant food scene of Napa Valley, where visitors can indulge in gourmet dining experiences and farm-to-table offerings.
Are all fees included in the Oakville holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Oakville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Oakville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Oakville holiday homes?
You can find great discounts on holiday homes in Oakville on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Oakville holiday home booking on Stayz?
To find Oakville holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oakville?
A long-stay holiday home in Oakville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oakville holiday home?
Book your Oakville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oakville?
Prices for holiday homes in Oakville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakville to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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