Oakville holiday homes

We found 2,248 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:15 Jan - 22 Jan

Private kitchen
Exterior
Living area
Bar (on property)
Exceptional
(12 reviews)

Stunning Private Estate in Wine Country - Carneros

Sonoma

8% off
NZ$65,767
for 7 nights, 1 home
NZ$9,395 per night
includes taxes & fees
Stunning Private Estate in Wine Country - Carneros
Huge 10' couch, chaise lounger, 1.5+ chair, gorgeous vaulted ceilings
Sun rise over the mountains
Carriage House: Chic room, custom lime-washed vintage walls. 
Love this room!!
10-foot outdoor dining table. 
- Built-in heaters just in case
Exceptional
(206 reviews)

Spa-like Estate, Wine Country Getaway, above the Sonoma Square, Amazing Views

Sonoma

5% off
NZ$22,231
for 7 nights, 1 home
NZ$3,176 per night
includes taxes & fees
Spa-like Estate, Wine Country Getaway, above the Sonoma Square, Amazing Views
Private kitchen
Living area
Pool
Terrace/patio
Excellent
(6 reviews)

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

Santa Rosa

7% off
NZ$15,336
for 7 nights, 1 villa
NZ$2,191 per night
includes taxes & fees
Vineyard Villa: Pool/Spa | Pickleball/Tennis | Dog
Living area
Pool
Property grounds
Interior
Exceptional
(7 reviews)

Sonoma Reserve - Architectural Luxury Estate

Sonoma

8% off
NZ$50,464
for 7 nights, 1 home
NZ$7,209 per night
includes taxes & fees
Sonoma Reserve - Architectural Luxury Estate
Counter sitting and wine room. Great for your private wine testing
Exterior
Outdoor dining
Living room. 75" Samsung smart tv
Exceptional
(24 reviews)

Wine Country Luxury Retreat - Pool Sauna Spa Views

Santa Rosa

8% off
NZ$14,367
for 7 nights, 1 home
NZ$2,052 per night
includes taxes & fees
Wine Country Luxury Retreat - Pool Sauna Spa Views
living room
Private kitchen
back yard dining table
living area with huge sectional to accommodate all guests
Exceptional
(177 reviews)

Turn of Century historic home DOWNTOWN NAPA sleeps 8

Napa

8% off
NZ$12,228
for 7 nights, 1 home
NZ$1,747 per night
includes taxes & fees
Turn of Century historic home DOWNTOWN NAPA sleeps 8
Master bedroom
Dining
Dining table
Pool
Excellent
(11 reviews)

Tranquil Escape: 4-Bedroom Home with Modern Amenities and pool

Vallejo

8% off
NZ$6,092
for 7 nights, 1 home
NZ$870 per night
includes taxes & fees
Tranquil Escape: 4-Bedroom Home with Modern Amenities and pool
Dining
Property grounds
Backyard and Bocce Court!
Great Room and Kitchen
Exceptional
(258 reviews)

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

Napa

8% off
NZ$16,211
for 7 nights, 1 home
NZ$2,316 per night
includes taxes & fees
Luxury Home for Family and Friends Near Downtown Napa - 5BDRs
Private kitchen
Room
Games room
Children’s area
Exceptional
(49 reviews)

Wine Country Backyard Escape

Santa Rosa

7% off
NZ$6,869
for 7 nights, 1 home
NZ$981 per night
includes taxes & fees
Wine Country Backyard Escape
Living area
Living area
Private kitchen
Dining
Exceptional
(5 reviews)

Magical Sunset and Vineyard Views

Santa Rosa

8% off
NZ$12,171
for 7 nights, 1 room
NZ$1,739 per night
includes taxes & fees
Magical Sunset and Vineyard Views
Room
Outdoor dining
Exterior
Dining
Exceptional
(233 reviews)

Historic Saint Helena farm house one block from Main Street

St. Helena

12% off
NZ$18,523
for 7 nights, 1 home
NZ$2,646 per night
includes taxes & fees
Historic Saint Helena farm house one block from Main Street
Property grounds
Dining
Pool
Living area
Exceptional
(16 reviews)

Estate Above the Clouds

St. Helena

9% off
NZ$11,880
for 7 nights, 1 home
NZ$1,697 per night
includes taxes & fees
Estate Above the Clouds
Fun awaits: Follow the stairs downstairs for exciting entertainment!
Begin your day with a view that takes your breath away - simply stunning.
Stroll the scenic pathway from house to garden and golf area.
Immerse yourself in the beauty of nature - this moment is Instagram-worthy!
Exceptional
(9 reviews)

Russian River Redwoods: Hot Tub, Fire Pit, Dogs OK

Forestville

7% off
NZ$6,192
for 7 nights, 1 home
NZ$885 per night
includes taxes & fees
Russian River Redwoods: Hot Tub, Fire Pit, Dogs OK
Stunning wraparound deck with rustic wood pergola, ancient oak canopy & endless vineyard and mountain views. The ultimate spot to sip your morning coffee or watch the Sonoma sun go down.
Stunning chef's kitchen where culinary dreams come alive! Soaring wood-beamed ceilings, a grand marble island with seating for 4, stainless steel appliances.  All flowing seamlessly into the dining area. Cook, gather & entertain in pure wine country style.
Lush manicured gardens framed by towering oaks, rolling vineyards & stunning mountain views under endless blue skies.
Exterior
Exceptional
(17 reviews)

Stunning Vineyard Villa: Pool·Spa·Games Rm·EV Chgr

Sonoma

8% off
NZ$10,542
for 7 nights, 1 villa
NZ$1,506 per night
includes taxes & fees
Stunning Vineyard Villa: Pool·Spa·Games Rm·EV Chgr
Exterior
Exterior detail
Living area
Dining
Exceptional
(70 reviews)

Beautiful Home in Northwest Napa

Napa

9% off
NZ$5,313
for 7 nights, 1 home
NZ$759 per night
includes taxes & fees
Beautiful Home in Northwest Napa
The lavender in July is spectacular.
Outdoor dining for lunches and long summer evening for 12 people
Private kitchen
50' Pool
Exceptional
(263 reviews)

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

Kenwood

8% off
NZ$23,909
for 7 nights, 1 home
NZ$3,416 per night
includes taxes & fees
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Dining Room to Outside Area - Two Leaves will Extend the Table
Fire Table Sitting Area
TV Room
Interior
Exceptional
(118 reviews)

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

Sonoma

7% off
NZ$12,423
for 7 nights, 1 home
NZ$1,775 per night
includes taxes & fees
Vineyard Views, Pool Hot Tub - Sleeps 8-12 - 4+ Bedrooms/3+ Bathrooms
Dining
Dining
Dusk by the pool
Interior
Exceptional
(97 reviews)

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

Sonoma

8% off
NZ$28,163
for 7 nights, 1 home
NZ$4,023 per night
includes taxes & fees
Private Sonoma Vineyard Estate: Modern Villa + Pool 10 Acre Winery Property
Swim at Ives Pool, just two blocks away! Reservations now required ivespool.org
Welcome home!
The other kitchen view
Living room
Exceptional
(197 reviews)

Spacious Sebastopol Home - 5-Minute Walk to Town, Wine Country at Your Doorstep

Sebastopol

9% off
NZ$3,984
for 7 nights, 1 home
NZ$569 per night
includes taxes & fees
Spacious Sebastopol Home - 5-Minute Walk to Town, Wine Country at Your Doorstep
Enclosed porch adjoining kitchen with dining area
Great room: formal dining area,  grand piano, fireplace, tv
Kitchen with large central island
Hot tub and solar heated pool.
Exceptional
(64 reviews)

Stay at Roche Winery's Sonoma Vineyard Retreat

Sonoma

15% off
NZ$11,931
for 7 nights, 1 home
NZ$1,704 per night
includes taxes & fees
Stay at Roche Winery's Sonoma Vineyard Retreat
Room
Pool
Living area
Property grounds
Exceptional
(34 reviews)

Cozy Wine Country Guesthouse with Private Pool & Yard

Santa Rosa

9% off
NZ$4,368
for 7 nights, 1 home
NZ$624 per night
includes taxes & fees
Cozy Wine Country Guesthouse with Private Pool & Yard
Outdoor spa tub
Outdoor dining
Spiral staircase leads to downstairs bedroom & bathroom
Interior
Exceptional
(279 reviews)

Italian Villa with Infinity Pool & Panoramic Views

Glen Ellen

8% off
NZ$14,804
for 7 nights, 1 villa
NZ$2,115 per night
includes taxes & fees
Italian Villa with Infinity Pool & Panoramic Views
2 Steps Up to Bedrooms
Picnic tables & Fire Pit
Interior
Living area
Exceptional
(40 reviews)

Beautiful Gated Winemaker’s Estate 1 mi to Historic Sonoma Town Square

Sonoma

12% off
NZ$19,342
for 7 nights, 1 home
NZ$2,763 per night
includes taxes & fees
Beautiful Gated Winemaker’s Estate 1 mi to Historic Sonoma Town Square
Living area
Room
Private kitchen
Outdoor dining
Exceptional
(121 reviews)

Sonoma Wine Country Madison Escape TOT #2380N

Sonoma

7% off
NZ$6,150
for 7 nights, 1 home
NZ$879 per night
includes taxes & fees
Sonoma Wine Country Madison Escape TOT #2380N
  • 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)
  • Domaine Chandon (3.4 mi / 5.5 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)
  • French Laundry Culinary Garden (3 mi / 4.9 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)

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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Oakville holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Oakville to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas