Oakville holiday homes

We found 2,292 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:4 Dec - 11 Dec

Exterior
Interior
Bedroom 7 with King bed and shared bathroom
Exterior
Exceptional
(150 reviews)

Casa Bella Estate in Wine Country w/ New Pool!

Kenwood

8% off
NZ$26,345
for 7 nights, 1 home
NZ$3,764 per night
includes taxes & fees
Casa Bella Estate in Wine Country w/ New Pool!
Exterior
Private kitchen
Pool
Exterior
Exceptional
(27 reviews)

Luxury Vineyard Creek Ranch Sonoma

Sonoma

8% off
NZ$20,515
for 7 nights, 1 home
NZ$2,931 per night
includes taxes & fees
Luxury Vineyard Creek Ranch Sonoma
Entry.
Dining room.
Cheers!
Enjoy the quiet serenity  around the pool and take in the lush landscape.
Exceptional
(148 reviews)

Amazing Get-Away! Enjoy the Views! Relax on Deck or by Pool. Minutes to Plaza.

Sonoma

8% off
NZ$9,401
for 7 nights, 1 home
NZ$1,343 per night
includes taxes & fees
Amazing Get-Away! Enjoy the Views! Relax on Deck or by Pool. Minutes to Plaza.
Master Bedroom (CAL King Bed!)
Sunset from the pool.
Dinning Room with table sitting for 12-14 adults
Full Dinner sets for 15 full dinner place settings.
Exceptional
(137 reviews)

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

Glen Ellen

16% off
NZ$17,708
for 7 nights, 1 home
NZ$2,530 per night
includes taxes & fees
Gorgeous Vineyard Views, Large private home w/heated Pool & Hot Tub included!
2 Steps Up to Bedrooms
Picnic tables & Fire Pit
Living area
Private kitchen
Exceptional
(39 reviews)

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

Sonoma

12% off
NZ$17,047
for 7 nights, 1 home
NZ$2,435 per night
includes taxes & fees
Beautiful Gated Winemaker’s Estate 1 mi to Historic Sonoma Town Square
Spiral staircase leads to downstairs bedroom & bathroom
Outdoor dining
Outdoor spa tub
Interior
Exceptional
(273 reviews)

Modern Italian Villa with Infinity Pool & Panoramic Views

Glen Ellen

8% off
NZ$13,712
for 7 nights, 1 villa
NZ$1,959 per night
includes taxes & fees
Modern Italian Villa with Infinity Pool & Panoramic Views
Carriage House: Chic room, custom lime-washed vintage walls. 
Love this room!!
Sun rise over the mountains
Huge 10' couch, chaise lounger, 1.5+ chair, gorgeous vaulted ceilings
10-foot outdoor dining table. 
- Built-in heaters just in case
Exceptional
(201 reviews)

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

Sonoma

8% off
NZ$15,191
for 7 nights, 1 home
NZ$2,170 per night
includes taxes & fees
Spa-like Estate, Wine Country Getaway, above the Sonoma Square, Amazing Views
Sauna
Dining room doors open to the outside patio for indoor/outdoor living.
Enjoy a beautiful sunset by the firepit.
Dining room has wet bar, wine fridge, and ice machine.
Exceptional
(155 reviews)

Wine Country Escape: Luxury Estate, Pool, Sauna, Steam, Spa, Views, 5+ Bedrooms

Santa Rosa

8% off
NZ$33,691
for 7 nights, 1 home
NZ$4,813 per night
includes taxes & fees
Wine Country Escape: Luxury Estate, Pool, Sauna, Steam, Spa, Views, 5+ Bedrooms
Sunset or Sunrise with coffee in hand, hard to pick a favorite.
Stunning views of Russian River Valley from upper level of the house.
Living area
Our scenic dining room seats 8 together with 2 additional at the kitchen bar top
Exceptional
(182 reviews)

Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

Healdsburg

8% off
NZ$6,511
for 7 nights, 1 home
NZ$930 per night
includes taxes & fees
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Interior
Dining
Interior
Dining
Exceptional
(96 reviews)

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

Sonoma

8% off
NZ$25,725
for 7 nights, 1 home
NZ$3,675 per night
includes taxes & fees
Private Sonoma Vineyard Estate: Modern Villa + Pool 10 Acre Winery Property
Private kitchen
Outdoor dining for lunches and long summer evening for 12 people
50' Pool
The lavender in July is spectacular.
Exceptional
(256 reviews)

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

Kenwood

8% off
NZ$20,979
for 7 nights, 1 home
NZ$2,997 per night
includes taxes & fees
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Dining
Property grounds
Backyard and Bocce Court!
Great Room and Kitchen
Exceptional
(253 reviews)

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

Napa

8% off
NZ$17,132
for 7 nights, 1 home
NZ$2,447 per night
includes taxes & fees
Luxury Home for Family and Friends Near Downtown Napa - 5BDRs
Large island with farmhouse double sink, bar seating and dining room
Open plan living room with sightlines to kitchen and all back yard amenities
Chat with the hot-tubers while preparing a gourmet meal
View of the main house deck and pool from the dining table
Exceptional
(161 reviews)

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

Sonoma

8% off
NZ$14,753
for 7 nights, 1 home
NZ$2,108 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
(89 reviews)

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

Sonoma

8% off
NZ$11,608
for 7 nights, 1 home
NZ$1,658 per night
includes taxes & fees
Single Story Ranch w/ Pool - 2.5 Acres close to Sonoma Square and Sonoma Raceway
Pool
Exterior detail
Large dining table
Living Room and back door exit to pool area
Exceptional
(84 reviews)

WOW! A little bit of France...in Sonoma!

Sonoma

8% off
NZ$10,832
for 7 nights, 1 home
NZ$1,547 per night
includes taxes & fees
WOW! A little bit of France...in Sonoma!
Exterior
Outdoor dining
Room
Private kitchen
Exceptional
(233 reviews)

Historic Saint Helena farm house one block from Main Street

St. Helena

12% off
NZ$17,441
for 7 nights, 1 home
NZ$2,492 per night
includes taxes & fees
Historic Saint Helena farm house one block from Main Street
Family Room
Living room with XL masonry fireplace
Al fresco dining on the back deck
Front of house.  Parking for up to 5 cars in the driveway and garage.
Exceptional
(128 reviews)

1-acre Private Backyard with Large Pool

Glen Ellen

20% off
NZ$9,548
for 7 nights, 1 home
NZ$1,364 per night
includes taxes & fees
1-acre Private Backyard with Large Pool
Open Plan living and dining area
Pool
outdoor seating under walnut tree
Dining area
Exceptional
(167 reviews)

A Stylish Getaway In The Heart Of Sonoma Wine Country

Kenwood

8% off
NZ$10,999
for 7 nights, 1 home
NZ$1,571 per night
includes taxes & fees
A Stylish Getaway In The Heart Of Sonoma Wine Country
Property grounds
Great room: formal dining area,  grand piano, fireplace, tv
Enclosed porch adjoining kitchen with dining area
Hot tub and solar heated pool.
Exceptional
(63 reviews)

Stay at Roche Winery's Sonoma Vineyard Retreat

Sonoma

16% off
NZ$10,864
for 7 nights, 1 home
NZ$1,552 per night
includes taxes & fees
Stay at Roche Winery's Sonoma Vineyard Retreat
Living room
Front Porch
Dining Room
Kitchen
Exceptional
(257 reviews)

Blackberry Cottage located next to Wineberry Lodge

Sebastopol

8% off
NZ$4,124
for 7 nights, 1 home
NZ$589 per night
includes taxes & fees
Blackberry Cottage located next to Wineberry Lodge
Room
Outdoor dining
Living area
Dining
Exceptional
(120 reviews)

Sonoma Wine Country Madison Escape TOT #2380N

Sonoma

7% off
NZ$4,989
for 7 nights, 1 home
NZ$713 per night
includes taxes & fees
Sonoma Wine Country Madison Escape TOT #2380N
Pool House
Cpurtyard
Pool house Looking to Pool
Back yard
Exceptional
(189 reviews)

Modern Hacienda Near Downtown Sonoma! ~ Walk to Plaza. Mid Week Discounts

Sonoma

8% off
NZ$13,794
for 7 nights, 1 home
NZ$1,971 per night
includes taxes & fees
Modern Hacienda Near Downtown Sonoma! ~ Walk to Plaza. Mid Week Discounts
Wine table that fits 8 people with views into both kitchen and living room.
Relax on main deck overlooking creek - direct access to living room & kitchen.
Interior
Chef's Kitchen with new dishwasher and new refrigerator.
Exceptional
(153 reviews)

Sonoma Valley, Glen Ellen Secluded Wine Country Sophistication

Glen Ellen

8% off
NZ$10,718
for 7 nights, 1 home
NZ$1,531 per night
includes taxes & fees
Sonoma Valley, Glen Ellen Secluded Wine Country Sophistication
Exterior
Private kitchen
Terrace/patio
Property grounds
Exceptional
(15 reviews)

Stunning Vineyard Villa | Pool · Hot Tub · Games Room · EV Charger

Sonoma

8% off
NZ$8,298
for 7 nights, 1 villa
NZ$1,185 per night
includes taxes & fees
Stunning Vineyard Villa | Pool · Hot Tub · Games Room · EV Charger
  • 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 most popular type of holiday home accommodation in Oakville?
The most popular types of holiday homes in Oakville are houses. Ready for more choices? Bookabach has a variety of options to match our guests' diverse needs, so you'll see properties in all sizes, and for all budgets. The perfect fit is ready and waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Oakville?
Several factors determine the price of a holiday home in Oakville, like the season, type of property and length of stay. Still, all our holiday homes have one thing in common — amazing value. Just add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Oakville?
Prices for beach houses in Oakville may differ depending on the size and type of the property and when you're travelling. Simply enter your travel dates into Bookabach and how many guests to see your home options and prices. From there you can use our filter tool to tailor your search by nearby activities, amenities, ratings and more.
What are popular home amenities in Oakville?
When it comes to home amenities that guests search for in Oakville, a garden, a barbecue grill and a fireplace rank the highest. With Bookabach holiday homes, you'll enjoy options to suit your style and taste, whether you're going on a holiday with family members, friends or even pets.
What are the top attractions for families in Oakville?
Keeping the kids occupied during your Oakville holiday is easy with these family-friendly attractions:
  • Napa Valley Museum
  • Robert Louis Stevenson Museum
  • The Christopher Hill Gallery
How old do you have to be to rent a holiday home in Oakville?
You'll have to check with the Oakville holiday property you're considering on Bookabach as age restrictions vary. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Oakville for?
The amount of time you can book an Oakville holiday home for is up to the property. Just tap in your preferred travel dates to browse options offering extended stays. They have everything you need to make your extended break more convenient and enjoyable, such as kitchens and air conditioning. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

More holiday ideas