Vacation rentals in Oakville

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Top-rated vacation rentals in Oakville

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

Guest favorite

Guesthouse in Glen Ellen

4.91 out of 5 average rating, 930 reviews

Crow Cottage ~ 3 min walk to town - restaurants

Crow Cottage is newly rebuilt and decorated in an eclectic whimsical style by the artist owners. It is light and airy with a private shade deck and sunny patio. The Cottage has a queen bed. There is a portable A/C. The cottage is well insulated so it doesn't get too hot in the summer. There is also a fan. Set on a country lane just a 3 min walk to great restaurants & a gourmet market. While we do have rescued cats in our yard we don't let them in any of the rooms. If highly allergic, reconsider.

Aug 12 – 19

R2,580 ZAR per night
Guest favorite

Condo in Napa

4.99 out of 5 average rating, 147 reviews

Chic 1 BR Condo Par Excellence at Silverado Resort

Distinctly modern and exquisitely curated, this newly-remodeled 2nd floor condo at Silverado Resort is sleek, subdued, and moody. It’s perfect for a couple's retreat, a girls' getaway, or a quiet place to stay after enjoying one of the many events hosted at this famed property! Blending urban sophistication with Wine Country charm, this exquisite condo features upscale amenities, 100% bamboo linens, a posh sleeper sofa, two fireplaces, and a premium King size mattress for next level sleep bliss.

Jun 8 – 15

R8,156 ZAR per night
Guest favorite

Guest suite in Sonoma

4.91 out of 5 average rating, 342 reviews

Wildwood Retreat and Pool

The Wildwood Retreat is located on a wooded 2 acre country property in the hills above Sonoma just minutes from the Historic Downtown Sonoma Plaza. The newly remodeled studio apt is very private on a separate level below the main house conveniently close to the pool. Amenities include a king size bed, kitchenette, private bath,sunny deck,pool access and convenient parking. Great walks are just outside your door. This tranquil retreat is ideally located for enjoying all the Wine Country offers.

Oct 15 – 22

R2,807 ZAR per night

Popular amenities for Oakville vacation rentals

Stay near Oakville's top sights

Oakville Grocery39 locals recommend
Robert Mondavi Winery23 locals recommend
Nickel & Nickel8 locals recommend

Other great vacation rentals in Oakville

Guest favorite

Condo in Napa

4.99 out of 5 average rating, 318 reviews

Silverado Resort! Large 1BR Mountain View, Balcony

Jul 11 – 18

R6,904 ZAR per night
Guest favorite

Guest suite in Napa

4.94 out of 5 average rating, 137 reviews

Sherrie's Vineyard View Retreat-Pool, Spa, N.Napa

Jul 25 – Aug 1

R5,245 ZAR per night
Guest favorite

Condo in Napa

4.96 out of 5 average rating, 107 reviews

Condo on PGA Silverado Course 15 min to BottleRock

Sep 12 – 19

R10,376 ZAR per night
Guest favorite

Guest suite in Napa

4.97 out of 5 average rating, 154 reviews

Luxury Private Poolside Suite

Aug 11 – 18

R3,576 ZAR per night
Guest favorite

Home in Napa

4.99 out of 5 average rating, 228 reviews

Peaceful home in the heart of Napa Valley

Jan 26 – Feb 2

R20,111 ZAR per night
Guest favorite

Apartment in Napa

4.87 out of 5 average rating, 229 reviews

Napa, Silverado Country Club Spotless 2 bd 2 ba

Aug 17 – 24

R7,664 ZAR per night
Guest favorite

Guest suite in Glen Ellen

4.96 out of 5 average rating, 186 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

Oct 6 – 13

R3,176 ZAR per night
Superhost

Home in Napa

4.88 out of 5 average rating, 99 reviews

w/ Hot Tub & Detached Office, Modern 3BR in Napa!

Aug 2 – 9

R15,808 ZAR per night
Guest favorite

Home in Napa

4.92 out of 5 average rating, 157 reviews

Casa Alta with Hot Tub near Oxbow Market!

Feb 9 – 16

R9,841 ZAR per night
Guest favorite

Condo in Napa

4.95 out of 5 average rating, 58 reviews

*Studio for Two at Silverado

R3,887 ZAR per night
Guest favorite

Guesthouse in Napa

4.97 out of 5 average rating, 75 reviews

*Minutes to Downtown ~ Napa Guest House*

May 5 – 12

R6,163 ZAR per night
Guest favorite

Home in Napa

4.97 out of 5 average rating, 33 reviews

Resort Living: Easy Access to Napa's Attractions

Jun 6 – 13

R10,398 ZAR per night

Destinations to explore

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  5. Oakville