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Oakville Holiday Rentals

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50 rentals in Oakville.
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Modern 3 Bedroom Wine Country Home Near Yountville, holiday rental in Oakville

Modern 3 Bedroom Wine Country Home Near Yountville

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The St. Helena House - Within Walking Distance To Downtown, holiday rental in Oakville

The St. Helena House - Within Walking Distance To Downtown

3 bedrooms
2 bathrooms
Sleeps 8
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St. Helena Cottage - Walk to Downtown!, holiday rental in Oakville

St. Helena Cottage - Walk to Downtown!

2 bedrooms
2 bathrooms
Sleeps 4
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Avail Christmas!  1 Block To St. Helena Main Street Shops/Gym/Pool/Restaurants!, holiday rental in Oakville

Avail Christmas! 1 Block To St. Helena Main Street Shops/Gym/Pool/Restaurants!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Historic Farm House with Vineyard in Downtown Saint Helena!, holiday rental in Oakville

Renovated Historic Farm House with Vineyard in Downtown Saint Helena!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Wine Country Vacation Home - St. Helena Permit #2012-34, holiday rental in Oakville

Beautiful Wine Country Vacation Home - St. Helena Permit #2012-34

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Charming Country Home Nestled In Kenwood Village the heart of the wine country., holiday rental in Oakville

Charming Country Home Nestled In Kenwood Village the heart of the wine country.

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Farm House Downtown St. Helena., holiday rental in Oakville

Charming Farm House Downtown St. Helena.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Kenwood House, a Place to Stay, holiday rental in Oakville

The Kenwood House, a Place to Stay

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to Restaurants, Wineries and More, holiday rental in Oakville

Walk to Restaurants, Wineries and More

3 bedrooms
3 bathrooms
Sleeps 6
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Fantastic Family Home - Walk to Town (STRP# PL20-006), holiday rental in Oakville

Fantastic Family Home - Walk to Town (STRP# PL20-006)

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Wine Country Oasis. Pool, hot tub, vineyard views, walk to Downtown St. Helena, holiday rental in Oakville

Wine Country Oasis. Pool, hot tub, vineyard views, walk to Downtown St. Helena

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private home in Sonoma Wine Country *Monthly Discounts*, holiday rental in Oakville

Private home in Sonoma Wine Country *Monthly Discounts*

3 bedrooms
3 bathrooms
Sleeps 8
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Breathtaking mountaintop sunset & city light views of the heart of the valley!!!, holiday rental in Oakville

Breathtaking mountaintop sunset & city light views of the heart of the valley!!!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spa-Like Paradise Walking Distance To Wineries, Shops, Restaurants, holiday rental in Oakville

Spa-Like Paradise Walking Distance To Wineries, Shops, Restaurants

3 bedrooms
3 bathrooms
Sleeps 6
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Lovely private getaway with pool and vineyard views., holiday rental in Oakville

Lovely private getaway with pool and vineyard views.

4 bedrooms
5 bathrooms
Sleeps 8
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Stunning  Vineyard View Home on Iconic Silverado Trail in Beautiful Napa Valley, holiday rental in Oakville

Stunning Vineyard View Home on Iconic Silverado Trail in Beautiful Napa Valley

4 bedrooms
3 bathrooms
Sleeps 8
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Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL19012, holiday rental in Oakville

Downtown St. Helena retreat with pool, bocce ball and privacy. Permit #PL19012

3 bedrooms
2 bathrooms
Sleeps 6
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Glen Ellen Stone Retreat. 5 bd 4.5 baths w/ pool, and hot tub, holiday rental in Oakville

Glen Ellen Stone Retreat. 5 bd 4.5 baths w/ pool, and hot tub

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Modern 3 Bedroom Home W/Pool in Sonoma on 2 acres along a seasonal creek., holiday rental in Oakville

Modern 3 Bedroom Home W/Pool in Sonoma on 2 acres along a seasonal creek.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quiet, private retreat - socially distant, close to nature!, holiday rental in Oakville

Quiet, private retreat - socially distant, close to nature!

3 bedrooms
2 bathrooms
Sleeps 6
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Elegant Yountville Retreat...Your Wine Country Vacation Begins at Your Doorstep, holiday rental in Oakville

Elegant Yountville Retreat...Your Wine Country Vacation Begins at Your Doorstep

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Romantic, Private Jewel - 3 blocks from Downtown St.Helena in the Napa Valley, holiday rental in Oakville

Romantic, Private Jewel - 3 blocks from Downtown St.Helena in the Napa Valley

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries, Bikes Included, holiday rental in Oakville

Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries, Bikes Included

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Lovely home in Old Town 1.5 blocks to French Laundry & Downtown!, holiday rental in Oakville

Lovely home in Old Town 1.5 blocks to French Laundry & Downtown!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Exclusive Tuscan Vineyard  View Property, holiday rental in Oakville

Exclusive Tuscan Vineyard View Property

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Yountville Retreat in the Heart of Napa Valley, holiday rental in Oakville

Yountville Retreat in the Heart of Napa Valley

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BELLISIMA- in the heart of the Napa Valley., holiday rental in Oakville

BELLISIMA- in the heart of the Napa Valley.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming, comfortable, quiet neighborhood living in the heart of Yountville., holiday rental in Oakville

Charming, comfortable, quiet neighborhood living in the heart of Yountville.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Casa Bella Estate in Wine Country, holiday rental in Oakville

Casa Bella Estate in Wine Country

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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WALK to Wineries from this Gorgeous Designer Home!, holiday rental in Oakville

WALK to Wineries from this Gorgeous Designer Home!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Your Home Away From Home, holiday rental in Oakville

Your Home Away From Home

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Retreat in Yountville, Napa Valley Home (Town of Yountville # TOYS17111), holiday rental in Oakville

Luxury Retreat in Yountville, Napa Valley Home (Town of Yountville # TOYS17111)

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Halfway between Napa and Sonoma - Villa Nel Bosco, holiday rental in Oakville

Halfway between Napa and Sonoma - Villa Nel Bosco

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Centrally located St. Helena retreat - 10 minute walk to wineries and downtown!, holiday rental in Oakville

Centrally located St. Helena retreat - 10 minute walk to wineries and downtown!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries, holiday rental in Oakville

Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ranch Home in the Heart of Napa Valley Vineyards, holiday rental in Oakville

Ranch Home in the Heart of Napa Valley Vineyards

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Stone Lodge in Kenwood ~ 5 bedroom/5 bath, holiday rental in Oakville

The Stone Lodge in Kenwood ~ 5 bedroom/5 bath

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Urban Retreat in the Heart of St. Helena, holiday rental in Oakville

Urban Retreat in the Heart of St. Helena

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BEAUTIFUL DOWNTOWN SAINT HELENA FARMHOUSE, holiday rental in Oakville

BEAUTIFUL DOWNTOWN SAINT HELENA FARMHOUSE

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 1 Level, 3,400 Sq. Ft., Pool, 4 Bedroom, 3.75 Bath, Pool, Pool Hse, Patio, holiday rental in Oakville

Luxury 1 Level, 3,400 Sq. Ft., Pool, 4 Bedroom, 3.75 Bath, Pool, Pool Hse, Patio

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Villa LaFleur Sonoma, holiday rental in Oakville

Villa LaFleur Sonoma

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated Farmhouse bordering Yountville!, holiday rental in Oakville

Newly Renovated Farmhouse bordering Yountville!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vineyard View Hideaway walk to Downtown SH, holiday rental in Oakville

Vineyard View Hideaway walk to Downtown SH

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Harvest House -  Steps From Everything in Yountville #TOY517167, holiday rental in Oakville

Harvest House - Steps From Everything in Yountville #TOY517167

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Blanca, holiday rental in Oakville

Casa Blanca

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Wine Country Estate Home with Pool, holiday rental in Oakville

Wine Country Estate Home with Pool

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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The Villa at The Estate Yountville – 5 Bedrooms, Outdoor Pool & Hot Tub, holiday rental in Oakville

The Villa at The Estate Yountville – 5 Bedrooms, Outdoor Pool & Hot Tub

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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RustRidge Bed and Breakfast - Rustridge Suite, holiday rental in Oakville

RustRidge Bed and Breakfast - Rustridge Suite

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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RustRidge Bed and Breakfast - Rustridge Cottage, holiday rental in Oakville

RustRidge Bed and Breakfast - Rustridge Cottage

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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