Vacation Rentals with Private Pool in Windsor Oaks Vineyards, CA: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  California

  5.  Windsor
  6.  Windsor Oaks Vineyards

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48 Best Vacation Rentals with Private Pool in Windsor Oaks Vineyards (Starting from $345)

Stella Campagna - Brand NEW 3 BD, Pool, Spa
Stella Campagna - Brand NEW 3 BD, Pool, Spa
House
Healdsburg, CA, 95448, United States
1.0k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1382
Average price / night
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Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
House
Healdsburg, CA, 95448, United States
1.4k from Windsor Oaks Vineyards center

AC, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

40 reviews

$1409
Average price / night
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Villa with Pool, Hot Tub and Tastings Included
Villa with Pool, Hot Tub and Tastings Included
House
Healdsburg, CA, 95448, United States
1.5k from Windsor Oaks Vineyards center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$1297
Average price / night
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Hidden Pocket: Private 1.5 Fenced Acres in Healdsburg Wine Country with Pool
Hidden Pocket: Private 1.5 Fenced Acres in Healdsburg Wine Country with Pool
House
Healdsburg, CA, 95448, United States
1.6k from Windsor Oaks Vineyards center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

104 reviews

$1317
Average price / night
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Healdsburg Luxe Reserve for 8, pool, spa, firepit
Healdsburg Luxe Reserve for 8, pool, spa, firepit
House
Healdsburg, CA, 95448, United States
1.6k from Windsor Oaks Vineyards center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1619
Average price / night
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Charming house in Healdsburg with Pool and Hot Tub
Charming house in Healdsburg with Pool and Hot Tub
House
Healdsburg, CA, 95448, United States
1.7k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.4

Superb

3 reviews

$798
Average price / night
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Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa
Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa
House
Healdsburg, CA, 95448, United States
1.7k from Windsor Oaks Vineyards center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

53 reviews

$1032
Average price / night
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Stay on the vineyard, hot tub &pool. 5 Queen suites, chef's kitchen, wrap porch
Stay on the vineyard, hot tub &pool. 5 Queen suites, chef's kitchen, wrap porch
House
Healdsburg, CA, 95448, United States
1.9k from Windsor Oaks Vineyards center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms10 Guests
10.0

Exceptional

94 reviews

$1314
Average price / night
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Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
House
Healdsburg, CA, 95448, United States
1.9k from Windsor Oaks Vineyards center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms10 Guests
10.0

Exceptional

66 reviews

$2100
Average price / night
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Luxury Private Pool Home near Healdsburg
Luxury Private Pool Home near Healdsburg
House
Windsor, CA, 95492, United States
2.8k from Windsor Oaks Vineyards center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$472
Average price / night
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Modern Hilltop Healdsburg Residence With 360' Views
Modern Hilltop Healdsburg Residence With 360' Views
House
Healdsburg, CA, 95448, United States
3.1k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

38 reviews

$2888
Average price / night
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The Quails Crossing-Healdsburg Vineyard Home
The Quails Crossing-Healdsburg Vineyard Home
House
Healdsburg, CA, 95448, United States
3.2k from Windsor Oaks Vineyards center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$2180
Average price / night
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Riverstone Estate sleeps 12 Pool Bocce Spa
Riverstone Estate sleeps 12 Pool Bocce Spa
House
Healdsburg, CA, 95448, United States
3.6k from Windsor Oaks Vineyards center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

5 Bedrooms12 Guests
10.0

Exceptional

22 reviews

$2938
Average price / night
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Perfect getaway! Riverside pool, river access, 5 min from Healdsburg square!
Perfect getaway! Riverside pool, river access, 5 min from Healdsburg square!
Apartment
Healdsburg, CA, 95448, United States
3.9k from Windsor Oaks Vineyards center

AC, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, Outdoor Space

2 Bedrooms4 Guests
10.0

Exceptional

31 reviews

$345
Average price / night
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Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
House
Healdsburg, CA, 95448, United States
4.3k from Windsor Oaks Vineyards center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

6 Bedrooms12 Guests
9.2

Superb

39 reviews

$1601
Average price / night
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Downtown Healdsburg Contemporary Home with Pool
Downtown Healdsburg Contemporary Home with Pool
House
Healdsburg, CA, 95448, United States
5.5k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$518
Average price / night
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Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ
Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ
Cottage
Healdsburg, CA, 95448, United States
5.7k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
8.6

Fabulous

19 reviews

$1000
Average price / night
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Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
Walk to Downtown Healdsburg--Luxury Healdsburg Vacation Rental
House
Healdsburg, CA, 95448, United States
5.8k from Windsor Oaks Vineyards center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
10.0

Exceptional

36 reviews

$1409
Average price / night
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Haven with Pool, Hot Tub and Tastings Included
Haven with Pool, Hot Tub and Tastings Included
House
Healdsburg, CA, 95448, United States
6.1k from Windsor Oaks Vineyards center

AC, Balcony, Barbecue, Dryer, Extra Bed, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
9.8

Exceptional

67 reviews

$1035
Average price / night
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Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
House
Healdsburg, CA, 95448-9029, United States
6.2k from Windsor Oaks Vineyards center

AC, Arcade, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms10 Guests
9.6

Exceptional

65 reviews

$2410
Average price / night
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Vista Breathtaking View Estate, 5 min to Healdsburg Square, Sleeps 12, Pool, Spa
Vista Breathtaking View Estate, 5 min to Healdsburg Square, Sleeps 12, Pool, Spa
House
Healdsburg, CA, 95448, United States
7.0k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms12 Guests
New to Booking
$1874
Average price / night
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Healdsburg Calif.: Amazing Resort-like Estate Healdsburg -- 4BD / 3BA
Healdsburg Calif.: Amazing Resort-like Estate Healdsburg -- 4BD / 3BA
House
Windsor, CA, 95492, United States
7.4k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$2533
Average price / night
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5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
House
Healdsburg, CA, 95448, United States
7.4k from Windsor Oaks Vineyards center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

196 reviews

$2307
Average price / night
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Private 3 Bed + Cottage Wine Country Estate With Pool And More
Private 3 Bed + Cottage Wine Country Estate With Pool And More
House
Healdsburg, CA, 95448, United States
7.6k from Windsor Oaks Vineyards center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
9.8

Exceptional

43 reviews

$1339
Average price / night
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'Villa Moderna' Ultimate Wine Country Estate. .WITH POOL
'Villa Moderna' Ultimate Wine Country Estate. .WITH POOL
House
Santa Rosa, CA, 95403, United States
7.6k from Windsor Oaks Vineyards center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$2009
Average price / night
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Secluded 4BDR Retreat w/ Pool, Hot Tub, Views | Shiloh Vista Estate by AvantStay
Secluded 4BDR Retreat w/ Pool, Hot Tub, Views | Shiloh Vista Estate by AvantStay
House
Santa Rosa, CA, 95403, United States
7.7k from Windsor Oaks Vineyards center

AC, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

4 Bedrooms10 Guests
New to Booking
$1645
Average price / night
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Sonoma Valley - Hot Tub, Pool, BBQ & Gym
Sonoma Valley - Hot Tub, Pool, BBQ & Gym
House
Santa Rosa, CA, 95404, United States
7.8k from Windsor Oaks Vineyards center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1399
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Windsor Oaks Vineyards.

Where to stay in Windsor Oaks Vineyards? Best neighborhoods & areas

Windsor Oaks Vineyards Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 48 verified vacation rentals with a private pool in Windsor Oaks Vineyards. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Windsor Oaks Vineyards vary depending on the property size, location, and travel season. Rates typically start from around $345 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Windsor Oaks Vineyards also welcome pets. Currently, 18 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Windsor Oaks Vineyards often include additional features such as Bedding/Linens, Fireplace/Heating, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Windsor Oaks Vineyards include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.