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5bd/4ba w/ Poolside Guest House - near Healdsburg

Photo gallery for 5bd/4ba w/ Poolside Guest House - near Healdsburg

Backyard w/pool and spa
Pool with lights
Back yard patio and dining area
Living Room
Living room

Reviews

10 out of 10, Loved by Guests
Top 10% based on
5 bedrooms4 bathroomsSleeps 82000 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Rooms & beds

5 bedrooms (sleeps 8)

Guest House

1 Queen Bed

Guest room #1

1 King Bed

Guest room #2

2 Single Beds

Primary bedroom

1 King Bed

Studio

1 King Bed

4 bathrooms

Guest bathroom

Bathtub · Toilet · Shower only

Guest House Bathroom

Bathtub or shower · Toilet

Primary bathroom

Toilet · Shower only

Studio Bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Office
Separate dining area
Garden

About this property

5bd/4ba w/ Poolside Guest House - near Healdsburg

Escape to wine country, just 5 minutes to Healdsburg! This fully furnished 5 bedroom, 4 bathroom single level home is centrally located in Windsor on a peaceful, oversized lot. The spacious, open floor plan includes an updated kitchen, dining table for 8 and opens to a serene backyard with a Pool/Spa and mature Oak Trees. The well-designed floor plan also includes a detached poolside guest house (perfect for extended family), office, and laundry room. 2 car garage and circular driveway provide ample off-street parking.

The space
- Plenty of storage is available in 2 hallway closets, large walk-in closet (primary), walk-in closet (guest house) and guestroom closets.
- Private Pool + Spa (Pool heating optional for an additional fee).
- Sonoma County Airport is just 5 miles away
- Less than a mile to Windsor Town Green with Summer Concert series, weekly Farmers market and Thursday Live Concerts
- Less than a mile to Oliver's Market
- 2 miles to Foothill Regional Park for hundreds of acres of hiking trails or fishing
- 5 miles to downtown Healdsburg with world class wineries and culinary cuisine, art galleries, museums, walking and hiking trails and shopping.
- For guests with mobility issues, there is a wheelchair, walker and toilet safety rail available for you to use.
- For families with young children, we have a pack n' play, highchair, baby changing pad, baby bath tub, and children's plates, bowls, cups and utensils.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted
Guests must sign rental agreement. NO parties, NO pets, NO smoking.
As a courtesy to our neighbors, please keep noise down after 9pm, quiet hours are 10:00pm and on.
Children under the age of 14 must be accompanied and supervised by an adult at all times. No jumping or diving.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Windsor

Windsor is home to this holiday home. Santa Rosa Plaza Shopping Center and Railroad Square Historic District are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Healdsburg Ridge Open Space Preserve and Safari West. Travelling with kids? Consider Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and mountain biking nearby.
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Map
Windsor, CA

What's nearby

  • Powell's Sweet Shoppe - Windsor - 17 min walk - 1.5 km
  • Dom Whitney Tasting Lounge - 19 min walk - 1.6 km
  • Russian River - 3 min drive - 6.3 km
  • Healdsburg Plaza - 5 min drive - 8.8 km
  • Dry Creek Vineyard - 11 min drive - 17.5 km

Getting around

  • Santa Rosa Station - 15 min drive
  • Santa Rosa, CA (STS-Sonoma County) - 8 min drive

Restaurants

  • ‪McDonald's - ‬17 min walk
  • ‪Starbucks - ‬3 min drive
  • ‪Taco Bell - ‬2 min drive
  • ‪Ana's Cafe & Espresso - ‬14 min walk
  • ‪Sweet T's Restaurant + Bar - ‬3 min drive

Frequently asked questions

Is 5bd/4ba w/ Poolside Guest House - near Healdsburg pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at 5bd/4ba w/ Poolside Guest House - near Healdsburg?

As of 5 Mar, 2026, prices found for a 1-night stay for 2 adults at 5bd/4ba w/ Poolside Guest House - near Healdsburg on 11 Feb, 2026 start from S$402, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at 5bd/4ba w/ Poolside Guest House - near Healdsburg?

On-site parking is available at the property.

What time is check-in at 5bd/4ba w/ Poolside Guest House - near Healdsburg?

Check-in begins at 3:00 PM.

What time is check-out at 5bd/4ba w/ Poolside Guest House - near Healdsburg?

Checkout is at 11:00 AM.

Where is 5bd/4ba w/ Poolside Guest House - near Healdsburg located?

This family-friendly Windsor holiday home is within 1 mi (2 km) of Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor. Windsor Oaks Vineyards is 3 mi (4.8 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 40 out of 40 reviews
Rating 8 - Good. 0 out of 40 reviews
Rating 6 - Okay. 0 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 0 out of 40 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Terry S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely Fantabulous! Our group loved every aspect and every minute of our stay! This is a five-star property and a five-star experience from start to finish. Sarah and Jeff are wonderful hosts - gracious, helpful and welcoming. Excellent location, kitchen is well-stocked, the beds are comfy. We spent many hours every day enjoying the pool, spa and backyard. We hope to be able to return for another wonderful stay!
Stayed 30 nights in Aug 2025

10/10 Excellent

carol s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family in wine country

Wonderful property, owners and great location!
Stayed 5 nights in Apr 2024

10/10 Excellent

Anjie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay

Awesome location and property for a group. We were very happy and the property managers were very responsive.
Stayed 3 nights in Apr 2023

10/10 Excellent

Angela K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Stayed here with multiple family members for a bike ride and wine touring. The house was in a great location, lots of room for everyone, and very comfortable. Thank you for a great stay.
Stayed 4 nights in Apr 2024

10/10 Excellent

Kevin Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Vacation Home!

We had a great experience at the Oak House. Great communication from the hosts, comfortable and spacious home for our group of 6 adults and 6 children. The pool/spa was perfect for the kids and adults. We would definitely stay here again!
Stayed 4 nights in Aug 2024

10/10 Excellent

Robin Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful retreat in Sonoma!

We picked this place to stay when a few friends were in town for a weekend. Plenty of room for everyone, close to wineries, and a beautiful place to hang out in while we recovered!
Stayed 4 nights in May 2024

10/10 Excellent

Corinne S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay

Super close to healdsburg. The host reaches out to you with instructions and is very helpful. Would stay again!
Stayed 2 nights in Mar 2024

10/10 Excellent

Tyler H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, spacious, and comfortable

This place was perfect for our large family. More than enough room for the 8 of us! Love the location and will definitely be staying here again.
Stayed 3 nights in Jul 2023

10/10 Excellent

Pamela H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time

Plenty of room for the 6 of us. More would still have been comfortable. Loved the location!
Stayed 7 nights in Feb 2025

10/10 Excellent

Elizabeth S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

Very comfortable home. Nice, big living room with great light. The pool and hot tub are excellent. The bedrooms are spacious and the beds are comfy.
Stayed 3 nights in Jul 2024

10/10 Excellent

Sean M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wine Tastings - Fun

Great place - highly recommend it especially for a larger group. Host were fantastic and very responsive
Stayed 4 nights in Apr 2024

10/10 Excellent

Ashley H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent place!

House is very nice and clean and had everything we needed. Beds were super comfortable. Communication with the property manager was seamless. House is close to downtown Healdsburg and many great wineries. Would definitely stay here again.
Stayed 3 nights in Oct 2024

10/10 Excellent

Myra R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sisters Getaway

The home was so comfortable and beautiful. The backyard pool and hot tub was perfect! We did not want to leave! We loved the whole home and can’t wait to go back again.
Stayed 3 nights in Oct 2024

10/10 Excellent

Lisa V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable and Relaxing!

We celebrated a friend's birthday in Napa. The house was perfect for our group! We went wine tasting in the morning, escaped the extreme afternoon heat in the pool, and enjoyed a 4th of July BBQ at night! We look forward to returning for another stay!
Stayed 4 nights in Jul 2024

10/10 Excellent

diane d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome!

Highly recommend this beautiful, well furnished clean, home with private yard yet close to town, country and vineyards. Would love to stay here again. Very helpful and caring owners!
Stayed 5 nights in Oct 2023

10/10 Excellent

TERESA M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

wonderful place for our long-time friends gathering

This delightful spot was just what we needed to gather with 6 long-time girlfriends to explore the Healdsburg/Windsor area. Hosts were very responsive. The house & yard were lovely and well maintained.
Stayed 3 nights in Oct 2023

10/10 Excellent

Meghan G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect stay in wine country!

This was the perfect property for our party of 10 for a recent wedding. The house was clean, spacious, and exactly as described. Jeff and Sarah were very responsive and flexible to accommodate our earlier than expected arrival. I would absolutely return and recommend to anyone traveling with a big group.
Stayed 2 nights in Sep 2024

10/10 Excellent

Sandra O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place for a wine country getaway!

This was a perfect place for me and my friends to spend my 60th Birthday!! Close enough to tube down the Russian River, plenty of room for the 10 of us with a great open floor plan for lots of festivities! We also enjoyed hanging out in the backyard lounging by the pool and relaxing in the hot tub! If you’re looking for a luxurious vacation with a big group, I would highly recommend this place!
Stayed 3 nights in Aug 2024

10/10 Excellent

SAL A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful & Restorative

Exceptionally clean, well maintained, spacious, a haven away from home, majestic oak trees, beautifully landscaped, elegant interior design, refreshing pool, quiet neighborhood, convenient to community’s amenities, our new preferred destination when traveling to Sonoma County.
Stayed 5 nights in Jun 2023

10/10 Excellent

Teresa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends getaway

Ideal property and location for friends gathering. Sonoma valley corridor and short drive from coastal shores. Property comfortably accommodated 3 couples with rooms to spare, large kitchen and seating, and beautiful private yard. This property is a great find and one to keep on the list for a return stay.
Stayed 3 nights in Nov 2023

10/10 Excellent

Michael K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious and comfortable

Great quiet neighborhood location, bright and airy large home with nice yard, pool and hot tub! Highly recommended.
Stayed 2 nights in Mar 2023

10/10 Excellent

Ann D., High Point, NC

Liked: Cleanliness, check-in, communication, location, listing accuracy

Calif. Trip

We had a group of 10 (5 couples) and everything was great. House and property were great. Even walked the neighborhood early in the morning as was a safe area. Would definitely stay again.
Stayed 6 nights in Sep 2023

10/10 Excellent

Bridget L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect house for a wine getaway

This house was perfect for our wine weekend getaway. It had plenty of space for everyone and was in a great location. The living spaces are open and there was seating for everyone at the table. We loved the decor. We also enjoyed the heated spa each night, which was a nice nightcap after wine tasting. Overall, would recommend for a large group and hope to be back!
Stayed 2 nights in Mar 2023

10/10 Excellent

David M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Barrel Tasting at Russian River

We had 5 couples staying in the house that had plenty of room to accommodate us all. Very clean and a fabulous location to wine tasting within the area. The owner was a very good communicator and we had no problems with the house. Plenty of parking areas, large kitchen and great backyard. Would definitely come back to this property.
Stayed 4 nights in Feb 2024

10/10 Excellent

Patricia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable home in wine country

We had an excellent stay at the Heritage Oak House ! It suited my family beautifully, lots of room, comfortable seating, big kitchen, and of course the pool and spa. Although the house is in a neighborhood, it’s a big yard, and you don’t feel intrusive to the neighbors. Location near market and stores is very convenient. Pristine clean, comfortable bedding, and well maintained. We will stay here again!
Stayed 3 nights in Oct 2023

About the host

Hosted by Jeff Minc

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Languages:

English

Premier Host

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