Entire home

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

Photo gallery for The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

Cozy outdoor deck with fire pit and rustic cabin charm
Spacious kitchen with modern island and vibrant seating
Stunning illuminated pool and spacious patio for evening gatherings
Modern kitchen sink with scenic backyard view and natural light
Spacious living room with vaulted ceilings and panoramic windows

Reviews

10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 42000 sq ft

Popular amenities

  • Hot tub on site
  • Garage parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Outdoor grill

Explore the area

View in a map
Healdsburg, CA
  • Place, Russian River
    ‪3 min drive‬
  • Place, Healdsburg Plaza
    ‪6 min drive‬
  • Place, Pezzi King Winery
    ‪6 min drive‬
  • Airport, Santa Rosa, CA (STS-Sonoma County)
    ‪13 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Living Room 1

1 King Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet

Spaces

Kitchen
Office
Balcony

About this property

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

Summary:

A luxurious villa with a private pool, hot tub, firepit, and complimentary tastings included!



The Space:

Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation rental offers an unforgettable experience, combining tranquility, elegance, and modern comfort. With its stunning outdoor area this property promises the ultimate retreat for adults seeking an escape from the hustle and bustle of everyday life.



As you enter the estate you'll be enchanted by the tastefully designed interior, adorned with high-end furnishings and captivating artwork. The open-concept living area provides a seamless flow between the stylishly furnished living room, dining area, and fully equipped gourmet kitchen, creating an ideal space for sophisticated gatherings and private relaxation.



The soothing breeze beckons you to unwind and indulge in leisurely afternoons under the warm sun. Surrounded by lush greenery and vineyard views, this private oasis offers a serene ambiance, perfect for lounging on the comfortable outdoor chairs with a glass of local wine in hand. The outdoor kids play area, bocce court and acreage will keep the kids running around and engaged!



For those who appreciate the art of culinary excellence, the outdoor kitchen is a true delight. Featuring top-of-the-line appliances and ample counter space, it invites you to create gourmet masterpieces while savoring the picturesque surroundings. Dine al fresco under the shaded patio, immersing yourself in the beauty of wine country and enjoying the company of your friends and family.



After a day of exploration, rejuvenate your senses in the inviting backyard. The soothing bubbles and captivating views create an atmosphere of pure bliss, ideal for unwinding and reflecting on the day's adventures.



We offer more than just a beautiful setting—we provide a personal touch. Guests appreciate our responsive, thoughtful approach that ensures every stay is smooth, supported, and relaxing.



Local Winery Partnerships | Elevate Your Stay with Complimentary Tastings



As our guest, you’re invited to elevate your Wine Country stay with complimentary tastings at several small, locally owned wineries (Guest of record must be present for all tastings and reservations are required):



• Merriam Vineyards – a family-owned estate crafting elegant, Old World–inspired Bordeaux-style wines; a $35 value per guest, complimentary for up to six guests. (within walking distance of the villa)

• Orsi Family Vineyards – a locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino; a $35 value per guest, complimentary for up to six guests.

• Stonemason Cellars – Small lot wines all sourced locally from Sonoma County grapes. Enjoy their "Nibbles & Wine" tasting experience ($35 value per person)



A unforgettable way to toast your Wine Country getaway — cheers to delicious moments ahead!



Book your stay at this gorgeous homestead and experience a luxury vacation like no other. Whether you're seeking a romantic escape, a retreat with friends or a multi-family get together, this exceptional property offers everything you need to create cherished memories in wine country.



Additional Info:

• House has 1 master en suite. The additional guest bedroom and a third room, both featuring King beds, share a Jack and Jill bathroom. (Third bed is in this third room, not in the living room as the breakdown suggests)

• House is equipped with a generator which will turn on automatically during power outages.

• Work out room has a Peloton bike, yoga mats, free weights, foam roller, & a split zone a/c / heater.

• Tesla Car Charger available for complementary use.

• Keurig and Drip Coffee maker as well as a bean grinder are available for guest use (Coffee not supplied).

• This is a whole house rental that is not shared with other guests or the owner. The pool house in the pictures is not part of the rental and will remain vacant and locked during your stay.

• Sonoma County quiet hours: 9PM-7AM. No amplified music at anytime per the Sonoma County ordinance thus this house does not have a bluetooth speaker.





Pool heating is currently unavailable. Hot tub heating is included in the rental rate.

With consistently warm weather, using the pool cover alone will raise the water temperature to the mid- to high-70s.



Permit#: TVR22-0045

TOT#: 4331N

VR License#: LIC23-0104



The Neighborhood:

Located in a quiet residential area.



Getting Around:

Uber/Lyft is available but wait times can vary.



Other Things to Note:

You may also see this home listed as “Villa with Pool, Hot Tub and Tastings Included” on some booking sites.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Hot Tub
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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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

No pets allowed
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Smoking

Smoking is not permitted
Smoking not allowed. Pets not allowed.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Property Registration Number TVR22-0045

About the neighborhood

Healdsburg

Healdsburg is home to this vacation home. The area's natural beauty can be seen at Russian River and Safari West. Traveling with kids? Consider Dom Whitney Tasting Lounge, or check out an event or a game at Redwood Empire Ice Arena.
Map
Healdsburg, CA

What's nearby

  • Russian River - 3 min drive - 3.5 km
  • Healdsburg Plaza - 6 min drive - 6.0 km
  • Raven Performing Arts Theater - 6 min drive - 6.0 km
  • Pezzi King Winery - 6 min drive - 5.3 km
  • Healdsburg Museum - 6 min drive - 6.0 km

Getting around

  • Santa Rosa Station - 18 min drive
  • Santa Rosa, CA (STS-Sonoma County) - 15 min drive

Restaurants

  • ‪Ana's Cafe & Espresso - ‬5 min drive
  • ‪Sweet T's Restaurant + Bar - ‬8 min drive
  • ‪Pizzaleah - ‬7 min drive
  • ‪Grata Italian Eatery - ‬7 min drive
  • ‪KIN Windsor - ‬6 min drive

Frequently asked questions

Is The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included?

As of Apr 15, 2026, prices found for a 1-night stay for 2 adults at The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included on Jun 29, 2026 start from $1,161, 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.

What time is check-in at The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included?

Check-in begins at 3:00 PM.

What time is check-out at The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included?

Check-out is at 11:00 AM.

Where is The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included located?

Located in Healdsburg, this family-friendly vacation home is 3 mi (4.8 km) from Pezzi King Winery, and within 6 mi (10 km) of Dom Whitney Tasting Lounge and Healdsburg Center for the Arts. Raven Performing Arts Theater and Russian River are also within 6 mi (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.2/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

KJ C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pool, spa and fire pit all were used a lot and enjoyed. House was beautiful with many wonderful amenities.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Cana M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My family & I stayed over Thanksgiving and had an incredible stay! We loved the amenities like the hot tub, on-site gym, & gas fire pit. The house was exceptionally well-stocked and had high end appliances like a Viking grill:) Host was extremely responsive with the one question we had. This was our second stay with this vacation rental company, and will certainly not be our last!!
Stayed 9 nights in Nov 2025
Verified

10/10 Excellent

Margaret T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a wonderful property! Everything is first class.We enjoyed the in and outside, all well done!
Stayed 14 nights in Aug 2025
Verified

10/10 Excellent

Whitney S.

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

Beautiful Property

The pictures didn’t do justice to how wonderful the property is. The outdoor space is amazing. Just wish the weather was warmer to enjoy it more. We will definitely be booking another stay here. Communication with property owner was responsive and helpful.
Stayed 8 nights in Mar 2025
Verified

10/10 Excellent

Michele P.

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

10 year anniversary!!!!

We are speechless!! Absolutely the best home and time ever!!!!! Thank you ☺️
Stayed 11 nights in Sep 2024
Verified

10/10 Excellent

Kevin H.

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

Amazing Property

I booked this house knowing it was more than I needed for this trip, but was comparing it to a suite at one of the nice hotels in the vicinity. This home feels like you’re staying at a family or friend’s home. I wish I would have had more time there. The kitchen was well-appointed, and worked well (I cooked in both nights). The furnishings are very nice and the instructions are easy to follow for the pool, fire pit, etc. I’ll be back with more friends or family next time!
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Thomas K.

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

Couples trip to Sonoma

Overall we were very happy with the property and its location. Really easy to get to from Santo Rosa airport. And we were able to Uber to and from the property. It was a perfect getaway for 2 couples. We enjoyed the pool and the fire pit in the evenings. We felt like we did not have enough time to fully utilize the property. We used the bocce court the last day. That’s the only repair needed - it hasn’t been maintained well. But we still enjoyed it. We would definitely recommend to anyone. And we hope to stay again. 5 stars for sure.
Stayed 3 nights in Jun 2024

About the host

Hosted by WC Lodging

Host profile image

What makes this property unique

A luxurious villa with a private pool, hot tub, firepit, and complimentary tastings at Merriam Vineyards and Orsi Family Vineyards!

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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