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Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful.

Bedrooms 3
Half Baths1
Space 3,300 sq. ft.
Property type house
Minimum Stay 2 nights


About the property

House, 3 Bedrooms + Other (See Description), 3.5 Baths, (Sleeps 8)

Nestled on 5+ acres at the end of a secluded country lane and shaded by a canopy of majestic oaks, Oak Leaf Retreat is a stunning, 3300 sq. ft., 2-story, luxury 3 bedroom, 3.5 bath custom home with a wrap around porch, abundant spectacular features, and gorgeous amenities. This elegant country Retreat offers the best of the two worlds of country and town, where you can enjoy the peace and serenity of a pastoral and vineyard setting that is only a 10 minute drive to the town square of charming and historic Healdsburg, the ‘crown jewel’ of Sonoma County’s Wine Country.

Oak Leaf Retreat is located near over 100 wineries in the Dry Creek Valley, Alexander Valley and Russian River Valley appellations. Naturally, there are dozens of fine restaurants within 15 minutes of Oak Leaf Retreat.

This special home in the ‘Tuscany’ of Northern California, has a fabulous gourmet kitchen, the heart of this very special retreat. The main level entry hall leads you to the expansive well-equipped kitchen, on your left, which opens to the dining and living areas, all with high ceilings, custom lighting, abundant windows and doors opening to the 3-sided porch and back patio, and the well designed flowing floor plan makes for nearly effortless transitions from room to room. With everything your ‘chef’ will want or need, this kitchen is truly heavenly and includes abundant custom lighting, marvelous maple cabinets, a large island with a professional Fisher&Paykal 5-burner gas cook top and prep sink, new appliances including a built-in oven, stainless steel Maytag fridge-over-freezer, dishwasher, Magic Chef microwave, and a large stainless steel sink

The lovely dining area conveniently awaits service of your culinary delights, just adjacent to the kitchen, with a rustic dining table, 6 luxurious leather high backed chairs and windows all around to let the splendor of nature ‘join’ you as you enjoy sipping, supping, and good conversation. From the kitchen/dining area, you can ‘flow’ into the large living and entertaining room with plenty of comfy seating for all including a large sectional sofa, 2 leather chairs, and an ottoman. The spacious living room’s audio/visual entertainment is provided by a 42” widescreen HD TV, which includes Netflix.

The Retreat’s main level is completed with 2 lovely bedrooms with full baths, a guest bathroom and a convenient laundry room. Situated to the left and right of the entry, the bedroom suites are on opposite sides allowing for maximum privacy. The bedroom suite on the left has a comfy queen bed, a full glass door to the side porch, and a private en-suite bath is well-appointed with a shower over tub and pedestal sink. You can use the available, trusty iMac computer. Also, WiFi delivers high-speed internet connection that reaches throughout the Retreat and outdoors more than 200 feet.

On the right front side of the home, ‘lives’ the second bedroom suite also with queen bed, peaceful décor, ceiling to floor silk drapes for the window, and full glass door, leading to the back deck and spa. There is also a wall-mounted 32' flat screen TV. A well appointed second en-suite bathroom features a huge walk-in, fully tiled shower with 2 showering stations with wands and a teak ‘in shower’ bench. Additionally, there is a private water closet, vanity, small dresser, and mirrored wall which completes this roomy and efficient ‘getting ready’ station. Finally, on the main level you'll find an additional half bath and a laundry with large washer and dryer, sink, wine fridge, and another full glass door to the side porch.

But wait! Climb the staircase to the upper level of this very special home to the expansive 1400+ sq. ft. multi-use Great Room suite. A private family retreat unto itself, this beautiful space creates a relaxing environment full of amenities and opportunities for play, watching TV or a movie, or a rejuvenating, restful sleep. Enter the upstairs expansive living entertainment area with sofa and loveseat and a 52” Panasonic HD widescreen TV with DVD player and an iHome Speaker/Charger System for your iPad, iPhone or iPod.

This very special haven’s alcoves include a bedroom ensemble with king bed and armoire, a queen bed, two single beds, a play area with game table, a desk/work station, and a wet bar. Spa inspired, the suite's bathroom is grand, and features a private bath and shower room that includes a jetted Jacuzzi soaking tub with wand and a large free standing shower with wand. Also, adjoining is a private water closet, and a private vanity with mirrored wall.

Considering the splendor of it all and spectacular and abundant amenities and features of this magnificent Retreat, you may never want to leave and may have to be ‘pried’ out to enjoy the beauty of Mother Nature and the many adventures to be enjoyed in Healdsburg, Windsor and the surrounding areas. The outdoor features of the Retreat include a 3-sided wrap-around porch, back deck with 2 tables and chairs for 10, another round table with umbrella and 4 chairs, two lounge chairs, a new high-end 7-person Belize 1500 hydrotherapy spa, a new gas grill for your BBQing pleasure, the shaded canopy of 100 year old oaks, over an acre of lawn, and the glorious sunsets over the vineyard. During the early morning hours of the ballooning season, you may also enjoy balloons overhead and, if you listen carefully, you'll hear distant conversations from above.

More Details

Property Manager
Andrew McGuire
Member since: 2009
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
March 28, 2017

About Andrew McGuire

My wife and I built our home in late 2003. After living in our dream home for 8 years we decided to return to the East Bay to be near (our two daughters and) our five granddaughters, all under the age of 5. We did not want to sell our home so we decided to provide our home as a vacation rental. This way we can return whenever the home is not occupied and show our granddaughters their goat and sheep friends on the neighboring property and help them indentify the birds (nearly 50 different birds appear throughout the year).

We intend to constantly upgrade our home with the amenities that make for a relaxing and memorable retreat or vacation. We encourage feedback from our guests so we can improve the 'wine country' experience for future guests.

Thank you for considering our home for your 'retreat.'

Kae and Andrew McGuire


Andrew McGuire purchased this house in 2003

What makes this house unique

Our home is at the end of a country lane and is peaceful and quiet.


Healdsburg House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 3300 sq. ft.
House Rules:
  • Max. occupancy 8
  • non smoking only
  • pets considered
  • Events Allowed
  • children welcome
Location Type:
  • Mountain View ...
  • Rural
  • Family
  • Romantic
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Computer Available ...
  • Hair Dryer
  • Heating ...
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Parking
  • Parking Off Street ...
  • Parking for RV/Boat/Trailer
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Coffee Maker ...
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 3 Bathrooms
  • 1 Half Bath
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 3 Bedrooms, Sleeps 8
  • King size beds (1), Queen size Beds (3), Twin or Single Beds (2), Porta Crib (1), 1 Double AeroBed
  • Books
  • CD Player
  • DVD Player
  • Games
  • Music Library ...
  • Satellite / Cable ...
  • Television ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • 2 garden chairs
  • wheelchair accessible ...
Pool / Spa:
  • Hot Tub ...
  • jetted tub ...
  • cinemas
  • health/beauty spa
  • museums
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • horseback riding
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • hot air ballooning
  • ice skating
  • kayaking
  • mountain biking
  • surfing
  • swimming
  • water skiing
Beautiful views grace this 5 acre, serene, secluded, retreat shaded by a canopy of 100+-year-old oaks.


Exceptional! 5/5 -
(24 traveler reviews)

Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful.
average rating of 5.0 based on 24 reviews

Most Relaxing stay we've had in years!

  • 5 of 5

The minute we drove up onto the property at Oak Leaf Retreat, we felt immediately relaxed. This 5 acre retreat felt private and restful. After a day of wine tasting at conveniently located nearby wineries, it was so perfect coming back to this beautiful property. We were able to cook dinner in the very open kitchen, which was stocked with everything we needed. Watching the sunset on the wrap-around deck felt incredible and so very memorable. In the distance you hear an array of birds, and can see jackrabbits bouncing about. It is truly a gem of an experience. You feel like you are a world away from everything, yet you are a short drive to the adorable town of Windsor and hip downtown Healdsburg. The location is perfection.

Communicating with wonderful owner Andrew, was very easy and he gave us all the information and help we needed. The house is not their primary home, so it didn't feel like we were intruding and staying amongst someone else's personal belongings. It is stocked with everything you need, yet truly feels like a vacation home.

I would recommend this home to anyone. It is great for a few families, a group getaway, or couples getaway. The price is outstanding for what you get. We looked at other rentals and nothing compared to this property with its very reasonable price point for the Healdsburg area. It is very versatile and you will absolutely enjoy every moment of your stay. I can't wait to visit again soon!

  • Submitted: Mar 9, 2017
  • Stayed: Feb 2017
  • Source: VRBO, from HomeAway
Owner's Response: Wow! Thank you for your observations and thoughts about our home. Do come back, Maggie.
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0 0
Fremont, CA

Beautiful House on a beautiful property!

  • 5 of 5

We found this home while looking for a weekend away to celebrate my husbands 60th birthday. We needed to take 2 dogs and had a person in a wheelchair so access was important. The hall ways are all super wide to accommodate a wheelchair and there is a full downstairs bedroom with a large shower that can also accommodate a chair. The house was beautiful with views all around! While we were only 6 you could easily have more guests! Upstairs there were beds aplenty. The kitchen was well appointed and while we didn't cook every meal there we found everything we needed for our purposes. We were there while it was quite cold so we didn't spend any time outside but I can imagine sitting outside with some appetizers and a bottle of wine under the beautiful trees on the property. We might just have to go back in the summer months! I would definitely recommend this property . . . you will not be disappointed!

  • Submitted: Dec 22, 2016
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
Owner's Response: Dear Barbara, Kae and I are so pleased that you and your friends enjoyed our home even though it was cold and rainy. Please come back and enjoy the outdoors. Kind Regards, Kae and Andrew
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2 0

Beautiful Home

  • 5 of 5

Homeowners are wonderful hosts, kind, responsive and accommodating. Their house is beautiful, cozy, charming, comfortable and equipped with absolutely everything you could need, including lovely touches like maps & guidebooks & info on the area and a detailed, helpful manual for the house. Beautifully designed and decorated home. The setting and the views are spectacular and it's a close drive to the plaza and great shops and restaurants. We only wished we had time for a longer stay. This is the perfect getaway spot and we can't wait to go back for a longer stay! It was the best find – can't recommend enough!

  • Submitted: Jun 19, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Mahshid. It gives us so much pleasure when our guests enjoy our home. Do come again. Kae and Andrew
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1 0

Great house, location, vineyards!!

  • 5 of 5

We had 3 couples that rented the house for a mini vacation. It was wonderful!! The house is rural, yet 10-15 minutes from town (Windsor or Healdsburg). Close to a lot of great wineries and right next to part of the J Vineyards property. We had plenty of space for the 6 of us - each with our own bathroom. I do agree with the last review - we had the upstairs bathroom and could only get warm water, not hot...but considering everything else, not a huge issue. We had planned on going out to eat every night, but ended up buying groceries and staying in. The kitchen was the perfect size. We enjoyed walking the vineyards - great views!! Thank you again Andrew and Kae for sharing your home!

  • Submitted: Oct 13, 2015
  • Stayed: Oct 2015
  • Source: VRBO, from HomeAway
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1 1

Perfect Combination of a retreat and yet close to it all

  • 5 of 5

A group of friends shared this house to celebrate some 50th birthdays, and we had a fabulouse time. We found the house to be clean, well maintained, and super comfortable, and well appointed. Also, the house is in a great location close to wineries as well as downtown Healdsburg. We even had a chef come in one evening to prepare dinner and he was impressed with the kitchen.

The upstairs did have a number of beds, but really best suited for kids (or a number of single folks), comfortable with sharing a room. The main floor master bedrooms were also nice with each having it's own bathroom. The only issue was the upstairs shower as we couldn't get the hot water to work, but we did not contact the owners as we just all shared the downstairs bathrooms.

I would definitely recommend this property to friends.

  • Submitted: Sep 20, 2015
  • Stayed: Aug 2015
  • Source: VRBO, from HomeAway
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1 0

A farmhouse dream

  • 5 of 5

Want the experience of a country farm house, but with all the goodies, look no farther. We rented this property for our sons rehearsal dinner, it was perfect for it. Plenty of room inside as well as outside. The kitchen was stocked with every kind of items you might need to entertain. Yet there you are in the pieceful country side enjoying all of Gods creatures just minutes from downtown Windsor. Enjoy sitting in the evening or morning on their large wrap around porch soaking in the vinyards.

Andrew was exceptional in helping to answer all our questions and making sure we had what we needed. Would definitely return to this property and would recommend to others.

  • Submitted: Aug 10, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
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Nearest Airport
5 Miles
Sonoma County Airport
Nearest Golf
4 Miles
Windsor Golf Course
Nearest Motorway
1.6 Miles
US 101
Nearest Restaurant
0.6 Miles
Kin, Lupe's , etc.
Car: necessary

Wine tasting, fine dining, old growth redwood preserve, Fort Ross Historical State Park, Skunk Train, sea, river, and lake.

Over 100 wineries within 20 minutes of Oak Leaf Retreat.


Rates & Availability

Healdsburg House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
My Standard Rate
2 night minimum stay
Notes: Rates are based on 4 guests; add $75 per night, per additional guest

Additional information about rental rates

Cleaning ($225-275) $275 + Tax
Pet Fee $75 + Tax
Tax Rate 12.0%

Our Standard Rate of $495/night is for 4 OR FEWER GUESTS. Add $75/night for EACH ADDITIONAL GUEST ABOVE 4. For example, the charge per night for 8 guests is: $495 + $75 X 4 = $795 per night (exclusive of tax and cleaning fee).


Manager's Cancellation Policy

  • 50% refund if canceled at least 7 days before arrival date.
  • 100% refund if canceled at least 14 days before arrival date.
Enter dates for accurate pricing

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