We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
other traveler has booked this property

Headland House*Two Homes*Marine Views* 3 King Beds

Great Room with expansive views of the sound
Bookings for this home are first-come, first served. Lock in your dates before they are gone
Great Room with expansive views of the sound
Upper level deck lounge area Dining area main house seating for 10 guests
Check Availability
Request to Book
Make Inquiry
4.5 of 5 stars
Very good
24 reviews
Great Room with expansive views of the sound
Upper level deck lounge area
Dining area main house seating for 10 guests
Views of the sound from Main house great room
Projection Media room system
#1 Master Bedroom main floor - King size bed
#1 Bedroom  Master Bedroom king size bed
#2 Bedroom Lower level West side King size bed
#3 Bedroom lower level East side King size bed
#3 Bedroom lower level patio and views
#4 Bedroom Retreat - Queen size sofa bed
#4 Bedroom Retreat dresser
#5 Bedroom - Guest house master - Queen size bed
#6 Bedroom Guest House Day bed with trundle
#6 Bedroom Guest House Day Bed
Game Room showing wall of windows water views
Game Room pool table
#1 Master Bedroom private deck area
Main House Kitchen
Main House Kitchen double ovens
Kitchen main house
Kitchen stove top
#1 Master Bathroom double sinks main house
#1 Master Bathroom soaking tub main house
#2 Bathroom Powder room main house
#3 Bathroom lower level main house
Entry Bridge leading to the main house
Enty bridge leading from Main House to Guest House
View of Main house and Guest House (homes face opposite direction lots of privacy)
Outdoor dining area
Outdoor dining and BBQ area
Main House Hot Tub
Guest house Hot Tub
Pathway to Guest house
Guest House balcony
Guest house views from dining area
Guest house great room
Guest House Kitchen
Guest House Dining Area
Guest House Living room area
Headland House Picnic and horseshoe pit area
Headland House outdoor lighting
View of great room showing projection screen
Dining area showing seating for 10 people
View into great room dining area and kitchen
This property is not available for these dates.
Don't give up! Inquire about other rentals just like this one that are available -
Show all rentals available
Rental Home -
6 Bedrooms, 4 Bathrooms, Sleeps 12
Deer Harbor, Orcas Island, San Juan Islands, Washington
If you are looking for the ultimate in a vacation home then consider Headland House. This Truly Spectacular property has TWO HOMES on the property. Located above the glistening waters of Deer Harbor on Orcas Island in the San Juan Islands. This 8-acre private haven with panoramic water views.

The Headland House property has two homes the main house has 4 bedrooms and the guest house has 2 bedrooms for a total of 6 bedrooms. The rate shown is based on the entire estate Maximum occupancy 12 guests (No Exceptions). Off season we offer the option to rent just the main house (maximum 9 guests) or guest house (maximum 3 guests)

When sending us an inquiry please tell us a little bit about yourself and the purpose of the stay. We ask that you please read through the entire listing before sending us an inquiry. To find our website... cli...
Read more
About the Owner, Vacation Holdings LLC L
Languages spoken: English
Response Rate: 100 %
Response Time: Within a few hours
Calendar Updated: 13 days ago
Listed since : Oct 2011
Overall rating: 4.5 / 5.0
Based on 24 reviews and 1 property
Contact Owner See more properties
Listing #FKN2383935 by: FlipKey
Reviews from our community
 of 5 stars
4.5 of 5 stars Very good - based on 24 reviews
Write a Review

Reviews from our community

Date | Rating
  • English first
  • Any
English first
Level Contributor
7 reviews
common_n_hotel_reviews_1bd8 6 helpful votes
1 of 5 stars Reviewed September 1, 2015 for a stay in August 2015
people found this review helpful

It's a lovely home that has some wear and the owners expect you to take an hour to inspect the house upon arrival and list the damage so that you won't be responsible for it. It would have taken well over an hour and would have been a long list. That's impossible....and we're on vacation--places to explore and fish to...

Management response:

Review is quite different than the voice message we received from Suzanne when she arrived. “Hi there Lisa and Richard it's Suzanne Randall”. “Sorry I'm so late in getting back to you but we are enjoying the home”. “We're about ready to sit down and have dinner and are setting the table noticing that there's a missing 12 ounce glass....


Report response as inappropriate
Nampa, Idaho
1 review
5 of 5 stars Reviewed April 1, 2015 for a stay in March 2015

The house was beautiful and clean. The bed was super comfy and the pillows were amazing. The house was fully stocked with every comfort and gadget imaginable! Truly a place you could come with just your clothes and not want for anything. The home was pretty secluded but easy to get to and had an amazing view of the water....

Management response:

Thank you Joy for all the sweet comments. We were delighted to hear that you and your husband enjoyed your stay and that you noticed the quality of our beds and our super comfy sleeping pillows. We really try hard to provide everything you would need as we recognize that it is part of island living. Nothing pleases us more...


Report response as inappropriate
Albany, New York
1 review
5 of 5 stars Reviewed April 1, 2015 for a stay in March 2015

I can't imagine a more wonderful home in which to stay, or more conscientious and gracious hosts. We appreciated the attention to detail and care that went into every aspect of the property. We were delighted with our stay in every single way. I have never had a rental experience nearly as flawless, and can't wait to return. We made...

Management response:

Thank you Beth for the kind words Richard and I really enjoyed having you and your family as or guests. Truly appreciated that you took the time to call and ask so many great questions before the stay. With the wonderful communication you made us feel as if our own family was arriving. We are looking forward to having you...


Report response as inappropriate
  • Air Conditioning
  • Alarm Clock
  • Balcony
  • Blender
  • Books
  • Ceiling Fans
  • Central Heating
  • Deck
  • Dining Seats (12)
  • Dishwasher
  • Dryer
  • DVD Player
  • En Suite Rooms (2)
  • Fax
  • Freezer
  • Game Room
  • Grill
  • Hairdryer
  • Highchair
  • Hot Tub
  • Internet Access
  • Iron
  • Kettle
  • King Beds:(3)
  • Linens Provided
  • Living Room Seats (12)
  • Local Guides/Maps
  • Microwave
  • Mountain Views
  • Ocean Views
  • Outdoor Dining Area
  • Paper Towels Provided
  • Parking
  • Patio
  • Porch
  • Private Yard
  • Queen Beds:(1)
  • Refrigerator
  • Safe
  • Satellite TV
  • Shared Yard
  • Single Beds:(2)
  • Soap/Shampoo Provided
  • Sofa Beds:(1)
  • Stereo System
  • Stove
  • Telephone
  • Terrace
  • Toaster
  • Towels Provided
  • TV
  • VCR
  • Washer
  • Water Views
  • Wi-Fi
  • Pets Allowed:
  • Smoking Allowed:
  • Kid Friendly:
Show Rates

Rates are calculated based on the latest information provided. Please contact the manager/owner to confirm actual rates for your requested dates.

Showing rates for up to guests.
Dates Min stay Per night Per week
Default 2 nights
Aug 4, 2017 -
Dec 31, 2017
6 Bedroom Rate Only
4 nights
  • Housekeeper fee: $335 / stay - Fee
  • Application Fee: $35 / stay - Fee
  • Security deposit: $250 / stay - Fee
  • Damage Insurance: $50 / stay - Fee
Hide Rates
Car advised
How to get there
Airport: Deer Harbor Marina Sea Planes: 1.0 mi
Ferry: Orcas: 5.0 mi
Headland House is walking distance from the Deer Harbor Marina. Kenmore Air Seaplanes fly into this marina. By Ferry from Seattle driving distance to the Anacortes Ferry Terminal is approximately 1.5 to 2 hour drive. Drive on Ferry distance to Orcas island is about an hour ferry ride. Washington State Ferry has a reservation system to San Juan Islands. San Juan Airlines and Northwest Ferry (Small Planes) offers flights from Bellingham and Boeing Field to the Orcas Airport.
Activities nearby
Fishing Nearby, There Is A Golf Course Within 30 Mins Drive, Nearest Beach: 0.5 mi.
About this property
How do I know if the property is available?
First, check the Availability tab on this page to see if your dates are available. If they are, contact the owner via the TripAdvisor Rental Inbox to confirm availability.
How can I contact the owner?
If the owner has provided contact information, you may contact him or her directly. If not, you can contact the owner via the TripAdvisor Rental Inbox. This inbox is created after you send your first message or booking request to the owner
How will the owner contact me?
This owner may contact you via the TripAdvisor Rental Inbox, your personal email, or phone.
What if I don't hear back from the owner?
You can send another message via the TripAdvisor Rental Inbox to check if the property is still available. If the owner has listed a phone number, you can also call to follow up. If you still don't hear from the owner, TripAdvisor recommends that you send inquiries to other properties.
How do I pay?
For this property, you may use a credit card to pay via the TripAdvisor Rental Inbox; the owner may also offer other payment options. \n You must pay via the TripAdvisor Rental Inbox if you want to be covered by our Payment Protection. Once the owner approves your stay, he or she will send you a quote, which will include payment instructions.
Is my payment insured in any way?
If you pay online via the TripAdvisor Rental Inbox, your payment will be covered by our Payment Protection.
Do you own a vacation rental? List it here.
Extra income
Earn money by renting out your home. With no up-front fees and no contract, you keep more for yourself.
Easy to manage
Confirm bookings in one click and track everything from inquiry to check-out – even while you're on the go.
Trusted by travelers
With millions of reviews and protected online payments, TripAdvisor helps travelers book your home with confidence.
Set up your free listing
Enter dates for more accurate prices
2 guests
Additional fees may be applied by owner
Make Inquiry
36 travelers
viewed this property in the past week
How to book this rental
Submit an inquiry to the owner using the above make inquiry button
The owner will respond with a quote.  We encourage owners to respond within 24 hours
You will be able to send additional messages and pay for the quote through the TripAdvisor Rental Inbox
Payments made through the TripAdvisor Rental inbox are covered by Payment Protection
this property has payment protection
Never pay for your vacation rental by wire transfer.
Learn more about paying safely.