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Headland House Estate * Two Homes * Marine Views *Theater System *3 King Beds

15 Reviews
Bedrooms 6
Half Baths1
Property type estate
Minimum Stay 1 - 4 nights

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Half Baths
Minimum Stay
1 - 4 nights


Deer Harbor Estate Rental Photos and Description

Estate, 6 Bedrooms + Convertible bed(s), 3.5 Baths, (Sleeps 12)

Maximum Occupancy "12 PEOPLE". NO EXCEPTIONS. Please do not submit inquires or reservation requests that exceed what we have posted as the max limit.

Headland House is a luxuriously appointed Orcas Island vacation rental home located on an 8 acre estate in the upscale community of Spring Point above the glistening waters of Deer Harbor. An open floor plan provides wonderful togetherness from the professionally outfitted gourmet kitchen to the cozy luxurious living area to the wraparound covered porches with numerous private decks and patio areas adorning this special home. This stunning estate property has panoramic water views, with a main house and guest house, 6 bedrooms and 3.5 baths, with occupancy up to 12 guests.

One feature that very few homes on Orcas Island have is Air Conditioning. Both the main house and guest house have air conditioning systems. Summer months tend to be quite warm so having this amenity is a benefit to guests that want to stay cool and comfortable while on vacation. When comparing rates please consider that we have the added energy costs to run our air conditioning systems.

Enter the home through a walkway bridge. Windows galore, bringing the outdoors in. As you enter the great room and dining room area you will be immediately drawn to the expansive ocean views with a full bank of windows that expands across the entire length of the room, large leather circular sofa which serves as a media room with a 105” projection theater room system with HD satellite TV, surround sound, DVD library in addition to a plethora of books for your reading pleasure.

The most discerning chef will find himself in heaven in this gourmet kitchen, as preparations for sumptuous meals using upscale appliances, panty features just about every small appliance, the dining area can comfortably seat 12 guests, laundry area with super large capacity washer and dryer.

Head downstairs to the African elephant theme game room where you can enjoy a game of pool, wet bar that features a margarita maker, flat screen TV, Sony Play station, Ipod station and large collection of board games. Guests that need to stay in touch with work will find a laptop workstation, wireless printer, and multi phone system both main house and guest house have separate telephone and wireless internet.

Outdoor covered BBQ area with pavilion dining area that features mosquito netting drapes, outdoor kitchen with fully stocked outdoor dinnerware.

Unique decorative accents will delight you as you make yourself at home. In the main house three of the bedrooms have king size beds with top of the line mattresses, TV's in most bedrooms hooked up to Dish network satellite, premium movie channels, luxurious linens and bath towels, robes, duvet covers, down alternative pillows and comforters to make your stay 'heavenly'.

Master bedroom suite located on main floor has been beautifully decorated in a Taj Mahal theme with a King size canopy bed with privacy panels, a 42” flat screen TV and DVD. The adjoining master bathroom features double sinks, shower and large soaking tub.

The second master bedroom suite is located on the lower level in the east wing. This bedroom has been decorated in a lovely Japanese Tea Garden theme with a King size platform style bed with adjoining bathroom. French doors lead out to the patio area with hot tub for the main house.

The third bedroom also has a king size platform bed and will cause you to day dream of far off places riding camels through the desert. This bedroom is located on the lower level east wing, features upscale quality furniture and bedding. French doors lead out to the outdoor dining and patio area.

The fourth bedroom is the retreat area that is adjoining bedroom two, features queen size sofa bed with triple dresser.

A special feature of Headland House is a fully detached guest house which is separated by a walkway bridge from the main house. Each home has its own separate entry and parking area. A cozy two bedroom one bath house in its own right, this delightful 'guest house' has a master suite with Queen size bed and has been decorated in a Serengeti theme with beautiful giraffe accent lamps and magnificent custom bedding.

The second bedroom in the guest house decorated in a magical tree monkey theme capturing your imagination for your restful repose at the end of the day, a trundle bed that makes up into two twin size beds.

The living room area of the guest house features, flat screen TV with DVD and DVD library, sofa with ottomans and a surprise waits as inside the ottomans as you will find books to read and more board games. Expansive views with open concept living, full kitchen complete with a stove, refrigerator, microwave. The guest house has its own laundry area with washer and dryer, and best of all - French doors opening up to the wrap around deck with the most amazing views where the ocean and mountains suddenly take on an unparalleled majesty. The guest house has a separate 3 person hot tub.

For planning sleeping capacity the bedroom layout for Headland House is as follows:

Main House

#1 Bedroom Master Bedroom Main floor – King size bed

#2 Bedroom Lower level West wing – King size bed

#3 Bedroom Lower level East wing - King size bed

#4 Retreat area - Queen size sofa bed

Guest House

#5 Bedroom – Master Bedroom Queen size bed

#6 Bedroom – two Twin size beds

* This listing is for the entire Headland House Estate (both main house and guest house). Winter, Off Season months and non holidays we offer the option to book the houses separately. Please refer to our other listing for booking just the Headland Main house or just the Headland Guest house.

* Time Change Option: Check in time 5:00 PM / Check out time is 10:00 AM we offer a time change for early or late check out the fee is $20.00/hr (not available months of June, July or August or on back to back stays). Please check ferry schedule before requesting this option as once the fee is paid it is not refundable.

Additional Information:

* No Visitor Policy

* Fireplaces not available for guest use.

* Sorry No Pets. We need to maintain the home as allergy free as members of our family have asthma. We also want to insure that our home maintains our high cleanliness standards.

*Suitability: This home is not suitable for young children. There are very steep cliffs on the view side of the property without railings and a wide and steep stairway next to the great room. The guest house also has steep cliffs as well as a spiral staircase next to the entry door that cannot be blocked off, during winter months the propane stove is hot to the touch. Young children are not free please be sure to include infants, babies and toddlers in the total guest count. Children 3 years and under there will be an extra baby fee of $75.00 to cover the costs to child proof the home, excess cleaning time and extra costs for removal of baby diapers.

*Cancellation Policy: No reservation holds are permitted. Once the property has been taken off the rental market with the calendar blocked and a booking confirmation receipt sent the terms of the cancellation policy will apply to all reservations. The cancellation fee is 20% for bookings made through our own website and 25% cancellation fee through the VRBOHomeAway booking site. No refund of previously paid deposits will be allowed unless the reserved property can be rebooked for the same reservation period and price. Refunds are based on any alternative revenue received, less a 20% cancellation fee of the total rental rate. Any such refunds will only be made once we have actually received the replacement reservation. Security deposits are fully refundable. It’s highly recommended that Trip Insurance is purchased should there be any unforeseen events that may require a cancellation.

Minimum Stay Requirements:

*July and August 7 nights (Friday to Friday preferred) less than 7 nights premium added to the high season rate.

*Thanksgiving minimum 4 nights

* Christmas & New Years Week minimum 4 nights.

*All other Federal Holidays 3 nights.

*Balance of the year flexible

Please tell us a little bit about yourself and the purpose of the stay. When sending us inquiries for pre-approval or a quote please include this simple code phase back to me. “Bonus points can be fun”. This code helps us confirm that guests have read through our listing.

More Details
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible

Lisa Strauss - Headland House
Member since: 2004
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
October 4, 2016
Call Owner

About Lisa Strauss - Headland House

My husband and I live on Orcas island and manage our own vacation homes so this enables us to respond to our guests needs quickly. You will find that we provide over the top amenities that are not typically found in most vacation homes as our goal is to exceed our guests expectations.

Lisa Strauss - Headland House purchased this estate in 2007

Why Lisa Strauss - Headland House chose Orcas Island

A few highlights. Awesome Marine Views because we sit out on a point. End of the road privacy. Main house has three king size beds making this property really ideal for a couples retreat.

What makes this estate unique

Headland House sits at the end of a point which is why the home has spectacular views. One of the nicest features of the property is that the main house and guest house face in opposite directions and have parking at both locations so each home has really nice privacy.

Guestbook comments from the owner

The house was beautiful, the views were amazing, and the kitchen was better stocked than our own! (which is saying something!) Not only was it a truly gourmet kitchen, which is rare to find in a vacation rental, but they also provided fun amenities such as donut mix and pancake/waffle mix - with the appliances to make them, of course! My husband LOVED the 105" projection TV with surround sound, especially for Thursday night football. I believe he called it a "mangasm". :) We enjoyed breakfast and dinner seated at the outdoor dining area most days, and got to relax in the hot tub in the evenings. I also tremendously enjoyed the soaking tub in the master suite bathroom. All in all, it was a perfect getaway. We definitely plan on going back, next time with friends so we can fully enjoy the entire property, including the game room with the pool table and margarita machine!

Date of Stay: 9/29 - 10/3/14

Original Review posted on Trip Advisor
Sep 2014
  • 1 of 28


based on 15 traveler reviews

Headland House Estate * Two Homes * Marine Views *Theater System *3 King Beds
average rating of 4.866667 based on 43 reviews

very nice

  • 5 of 5

plenty of space had all the kitchen utensils and gadgets you could want quiet location great views all good

  • Submitted: Aug 15, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
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Bremerton, WA

Beautiful home and very relaxing stay

  • 5 of 5

We had a fantastic time enjoying this beautiful home (the main house). The owners spared no detail making us feel welcome. The setting was serene and quiet perched on a rock surrounded by madrona and evergreen. The views were fantastic even with the rainy weather. We really appreciated every detail of the home and activity at our finger tips, especially the hot tub and pool table. Don't be intimidated by the rules, they are by and large just common sense so all can have an opportunity to enjoy this well-built home. We appreciated the fully stocked kitchen and pancake smorgasbord too! Thanks much :)

  • Submitted: Feb 5, 2016
  • Stayed: Dec 2015
  • Source: HomeAway
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Peaceful Location, Beautiful House

  • 5 of 5

The house was exactly as shown in the listing, in terms of rooms and amenities. The clear instructions throughout the house were very helpful. We appreciated the extra touches throughout, such as the popcorn maker in the living room. The owner was available by phone when we had questions.

  • Submitted: Nov 26, 2015
  • Stayed: Nov 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for the kind words. Your group were outstanding guests and took exceptional care of the house. We were delighted that you selected our home for your company retreat and are hoping that you will be back for your next planning meeting.
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The best

  • 5 of 5

This was an amazing property and the owners were such great hosts. Everything would could possibly need was made available in the home. I really hope I get the opportunity to come back. It really felt like "home" for the time I was there.

Thanks for everything!

  • Submitted: Sep 25, 2015
  • Stayed: Sep 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for your stay we truly enjoyed having you and your family as our guests.
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Arlington, TX


  • 5 of 5

What an amazing property. Our family was on Orcas for my brother's 50th the week of July 4th, 10 of us stayed at Headland House, and absolutely loved the property. Do not let the "check-out" to do list scare you, the truth is, it was a piece of cake because the owners have made sure that everything is in it's place when you arrive, everything is labeled, so putting things back and catching the early ferry was no problem. The property is so well maintained and basically you are expected to treat the house like you would treat your own house. We ranged in age from 80-14 and we all loved the house, the kids loved all the "surprise" amenities! We all loved watching the USA women's soccer finals are the movie screen, grilled, and took full advantage of the hot tub every day! We would highly recommend the property and hope to stay there again in the future!

  • Submitted: Jul 12, 2015
  • Stayed: Jun 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for the kind words we absolutely loved hosting your family. We are looking forward to having you back again and creating even more fun surprises for our guests next year.
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Los Angeles, California

Gorgeous, peaceful getaway!

  • 5 of 5

I stayed at the guesthouse in November. I came to Orcas Island to get away from the hustle and bustle of Los Angeles for a few days. What a wonderful, peaceful oasis with the most amazing views! This place is absolutely gorgeous with plenty of wildlife all around (I think I saw about 5 deer during my two day stay).

The owners are very meticulous about their rental and rightly so. Everything is neat and clean and the thought they put into the guesthouse is evident. I really appreciated every detail they thought of. It was such a luxurious space and I really couldn't believe I had the luck to come across this fabulous rental!

I'm really looking forward to coming back here soon. Orcas Island is truly a magical place.

  • Submitted: Feb 24, 2015
  • Stayed: Nov 2014
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for the kind words. We are so pleased to hear that you enjoyed you stay.
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Rates & Availability

Deer Harbor Estate Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Oct 1 2016 - Oct 31 2016
4 night minimum stay
Nov 1 2016 - Nov 23 2016
2 night minimum stay
Dates Holiday Sold
Nov 24 2016 - Nov 27 2016
4 night minimum stay
Nov 28 2016 - Dec 20 2016
2 night minimum stay
Dec 21 2016 - Dec 27 2016
4 night minimum stay
Dec 28 2016 - Jan 3 2017
4 night minimum stay
Jan 4 2017 - Jan 26 2017
2 night minimum stay
Dates Event
Jan 27 2017 - Feb 6 2017
3 night minimum stay
Feb 7 2017 - Feb 15 2017
2 night minimum stay
Dates Holiday
Feb 16 2017 - Feb 21 2017
3 night minimum stay
Feb 22 2017 - Mar 31 2017
2 night minimum stay
Apr 1 2017 - Jun 30 2017
2 night minimum stay
Jul 1 2017 - Sep 8 2017
4 night minimum stay
Sep 9 2017 - Oct 31 2017
4 night minimum stay
Nov 1 2017 - Nov 19 2017
2 night minimum stay
Dates Holiday
Nov 20 2017 - Nov 27 2017
4 night minimum stay
Nov 28 2017 - Dec 20 2017
2 night minimum stay
Dates Holiday
Dec 21 2017 - Dec 27 2017
4 night minimum stay
Dates Holiday
Dec 28 2017 - Jan 2 2018
4 night minimum stay
My Standard Rate
1 night minimum stay

Additional information about rental rates

Security Deposit $250
Damage Insurance $50
Application Fee $35
Housekeeper Fee $300 + Tax
Tax Rate 10.1%

To simplify our rate structure the rate shown is "One Flat Rate" for the "Entire Headland House Estate" includes Main House and Guest House all 6 bedrooms. Rate posted is the same rate from 1 - 12 guests.

Guests can book a 1 night stay during the off season with a $100.00 cleaning fee added to the rate. Time change option for early and late check out available at $20.00/hr.

Refer to our other listings for booking just the main house or guest house as winter and non holidays we offer the ability to book each of the houses separately. We also offer a "Book by Bedroom Option" which makes the rate affordable for just one couple.

We do not have a standard rate $1.00 shown is a placeholder only.

Owner's Cancellation Policy

  • 0% refund if canceled at least 0 days before arrival date.
Enter dates for accurate pricing
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Deer Harbor Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 5750 sq. ft.
Location Type:
  • Beach View
  • Ocean View ...
  • Water View ...
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Air Conditioning ...
  • Clothes Dryer ...
  • Free Long Distance ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Parking ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Wood Fireplace ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 3 Bathrooms
  • 1 Half Bath
  • Bathroom 1 Master Upper - toilet , tub , shower
    Bathroom 2 Master Lower - toilet , combination tub/shower
    Bathroom 3 Guest House - toilet , shower
    Powder Room - toilet
  • 6 Bedrooms, Sleeps 12
  • #1 Main floor Master - King size bed - 1 king
    #2 Lower Level West Wing - King size bed - 1 king
    #3 Lower Level East Wing - King size bed - 1 king
    #4 Retreat - Queen size Sofa Bed - 1 sleep sofa /futon
    #5 Guest House Master - Queen size bed - 1 queen
    #6 Guest House - Two Twin Beds - 2 twin/ single , Day bed with twin trundle bed cannot be made up as a king
    Game Room - Queen size Sofa Bed - 1 sleep sofa /futon , Extra sleeping capacity (extra fee)
  • Sofa bed in the game room is not included in the rate must be ordered separately. The Sofa bed in the guest house is locked and not available for guest use.
  • Books ...
  • DVD Player ...
  • Game Room ...
  • Games ...
  • Music Library ...
  • Pool Table
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Toys
  • Video Game Console ...
  • Video Games
  • Video Library ...
  • Balcony ...
  • Deck / Patio ...
  • Lanai / Gazebo
  • Outdoor Grill
  • 10 garden chairs
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible
Pool / Spa:
  • Hot Tub ...
  • live theater
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • horseshoes
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • fitness center
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • kayaking
  • mountain biking
  • sailing
  • snorkeling/diving
  • sound/bay fishing
  • swimming
Amenity soaps, shampoo, spa towels and bath robes. Home Security Systems: The home has a central burglar and central fire alarm as well as a video surveillance system which monitors the driveway entrance, parking area and entry way.

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