45 Best San Juan Island Vacation rentals on Holiday Lettings - Cabins

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127 Vacation rentals

23

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 9 4 nights min

  • 3 bedrooms
  • Sleeps 9
  • 4 nights min
  • Ask about children
  • Pet friendly
WHALES, EAGLES, SUNSETS & KAYAK LAUNCH ON THE SPECTACULAR WEST SIDE - DOG FRIENDLY TOO! When you stay at Three Coves Hideaway, you’ll enjoy a San Juan Island location that is second to none. The home faces west over Haro Straight, so you will bask in amazing sunsets an …see more

from $359 / night

$2,159 - $3,899 / week

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from $359 / night

15

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
WHALE WATCH FROM THIS WATERFRONT VACATION RENTAL HOME ON SAN JUAN ISLAND One stay in Writer’s Retreat almost always leads to another. Year after year, guests reserve "their" customary week in this San Juan Island vacation home because it is simply exceptional in every …see more

from $325 / night

$1,950 - $2,699 / week

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from $325 / night

(9) Excellent 

23

Friday Harbor Vacation b&b rental

San Juan Island / Friday Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Private garden
Let me host you in our charming beach house. Located near Roche Harbor and a 5 Minute Walk to Reuben Tarte Beach. Enjoy a Spacious Master bedroom Suite Queen Bed and Spacious Bathroom. Second Large Bedroom with Queen Bed Beautifully appointed. Shared kitchen w …see more

from $200 / night

$1,274 / week

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from $200 / night

15

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
This spacious waterfront house is situated on a private beach just 1.5miles from the town of Friday Harbor but featuring privacy for your dream island getaway. The beach is perfect for leisurely walks, sea glass hunts, fort building, launching a kayak or even swimming …see more

from $350 / night

$2,450 / week

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from $350 / night

(4) Excellent 

24

Home rental in Friday Harbor

San Juan Island / Friday Harbor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Have the ultimate Friday Harbor getaway by escaping to this gorgeous 2-bedroom, 2-bathroom waterfront vacation rental house that comfortably sleeps 4. Overlooking Griffin Bay and steps away from the beach, this house is the perfect home base for endless outdoor exciteme …see more

from $265 / night

$1,855 - $4,025 / week

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Responds fast!
avg. 1 hour 0 minutes

from $265 / night

(1) Excellent 

20

Friday Harbor Vacation apartment rental

San Juan Island / Friday Harbor

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
Why pay more? Affordable condo rental in Friday Harbor. This one-bedroom garden apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaur …see more

from $125 / night

$875 / week

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from $125 / night

(8) Very Good 

17

Vacation home rental

San Juan Island / Friday Harbor

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
If you are looking for a truly unique place on San Juan Island that is affordable, private, with an open view setting, beautiful furnishings, indoor and outdoor spaces, at an ideal location; you have found it! Escape the crowds and enter your own world, up a winding …see more

from $199 / night

$1,393 - $1,743 / week

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Responds fast!
avg. 3 hours 44 minutes

from $199 / night

(5) Excellent 

25

Friday Harbor Vacation home rental

San Juan Island / Friday Harbor

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
San Juan Bay is 1700+sf and on over 1.5 acres that includes over 100 ft of waterfront. The cabin has a spacious living room and dining area with floor to ceiling windows taking in the waterviews and abundance of wildlife! The living room offers a 50’ flat screen televis …see more

from $200 / night

$1,200 - $2,370 / week

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from $200 / night

(1) Excellent 

15

Apartment rental in Friday Harbor

San Juan Island / Friday Harbor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
Why pay more? Affordable condo rental in Friday Harbor. This one-bedroom apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, king-sized bed, parking, and easy access to restauran …see more

from $125 / night

$875 / week

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from $125 / night

(2) Very Good 

15

Vacation apartment rental

San Juan Island / Friday Harbor

2 1 night min

  • Sleeps 2
  • 1 night min
  • Swimming pool
Why pay more? Affordable condo rental in Friday Harbor. This studio apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants and all …see more

from $95 / night

$665 / week

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from $95 / night

4

Vacation log cabin in Friday Harbor

San Juan Island / Friday Harbor

2 2 nights min

  • Sleeps 2
  • 2 nights min
  • Pet friendly
The cabin is 12X18,...... small but complete with shower, kitchen with fridge, stove, toaster, microwave, and coffee maker. Propane BBQ on the deck. WiFi and DirectTV Great location ...perfect for bicyclists...park your car on the mainland for quick on and off the islan …see more

from $175 / night

$1,050 / week

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Responds fast!
avg. 2 hours 31 minutes

from $175 / night

(2) Very Good 

16

Vacation apartment in Friday Harbor

San Juan Island / Friday Harbor

2 1 night min

  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Car not necessary
Why pay more? Affordable condo rental in Friday Harbor. This studio apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants and all …see more

from $95 / night

$665 / week

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from $95 / night

(2) Very Good 

15

Vacation apartment in Friday Harbor

San Juan Island / Friday Harbor

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Why pay more? Affordable condo rental in Friday Harbor. This one-bedroom apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants an …see more

from $125 / night

$875 / week

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from $125 / night

(1)  

16

Vacation studio in Friday Harbor

San Juan Island / Friday Harbor

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
Why pay more? Affordable condo rental in Friday Harbor. This studio apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants and all …see more

from $105 / night

$735 / week

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from $105 / night

(1) Excellent 

24

Studio rental in Friday Harbor

San Juan Island / Friday Harbor

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
Your perfect romantic getaway awaits you at this eclectic vacation rental cottage in Friday Harbor. As soon as you arrive onto the island, you'll be surrounded by the natural splendor of the Pacific Northwest and feel all your stresses melt away! Located on the serene S …see more

from $125 / night

$875 - $1,645 / week

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Responds fast!
avg. 45 minutes

from $125 / night

(11) Very Good 

22

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Ask about pets
Happy Sunny Days!Wake up to the singing of birds and not city noises. With either romance and/or relaxation in mind, rent this charming, clean one bedroom with bathroom located in a separate wing of my home accessible thru your own individual entrance. The hot tub loca …see more

from $98 / night

$650 / week

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Responds fast!
avg. 3 hours 19 minutes

from $98 / night

16

Vacation home in Lime Kiln

San Juan Island / Lime Kiln

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
Prepare to enjoy the peace and serenity of this island retreat, and the amazing views of the Haro Strait, the Strait of Juan de Fuca, the Olympics and Victoria. Our spacious home is a comfortable 2000 square foot rambler, situated on four rolling acres overlooking the H …see more

from $250 / night

$1,500 - $1,900 / week

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from $250 / night

(2) Excellent 

23

Vacation studio with golf nearby in Friday Harbor

San Juan Island / Friday Harbor

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
Please Note: Etta's Suite studio is available for longer stays on a month-to-month basis for fall 2017 and winter 2018 at $1050 per month with a $350 security/cleaning deposit. Please send a request for more information to owner. Etta's Suite, upstairs, is a studio sui …see more

from $149 / night

$950 - $1,240 / week

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Responds fast!
avg. 2 hours 15 minutes

from $149 / night

(5) Very Good 

19

Vacation apartment in Friday Harbor

San Juan Island / Friday Harbor

2 1 night min

  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Why pay more? Affordable condo rental in Friday Harbor. This studio apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants and all …see more

from $105 / night

$735 / week

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from $105 / night

21

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
The Harbor Passage is a year old, 2500+ sf home with breathtaking views down Presidents Channel as well to San Juan and Spieden Channels, Waldron, Jones and Orcas Islands, and glimpses of Spieden Island and the Canadian San Juans. The Harbor Passage was designed to t …see more

from $425 / night

$2,550 / week

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from $425 / night

(3) Good 

15

Friday Harbor Vacation apartment accommodation

San Juan Island / Friday Harbor

2 1 night min

  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
Why pay more? Affordable condo rental in Friday Harbor. This studio apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants and all …see more

from $95 / night

$665 / week

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from $95 / night

(9) Excellent 

39

Friday Harbor Vacation apartment rental

San Juan Island / Friday Harbor

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Private garden
"Artists's Retreat", lovely and quiet on 10 acres with tall cedar trees, winding walks and charming gardens. Located next to a private professional Art Studio. Freshly redone, new bedding, and a full bath. Small, (the size of a nice hotel room) but complete, the kitch …see more

from $129 / night

$775 - $900 / week

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from $129 / night

(3) Good 

11

Vacation apartment in Friday Harbor

San Juan Island / Friday Harbor

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
Why pay more? Affordable condo rental in Friday Harbor. This one-bedroom apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants an …see more

from $125 / night

$875 / week

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from $125 / night

(5) Good 

15

Friday Harbor Vacation apartment rental

San Juan Island / Friday Harbor

2 1 night min

  • Sleeps 2
  • 1 night min
  • Swimming pool
Why pay more? Affordable condo rental in Friday Harbor. This studio apartment, located just an 8 minute walk from the ferry landing, has everything you need for your stay on San Juan Island: kitchen, bathroom, queen bed, parking, and easy access to restaurants and all …see more

from $95 / night

$665 / week

Book View

from $95 / night

(1) Excellent 

25

Friday Harbor Vacation home rental

San Juan Island / Friday Harbor

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Get away from it all in this luxuriantly appointed, beautiful 4-bedroom home with spectacular water and territorial views. So quiet all you can hear is the swish of birds' wings. Samadhi House is perched atop Mt. Dallas, the highest point on San Juan Island in Washi …see more

from $585 / night

$4,700 / week

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from $585 / night

(27) Excellent 

17

Home rental in Friday Harbor

San Juan Island / Friday Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
WATERFRONT VACATION RENTAL HOME ON SAN JUAN ISLAND This San Juan Island vacation rental home offers sweeping views across San Juan Channel to Orcas Island and other surrounding islands. Floor to ceiling windows invite the exquisite beauty of nature into your living roo …see more

from $299 / night

$1,799 - $2,699 / week

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from $299 / night

(19) Excellent 

36

Vacation log cabin in Friday Harbor

San Juan Island / Friday Harbor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 mi
  • Ask about children
  • Car not necessary
Westcott Woods A San Juan Island Waterview Vacation Rental. Find link to website under Manager Info on Flipkey.com A unique waterview retreat, Westcott Woods cabin is the perfect place to spend both an active and restorative break. Perfect for a small group of friend …see more

from $200 / night

$1,300 - $1,430 / week

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Responds fast!
avg. 2 hours 6 minutes

from $200 / night

33

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 11 Min stay varies

  • 3 bedrooms
  • Sleeps 11
  • Min stay varies
  • Ask about children
  • Air conditioning
PRIVATE BEACH, HOT TUB, VIEW OF MOUNT BAKER, CLOSE TO GOLF COURSE, TENNIS COURSE & FRIDAY HARBOR, EVEN A MOORING BUOY! Before San Juan Island was discovered as a travel destination, Friday Harbor was a cluster of modest houses on a few central streets. When the commerc …see more

from $459 / night

$2,759 - $3,779 / week

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from $459 / night

13

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
CLASSIC WATERFRONT CABIN WITH GREAT SUNSETS, AND A SUPER LOCATION NEAR ROCHE HARBOR This classic waterfront vacation cabin on San Juan Island reminds many visitors of blissful childhood vacations, when things were not expected to be fussy or complicated. Our guests wh …see more

from $249 / night

$1,439 - $2,099 / week

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from $249 / night

13

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
NEW LISTING - Welcome to this beautiful Garrison Bay Waterfron Chalet! You can be one of the first guests to stay in this exceptional property. When you arrive at Garrison Bay Chalet, you’ll understand why the exquisite detailing and fine craftsmanship of this special …see more

from $399 / night

$2,399 - $3,599 / week

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from $399 / night

20

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
WATERFRONT VACATION RENTAL HOME NEAR FRIDAY HARBOR ON SAN JUAN ISLAND This vacation home on San Juan Island perches right over the sea. Amazing views of the water set the stage for a classic Island vacation - in fact there's so much blue water right out front of the wi …see more

from $299 / night

$1,799 - $2,699 / week

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from $299 / night

17

Private room rental in Friday Harbor with golf nearby

San Juan Island / Friday Harbor

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Please Note: Newt's Suite is currently fully booked from October 2017 through February 2018. Newt's Suite, main floor, is a hotel room with: • queen bed • refrigerator/freezer • microwave • coffeemaker • private bath • This suite is …see more

from $139 / night

$940 - $1,185 / week

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Responds fast!
avg. 2 hours 15 minutes

from $139 / night

(6) Excellent 

23

Vacation home in Lime Kiln

San Juan Island / Lime Kiln

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Private garden
Haro Haiku on the West side of beautiful San Juan Island The house is nestled just below the ridge line - with the Olympic mountains, the Strait of Juan de Fuca beyond, and Haro Straits immediately below. Approaching the house, you pass by a Japanese-inspired garden wit …see more

from $420 / night

$2,940 / week

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from $420 / night

(2) Excellent 

7

Home rental in Friday Harbor

San Juan Island / Friday Harbor

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Ask about children
RIGHT IN THE HEART OF FRIDAY HARBOR ON SAN JUAN ISLAND. ABSOLUTELY DELIGHTFUL FERRY LANDING SUITE WITH TWO BEDROOMS, DECK, PARKING. You will feel like you’re living in a postcard when you stay at The Ferry Landing Suites! The Elwha Suite is a delightful two bedroom co …see more

from $299 / night

$2,099 - $2,699 / week

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from $299 / night

15

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
AVAILABLE ONLY FOR 30 DAY MINIMUM RENTAL. YOU WILL SHARE THE LOFTY PERSPECTIVE OF A SOARING EAGLE WHEN YOU BOOK THIS SPACIOUS RENTAL ON SAN JUAN ISLAND. This comfortable residence offers a 180 degree bird’s-eye view of wooded hillsides, northern waterways, neighboring …see more

from $54 / night

$378 / week

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from $54 / night

14

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
ANOTHER NEW HOME FOR 2017! Orca Overlook sits perched on a hillside overlooking some of the most Orca traveled waters in Haro Strait and the Salish Sea. A brand new large deck, surrounded by trees, gives one the feeling of being in a tree house. After you watch the sun …see more

from $249 / night

$1,499 - $2,099 / week

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from $249 / night

(15) Very Good 

10

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
VACATION RENTAL HOME ON SAN JUAN ISLAND WITH DOCK! NEAR ROCHE HARBOR There’s nothing like exploring the beautiful San Juan Islands from the water. Boating enthusiasts will love tying up to the private 50 foot float/dock in the “backyard” of Afterglow Cottage, an immacu …see more

from $269 / night

$1,619 - $2,279 / week

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from $269 / night

9

Cottage rental in Friday Harbor

San Juan Island / Friday Harbor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
NEW LISTING! The Captain's Cottage enjoys a truly wonderful location on Davidson Head overlooking the Isthmus that connects it to San Juan Island and Roche Harbor Resort! From this location you can visit the Isthmus beach, a popular spot to relax and watch boats go by …see more

from $199 / night

$1,439 - $1,799 / week

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from $199 / night

22

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
ANOTHER NEW HOME FOR 2017! Welcome to Westcott Bay Crab Trap! This home is the perfect mix of the new, with its modern interior and beautiful high-quality furnishings, and the classic with its beach front charm and location. This unique combination of characteristics …see more

from $279 / night

$1,679 / week

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from $279 / night

24

Vacation home in Friday Harbor

San Juan Island / Friday Harbor

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
LARGE, SPACIOUS WATERFRONT HOME WITH 32 FOOT DOCK _Rocky Bay Retreat has just released its Prime Peak Season dates for 2017 occupancy, but don’t wait to make your reservation – large waterfront homes of this caliber are rarely available for vacation rental and they fil …see more

from $549 / night

$3,299 - $5,399 / week

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from $549 / night