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San Juan Island Holiday Rentals

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44 rentals in San Juan Island.
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Peaceful waterfront cottage, close to town!, holiday rental in San Juan Island

Peaceful waterfront cottage, close to town!

1 bedroom
1 bathroom
Sleeps 2
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WATER VIEWS of Puget Sound and the Olympic Mountains with Expansive Gardens, holiday rental in San Juan Island

WATER VIEWS of Puget Sound and the Olympic Mountains with Expansive Gardens

1 bedroom
2 bathrooms
Sleeps 2
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Brand New Custom Waterfront Home next to Picnic Island-Easy walk to Roche Harbor, holiday rental in San Juan Island

Brand New Custom Waterfront Home next to Picnic Island-Easy walk to Roche Harbor

4 bedrooms
3 bathrooms
Sleeps 8
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Enticing Waterfront Cottage!, holiday rental in San Juan Island

Enticing Waterfront Cottage!

1 bedroom
1 bathroom
Sleeps 2
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Water View Cape Cod Home Near Town, holiday rental in San Juan Island

Water View Cape Cod Home Near Town

2 bedrooms
2 bathrooms
Sleeps 4
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Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor., holiday rental in San Juan Island

Westcott Bay Waterfront pet friendly home. just minutes from Roche Harbor.

2 bedrooms
1 bathroom
Sleeps 5
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Beachfront with Spectacular Sunsets.  Lopez Island, holiday rental in San Juan Island

Beachfront with Spectacular Sunsets. Lopez Island

2 bedrooms
2 bathrooms
Sleeps 4
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Utter Seclusion on 600 Feet of Waterfront , Free WiFi, holiday rental in San Juan Island

Utter Seclusion on 600 Feet of Waterfront , Free WiFi

2 bedrooms
1 bathroom
Sleeps 6
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Amenity-Packed Waterfront Island Retreat, holiday rental in San Juan Island

Amenity-Packed Waterfront Island Retreat

4 bedrooms
3 bathrooms
Sleeps 10
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Unique Waterfront Beach House, brand new, 1 mile from Downtown Friday Harbor, holiday rental in San Juan Island

Unique Waterfront Beach House, brand new, 1 mile from Downtown Friday Harbor

3 bedrooms
2 bathrooms
Sleeps 6
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BEAUTIFUL, SPACIOUS, SANITARY, MODERN HOME NEAR GOLF COURSE, holiday rental in San Juan Island

BEAUTIFUL, SPACIOUS, SANITARY, MODERN HOME NEAR GOLF COURSE

3 bedrooms
2 bathrooms
Sleeps 6
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Mountain & meadow views among old growth oaks, holiday rental in San Juan Island

Mountain & meadow views among old growth oaks

2 bedrooms
2 bathrooms
Sleeps 5
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Relaxing Waterfront Cabin - Private Beach and Hot Tub with a View!, holiday rental in San Juan Island

Relaxing Waterfront Cabin - Private Beach and Hot Tub with a View!

2 bedrooms
1 bathroom
Sleeps 6
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Waterfront Studio Apt, holiday rental in San Juan Island

Waterfront Studio Apt

3 bedrooms
3 bathrooms
Sleeps 6
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Sunsets on Mitchell Bay, holiday rental in San Juan Island

Sunsets on Mitchell Bay

3 bedrooms
4 bathrooms
Sleeps 8
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Studio with a View!!, holiday rental in San Juan Island

Studio with a View!!

0 bedrooms
1 bathroom
Sleeps 2
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San Juan Bay - Private Cabin in the Woods on Garrison Bay!, holiday rental in San Juan Island

San Juan Bay - Private Cabin in the Woods on Garrison Bay!

2 bedrooms
2 bathrooms
Sleeps 6
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Westcott Woods - A San Juan Island Waterview Cabin, holiday rental in San Juan Island

Westcott Woods - A San Juan Island Waterview Cabin

2 bedrooms
1 bathroom
Sleeps 4
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Contemporary in the Woods 2016, holiday rental in San Juan Island

Contemporary in the Woods 2016

2 bedrooms
3 bathrooms
Sleeps 6
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Nowak House - Lopez Island's One of a Kind Intimate Getaway, holiday rental in San Juan Island

Nowak House - Lopez Island's One of a Kind Intimate Getaway

1 bedroom
1 bathroom
Sleeps 2
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Fisherman’s Bay view 1910 Lopez Island farmhouse with beautiful views, holiday rental in San Juan Island

Fisherman’s Bay view 1910 Lopez Island farmhouse with beautiful views

3 bedrooms
2 bathrooms
Sleeps 6
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San Juan Island Private Studio on 10 Acres, holiday rental in San Juan Island

San Juan Island Private Studio on 10 Acres

1 bedroom
1 bathroom
Sleeps 2
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Charming 4 br gated waterfront estate on acreage with private beach and buoy., holiday rental in San Juan Island

Charming 4 br gated waterfront estate on acreage with private beach and buoy.

4 bedrooms
3 bathrooms
Sleeps 10
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Lovely Cottage Offering Style, Sophistication, Comfort and Tranquility, holiday rental in San Juan Island

Lovely Cottage Offering Style, Sophistication, Comfort and Tranquility

1 bedroom
1 bathroom
Sleeps 2
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Seaview condo w/ deck & grassy lawn - walk to trails, restaurants & more!, holiday rental in San Juan Island

Seaview condo w/ deck & grassy lawn - walk to trails, restaurants & more!

2 bedrooms
2 bathrooms
Sleeps 2
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1 Bedroom, Sleeps 6 Steps From Friday Harbor San Juan Island Ferry, Washington, holiday rental in San Juan Island

1 Bedroom, Sleeps 6 Steps From Friday Harbor San Juan Island Ferry, Washington

2 bedrooms
2 bathrooms
Sleeps 6
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Enjoy Roseberry Cottage! Updated westside beach access with stunning views, holiday rental in San Juan Island

Enjoy Roseberry Cottage! Updated westside beach access with stunning views

2 bedrooms
1 bathroom
Sleeps 4
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Fisherman’s Bay view converted boathouse, holiday rental in San Juan Island

Fisherman’s Bay view converted boathouse

1 bedroom
1 bathroom
Sleeps 2
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Modern home w/multiple decks, amazing views, peaceful location, holiday rental in San Juan Island

Modern home w/multiple decks, amazing views, peaceful location

4 bedrooms
3 bathrooms
Sleeps 10
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Convenience Of Town, Relaxation Of Country Life, Incredible Views, Kid Friendly, holiday rental in San Juan Island

Convenience Of Town, Relaxation Of Country Life, Incredible Views, Kid Friendly

3 bedrooms
2 bathrooms
Sleeps 6
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Luxury Mitchell Bay Hideaway - Escape to this 4,000 sq ft retreat with Hot Tub!, holiday rental in San Juan Island

Luxury Mitchell Bay Hideaway - Escape to this 4,000 sq ft retreat with Hot Tub!

3 bedrooms
4 bathrooms
Sleeps 8
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The Best Home On Roche Harbor Waterfront, holiday rental in San Juan Island

The Best Home On Roche Harbor Waterfront

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern, dog-friendly, waterfront home w/ a bay view!, holiday rental in San Juan Island

Modern, dog-friendly, waterfront home w/ a bay view!

3 bedrooms
3 bathrooms
Sleeps 4
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Picturesque Westcott Bay Cape Cod on 5 Acre Estate -Walk to Roche Harbor, holiday rental in San Juan Island

Picturesque Westcott Bay Cape Cod on 5 Acre Estate -Walk to Roche Harbor

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Rainbow's End - Spacious Beach House, pet friendly with mooring, holiday rental in San Juan Island

Rainbow's End - Spacious Beach House, pet friendly with mooring

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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HARO HAIKU - San Juan Island, West side, views! CLOSED DUE TO COVID-19, sorry., holiday rental in San Juan Island

HARO HAIKU - San Juan Island, West side, views! CLOSED DUE TO COVID-19, sorry.

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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San Juan Island Samadhi House, holiday rental in San Juan Island

San Juan Island Samadhi House

4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Cozy & quiet cabin w/ natural beauty close to all the sights of southern Lopez!, holiday rental in San Juan Island

Cozy & quiet cabin w/ natural beauty close to all the sights of southern Lopez!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy cabin with peaceful atmosphere, breathtaking ocean views moments from beach, holiday rental in San Juan Island

Cozy cabin with peaceful atmosphere, breathtaking ocean views moments from beach

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Modern waterfront home moments from shopping, dining, & beaches!, holiday rental in San Juan Island

Modern waterfront home moments from shopping, dining, & beaches!

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing Historic Farm House on Westcott Bay - Walk to Roche -, holiday rental in San Juan Island

Amazing Historic Farm House on Westcott Bay - Walk to Roche -

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Secluded Modern Home on 2 Acres, Bike to Roche Harbor, Fire pit, 2 Bikes, holiday rental in San Juan Island

NEW! Secluded Modern Home on 2 Acres, Bike to Roche Harbor, Fire pit, 2 Bikes

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Amazing Estate on Westcott Bay- 10 Acre, 2 Home Estate - Next to Roche, holiday rental in San Juan Island

Amazing Estate on Westcott Bay- 10 Acre, 2 Home Estate - Next to Roche

7 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
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Spyglass Hill, holiday rental in San Juan Island

Spyglass Hill

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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