Vacation rentals in Eastsound

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Top-rated vacation rentals in Eastsound

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A light-filled living space features a gray sleeper sofa adorned with a cozy blanket. An oval mirror reflects the bright interior, while a dining table and chairs are positioned near a large window offering scenic views. Soft textures create a welcoming atmosphere.
Guesthouse in Olga
4.88 out of 5 average rating, 224 reviews

Little Stuga | Water Views, Cozy, Great Location

Located in the Historic Hamlet of Olga, Little Stuga provides a quiet retreat conveniently located within steps of the water, two beaches, and a public dock. Light-filled interior spaces provide simple comfort and convenience, great for couples, small families, or remote work travel. Moran State Park, Doe Bay, and Mt Constitution are a quick 5 min drive, with Eastsound only 10 min away. Water views on both levels, high-end linens, fully stocked kitchenette, all in a thoughtfully designed space

Top guest favorite
A vintage cabin is framed by trees and lush green grass, illuminated by soft evening light. A wooden picnic table sits on the lawn, enhancing the inviting outdoor space. The cabin’s porch leads to scenic views of the nearby water.
Guesthouse in Eastsound
4.99 out of 5 average rating, 143 reviews

Waterfront Guest Cabin on private beach estate

See our other two available cabins listed on this waterfront estate by clicking my host profile. Welcome to the vintage 100 year old original guest Cabin, nestled over the Salish Sea on a private estate with two cabins, beach, camp fire, kayaks & paddle boards. Seals, otters, eagles and deer are your neighbors. Walk to Turtleback Mountain south trailhead for grand views above. The secluded Hot Tub is tucked under cedar trees, over the beach, private for either cabin, but not at the same time.

Guest favorite
A wooden table is set on a private sun deck, featuring two glasses of white wine and a plate of fresh strawberries. Lush green foliage is placed in a small pot beside the table, while a tranquil water view and distant mountains create a serene backdrop.
Condo in Eastsound
4.93 out of 5 average rating, 170 reviews

Water View! PORT SUITE

Water view! 1,100+ sf. Luxury Suite in the heart of Orcas Island. Located in Eastsound Village-- walk to shops, restaurants, galleries & the beach! * Master bedroom (K): organic latex mattress, luxury linens, down duvet and pillows * Spacious bath: 2-person jetted tub & steam shower * Full kitchen open to living area * 2-sided gas fireplace * Private sun deck with water view Note: if PORT is booked, check the Eastsound Suites STARBOARD listing. Suites are identical- same Fishing Bay view!

Guest favorite
A small table holds a bottle of wine and two glasses on a balcony overlooking the serene waterfront. Views of the calm sea and lush green hills are visible in the distance, with scattered clouds framing the scenic landscape.
Loft in Eastsound
4.95 out of 5 average rating, 330 reviews

The Windward Studio at SeaStar Lofts

Enjoy gorgeous views from this beautifully appointed condo perched right on the shore! Every convenience for your stay: fine linens, eco-friendly amenities, compact kitchen, locally roasted coffee, tasteful furnishings, and more. SeaStar Lofts are in the heart of charming Eastsound Village, with shops and restaurants just steps away. MARCH 2020 UPDATE: due to Corona Virus concerns we're offering a full refund should you need to cancel. And rest assured, we THOROUGHLY disinfect between guests.

Guest favorite
The cabin's exterior is gently illuminated in the evening, highlighting its log construction and welcoming porch. Soft lighting reveals comfortable seating on the porch, surrounded by lush greenery and stone pathways, creating a serene atmosphere amidst the trees.
Tiny home in La Conner
4.98 out of 5 average rating, 782 reviews

The Coho Cabin - A Beachfront Getaway

Welcome to the Coho Cabin, a tiny house/log cabin perched atop Skagit Bay with direct westerly waterfront views of wildlife, Whidbey Island and the Olympic Mts. Built in 2007, it's an authentic log cabin, custom designed out of Alaskan Yellow Cedar. Enjoy the rustic-yet-elegant vibe, radiant heated floors, cozy loft bed, outdoor bbq and private location. Located 10 min. west of La Conner, guests can browse shops, adventure on unique hikes, or enjoy a relaxing beach stroll.

Top guest favorite
A private deck is visible, featuring a couple of red chairs and a potted plant. The view showcases calm waters reflecting the sky and surrounding hills, with trees lining the shoreline, creating a serene landscape.
Condo in Eastsound
4.99 out of 5 average rating, 223 reviews

Templin Haven

This is a special place right on the water, facing west, overlooking Fishing Bay and Indian Island in Eastsound on Orcas Island. I am one of three waterfront units in Eastsound and have tried to provide everything you will need for a wonderful experience on Orcas. This unit is steps away from all the shops, restaurants, bakery, museum and galleries of our little village of Eastsound. Also, I am a fourth generation islander so ask me some Orcas Island history!

Top guest favorite
A charming cottage with bright orange siding is showcased, surrounded by lush greenery. A round table with four wooden chairs is positioned on a grassy area, inviting relaxation. The entrance features a single door, complemented by windows that allow natural light.
Cottage in Eastsound
4.97 out of 5 average rating, 268 reviews

Farm cottage, close to Eastsound!

Buckhorn Farm Bungalow is located on ten-acres near the north shore of Orcas Island. This family vacation cottage enjoys a wonderful country-farm atmosphere but is only a 5 minute drive from the village of Eastsound, our island's version of “downtown.” Guests can easily walk or ride bicycles along level roads to restaurants, shops or to the nearby semi-private beach to enjoy beach strolls, tide-pooling and spectacular views from Mt. Baker to Vancouver Island.

Guest favorite
A cozy living area features large French doors that open to a deck, allowing natural light to fill the space. Comfortable seating includes a dark chair with a soft throw and a light sofa adorned with decorative pillows. A small wooden coffee table sits on a textured rug.
Guesthouse in Eastsound
4.94 out of 5 average rating, 358 reviews

Northbeach Cabin

Sweet cedar shingled cabin on Sunset Avenue just a short walk to town, and an even shorter walk to the beach! Queen size bed tucked upstairs under the vaulted ceiling with peek-a-boo view of the water. Freshly renovated, old school Orcas style. Hardwood & Marmoleum floors throughout, pine paneling & subway tile in kitchen and bathroom. French door slider opens to deck, perfect for enjoying your morning coffee. #weaccept. PPROVO-17-0042

Guest favorite
Home in Eastsound
4.96 out of 5 average rating, 146 reviews

Beautiful WaterViews, Pet-Friendly, Close to Town

Welcome to our home Cool Breeze, a well-appointed home offering water views in a peaceful neighborhood, just a short walk to downtown Eastsound. 🍽️ Gourmet Kitchen – Fully equipped for home-cooked meals, or explore local dining and craft drinks nearby. 🌿 Outdoor Adventures – Paddleboarding, kayaking, hiking, and golfing are all easily accessible. 🐾 Family & Pet-Friendly – A welcoming space for guests of all ages, including pets.

Top guest favorite
A serene water view reflects soft pastel hues of pink and blue in the sky, surrounded by lush green hills. The stillness of the water is complemented by distant tree-covered slopes, creating a peaceful natural setting.
Guest suite in Eastsound
4.98 out of 5 average rating, 298 reviews

The Salish Waterfront Retreat

Fishing Bay. Ground-level suite. On the water right next to the village of Eastsound. No Pets or ESA with hair or dander. An exclusive location with amazing views, private beach, kayak launch, above water deck, a Japanese Soaking Tub, and outdoor fire pit. All within a five minute walk to Eastsound. Kayaks, bicycles, mooring buoy, and crab trap are available for free on site for use with a signed Release of Liability.

Guest favorite
A modern two-story home is displayed, featuring large windows and a balcony with partial awning. The exterior is clad in white siding, contrasted by natural stone steps and a horizontal wood fence. Lush greenery surrounds the building, creating a serene environment.
Townhouse in Eastsound
4.94 out of 5 average rating, 119 reviews

New home in Center of Town, Walk Everywhere

Bright, light-filled modern home w/2 bedrooms & 1.75 baths, in the heart of the Eastsound, the center of Orcas Island, w/many shops, restaurants, public beaches, just steps from your front door. Enjoy beautiful views across Eastsound to the bay from the balcony. There is an office nook for remote work. 2 king-size beds, one upstairs & one down, make this perfect for 2 couples. Signed rental agreement required.

Guest favorite
A scenic view captures a calm waterfront at sunset, with layers of distant islands against a colorful sky. The foreground includes silhouettes of towering trees, adding depth to the landscape and enhancing the peaceful atmosphere.
Home in Eastsound
4.98 out of 5 average rating, 101 reviews

Beautiful Modern Home- Water View- Dog Friendly

Enjoy spectacular sunsets from our NEW larger deck at our beautiful home located in the VERY POPULAR Rosario area. 1.5 miles to the entrance of Moran State Park with lakes, hiking and Mt. Constitution. 2 miles in the other direction is the Rosario Resort. The large Master Suite has a jetted tub, shower and private access to the deck. Guest Bedroom has separate full bath and queen bed

Popular amenities for Eastsound vacation rentals

When is the best time to visit Eastsound?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR3,437 ZARR3,368 ZARR3,540 ZARR4,127 ZARR4,248 ZARR5,613 ZARR6,563 ZARR6,822 ZARR5,285 ZARR4,317 ZARR3,972 ZARR3,627 ZAR
Avg. temp6°C6°C7°C10°C13°C15°C18°C18°C15°C11°C8°C6°C

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Eastsound?

    Four-legged friends are welcome in Eastsound. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Eastsound?

    Yes! Work meets play with ease at over 30 vacation rentals in Eastsound featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Eastsound?

    Experience the best of Eastsound with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Eastsound have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Eastsound. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Eastsound have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Eastsound. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Eastsound have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Eastsound. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Eastsound?

    Eastsound has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Eastsound?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Eastsound

  • Total vacation rentals

    Explore 60 vacation rentals in Eastsound

  • Nightly prices starting at

    Eastsound vacation rentals start at R2,072 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 4,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Eastsound vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Eastsound rentals

  • 4.9 Average rating

    Eastsound stays are highly rated by guests—averaging 4.9 out of 5!

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