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Pet-friendly vacation rentals in Westport Island

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Quick stats about vacation rentals that are pet-friendly in Westport Island

  • Total vacation rentals

    Explore 30 vacation rentals in Westport Island

  • Nightly prices starting at

    Westport Island vacation rentals start at G$27,197 GYD per night before taxes and fees

  • Verified guest reviews

    Over 850 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Westport Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Westport Island rentals

  • 4.9 Average rating

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

Top-rated pet-friendly home rentals in Westport Island

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
Cottage in Harpswell

Quaint & Peaceful Designer's Oceanfront Cottage

Coco Cottage is a peaceful, cliffside escape with stunning 180° views of Harpswell Sound. Located at the end of a private road, it’s perfect for a designer’s retreat or family getaway. Three bedrooms—two queens, plus a twin/office combo—make it ideal for remote work or rest. Relax fireside and watch a movie, dine on the patio, read on the dock, or explore the amazing trails, beaches, seafood and sunsets of Harpswell. Enjoy oceanfront tranquility just 15minutes from Bowdoin College and Brunswick.

PetsWalkabilityCleanliness

4.87 out of 5 average rating, 239 reviews
Guest favorite
A modern A-frame structure is nestled within a wooded setting, featuring a dark exterior with wooden accents. Adjacent, a spacious gazebo is set on a gravel patio, furnished with a dining table and a comfortable seating area, surrounded by trees offering a sense of privacy.
Tiny home in Wiscasset

Tiny A-Frame Romantic Getaway

Camp Lupine is a brand new Luxury 400 sq ft Tiny A-Frame tucked away on a private wooded lot with a small stream just a quarter mile off Coastal Route 1. With Historic Wiscasset, Booth Bay, Bath, Freeport, and Portland all at your fingertips, it’s the perfect romantic getaway. Spend your days exploring coastal Maine and your nights soaking in the hot tub with a glass of Malbec. Stay for a while and explore the growing restaurant scene in Wiscasset and the entire Midcoast region. See you soon!

WalkabilityPetsAir conditioning

4.91 out of 5 average rating, 169 reviews
Top guest favorite
A wooden dock extends into calm water, reflecting the clear blue sky and surrounding greenery. Trees line the shore, creating a serene backdrop for peaceful moments by the water.
Home in Friendship

Maine Waterfront Hideaway

You won't find mobs of tourists here but you will experience a working lobstering village in Maine. Sit back, relax and enjoy the quiet and privacy of 2+ acres at the end of a dirt road with a huge dock located on a tidal cove. Great for family reunions with lots of space and activities for folks of all ages. We focus on making the house comfortable and don't want you to worry about the little things like feet on the couch, water rings on the table or a broken glass. Life happens :-)

Outdoor spacesPetsGetting around

4.96 out of 5 average rating, 130 reviews
Guest favorite
The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.
Cottage in Edgecomb

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

PetsWalkabilityLayout

4.97 out of 5 average rating, 381 reviews
Guest favorite
The front entrance showcases a vibrant red door framed by two sconces, inviting guests inside. Steps lead up to a spacious deck, which is flanked by decorative flower pots. The house features a classic shingle exterior, accented by charming dormer windows.
Home in Boothbay Harbor

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

PetsOutdoor spacesQuiet

4.92 out of 5 average rating, 166 reviews
Guest favorite
Townhouse in Boothbay

Captain Fuller House: Boat Builders Retreat - Main

Wake up to sweeping views of Linekin Bay at this pet-friendly coastal retreat . Nestled in a quiet neighborhood, the home sleeps 6–8 guests with three bedrooms and two full bathrooms, perfect for families or small groups. Enjoy peaceful waterfront scenery, fresh ocean air, and easy access to Boothbay Harbor. Modern comforts include an on-site EV charger, while classic Maine charm makes it an ideal place to relax, recharge, and enjoy life by the bay—paws included.

Outdoor spacesPetsLocation

4.78 out of 5 average rating, 132 reviews
Top guest favorite
A well-maintained cottage is positioned beside a tranquil body of water, surrounded by lush greenery. A spacious lawn is visible in the foreground, showcasing an outdoor seating area with a patio umbrella. The scenic view of the water complements the serene setting.
Home in Harpswell

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

Outdoor spacesWalkabilityLayout

4.98 out of 5 average rating, 240 reviews
Top guest favorite
The exterior of a rustic mid-century cabin is framed by lush greenery, featuring a screened-in porch and wooden deck. Stairs lead up to the entrance, and natural stone accents create a seamless blend with the surrounding landscape.
Cabin in Boothbay Harbor

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

Outdoor spacesPetsAmenities

4.98 out of 5 average rating, 284 reviews
Top guest favorite
A spacious waterfront view captures the serene Kennebec River, adorned with small islands and surrounded by lush green trees. The sky is bright blue with scattered clouds, reflecting a tranquil natural setting.
Guesthouse in Bath

Waterfront Sunrise Cove Cottage

Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Owners live on property with small dog.

PetsWalkabilityAccess

5.0 out of 5 average rating, 180 reviews
Guest favorite
A charming beach house is surrounded by trees, featuring a light green exterior with white trim. The front porch has steps leading to the entrance, which is framed by large windows. A landscaped yard with shrubs provides a welcoming view.
Home in Phippsburg

Classic Maine, Modern Comfort

NOTE: Summer Bookings are 7 Days from Saturday-Saturday and tend to fill up by February/March or sooner. All the comforts of home while you're away from home. Come enjoy a newly built beach house (2008) just short walk from beautiful Popham Beach - one of Maine's most beautiful and expansive beaches, one hour north of Portland, Maine.

Outdoor spacesWalkabilityAmenities

4.94 out of 5 average rating, 297 reviews
Top guest favorite
Home in Bath

Beautiful Fall River Retreat

Charming victorian house on the Kennebec River on the outskirts of historic and beautiful Bath, Maine. Close to great shops, restaurants, ski slopes and beaches, and just a 20-minute drive from Bowdoin College. Adjacent to a boat launch, and a short walk from the Bath Maritime Museum and a scenic dog park.

WalkabilityPetsParking

4.91 out of 5 average rating, 449 reviews
Top guest favorite
A charming cottage is presented with a spacious front porch featuring multiple windows and a balcony above. The exterior showcases a combination of textured siding and stone accents, flanked by a neatly landscaped yard with a rock border.
Cottage in Edgecomb

Sheepscot Harbour Village - 3 Bd Condo Waterview

Relax with the whole family at this peaceful place to stay. This newly renovated and well kept cottage features water views and easy access to all attractions. Located with in Sheepscott Bay Village with Deep Water dock and on site restaurant (seasonal pop-up). You will be in the middle of it all.

WalkabilityOutdoor spacesIndoor spaces

4.95 out of 5 average rating, 117 reviews

Popular amenities for Westport Island pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favorite
The two-story cottage features a welcoming front porch with a green roof and an American flag. A gravel driveway leads to the house, surrounded by trees and green lawns, offering a peaceful and private setting.
Home in Bristol

Coastal Maine Retreat · Fire Pit · Walk to Harbor

WalkabilityOutdoor spacesRiver

4.96 out of 5 average rating, 105 reviews
Guest favorite
A fire pit is positioned near the water's edge, surrounded by two adirondack chairs. The setting sun reflects off the river, casting warm hues across the sky and water. Green trees frame the tranquil scene, creating a peaceful atmosphere.
Home in West Bath

Oak Leaf

Outdoor spacesPetsKitchen

4.89 out of 5 average rating, 186 reviews
Guest favorite
A three-story cottage is nestled on a hillside, showcasing large bay windows and a charming balcony adorned with decorative elements. Lush greenery surrounds the home, complementing its gentle color scheme against a clear blue sky.
Home in Southport

Maine Cottage/Your Year-Round Destination

WalkabilityPetsComfort

4.92 out of 5 average rating, 106 reviews
Top guest favorite
A screened-in porch features comfortable seating arranged around a central table. Natural wood beams adorn the ceiling, and a ceiling fan is present for air circulation. Views of the outdoor area can be appreciated through the screens, enhancing relaxation in this inviting space.
Home in Bath

Little Cottage on the Kennebec

PetsWalkabilityAir conditioning

4.94 out of 5 average rating, 129 reviews
Superhost
A bright living space features a light blue couch and a gray armchair positioned around a wooden coffee table. Green plants add a natural touch, while framed artwork decorates the walls. Soft textiles are draped on the couch, and large windows allow for ample daylight.
Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay

PetsWalkabilityTV

4.88 out of 5 average rating, 112 reviews
Top guest favorite
An airy living space is highlighted by tall windows that bring in natural light and showcase views of the surrounding trees. A large sectional sofa faces a flat-screen TV, complemented by a wood stove for warmth. A dining area is visible in the background.
Home in Freeport

Waterfront 5 BR Home | On Casco Bay in Freeport

WalkabilityOutdoor spacesRiver

4.96 out of 5 average rating, 145 reviews
Guest favorite
A serene view of a lake at sunset is presented, showcasing soft hues of orange, pink, and purple reflected on the water. Silhouettes of trees line the shore, while the calm surface creates gentle ripples, inviting relaxation and contemplation.
Home in Manchester

Lakeside retreat on quiet cove on Cobbessee Lake!

Outdoor spacesPetsLayout

4.85 out of 5 average rating, 112 reviews
Top guest favorite
Home in Wiscasset

Cozy Midcoast Island Cottage

Outdoor spacesPetsCheck-in

5.0 out of 5 average rating, 29 reviews

Pet-friendly home rentals with a pool

Top guest favorite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Outdoor spacesWalkabilityCleanliness

4.97 out of 5 average rating, 174 reviews
Guest favorite
Home in South Thomaston

Large private area, close to Rockland

PetsOutdoor spacesGetting around

4.94 out of 5 average rating, 113 reviews
Top guest favorite
Home in Old Orchard Beach

OOB Oasis: 6BR Home w/ Private Pool Near Beach

WalkabilityPetsCheckout

4.95 out of 5 average rating, 155 reviews
Guest favorite
Cabin in Freeport

A-frame w/ towering 18ft glass wall & deck - 15

WalkabilityOutdoor spacesIndoor spaces

4.95 out of 5 average rating, 116 reviews
Guest favorite
A log cabin is nestled among tall trees on a gentle slope. Large windows create airy views from the exterior, showcasing a front deck that extends along the house. The natural surroundings provide a peaceful and serene setting.
Home in Peru

the lake house

Outdoor spacesPetsHiking

4.94 out of 5 average rating, 236 reviews
Guest favorite
A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.
Apartment in Cape Elizabeth

Portland & Beach & Lighthouses! Romantic! Lovely

Outdoor spacesPetsIndoor spaces

4.87 out of 5 average rating, 611 reviews
Guest favorite
Home in Mechanic Falls

Back street!

Outdoor spacesHospitalityCleanliness

4.83 out of 5 average rating, 24 reviews
Top guest favorite
Home in Biddeford

Bubbles & Pines - Pool, HotTub, Lg Deck, ME Coast

Outdoor spacesWalkabilityHospitality

4.99 out of 5 average rating, 76 reviews

Private, pet-friendly home rentals

Guest favorite
A fire pit area features a circular arrangement of brightly colored chairs on a well-maintained lawn. The ocean view is visible in the background, framed by trees. Gentle waves can be seen at a distance, enhancing the tranquil outdoor space.
Cottage in New Harbor

Captains View at Pemaquid Point

WalkabilityOutdoor spacesBathroom

4.97 out of 5 average rating, 104 reviews
Top guest favorite
The exterior of a charming cottage is captured, featuring rustic wooden shingles. A set of double French doors is framed by greenery and shadows from surrounding trees. A small porch area is visible, leading to a well-maintained lawn.
Cabin in Edgecomb

The Highland Cottage on Sheepscot

Outdoor spacesWalkabilityDecor

4.88 out of 5 average rating, 1012 reviews
Top guest favorite
An open space features a vaulted wooden ceiling with beams and skylights. A cozy seating area includes a brown sofa and a modern coffee table. A wood stove adds warmth, while a well-equipped kitchen with dark green cabinets is visible in the background.
Tiny home in Freeport

Cozy Rock Cabin #thewaylifeshouldbe

Outdoor spacesPetsComfort

4.99 out of 5 average rating, 389 reviews
Guest favorite
A serene view captures the sunset over the water, with the sun reflecting on the surface. Silhouetted trees are positioned in the foreground, creating a natural frame. The grassy landscape leads towards the water, enhancing the tranquil setting.
Cabin in New Harbor

Rustic Oceanfront Log Cabin

PetsWalkabilityValue

4.91 out of 5 average rating, 158 reviews
Top guest favorite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston

Timeless Tides Cottage

Outdoor spacesPetsTV

4.96 out of 5 average rating, 212 reviews
Top guest favorite
A welcoming living space features a large sectional sofa in blue-gray fabric, complemented by a rustic coffee table. Natural light floods in through skylights and sliding glass doors that open to views of the waterfront. A dining table for ten and stylish decor enhance the inviting atmosphere.
Home in Phippsburg

Waterfront Home Phippsburg Maine

Outdoor spacesPetsHeating

5.0 out of 5 average rating, 29 reviews
Top guest favorite
A wooden dock leads towards a house set among tall trees, featuring a flag waving above. The waterfront view showcases rocky shoreline and calm waters, while the greenery adds a natural touch to the serene environment.
Home in Southport

Waterfront cottage with private dock Southport, ME

Outdoor spacesPetsLaundry

5.0 out of 5 average rating, 17 reviews
Top guest favorite
The single-level home is set amidst a lush green lawn, featuring a covered front porch with white railings and blue shutters on the windows. The pathway leads to the entrance, framed by well-maintained landscaping and trees in the background under a partly cloudy sky.
Home in Boothbay

Morning View: One Level, Dog-Friendly, Water View

PetsOutdoor spacesCleanliness

5.0 out of 5 average rating, 13 reviews

When is the best time to visit Westport Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,749 GYDG$43,305 GYDG$37,238 GYDG$38,494 GYDG$59,414 GYDG$49,791 GYDG$46,443 GYDG$52,929 GYDG$55,230 GYDG$56,276 GYDG$57,531 GYDG$52,301 GYD
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

Destinations to explore