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Family-friendly vacation rentals in Westport Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Westport Island

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

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Top guest favorite

A scenic view is captured from the deck, showcasing the tranquil waters of Jones Cove with lush greenery lining the shore. In the distance, small islands are visible under a clear blue sky, creating an inviting atmosphere for relaxation.

Guesthouse in South Bristol

4.98 out of 5 average rating, 400 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

The cottage exterior features a welcoming front porch with white railings and blue steps. A red door is flanked by blue shutters and adorned with vintage-style lanterns. Lush green plants and vibrant flowers enhance the inviting atmosphere, while a small blue bistro set provides a cozy spot for outdoor seating.

Cottage in Bristol

4.76 out of 5 average rating, 111 reviews

POST OFFICE COTTAGE Pemaquid Point

We now have a social media page! @pemaquidpostofficecottage Enjoy the relaxing, picturesque coast of Maine in this cozy, comfortable cottage...like a dolls house. Centrally located to local attractions, Pemaquid Lighthouse is 1/2 mile walk.Pemaquid beach only a 5 minute drive. Tiny Cottage sleeps two, with a full size bed or use pull-out couch, efficiency kitchen, and compact bathroom , shower stall. ( 16’ x 20’ square footage) Located with access to tide pools, glorious sunsets!

The rustic exterior of the historic retreat features a weathered brown shingle facade and a vibrant red front door. A spacious deck extends towards the water, surrounded by greenery and providing a serene view of the tidal Sheepscot River at sunset.

Farm stay in Westport Island

4.83 out of 5 average rating, 125 reviews

The Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

Top guest favorite

The studio's interior displays rustic charm with original rough-hewn beams overhead. A spacious bed is visible in the back area, while a comfortable seating arrangement and TV are situated in the front. Natural light streams through multiple windows, enhancing the welcoming atmosphere.

Guesthouse in Harpswell

4.95 out of 5 average rating, 461 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, spacious, colorful, comfy, bright! New king bed! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away. Enjoy the trails in the woods with spectacular views or walk on the beach at one of the state parks! So beautiful!

A charming white cottage with a sloped roof is situated near the water's edge. Orange window boxes add a pop of color to the exterior, while a stone patio features several wooden chairs. Lush greenery surrounds the property, providing a natural backdrop.

4.91 out of 5 average rating, 341 reviews

Gorgeous Studio on the Kennebec

Gorgeous riverside studio, the smaller of two AirBnB houses on the same property on the outskirts of beautiful and historic Bath, Maine. (The other, “Beautiful Summer River Retreat,” is a separate Airbnb rental.) Kitchenette, bathroom/shower, living room, and bedroom. Simple, modern decor. Close to great shops, restaurants, and beaches, and just a 20-minute drive from Bowdoin College. Adjacent to a boat launch, and a short walk from the Bath Marine Museum and a scenic dog park.

Top guest favorite

A bright living area is visible, featuring a light-colored sofa and a comfortable armchair. A wooden dining table with two chairs occupies the foreground. Windows allow natural light to illuminate the space, while soft curtains frame the views of the surrounding forest.

Loft in Edgecomb

4.91 out of 5 average rating, 335 reviews

Cozy Loft in the Woods (Dogs Welcome)

Bright, cozy loft, surrounded by deep woods, separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

The exterior of a Victorian farmhouse is showcased, featuring classic white siding and multiple large windows. Lush green trees frame the house, while vibrant pink and purple flowers add color to the front yard. A covered porch invites relaxation.

Apartment in Lisbon falls

4.94 out of 5 average rating, 465 reviews

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

The exterior of the cottage displays a warm wood façade with a porch adorned with potted flowers. Surrounding landscaping includes low shrubs and rocky features, contributing to a natural setting. A gravel pathway leads to the entrance, framed by greenery.

Condo in Edgecomb

4.91 out of 5 average rating, 190 reviews

A Spacious Vacation Cottage in Sheepscot Harbour

A large and stylish one bedroom cottage with water views. Newly renovated and offering style and convenience. Located within walking distance to Wiscasset. A great home base for exploring Boothbay Harbor and many more midcoast Maine destinations! Plan a day excursion, or relax inside with the view of the harbor. Make yourself at home in the cottage! Enjoy and walk the resort common areas including a gazebo, riverside lawn, and a 100 ft pier.

Top guest favorite

An entryway is displayed, featuring a nautical map mounted on the wall. A wooden bench sits beneath the map, accompanied by a woven bag hanging from hooks. A striped area rug lines the floor, complemented by a pair of sandals positioned nearby.

Guest suite in Bath

4.99 out of 5 average rating, 217 reviews

Bath Historic District Apartment

Located in the Bath historic district, this one bedroom apartment is located just a few blocks from downtown. The apartment has a queen bed in the bedroom and also a queen sleeper sofa in the living room. The home was built in the late 1700's, but with the recent upgrades, it now feels fresh with classic elements. Located in Midcoast Maine, this apartment is an quick drive to the beach, hiking trails and museums.

A spacious living room is featured, furnished with a comfortable couch and two recliners. Natural light filters through the covered windows, highlighting the neutral-colored decor. A small side table holds a lamp, complementing the cozy atmosphere.

Home in Brunswick

4.93 out of 5 average rating, 253 reviews

A cozy, cute and comfortable house.

Cute and comfortable, 5 min. walk to restaurants, fast food, coffee shop, groceries and shopping centers. Also, bowling alley, miniature golf, driving range and cinema. Minutes by car to The Brunswick Executive Airport Downtown Brunswick Bowdoin College Maine State Music Theater Mid Coast Hospital Bailey Island Historic town of Bath

A wooden tree dwelling is nestled among the trees, featuring large windows that allow ample natural light. A welcoming entry door is visible, and a small private deck extends from the structure, surrounded by greenery and a hammock underneath.

Treehouse in Georgetown

4.97 out of 5 average rating, 340 reviews

Tree Dwelling with Water Views & Cedar Hot Tub (2)

Experience the airiness of life up among the pines in Georgetown, ME. Unique tree dwelling with cedar hot tub perched atop 21-acre wooded hill sloping to water views. Set in classic coastal Maine village w/ Reid State Park beaches and famed Five Islands Lobster Co. River views from the King size bed, through wall of windows.

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Popular amenities for Westport Island family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A colorful cabin is nestled among greenery, featuring a blue exterior with red accents. A spacious porch is shaded by a roof, with a stone seating area nearby. A fire pit is situated in front, surrounded by grass, creating a peaceful outdoor setting.

Cabin in Appleton

4.89 out of 5 average rating, 307 reviews

Raven's Crossing - Kate's Cottage

An aerial view showcases the cozy ranch home nestled in a vast pasture, surrounded by vibrant autumn foliage. The backdrop features rolling mountains under a clear blue sky, while winding roads and scattered trees create a picturesque rural scene.

4.95 out of 5 average rating, 159 reviews

Brownie- Comfy Modern Ranch Home w/Hot Tub

Top guest favorite

A spacious log cabin is featured, set in a natural landscape surrounded by trees. A wide wraparound deck is accessible via a wooden ramp, leading to a welcoming front door. Lush greenery and decorative plant beds border the cabin, complementing its rustic charm.

Cabin in Chesterville

4.89 out of 5 average rating, 53 reviews

Lakefront Log Cabin escape-boats-fishing-hot tub

The three-story beach house features a prominent grey exterior with multiple large windows allowing natural light. A spacious patio is surrounded by landscaped greenery, offering seating areas with chairs and sun beds. Balconies extend from the upper levels, providing outdoor spaces with relaxing views.

Home in Old Orchard Beach

4.96 out of 5 average rating, 147 reviews

Luxury 6 bedroom Beach House 50 ft from beach

Top guest favorite

A spacious outdoor area features several horses roaming in a fenced pasture, with trees providing a natural backdrop. A rustic barn and a house are visible in the distance, surrounded by lush greenery. Paths lead towards a gravel road nearby.

Loft in Andover

4.98 out of 5 average rating, 169 reviews

Private studio loft, decks and hot tub

A private deck area showcases a hot tub, emitting a soft blue light. Two chairs are positioned nearby, with a decorative cushion displayed on one. Lattice fencing and greenery provide privacy, creating an inviting setting for relaxation at night.

Apartment in Topsham

4.87 out of 5 average rating, 547 reviews

Cozy hot tub haven

The exterior of a charming farmhouse is depicted, showcasing a spacious deck with a hot tub and outdoor seating. String lights are seen illuminating the area, while a green lawn and surrounding trees add to the tranquil setting during sunset.

4.89 out of 5 average rating, 83 reviews

Charming Farmhouse: Game Room, Hot Tub, Firepit

The exterior of a two-story house is surrounded by a green lawn and neatly trimmed bushes. The home features multiple windows and a balcony. A flag is displayed on a pole, while trees and landscaping create a natural backdrop.

Cottage in Verona Island

4.89 out of 5 average rating, 170 reviews

Nashport on the Penobscot

Family- and pet-friendly home rentals

A charming two-story blue house with a welcoming front porch is surrounded by lush green grass and trees. The structure features multiple windows and a contrasting red house visible in the background, providing a sense of space and community.

4.96 out of 5 average rating, 116 reviews

Sunday River Bethel Village ! Walk to Restaurants

Top guest favorite

A spacious living area features a sectional leather couch adorned with decorative pillows, complemented by an ottoman and wooden flooring. Natural light filters through large windows covered with dark shades, enhancing the room's cozy ambiance. A television and wooden shelving unit are visible in the background.

Home in Rumford

4.91 out of 5 average rating, 190 reviews

Charming Home Getaway near Sunday River & Hikes

A yurt is set against a wooded backdrop, surrounded by trees. A wooden deck features a seating area and an umbrella, providing shade. Access to the deck is facilitated by a small ramp, ensuring easy entry.

4.93 out of 5 average rating, 263 reviews

Fire Fly Yurts on Funky Bow Lane

Top guest favorite

A well-maintained backyard garden features a stone fire pit surrounded by seating. Flower beds with various plants provide color and texture. A wooden swing set and a shed are visible in the background, with a stone path leading through the grassy area.

Home in South Portland

4.91 out of 5 average rating, 117 reviews

Cottage style home 2 blocks from the beach!

A cozy living area features a black wood stove providing warmth. A wooden table is set with two glasses and a bottle, inviting relaxation. Windows offer views of the water, while comfortable seating is arranged nearby, enhancing the inviting space.

Guest suite in Penobscot

4.88 out of 5 average rating, 109 reviews

Waterfront Getaway on the coast of Maine.

A cozy living room is depicted, featuring two brown leather sofas with colorful cushions. A wooden coffee table sits center stage. Large windows adorned with patterned curtains allow natural light to fill the space, while shelves decorated with various items line the walls.

Apartment in East End

4.94 out of 5 average rating, 304 reviews

Monument SWEET!

A serene waterfront scene captures calm waters dotted with boats gently bobbing in the harbor. Rocky shores lead to lush greenery in the background, with a clear blue sky above, creating an inviting coastal atmosphere in this Maine setting.

Apartment in Falmouth

4.96 out of 5 average rating, 155 reviews

Falmouth Waterfront Carriage House Apt

Top guest favorite

An aerial view showcases a spacious home surrounded by lush greenery and a golf course. Nearby, a parking area is visible, along with manicured fairways and trees in the distance, providing a sense of tranquility and openness.

Home in Bridgton

4.95 out of 5 average rating, 100 reviews

Beautiful Views, Bridgton Maine

Family-friendly home rentals with a pool

A large outdoor pool area is surrounded by lounge chairs in vibrant colors. The pool is complemented by neighboring buildings with multiple windows, providing a welcoming atmosphere. The concrete patio offers ample space for relaxation and sunbathing, with a barbecue area visible in the background.

4.85 out of 5 average rating, 184 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

A spacious outdoor pool area is seen, surrounded by a paved deck. Sun loungers are positioned neatly along the perimeter, with blue umbrellas providing shade. A clubhouse with a large deck overlooks the pool, set against a backdrop of trees.

Cottage in Wells

4.88 out of 5 average rating, 42 reviews

Beach Dreaming

A serene view of Penobscot Bay at sunrise, featuring a pastel sky in shades of pink and purple. Small boats are visible on the water, while a lighthouse stands on the shoreline. A grassy area has benches and picnic tables, inviting outdoor enjoyment.

Apartment in Rockland

Heart of Rockland Maine

An outdoor pool is center stage, surrounded by a wooden deck that extends to a grassy area with playground equipment visible in the background. A patio table and chairs, along with an umbrella, offer shaded seating options nearby.

4.91 out of 5 average rating, 45 reviews

Caribou Run Private Retreat with Mountain Views

An aerial view showcases an A-frame cabin nestled among greenery, surrounded by trees and a tranquil pond. A winding path leads to the cabin, highlighting the seamless integration of nature and architecture. The setting reflects a peaceful and private retreat.

Home in Harrison

4.9 out of 5 average rating, 306 reviews

EPIC VIEWS, Hot Tub, Pond, River, 14 Acres A Frame

A small cottage is framed by a white picket fence, with lush greenery and flowering bushes surrounding its exterior. The front porch features large windows, enhancing natural light, while a gravel path leads to the entrance.

Cottage in Wells

4.64 out of 5 average rating, 102 reviews

Appledore Cottage is a Family Vintage Cottage

An aerial view of a spacious backyard showcases a well-maintained heated pool surrounded by a patio area with seating. Lush greenery and trees frame the property, enhancing the outdoor space, while a shaded fire pit area and landscaped garden beds are visible.

Home in Portland

5 out of 5 average rating, 11 reviews

The Hill's on Buttonwood

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.

4.95 out of 5 average rating, 218 reviews

the lake house

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

Total rentals
50 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi

Destinations to explore