Family-friendly vacation rentals in Boothbay Harbor

A charming turn-of-the-century Victorian farmhouse is visible, surrounded by lush greenery and colorful flowers. Purple lupines and white daisies create a natural border in the foreground, while the house features multiple windows reflecting the daylight.

4.88 out of 5 average rating, 128 reviews

Rosie's Hideaway By the Sea

Rosie's Hideaway By The Sea is in a lovely turn of the century Victorian farm house filled with paintings by Maine artists and beautiful hardwood floors. The front yard has gorgeous shade trees and a stone wall. Fabulous views of the harbor is a short walk away. . Follow the road along the harbor and you'll end up downtown Boothbay Harbor where all the shops and restaurants are. While we love children and animals, the space is not appropriate / safe for children under 8 or pets of any kind.

4.99 out of 5 average rating, 118 reviews

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

Home in Georgetown

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

4.89 out of 5 average rating, 131 reviews

A tranquil view of the water is framed by trees and a wooden pathway leading to a sandy beach area. Calm waters reflect the surrounding clouds and greenery, providing a serene escape in the natural landscape.

Cabin in Boothbay Harbor

Sebasco Sprucewold Cabin@ the Beach

This quaint and cozy log cabin built in the 1940's is located in the summer colony of Sprucewold. It is just about 1 mile from downtown Boothbay Harbor. At 750 square feet, this adorable cabin is suited for no more than 4 people. You will have access to a small, private, sandy beach; a rare find on the rocky coast of Maine. There is so much to see and do in the Boothbay area. Life slows down and there is no better place to experience that "Maine, the way life should be" feeling.

4.92 out of 5 average rating, 157 reviews

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.

An exterior view of the apartment's entrance is presented, featuring a small deck with two wooden chairs and a table. Colorful potted flowers line the steps leading up to the entrance, while a decorative red paddle hangs by the door, reflecting a nautical theme.

4.99 out of 5 average rating, 109 reviews

Chic 1-Bedroom at the Heart of Boothbay Harbor

Welcome to Oak Ledge! Stay for Windjammer 2026: June 21-27! Oak Ledge is a beautifully-renovated 2-storey 1-bedroom apartment in the heart of Boothbay Harbor. Bedroom and Bathroom on the upper level. 5-night maximum This is an adults only listing. Sorry, no pets. Our friendly rescue dog "Oscar" roams freely on the property. Off-street parking for one car. Self check-in. Smart TV with streaming - remember to have your log-ins.

A welcoming living space features two comfortable armchairs and a soft couch, with a wooden coffee table at the center. Large windows provide abundant natural light and views of the water. A well-equipped kitchen is visible in the background, along with light-colored cabinetry.

5 out of 5 average rating, 135 reviews

Sail Loft: Oceanfront Apartment on a Pier.

Experience a one-of-a-kind waterfront escape at the Sail Loft in Boothbay Harbor! This unique 1-bedroom apartment is located directly over the water in a working marina, offering stunning panoramic views from every window. It feels like being on a private yacht. Perfect for a couple's getaway, you're just a short walk from all the downtown shops and restaurants. Enjoy a truly memorable stay with free parking included.

4.97 out of 5 average rating, 274 reviews

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).

Guesthouse in Boothbay Harbor

The cottage exterior features light-colored siding and a distinctive steeply pitched roof with a prominent window above the entrance. Double doors framed by a large glass panel invite visitors inside, surrounded by lush greenery and flowering shrubs.

5 out of 5 average rating, 264 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

A furnished space includes a spacious bed with decorative pillows, a comfortable sofa, and a dining table with chairs. Soft lighting is provided by a hanging pendant light and lamps. Wooden accents are featured throughout, complemented by a small kitchenette and a decorative rug.

5 out of 5 average rating, 133 reviews

Harbor for Two

Absorbed in ship-building tradition, picturesque Boothbay Harbor is still about boats-boats from around the world bobbing in the harbor, lobster boats unloading the day's catch, sea-kayaks exploring the rocky shoreline. Paddle, shop or gallery-hop along the charming waterfront or discover some of the endless hiking trails.

4.94 out of 5 average rating, 483 reviews

A charming log cabin nestled among lush greenery, featuring a sloped roof and multiple windows. A picnic table is positioned in front, surrounded by natural landscaping. The peaceful outdoor setting invites relaxation and exploration in the surrounding forest.

Cabin in Boothbay

Simple Boothbay Log Cabin on Water

Relax, reflect, & let time stand still when you visit this tiny, off-the-grid (NO ELECTRICITY) log cabin. Lobster bakes, swim, paddle the cove, swing the hammock, enjoy an hypnotic fire and unplug. Looking for pure Maine experience in the Mid-Coast?

4.93 out of 5 average rating, 228 reviews

A rustic cabin is nestled among tall trees, featuring large glass windows that allow natural light to fill the interior. The wooden exterior blends harmoniously with the surrounding greenery, while a small deck extends from the front, offering a serene view of the landscape.

Cabin in Boothbay

Peaceful & private waterfront cabin

Enjoy uninterrupted quiet on the Maine coast in our light-filled waterfront cabin. Just 5 minutes from lovely Boothbay Harbor for kayaking, sailing, hiking, seafood tasting, you name it! Or just relax at the cabin in a stunning natural setting.

4.99 out of 5 average rating, 170 reviews

The treehouse, shaped like a fox, is elevated among the trees with large windows that allow natural light to flood the interior. Its unique architecture features a copper roof and warm illumination, creating a welcoming appearance against the tranquil forest backdrop.

Treehouse in Pownal

The Copper Fox Treehouse

At The Copper Fox Treehouse enjoy relaxing in the treetops in a red fox head shaped treehouse. Discover many locally and custom made fox finishings inside. How many foxes can you find? Follow our journey on IG at @thecopperfoxtreehouse

Popular amenities for Boothbay Harbor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Tiny home in New Gloucester

A modern tiny house is set amidst lush greenery, featuring a spacious wooden deck with clear railings. A swing hangs from a nearby frame, and rustic stone landscaping encircles a small fire pit. Sunlight filters through the trees, highlighting the tranquil outdoor space.

4.94 out of 5 average rating, 246 reviews

Tiny house in the Birch Grove with private HOT TUB

4.91 out of 5 average rating, 155 reviews

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

4.98 out of 5 average rating, 457 reviews

The tree dwelling is elevated among sturdy trees, featuring a wraparound balcony surrounded by foliage. Large windows invite natural light, offering views of the lush surroundings. A rope bridge connects to another elevated structure, enhancing the unique treehouse experience.

Treehouse in Georgetown

Modern Treehouse w/Water Views+Cedar Hot Tub

4.98 out of 5 average rating, 184 reviews

The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.91 out of 5 average rating, 763 reviews

An inviting living area showcases a modern spiral staircase leading to the loft. A sleek kitchen is visible, featuring patterned backsplash tiles and stainless-steel appliances. A comfortable sofa and a coffee table create a cozy seating arrangement, complemented by natural light from the large windows.

Apartment in Brunswick

Downtown Hideaway-Loft HotTub Modern Clean Private

Place to stay in Owls Head

A charming off-grid cabin stands amidst lush greenery, featuring large front windows framed by wooden trim. A picnic table with potted flowers occupies a gravel area in front, inviting outdoor gatherings. Solar panels are visible on the roof, showcasing eco-friendly energy use.

4.98 out of 5 average rating, 282 reviews

A comforting sweet off grid cabin near the beach!

4.96 out of 5 average rating, 219 reviews

A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.

Home in Augusta

Lakefront: Private Hot Tub, Sauna & Free Massages!

4.96 out of 5 average rating, 110 reviews

Two Adirondack chairs are positioned on a rocky area overlooking a serene waterfront. Trees frame the scene, with the sky displaying soft hues of pink and orange during sunset. The calm water reflects the natural beauty of the surroundings.

Home in Phippsburg

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 117 reviews

A modern kitchen is equipped with a stainless-steel microwave and stove beneath a stylish backsplash. The countertop features a sink and invites meal preparation. A comfortable nook with a raised twin bed can be seen in the background, surrounded by decorative plants.

Guest suite in Freeport

Studio Apartment in Freeport

4.92 out of 5 average rating, 104 reviews

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

Cottage in South Thomaston

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.

4.96 out of 5 average rating, 203 reviews

Timeless Tides Cottage

4.98 out of 5 average rating, 262 reviews

An aerial view captures a secluded log cabin surrounded by lush greenery on a private island. A wooden dock extends over the tranquil water, providing access to the cabin, which is nestled among trees. Sunlight glistens on the lake's surface.

Island in Monmouth

Naughty Dog Private Island Log Cabin

4.88 out of 5 average rating, 165 reviews

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

4.91 out of 5 average rating, 383 reviews

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.

Home in Bath

Gorgeous Studio on the Kennebec

4.95 out of 5 average rating, 184 reviews

A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.

Cabin in Bridgton

Writers Cabin in the Woods with Sauna!

4.98 out of 5 average rating, 356 reviews

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

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 132 reviews

The outdoor area features a circular pool surrounded by reclining lounge chairs with blue and white stripes. A stone patio is adorned with a wooden table and chairs, while lush greenery and flowering shrubs frame the scene under a clear blue sky.

Guest suite in Portland

Resort-like 2 bed/1 bath - seasonal pool/hot tub

4.96 out of 5 average rating, 187 reviews

A warm orange wall serves as a backdrop for a vibrant deer painting. A purple sofa is positioned in front, accompanied by a patterned pillow and a modern lounge chair. A tall plant adds texture, while a decorative oriental carpet covers the floor.

Apartment in Westbrook

A Riot of Color at an Artist's Retreat on the Portland Line

4.95 out of 5 average rating, 108 reviews

A spacious living area features a plush leather sofa and an easy chair, arranged around a circular coffee table atop a textured area rug. A wall-mounted smart TV is visible, while a dining space with multiple chairs is seen in the background.

Apartment in Portland

Portland Sweet Escape

4.96 out of 5 average rating, 163 reviews

A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.

Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

4.97 out of 5 average rating, 113 reviews

A refreshing pool area is surrounded by well-kept landscaping and seating options. Two blue umbrellas provide shade over metal chairs and tables. Colorful pool floats are positioned in the clear water, and a charming white structure is visible in the background.

Apartment in Falmouth

Poolside Suite-Gateway to Portland

4.95 out of 5 average rating, 687 reviews

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

Loft in Falmouth

Loft Apartment on Tree-Lined Street in Falmouth

Home in Old Orchard Beach

4.95 out of 5 average rating, 141 reviews

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