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Family-friendly vacation rentals in Rockland

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Rockland

  • Total vacation rentals

    Explore 80 vacation rentals in Rockland

  • Nightly prices starting at

    Rockland vacation rentals start at G$25,101 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,840 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Rockland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Rockland rentals

  • 4.9 Average rating

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

Top-rated family-friendly rentals in Rockland

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

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Top guest favorite
The exterior of a two-story coastal home is presented with light blue siding and white trim. A white picket fence surrounds the front yard, which features green grass and small shrubs. Large windows allow natural light to illuminate the interior spaces.
Home in Rockport

Seaside House/Downstairs

Enjoy everything coastal Maine has to offer in this coastal home with great ocean views. The space is light and bright and yet cozy! The house has a well appointed kitchen and is well maintained. You will find everything you need and more in this comfortable seaside retreat. Access to the beach is a short walk away. The house sits across the street from Clam Cove and is not directly on the beach. Beach access is private, quick and easy. There is also a large back yard to play or relax in.

4.92 out of 5 average rating, 172 reviews
Top guest favorite
The exterior of the tiny house displays a simple structure with light-colored siding and multiple windows. Decorative butterflies adorn the side wall. A gravel pathway leads up to wooden steps, providing access to the entrance. Green grass surrounds the house, contributing to the serene setting.
Tiny home in Rockland

Simplicity-Just what you need! STR24-20

The first legal tiny house in Rockland! All the comforts of home in this sweet tiny house. First floor living, open floor plan. Small but roomy. In walking distance to Main St, South end beach, the Lobster Festival, Blues Festival, Boat Show and more. You will love the simple concept this little gem offers whether just staying the weekend or for weeks. It is quiet and serene as you sit in the living space and have a warm cup of tea or a cold lemonade. We love our tiny house and hope you do too!

4.96 out of 5 average rating, 194 reviews
Top guest favorite
An open living area features a dining table with two wooden chairs, a sofa, and a light-colored coffee table. The kitchen showcases full-size appliances and a window illuminating the space. A warm orange wall adds a touch of character, while bamboo flooring runs throughout.
Guesthouse in Rockland

Sweet Willow Suite, Rockland, private 1st floor

Clean, cozy, and quiet, 1-bdrm apartment in Rockland, 2 blocks to Main St. & the waterfront. 1st fl, 1-story separate building, private entrance, queen bed, walk-in shower. Suite includes many safety features. Host is hands-on, happy to greet you at check-in, then respect your privacy. Licensed with the City of Rockland #STR26-12. Airbnb has a new fee structure. They now take the guest service fees out of the nightly rate rather than add them to your total as separate line item when you pay.

4.9 out of 5 average rating, 423 reviews
Guest favorite
The exterior of the cottage features a light gray shingle facade, complemented by white trim around the windows and front door. A set of three windows with flower boxes is situated on each side of the door. A welcoming porch leads to the entrance.
Home in Rockland

Downtown-Walk to All Things Rockland

Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

4.94 out of 5 average rating, 435 reviews
Top guest favorite
A cottage is positioned near the water's edge, surrounded by trees. Outdoor seating in the form of Adirondack chairs is visible, offering a view of the ocean. Steps lead from the door to the grassy area, which features a barbecue grill.
Cottage in Rockport

Cottages at Oakland Seashore (Cottage #8)

Nestled on 70 acres of oceanfront property in Rockport, Maine, the cottages at Oakland Seashore are the perfect choice for a romantic getaway, vacation with friends, or a family gathering. Formerly the Oakland Seashore Motel & Cabins, I recently purchased the property and have decided to rent a few of the cottages this summer and fall on a weekly basis. Reminiscent of a bygone era, these cottages are simple and provisioned with the basics, but have the most remarkable ocean views.

4.95 out of 5 average rating, 106 reviews
Top guest favorite
A charming yellow house features white trim and a welcoming front door. Flower boxes are filled with vibrant blooms beneath the windows, surrounded by a neatly tended garden. A stone wall provides a defined border, enhancing the inviting exterior.
Guest suite in Rockland

5 Laurel Studio private entrance STR26-47

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

4.98 out of 5 average rating, 515 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

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

4.96 out of 5 average rating, 216 reviews
Top guest favorite
Home in Rockland

Charming, Family-Friendly Historical In Town Home

STR26-48 Sadler House is an in-town historic home located just blocks from Main Street. We have made it truly convenient for families, with flexible sleeping arrangements in three cozy upstairs bedrooms, two full baths, a fully equipped kitchen, large dining table, living room, and sun room. Walk to shops, restaurants, museums and the harbor in minutes. Our house is the perfect home base for exploring all that the beautiful midcoast has to offer.

4.98 out of 5 average rating, 133 reviews
Top guest favorite
The exterior of the home is featured, showcasing a single-story structure with a light grey façade. A brick pathway leads to the front entrance, accompanied by well-maintained lawns and decorative flower beds. Surrounding trees provide a natural setting, enhancing the peaceful atmosphere.
Home in Rockport

Sweet home away (pet friendly)

Single floor living at its finest. Conveniently located to both Camden and Rockland, enjoy this 3 bdrm 1.5 bath home in a great country setting. Just 1/2 mile to route 1 and very close to the ocean. Come enjoy the large back deck over looking the peaceful maine woods. The front door in about 50’ from the road, which can be busy at certain time of the day. There is 1 ring doorbell for everyone’s security outside the front door of the house.

4.96 out of 5 average rating, 378 reviews
Top guest favorite
The front of the home features a charming covered porch with red chairs and hanging flower baskets. A light-colored door with glass paneling is centered between two windows. A well-maintained lawn and a slight stone pathway enhance the inviting entrance.
Apartment in Owls Head

Coastal Vintage Living

This is a spacious 1000 sq. ft. apartment in my childhood home that has been renovated in Spring 2020 with a modern coastal theme and well appointed with vintage items. We have a well stocked kitchen, cozy dining/living room with a 43" Roku TV, and full laundry. Try a pastry from the professional baker across the road, take a walk down the street to Crockett's Beach, or go for a stroll in downtown Rockland. Remote check-in available.

4.97 out of 5 average rating, 185 reviews
Top guest favorite
A multi-level outdoor deck is shown, featuring a wooden table surrounded by four chairs. In the background, expansive views of the water and distant boats are visible. Lush greenery frames the scene, enhancing the connection to nature.
Home in Owls Head

Extreme Oceanfront House

This open concept, updated Ranch boasts expansive water views from the living room, dining room, kitchen & master bedroom. Start & end your day in the adjacent sitting or dining area with an enormous plate glass window framing an ever-changing view of sea birds, boats & islands. Step out onto the multi-level decks & terraces & stroll across the nicely landscaped yard to the water's edge.

4.95 out of 5 average rating, 101 reviews
Top guest favorite
A bright entryway features a light-colored door flanked by windows. A simple staircase leads to the second floor, while a small hall opens to the kitchen area. Natural materials are incorporated through woven basket and striped textiles hanging on hooks.
Apartment in Rockland

1 Block to Beach • Walk Downtown • Peaceful Escape

Renovated 1860s Cape Cod in Rockland’s coveted South End, just 1 block from the beach. Enjoy the scenic boardwalk into town to restaurants, galleries, shops, and the seasonal farmers’ market. Bright, uncluttered spaces with modern amenities create a peaceful retreat — perfect for couples, small families, or anyone seeking a quiet coastal getaway.

4.99 out of 5 average rating, 129 reviews

Popular amenities for Rockland family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A charming modern cottage with a red exterior and a pitched roof stands amidst lush greenery. The covered porch is furnished with comfortable seating, inviting relaxation. Large windows allow natural light to enter, enhancing the welcoming atmosphere of the property.
Home in Northport

Cute Midcoast Cottage w Hot Tub

4.98 out of 5 average rating, 281 reviews
Top guest favorite
Cabin in Chesterville

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

5.0 out of 5 average rating, 213 reviews
Guest favorite
A spacious wooden yurt is illuminated from within, showcasing its round shape against a starlit sky. Surrounding trees are visible, with a welcoming atmosphere created by the warm glow emanating from the windows.
Yurt in Appleton

SUMMER ROSE a Yurt for ALL Seasons

4.96 out of 5 average rating, 365 reviews
Top guest favorite
The image features an expansive view of a well-maintained garden, showcasing various plants and trees surrounded by a wooden fence. A greenhouse is visible, along with a garage and paths leading to cultivated garden beds. The background includes lush greenery and a cloudy sky.
Loft in Camden

Lovely new loft in permaculture gardens

4.99 out of 5 average rating, 134 reviews
Top guest favorite
A serene deck area features two wooden chairs and a small table overlooking a lush green lawn and tranquil water. The peaceful view includes trees framing the shoreline, offering a calming ambiance and connection to nature.
Home in Belfast

[Trending Now]Belfast City Park Ocean House

4.93 out of 5 average rating, 259 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

4.99 out of 5 average rating, 394 reviews
Guest favorite
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, 468 reviews
Top guest favorite
The exterior of a cozy cabin is showcased, featuring wooden shingles and a dark roof. A small deck includes a two-chair dining set and a hot tub nearby, surrounded by lush greenery and a well-maintained lawn.
Cabin in Searsmont

Birch Hill Cabin w/Hot Tub

4.99 out of 5 average rating, 245 reviews

Family- and pet-friendly home rentals

Top guest favorite
A modern cabin exterior showcases a deep blue facade and a welcoming entry, highlighted by a wooden deck adorned with an outdoor seating area. The surrounding landscape features various plants and autumn decor, enhancing the serene setting within the woods.
Tiny home in Appleton

Little Apple Cabin on 5 acres, amazing stargazing!

4.95 out of 5 average rating, 148 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

4.96 out of 5 average rating, 133 reviews
Top guest favorite
Apartment in Belfast

Belfast Harbor Loft | Downtown

4.96 out of 5 average rating, 431 reviews
Top guest favorite
A serene ocean view showcases a sailboat gliding across calm waters, framed by lush greenery and a rocky coastline. The expansive sky is filled with soft clouds, creating a tranquil atmosphere that invites relaxation and reflection.
Cottage in South Thomaston

Cottage by the sea private oceanfront shoreline

4.94 out of 5 average rating, 152 reviews
Top guest favorite
A scenic view captures a grassy area leading to a dock over Hobb's Pond. Four red Adirondack chairs are arranged around a fire pit made of stones. A mountain rises in the background, framed by fluffy clouds in a blue sky.
Cabin in Hope

Hobb’s House - Year Round Log Cabin on the Water

4.97 out of 5 average rating, 140 reviews
Top guest favorite
A spacious balcony offers stunning views of a vast natural landscape filled with greenery and wildflowers. A railing made of metal cables encircles the space, enhancing the sense of openness to the tranquil surroundings.
Apartment in Rockland

Mountain to Sea Serenity

4.96 out of 5 average rating, 160 reviews
Guest favorite
Home in South Thomaston

Large private area, close to Rockland

4.94 out of 5 average rating, 117 reviews
Top guest favorite
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

4.94 out of 5 average rating, 505 reviews

Family-friendly home rentals with a pool

Top guest favorite
A charming exterior of the historic residence showcases a well-maintained garden filled with vibrant purple flowers and greenery. The pale yellow siding of the house complements the octagonal window and green door, offering a welcoming appearance.
Apartment in Brunswick

Charming Saltwater Farm apartment

4.99 out of 5 average rating, 249 reviews
Guest favorite
The modern cabin features a sleek design surrounded by lush greenery. Soft bistro lights create a warm glow, illuminating the outdoor seating area with two Adirondack chairs. The deck can be seen in the background, enhancing the inviting atmosphere of the natural setting.
Cabin in Freeport

Romantic hideaway cabin w/ access to spa - 26

4.96 out of 5 average rating, 125 reviews
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!

4.96 out of 5 average rating, 179 reviews
Top guest favorite
A spacious suite is showcased with large windows allowing natural light. A comfortable couch faces a marble-topped coffee table, and a custom-built king bed is nestled against a natural pine headboard. The decor reflects minimalism, offering a peaceful setting for relaxation.
Apartment in Portland

Luxury Retreat In Back Cove | 10 Min to Downtown

5.0 out of 5 average rating, 116 reviews
Guest favorite
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

4.95 out of 5 average rating, 702 reviews
Top guest favorite
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

4.93 out of 5 average rating, 147 reviews
Guest favorite
Home in Bangor

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

4.97 out of 5 average rating, 372 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

4.87 out of 5 average rating, 615 reviews

When is the best time to visit Rockland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,534 GYDG$37,651 GYDG$44,972 GYDG$44,136 GYDG$50,202 GYDG$61,706 GYDG$62,124 GYDG$62,124 GYDG$53,967 GYDG$49,156 GYDG$37,233 GYDG$40,998 GYD
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

Destinations to explore