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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$25,104 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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Guest favorite
The kitchen area features a spacious countertop with dark cabinetry and modern appliances. Bright, sloped ceilings are complemented by large windows that provide abundant natural light. A cozy living area is visible, adorned with comfortable seating and decorative elements that reflect the coastal theme.
Apartment in Owls Head

Oceanview Escape near Maine Beaches

Located at the end of a private road you will find the area very peaceful with beautiful ocean view sunrises and sunsets and lots of wildlife sightings. This cozy 1000 square foot apartment has been recently renovated for a clean coastal vibe. The house was originally hand built in 2000 by the owner. You will notice the craftsmanship detail, built ins, hand made furniture and unique nautical style throughout the apartment. The kitchen is fully stocked and equipped with stove, full fridge and a new microwave and dishwasher. The living space provides a 50 inch smart TV and queen pull out sofa. Enjoy the vast ocean views from the large living room picture windows. Watch the boats cruising through Penobscot Channel or a local lobsterman hauling their traps. The bedroom offers a queen bed and plenty of closet/storage space. There is a large jacuzzi tub and separate hand tiled shower in the bathroom. Spacious deck off the kitchen/living area provides an outdoor dining area and grill. Enjoy dinner or drinks taking in the salty ocean air and views. At the base of the entry stairs is a separate patio space with propane fire pit shared amongst both living spaces. Located behind the apartment is an adorable playhouse with slide, saucer swings and a rock climbing wall that is shared amongst the neighborhood. Please play at your own risk. WiFi included

Indoor spacesKitchenGetting around

4.92 out of 5 average rating, 123 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!

Indoor spacesFamilyOutdoor spaces

4.94 out of 5 average rating, 431 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 :-)

FamilyIndoor spacesGetting around

4.96 out of 5 average rating, 130 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.

Indoor spacesFamilySleep quality

4.95 out of 5 average rating, 103 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 STR20-69

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

Indoor spacesFamilyHospitality

4.98 out of 5 average rating, 511 reviews
Top guest favorite
The exterior of the house features a charming gray shingle facade with white trim, complemented by blooming purple azalea bushes. A neatly paved driveway leads to the entrance, while green grass surrounds the base of the structure and tall evergreen trees provide a natural backdrop.
Home in Rockport

Seaside House/Upstairs

Enjoy everything coastal Maine has to offer with this as your home base. The views are outstanding and the house is well appointed and well maintained. This house encompasses the second and third floors, with great ocean views. The first floor is a separate apartment. The property has a large back yard to relax or play in and a dedicated BBQ. The house sits across the street from Clam Cove and is not directly on the beach. Beach access is private, quick and easy.

FamilyIndoor spacesCheckout

4.95 out of 5 average rating, 125 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.

FamilyKitchenAccess

4.96 out of 5 average rating, 212 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.

KitchenIndoor spacesTV

4.98 out of 5 average rating, 129 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.

KitchenFamilyHeating

4.96 out of 5 average rating, 373 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.

KitchenFamilyGrill

4.97 out of 5 average rating, 183 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. Sweet Willow is downtown Rockland, 2 blocks from Main St. and the waterfront. 1st floor, 1-story separate building, with private entrance, light-filled open area, queen bed, full bath with walk-in shower. Suite includes many safety features. Host is hands-on and is happy to greet you at check-in, then respect your privacy. Licensed with the City of Rockland #STR26-12.

KitchenFamilyBreakfast

4.9 out of 5 average rating, 420 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.

Indoor spacesFamilyAccess

4.99 out of 5 average rating, 127 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

FamilyIndoor spacesWalkability

4.98 out of 5 average rating, 274 reviews
Top guest favorite
Cabin in Chesterville

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

FamilyIndoor spacesCleanliness

5.0 out of 5 average rating, 209 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

KitchenFamilyCleanliness

4.98 out of 5 average rating, 467 reviews
Superhost
A spacious white tipi is nestled among trees, with a clear view of a quiet lake. A picnic table sits nearby, accompanied by a hammock stretched between two trees, inviting relaxation in this serene natural setting.
Tent in Brooks

Waterfront Tipi Glamping // Phoenix Landing

Indoor spacesFamilyPets

4.9 out of 5 average rating, 272 reviews
Guest favorite
A hot tub bubbling gently is positioned on lush green grass, with a serene view of Lake Saint George in the background. Colorful autumn trees line the water's edge, and a clear blue sky adds to the tranquil setting.
Home in Liberty

Modern Lakefront Home w/ Hot Tub • Summer Vacation

Indoor spacesFamilyAmenities

4.87 out of 5 average rating, 121 reviews
Top guest favorite
The exterior of a contemporary yurt is illuminated at night, set among trees in a wooded area. The structure features a circular design with a central roof vent and a wrap-around deck. Soft lighting highlights seating areas on the porch.
Yurt in Appleton

SILVER MOON, a Yurt for All Seasons

Indoor spacesFamilyAir conditioning

4.95 out of 5 average rating, 349 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

FamilyIndoor spacesAccess

4.99 out of 5 average rating, 238 reviews
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

FamilyIndoor spacesShared spaces

4.93 out of 5 average rating, 253 reviews

Family- and pet-friendly home rentals

Guest favorite
Home in South Thomaston

Large private area, close to Rockland

Indoor spacesKitchenBeach

4.94 out of 5 average rating, 113 reviews
Guest favorite
A living area features a blue sofa and a loveseat, both adorned with soft pillows. A wooden coffee table sits at the center, surrounded by natural light from large windows. A piece of artwork hangs on the wall, complementing the neutral tones of the space.
Home in Rockport

Fully Updated Airy Historic Home in West Rockport

Indoor spacesFamilyOutdoor spaces

4.84 out of 5 average rating, 153 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

KitchenFamilyDecor

4.96 out of 5 average rating, 159 reviews
Guest favorite
Cottage in Lincolnville

Call of the Loon - Water Edge Lake House

KitchenFamilyHiking

4.83 out of 5 average rating, 115 reviews
Guest favorite
A winter landscape features a wide expanse of untouched snow leading to a serene bay. Snow-covered homes dot the shoreline, and trees line the background against a clear blue sky, providing a peaceful view of the water.
Home in Owls Head

Island View

KitchenFamilyCleanliness

4.92 out of 5 average rating, 241 reviews
Guest favorite
A modern living area is highlighted by a sleek fireplace, framed by large windows allowing natural light to fill the space. A flat-screen television is mounted above the hearth. A potted plant and decorative artwork enhance the room's aesthetic, creating a cozy atmosphere.
Home in Thomaston

Monarch Landing · Riverfront House · Walk to Town

KitchenIndoor spacesTV

4.93 out of 5 average rating, 131 reviews
Top guest favorite
The image captures a serene view of the water at sunset, with the sun reflecting on the surface. Framed by lush green foliage, a small rustic bench is positioned on the shore, inviting quiet moments of contemplation.
Cottage in Belfast

Quiet cottage on the bay

Indoor spacesKitchenBiking

4.98 out of 5 average rating, 212 reviews
Top guest favorite
A spacious two-story colonial home features a welcoming covered porch with seating. Large windows allow natural light, while the well-maintained yard offers an inviting green landscape. Sunlight casts soft shadows on the exterior, enhancing its classic design amidst surrounding trees.
Home in Rockport

Walk Anywhere, Immaculate , Fishing, Pet Friendly

FamilyKitchenCondition

4.91 out of 5 average rating, 148 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

Indoor spacesFamilyCheckout

4.99 out of 5 average rating, 245 reviews
Guest favorite
Cabin in Freeport

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

Indoor spacesFamilyDecor

4.95 out of 5 average rating, 116 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!

KitchenFamilyComfort

4.97 out of 5 average rating, 174 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

KitchenIndoor spacesLayout

5.0 out of 5 average rating, 113 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

FamilyIndoor spacesView

4.95 out of 5 average rating, 700 reviews
Guest favorite
Home in Bangor

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

KitchenFamilySkiing

4.97 out of 5 average rating, 369 reviews
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

FamilyKitchenCleanliness

4.93 out of 5 average rating, 146 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

KitchenIndoor spacesCheckout

4.87 out of 5 average rating, 611 reviews

When is the best time to visit Rockland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$39,540 GYDG$37,657 GYDG$44,979 GYDG$44,142 GYDG$50,209 GYDG$61,715 GYDG$62,134 GYDG$62,134 GYDG$53,975 GYDG$49,163 GYDG$37,238 GYDG$41,004 GYD
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

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