
Family-friendly vacation rentals in Bailey Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Bailey Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.
FamilyKitchenComfort
4.86 out of 5 average rating, 242 reviews
Waterfront Coastal Apartment | 5 Min to LLBean
Private waterfront guest apartment with king bed, pull-out sofa, kitchenette, walk-in shower, private entrances, and porch overlooking Harraseeket Cove for a relaxing coastal Maine getaway. Set on 8 private wooded acres with waterfront access to South Freeport Harbor, perfect for kayaking, wildlife, and enjoying nature. Peaceful and tucked away in the woods, yet only 5 minutes from LLBean, Freeport’s shops, restaurants, breweries, and bars. Wolfe’s Neck Woods State Park is less than a mile away.
FamilyIndoor spacesAmenities
4.97 out of 5 average rating, 287 reviews
Luxury Year-round Treehouse with private hot tub
The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.
KitchenIndoor spacesValue
4.91 out of 5 average rating, 604 reviews
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.
KitchenFamilyCleanliness
4.99 out of 5 average rating, 144 reviews
Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax with ocean views, warm up in the sauna or take a refreshing dip. Our cottage is part of Gurnet Village, an over 100-year-old working lobstering & oyster farming property on historic Route 24, between Brunswick & Harpswell. Expect boats, workers, road traffic, gear, and the occasional sounds & smells of a real Maine working waterfront. All rooms have ocean views, with access to the tidal beach & floating dock (May-Dec).
FamilyKitchenCheck-in
5.0 out of 5 average rating, 226 reviews
The Copper Fox Treehouse
Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse
FamilyIndoor spacesDecor
4.99 out of 5 average rating, 198 reviews
Classic Maine Cottage - dock, sauna & kayaks
The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.
Indoor spacesFamilyGetting around
4.9 out of 5 average rating, 182 reviews
Shore House, Leona Unit - Ocean Front Property
This is the ground level of a multi-unit house. It is wheelchair friendly, with cathedral ceilings, a modern kitchen, and wide plank pine floors. The expansive deck will only enhance you experience overlooking a working wharf on Garrison Cove and Casco Bay. Dogs allowed upon approval. Must not be big barkers and owners are responsible for any waste. We want to be courteous with all renters and their pets. Weekly rentals preferred in July and August months (Saturday - Saturday)
FamilyIndoor spacesComfort
4.95 out of 5 average rating, 112 reviews
The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.
FamilyKitchenQuiet
5.0 out of 5 average rating, 155 reviews
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.
KitchenIndoor spacesHeating
4.98 out of 5 average rating, 244 reviews
Drakes Island Beach Front Breathtaking Property !
Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !
FamilyIndoor spacesLayout
4.88 out of 5 average rating, 144 reviews
Rising Tide Times - quintessential Maine cottage
Classic Maine cottage on the end of a point, surrounded by water on 3 sides provides stunning views. The perfect backdrop for the quintessential cottage vacation. Features spacious decks, direct tidal access for kayaking, and outdoor firepit. 15 min to downtown Brunswick/45 min to Portland. We even have Kayaks onsite for guests to paddle around Cards Cove. Perfect for couples and families!
KitchenFamilyWalkability
4.88 out of 5 average rating, 136 reviewsPopular amenities for Bailey Island family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Treehouse w/Water Views+Cedar Hot Tub
Indoor spacesKitchenTV
4.98 out of 5 average rating, 468 reviews
Romantic hideaway cabin w/ access to spa - 26
KitchenFamilyAmenities
4.97 out of 5 average rating, 124 reviews
A comforting sweet off grid cabin near the beach!
KitchenIndoor spacesLocation
4.98 out of 5 average rating, 310 reviews
LUX Designer Private Waterfront Hot Tub - Secluded
FamilyKitchenOutdoor spaces
4.98 out of 5 average rating, 200 reviews
Oceanfront Escape • Walk to Beach • Sleeps 14
KitchenIndoor spacesLocation
4.98 out of 5 average rating, 175 reviews
LuxuryTreehouse w/ Hot Tub Near Sunday River
KitchenIndoor spacesCleanliness
4.98 out of 5 average rating, 330 reviews
Solar Powered Bus in Forest | Hot Tub + Wellness
KitchenFamilySleep quality
4.91 out of 5 average rating, 148 reviews
HotTub+Firepit/5 min to DockSquare, Dining, Beach
Indoor spacesFamilyParking
4.96 out of 5 average rating, 229 reviewsFamily- and pet-friendly home rentals

Lakeside 3 BR Cabin in Boothbay Harbor
FamilyIndoor spacesAccess
4.98 out of 5 average rating, 290 reviews
Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit
KitchenIndoor spacesLocation
4.99 out of 5 average rating, 235 reviews
Simple Boothbay Log Cabin on Water
KitchenFamilyCheck-in
4.94 out of 5 average rating, 505 reviews
Charming Historic Freeport House
KitchenFamilyView
4.89 out of 5 average rating, 114 reviews
Charming Cottage With Spectacular Water View
FamilyKitchenHiking
4.97 out of 5 average rating, 389 reviews
Naughty Dog Private Island Log Cabin
FamilyKitchenNearby
4.98 out of 5 average rating, 276 reviews
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
KitchenFamilyLong stay
4.96 out of 5 average rating, 179 reviews
On the water Boathouse!
FamilyIndoor spacesDecor
4.9 out of 5 average rating, 178 reviewsFamily-friendly home rentals with a pool

Charming Saltwater Farm apartment
FamilyIndoor spacesQuiet
4.99 out of 5 average rating, 249 reviews
Luxury Retreat In Back Cove | 10 Min to Downtown
KitchenIndoor spacesSleep quality
5.0 out of 5 average rating, 116 reviews
Loft Apartment on Tree-Lined Street in Falmouth
Indoor spacesFamilyDecor
4.95 out of 5 average rating, 702 reviews
Starfish Condo Wells Beach
FamilyIndoor spacesGetting around
4.9 out of 5 average rating, 120 reviews
OOB Oasis: 6BR Home w/ Private Pool Near Beach
KitchenIndoor spacesAmenities
4.96 out of 5 average rating, 159 reviews
Historic Schoolhouse c1866 + Pool + Lake + Hot tub
KitchenFamilyWalkability
5.0 out of 5 average rating, 144 reviews
Resort-like 2 bed/1 bath - seasonal pool/hot tub
FamilyKitchenSleep quality
4.93 out of 5 average rating, 147 reviews
Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
KitchenFamilyNearby
4.98 out of 5 average rating, 525 reviewsDestinations to explore
- New York City Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Mont-Tremblant Vacation rentals
- Salem Vacation rentals
- Providence Vacation rentals
- Newport Vacation rentals
- York County Vacation rentals
- Rentals with beach access Bailey Island
- Pet-friendly rentals Bailey Island
- Waterfront rentals Bailey Island
- Cottage rentals Bailey Island
- House rentals Bailey Island
- Family-friendly rentals Harpswell
- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- Cape Neddick Beach
- Scarborough Beach
- Footbridge Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Hills Beach
- Gooch's Beach
- Fortunes Rocks Beach
- East End Beach
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Funtown Splashtown USA
- Palace Playland
- Portland Museum of Art
- Maine Maritime Museum





