
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.
4.87 out of 5 average rating, 240 reviews
Little Harbor Cottage
Waterfront cottage on perfect for the whole family. Newly renovated in 2024, this 5 bedroom, 2.5 bath house features ocean views from each bedroom and easy access to rocky beaches. Well appointed kitchen, high speed WiFi, and AC in each room make this the perfect place for your next Maine vacation. Centrally located on Bailey Island in Casco Bay, an easy home base for your coastal adventures. If the specific dates you’re looking for aren’t available, reach out to see if we have any flexibility
5.0 out of 5 average rating, 13 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).
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
4.99 out of 5 average rating, 197 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.
4.9 out of 5 average rating, 181 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)
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.
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.
4.98 out of 5 average rating, 244 reviews
Well located, spacious home on Bailey Island!
The Fairwinds Home ~ Enjoy this beautifully landscaped, Spacious home conveniently located on Bailey Island, ME. Charming , comfortable home, 3 bedroom, 2.5 bath, Fresh Maine seafood ! Large deck attached to the living area, perfect for that morning coffee and those afternoon cocktails ! Fully stocked kitchen, as well as a propane grill~ 7 night minimum from mid June-mid Sept. Inquire for long term winter rentals.
4.81 out of 5 average rating, 16 reviews
Comfortable studio apartment in quiet location
Peaceful, rural second story studio apartment. Near Middle Bay in beautiful Harpswell, Maine. Enjoy our farmer's porch or walks to the shore deck to look out over the water and enjoy a sunset or go the shore for a swim in summer. Short distance to Brunswick and Bowdoin College, local restaurants. The host also teaches porcelain doll making. You could learn to make porcelain dolls while enjoying the Maine coast.
4.93 out of 5 average rating, 236 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!
4.88 out of 5 average rating, 135 reviews
Cottage on Todd Bay
Autumn is nearly here, and the maples are turning red along the road down from Bath. Days are warm but crisp, and nights are chilly; our guests on Todd Bay have begun building evening fires in the wood stove. We still have a few more available nights in October for fall getaways -- and we're starting to look ahead to May and the 2027 season!
4.98 out of 5 average rating, 155 reviewsPopular amenities for Bailey Island family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Treehouse w/Water Views+Cedar Hot Tub
4.98 out of 5 average rating, 468 reviews
Luxury Year-round Hobbit House w/ private hot tub
4.92 out of 5 average rating, 132 reviews
Romantic hideaway cabin w/ access to spa - 26
4.98 out of 5 average rating, 122 reviews
Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub
4.96 out of 5 average rating, 118 reviews
LUX Designer Private Waterfront Hot Tub - Secluded
4.97 out of 5 average rating, 199 reviews
Oceanfront Escape • Walk to Beach • Sleeps 14
4.98 out of 5 average rating, 175 reviews
Solar Powered Bus in Forest | Hot Tub + Wellness
4.9 out of 5 average rating, 146 reviews
A comforting sweet off grid cabin near the beach!
4.98 out of 5 average rating, 309 reviewsFamily- and pet-friendly home rentals

Newly renovated 3BR house w/ stunning ocean views
4.96 out of 5 average rating, 128 reviews
Lakeside 3 BR Cabin in Boothbay Harbor
4.98 out of 5 average rating, 287 reviews
Charming Historic Freeport House
4.89 out of 5 average rating, 114 reviews
Naughty Dog Private Island Log Cabin
4.98 out of 5 average rating, 275 reviews
Studio Apartment in Freeport
4.97 out of 5 average rating, 146 reviews
Classic Maine, Modern Comfort
4.94 out of 5 average rating, 299 reviews
Charming Cottage With Spectacular Water View
4.97 out of 5 average rating, 387 reviews
On the water Boathouse!
4.9 out of 5 average rating, 177 reviewsFamily-friendly home rentals with a pool

Loft Apartment on Tree-Lined Street in Falmouth
4.95 out of 5 average rating, 702 reviews
Luxury Retreat In Back Cove | 10 Min to Downtown
5.0 out of 5 average rating, 116 reviews
Charming Saltwater Farm apartment
4.99 out of 5 average rating, 249 reviews
OOB Oasis: 6BR Home w/ Private Pool Near Beach
4.96 out of 5 average rating, 158 reviews
Resort-like 2 bed/1 bath - seasonal pool/hot tub
4.93 out of 5 average rating, 147 reviews
Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
4.98 out of 5 average rating, 522 reviews
Ogunquit Village 5 BDR, Heated Pool, Walk to Beach
5.0 out of 5 average rating, 105 reviews
Portland & Beach & Lighthouses! Romantic! Lovely
4.87 out of 5 average rating, 614 reviewsDestinations to explore
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