
Family-friendly vacation rentals in Chebeague Island
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Chebeague Island

Total vacation rentals
Explore 160 vacation rentals in Chebeague Island

Nightly prices starting at
Chebeague Island vacation rentals start at G$27,189 GYD per night before taxes and fees

Verified guest reviews
Over 3,280 verified reviews to help you choose

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
160 of Chebeague Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chebeague Island rentals

4.8 Average rating
Chebeague Island stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Chebeague Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Loft Apartment on Tree-Lined Street in Falmouth
Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.
KitchenFamilyAir conditioning

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.
FamilyIndoor spacesHiking

Large Historic 7 Bedroom home with Pool & Hot Tub
Very Unique, large historial home in beautiful Falmouth, Maine. Originally built in 1725, this nearly Three-Hundred-Year old Federal-style farmhouse still retains some original features. In the early 1900's, this home served as a bootleg hard cider mill, and more recently, an oriental rug business. Great place for families with kids to stay while enjoying coastal Maine and Portland. Less than a mile from Portland and 4 miles from the historic Old Port district. (Hot tub open year-round)!
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Yurt on Chebeague Island
Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.
KitchenIndoor spacesPets

4br2ba House+parking@PeacefulOasis on Munjoy Hill
This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.
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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
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The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!
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Peaks Island Master Bedroom Suite
Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.
FamilyIndoor spacesCheck-in

Harborview - Curated East End Escape w/ Parking
Harborview is a newly renovated, top-floor apartment perched on the edge of Munjoy Hill in Portland's East End. This home is a short stroll to the Eastern Promenade and the East End Beach, the Casco Bay Islands Ferry Terminal, and the historic Old Port. The apartment features a spacious open kitchen, dining, and living room floor plan adjoined by a large private deck. It's the perfect spot to gather, relax, and dine while enjoying the breathtaking views of Casco Bay!
FamilyIndoor spacesTV

Beach, Parks, Trails, Tranquil, Quiet, Peaceful
The Kettle Cove neighborhood is beautiful, relaxing, safe, quiet. Kettle Cove and Crescent beaches are a stroll away. We live in a 200 year-old farmhouse, and we love to host guests at our guesthouse, which is separate and private. The wide lawn, fire-pit, and BBQ are open for our guests. We are quiet, friendly, inviting, and respectful of our guests' space and privacy. ***WEEKEND STAY WE REQUIRED FRIDAY/SATURDAY/SUNDAY NIGHTS***
Indoor spacesFamilyTV

Stone Isle. 8 acres next 2 little john preserve.
Nestled on 8 acres overlooking Casco Bay, the Stone Isle guest house has 2 bedrooms, 1 bathroom and amazing water views. The guest house includes an open plan layout with a full kitchen, living room (with sleeper sofa) and a dining table for 4. Last but not least the guest house is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!
FamilyKitchenLong stay

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.
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Popular amenities for Chebeague Island family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Treehouse w/Water Views+Cedar Hot Tub
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Oceanfront Escape • Walk to Beach • Sleeps 14
Indoor spacesFamilyComfort

Easy Old Port Access & Casco Bay View Craftsman
Indoor spacesKitchenBeach

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub
Indoor spacesKitchenOutdoor spaces

Romantic hideaway cabin w/ access to spa - 26
KitchenFamilyDecor

Secluded Cabin: Mountain View, Hot Tub + Fireplace
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HotTub/5min to K-port, Pet friendly, @anchorunwind
FamilyKitchenAccess

The Modern Lakehouse
FamilyKitchenAmenities
Family- and pet-friendly home rentals

Waterfront 5 BR Home | On Casco Bay in Freeport
KitchenIndoor spacesAmenities

Studio Apartment in Freeport
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Newly renovated 3BR house w/ stunning ocean views
KitchenFamilyBeach

Portland + Cape Elizabeth + Beaches + luxurious!
Indoor spacesFamilyHeating

Top Deck - Portland Property with Views!
Indoor spacesFamilyPets

Year-Round: Peaceful and Quiet Island Getaway
FamilyIndoor spacesNearby

Lakeside 3 BR Cabin in Boothbay Harbor
Indoor spacesKitchenLocation

Classic Maine, Modern Comfort
KitchenFamilyCondition
Family-friendly home rentals with a pool

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Indoor spacesKitchenLocation

Luxury Retreat In Back Cove | 10 Min to Downtown
KitchenFamilyCleanliness

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

Charming Saltwater Farm apartment
Indoor spacesFamilyDecor

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach
FamilyIndoor spacesHospitality

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
Indoor spacesFamilyParks

Beach House w/ Heated Pool · Fire Pit · Kennebunk
FamilyIndoor spacesAccess

Cozy Cottage with Ocean Views, Wells Maine
FamilyIndoor spacesCheck-in
When is the best time to visit Chebeague Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$77,175 GYD | G$60,025 GYD | G$56,260 GYD | G$52,078 GYD | G$56,260 GYD | G$68,391 GYD | G$75,920 GYD | G$74,038 GYD | G$67,764 GYD | G$57,515 GYD | G$57,515 GYD | G$69,437 GYD |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°C | -1°C |
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- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Short Sands Beach
- Willard Beach
- York Harbor Beach
- Scarborough Beach
- Cape Neddick Beach
- Footbridge Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Gooch's Beach
- Hills Beach
- Fortunes Rocks Beach
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Funtown Splashtown USA
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