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

Pet Friendly Audubon Bring Your Fishing Gear!
Enjoy the view from this wonderful 1940's waterfront cottage on the Sasanoa River in Woolwich. From here access Reid or Popham Beach State Parks with ease. Visit Maine Maritime museum in Bath, the "City of Ships." Head to Portland for a night out. Just relax and watch the seals, osprey and eagles. Rent a boat to enjoy all this extremely special waterway has to offer. Around the corner is the Kennebec River and Merrymeeting Bay, to the south you'll discover Phippsburg and historical Fort Popham.

Tiny A-Frame Romantic Getaway
Camp Lupine is a brand new Luxury 400 sq ft Tiny A-Frame tucked away on a private wooded lot with a small stream just a quarter mile off Coastal Route 1. With Historic Wiscasset, Booth Bay, Bath, Freeport, and Portland all at your fingertips, it’s the perfect romantic getaway. Spend your days exploring coastal Maine and your nights soaking in the hot tub with a glass of Malbec. Stay for a while and explore the growing restaurant scene in Wiscasset and the entire Midcoast region. See you soon!

1820s Maine Cottage with Garden
Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

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.

The Stilt House
Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

Renovated home with amazing waterfront views
Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit
Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

Private Guest Apartment with separate entrance.
Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking. sitting room with a dining table that looks out onto the deck, queen bedroom, private bathroom with jetted tub and separate shower, fully equipped kitchenette; NEW FURNACE-quiet and efficient.

Bath Historic District Apartment
Located in the Bath historic district, this one bedroom apartment is located just a few blocks from downtown. The apartment has a queen bed in the bedroom and also a queen sleeper sofa in the living room. The home was built in the late 1700's, but with the recent upgrades, it now feels fresh with classic elements. Located in Midcoast Maine, this apartment is an quick drive to the beach, hiking trails and museums.

The Sparrow’s Nest Charming Country Cottage
The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

Fully Renovated "Saltbox" Home in Boothbay
Start creating memories in this private setting, minutes away from Boothbay Harbor, Ocean Point, Botanical Gardens, and all the splendor that the mid-coast has to offer. Enjoy the grounds including an wonderful deck and a fire pit on the second level overlooking the property. It is a fantastic home-base for exploring Midcoastal Maine while enjoying close proximity to dining and shopping in Boothbay Harbor.

Waterfront Sunrise Cove Cottage
Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Owners live on property with small dog.
Popular amenities for Westport Island family-friendly rentals
Family-friendly home rentals with a hot tub

Tiny house in the Birch Grove with private HOT TUB

Cute Midcoast Cottage w Hot Tub

Treehouse with Water Views + Cedar Hot Tub

Cozy, Efficiency Apartment with Hot Tub

LUX Designer Private Waterfront Hot Tub - Secluded

Private Oceanfront Home 🔆2 min to Popham ✔️Hot Tub

Cozy log cabin on private pond, near Reid St Park!

SNOW SWEET, A Yurt for All Seasons
Family- and pet-friendly home rentals

The Chickadee Tiny House

Studio Apartment in Freeport

Maplenook Tiny Cabin - A Cozy Woodland Oasis

Oak Leaf

The Byre at Piper’s Pond

Yurt on Chebeague Island

Waterscape Cottage - private waterfront

Linekin Guest Suite
Family-friendly home rentals with a pool

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

A Riot of Color at an Artist's Retreat on the Portland Line

House in the woods

Portland Sweet Escape

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Starfish Condo Wells Beach

Steep Falls Escape, river & falls just steps away

Luxury Retreat In Back Cove | 10 Min to Downtown
When is the best time to visit Westport Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £222 | £294 | £297 | £357 | £220 | £189 | £215 | £232 | £199 | £204 | £274 | £283 |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Quick stats about holiday rentals that are family-friendly in Westport Island

Total holiday rentals
Explore 60 holiday rentals in Westport Island

Nightly prices starting at
Westport Island holiday rentals start at £105 per night before taxes and fees

Verified guest reviews
Over 1,290 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Westport Island holiday rentals include wifi access

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

4.8 Average rating
Westport Island stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with a patio Westport Island
- Rentals with a washing machine and dryer Westport Island
- Rentals with a firepit Westport Island
- House rentals Westport Island
- Rentals with outdoor seating Westport Island
- Waterfront rentals Westport Island
- Pet-friendly rentals Westport Island
- Rentals with a fireplace Westport Island
- Family-friendly rentals Lincoln County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Popham Beach, Phippsburg
- Willard Beach
- Scarborough Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- East End Beach
- Popham Beach State Park
- Coastal Maine Botanical Gardens
- Hills Beach
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Fortunes Rocks Beach
- Palace Playland
- Funtown Splashtown USA
- The Camden Snow Bowl
- Rockland Breakwater Light
- Portland Museum of Art
- Maine Maritime Museum
- Bradbury Mountain State Park
- Farnsworth Art Museum
- Bug Light Park
- Cellardoor Winery
- Aquaboggan Water Park





