
Family-friendly vacation rentals in Winslow
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winslow
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winslow family-friendly rentals
Family-friendly home rentals with a hot tub

Raven's Crossing - Kate's Cottage

Cute Midcoast Cottage w Hot Tub

Hilltop Retreat with A/C, Hot Tub & Sauna

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Birch Hill Cabin w/Hot Tub

LUX Designer Private Waterfront

Secluded Retreat w/ Luxe Hot Tub & Forest Views

SkyView Treehouse | Lakefront • Private Hot Tub
Family- and pet-friendly home rentals

Modern Home on Working Farm

Cozy Cabin on the Carrabassett River

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Simple Boothbay Log Cabin on Water

Peaceful & private waterfront cabin

Hammock Haven Island Dome

Moore's place

Wild Acres Yurt on 36 acres.
Family-friendly home rentals with a pool

Large Home with Great View next to horse farm

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

New Listing! Pool, Hot tub & Lakes! Mins to Sebago

Luxe Liberty: Getaway with Heated Indoor Pool!

Coastal Retreat with Pool and Cheerful Vibes

Ocean View Retreat with Pool / Hot Tub

Retreat In The Orchards

Cabin on the hill!
Quick stats about vacation rentals that are family-friendly in Winslow
Total rentals
20 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
990 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Pemaquid Beach
- Pemaquid Point Lighthouse
- Samoset Resort
- Belgrade Lakes Golf Club
- Coastal Maine Botanical Gardens
- Fox Ridge Golf Club
- Dragonfly Farm & Winery
- Brunswick Golf Club
- Hermon Mountain Ski Area
- Spragues Beach
- Sugarloaf Golf Club
- Three Island Beach
- Eaton Mountain Ski Resort
- Sandy Point Beach
- Maine Maritime Museum
- Wadsworth Cove Beach
- Black Mountain of Maine
- The Camden Snow Bowl
- Islesboro Town Beach
- Narrow Place Beach
- Bear Island Beach
- Lost Valley Ski Area
- Titcomb Mountain
- Farnsworth Art Museum
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