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

Nana-tucket Inn

Your Cozy 1 BR Apt & Relaxing Retreat

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Stunning Waterfront Condo with Boston Skyline View

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

Luxury Scandinavian-Inspired house in Kendall

Lakeside apartment, patio, hot tub, outside shower

Beach Home with Jacuzzi and Direct Ocean Access
Family- and pet-friendly home rentals

Spacious 3 Bedroom Apartment with King Bed

2bed/2bath Apt at Waltham Landing. Corner Unit

Beechwood Cottage

Pretzel Factory Loft w/Peloton

Tiny farm house on horse farm

Lionsgate at Cohasset

Flower Farm Getaway 2BR, 20 Min To Boston

Ocean views, Large Deck, Grill, Kid/Dog Friendly
Family-friendly home rentals with a pool

Villa with private Pool in Boston's Elite Enclave

Large Pool, Nature Trails, Redd's Pond, 4-Bed

Cute mill house: 3BR•Wood stove *Brkfst included*

the house of id; vintage shop, accessible space

Ideal for long stays | Spacious suite in Boston

Modern Space With Pool Close To Singing Beach

Stylish and Cozy at Revere Beach

Country Cottage in the City
Quick stats about holiday rentals that are family-friendly in Winthrop
Total rentals
70 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
3.5K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
Destinations to explore
- Plainview Holiday rentals
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- Rentals with a fireplace Winthrop
- Rentals with outdoor seating Winthrop
- House rentals Winthrop
- Waterfront rentals Winthrop
- Rentals with a washing machine and dryer Winthrop
- Beachfront rentals Winthrop
- Rentals with a patio Winthrop
- Rentals with beach access Winthrop
- Flat rentals Winthrop
- Fitness-friendly rentals Winthrop
- Pet-friendly rentals Winthrop
- Family-friendly rentals Suffolk County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
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- House Rentals with a Pool United States
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- Apartments with a Hot Tub United States
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- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
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- Hampton Beach
- Fenway Park
- Boston Common
- Revere Beach
- TD Garden
- Harvard University
- Brown University
- Lynn Beach
- Duxbury Beach
- Onset Beach
- New England Aquarium
- Canobie Lake Park
- Crane Beach
- Good Harbor Beach
- Freedom Trail
- Faneuil Hall Marketplace
- Rye North Beach
- MIT Museum
- Jenness State Beach
- North Hampton Beach
- Museum of Fine Arts, Boston
- Quincy Market
- Prudential Center
- White Horse Beach