
Family-friendly vacation 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.

Licensed Boston airport studio 5 stars, subway
We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

Oceanfront Pool. Close to Boston. Free Parking.
Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Truly Ocean-Front! Spacious Family Home w/ Pets
Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Cozy place to relax! 14min to Salem - 25 to Boston
Due to your allergies, we are unable to Host any animals Private entrance-Basement - H 6' - entrance 5' 6" Relax in this calm, stylish space after a day of exploration! Perfect for travelers /work trips. Stay with US! I live on-site to ensure a safe and welcoming stay You will get to enjoy: - Salem MA - - Boston MA - Beaches - Beverly MA - Gloucester MA - Marblehead MA - Trails Our mattress is fairly firm, which can provide a very good night sleep! - Illegal activities will be reported -

Beachmont Guest Suite
Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

J&K's BnB .... Private studio Airbnb with parking
Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

The Price is Right Boston Airport Beach Park Free
Private spacious 1 bedroom 1 bath attic apartment with new rug/paint/ac. Nice little skyline view of Boston in a beautiful safe quiet residential neighborhood. Great place to rest your head or use as a base to Boston The Encore Casino Salem & beyond! Bedroom comfy mattress/sheets 55” Smart TV blackout shade ceiling fan nightstands lamps 2 chairs Living Areas sofa bed 55” Smart TV sitting chair table 2 chairs/lamps Kitchenette fridge microwave Keurig toaster oven dishes silverware glass

Renovated Cozy City Getaway
Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

Stylish and Cozy at Revere Beach
Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Cozy studio, near beaches and city skyline views
The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Corner Cottage - cozy studio just north of Boston
Whether you’re a tourist visiting Boston for the weekend, a traveling nurse in search of a medium-term stay, or a pilot/flight attendant needing overnight accommodations, this completely renovated and professionally cleaned AirBnB is perfect for you! Finding living accommodations is tough; finding a reliable and responsive host is even tougher. Not only is this unit well equipped with almost everything you may need, but I will do my best to ensure your stay is the most comfortable.

Prime location near Boston
Home in Everett, MA. Located just a 20 minute walk from Encore Boston Harbor Casino. This location is also just a 15 minute drive from downtown Boston. Room in the basement has a microwave, refrigerator, coffee maker, and hot water for making tea which is provided along with light snacks and coffee. There is a desk for laptop. Queen Tempurpedic Mattress topper as well as a pull out sofa. Private bathroom with spacious shower. See guide book for more info on the area!
Popular amenities for Winthrop family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy & convenient place with sunset & garden view

Your Cozy 1 BR Apt & Relaxing Retreat

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

Headers’ Haven

4Bed AP/5 min walk to T-Logan- downtown to Boston

Lakeside apartment, patio, hot tub, outside shower

Newly renovated, close to Foxboro and Boston

Cozy Waterfront Home with Jacuzzi and Fireplace
Family- and pet-friendly home rentals

Family Home + Near Downtown + Cool Backyard!

Spacious 3 Bedroom Apartment with King Bed

Lionsgate at Cohasset

Coastal Home Walk to Beach

Ocean view studio with hot tub & access to Boston

Peaceful 2BR near US Route 1 and Boston.

Quincy Beach Home Next to Boston & T, Free Parking

Heart of Old Town Duplex (LEFT), Steps from Harbor
Family-friendly home rentals with a pool

Peaceful suite in Boston with city views

NEW! Walk To Beach! Sunshine House

Boston Modern Apt: Luxe Stay w/ Gym, Parking

Spacious vacation unit in premium suburban town

Modern Space With Pool Close To Singing Beach

Country Cottage in the City

Monthly Skyline Apartment

Cozy Private Studio Unit w/ Laundry and Parking!
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $217 CAD | $233 CAD | $259 CAD | $301 CAD | $334 CAD | $321 CAD | $331 CAD | $334 CAD | $320 CAD | $349 CAD | $314 CAD | $262 CAD |
| Avg. temp | -1 °C | 0 °C | 4 °C | 9 °C | 15 °C | 20 °C | 23 °C | 23 °C | 19 °C | 13 °C | 7 °C | 2 °C |
Quick stats about vacation rentals that are family-friendly in Winthrop

Total vacation rentals
Explore 70 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at $126 CAD per night before taxes and fees

Verified guest reviews
Over 4,090 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Winthrop vacation rentals include wifi access

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

4.8 Average rating
Winthrop stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Winthrop’s top spots, include Orient Heights Station, Beachmont Station, and Suffolk Downs Station
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- Family-friendly rentals United States
- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- New England Aquarium
- Duxbury Beach
- Good Harbor Beach
- Freedom Trail
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Onset Beach
- Jenness State Beach
- Quincy Market
- Rye North Beach
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- Prudential Center
- White Horse Beach
- Roger Williams Park Zoo




