Family-friendly vacation rentals in Winthrop

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

4.97 out of 5 average rating, 348 reviews

Private Suite• Pool • Sleeps 4 • Boston • Airport

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

4.92 out of 5 average rating, 1406 reviews

A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.

Guest suite in Winthrop

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.

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

4.96 out of 5 average rating, 286 reviews

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.

4.92 out of 5 average rating, 261 reviews

A light-filled corner of the living area features a sectional sofa in soft gray, complemented by a small coffee table. Three windows dressed in blinds allow natural light to filter in, enhancing the cozy and inviting atmosphere.

Apartment in Revere

Quiet Neighborhood Luxury Stay

The apartment is brand new with a modern feel to it. Available with all the amenities needed for your convenience. Very quiet, clean, and safe neighborhood. Close to everything you desire, 1 minute to the beach, 8 minutes away from the train station, 1 minute away from the T-Bus stop, 9 minutes to Logan Airport, 12 minutes to Downtown Boston, 15 minutes away from Encore Casino, food and coffee shops, such as Starbucks and Dunkin' Donuts in the area. Perfect for a family stay or a business trip.

4.99 out of 5 average rating, 242 reviews

Condo in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

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.

4.95 out of 5 average rating, 182 reviews

A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.

Apartment in Nahant

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

4.98 out of 5 average rating, 123 reviews

The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.

Condo in Winthrop

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. An historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two condos and renovated).

4.98 out of 5 average rating, 507 reviews

The exterior of the private studio is shown, featuring a light blue siding with a gray shingled roof. A welcoming front door is flanked by a light fixture and a decorative sign. Flowering plants are arranged in front, enhancing the outdoor space.

Cottage in Winthrop

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.

4.78 out of 5 average rating, 247 reviews

A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.

Home in East Boston

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.

A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.

4.84 out of 5 average rating, 133 reviews

Sunny 3 bedroom on beach

Welcome to our beautiful 3 bedroom apartment on the beach! Enjoy stunning ocean views and easy access to Winthrop Beach, only 2 minutes away. Accommodations for up to 8 guests, making it perfect for families or groups of friends. Located on the 2nd floor of a historic building, this home offers a bright and airy living area with plenty of natural light and a cozy seating area, perfect for relaxing after a long day at the beach. The dining area, kitchen and private deck with ocean views.

5.0 out of 5 average rating, 178 reviews

A pathway lined with brick leads to a cozy cottage with maroon siding, framed by lush greenery. A seating area with chairs is positioned on a well-maintained lawn, inviting relaxation on a sunny day. Tall trees provide shade, enhancing the tranquil ambiance.

Barn in Nahant

Entire Beach-Town Cottage, Barn Charm, near Boston

A nicely renovated, old barn, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. The ideal location for a short getaway with family or friends. Only 25' from downtown Boston and other North Shore towns with restaurants and bars. For pricing transparency: AirBnb now includes cleaning and all service fees and taxes in the total. Hosts nightly fees are 20-25% lower (bc cleaning is included)! 15% of fees go to Airbnb!

The exterior of a stylish two-family home is depicted, featuring a welcoming porch with white railings and a neatly landscaped front yard. Flowering plants, small trees, and a paved pathway lead to the entrance. The upper floor includes strategically placed windows, allowing natural light to filter in.

4.96 out of 5 average rating, 118 reviews

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

Popular amenities for Winthrop family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 221 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

4.93 out of 5 average rating, 242 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

4.93 out of 5 average rating, 116 reviews

A modern open-concept living space features a well-equipped kitchen with stainless steel appliances and a large island with seating for five. A cozy living area displays a sectional couch facing a wall-mounted TV, with large windows allowing natural light to brighten the room.

Home in South Boston

Heart of Southie - Hot Tub + Walk to Top Bars

4.78 out of 5 average rating, 359 reviews

The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.

Apartment in Roxbury

Modern, Spacious 1BR for 4 - Easy Marathon Access!

Guest suite in Marblehead

Headers’ Haven

5.0 out of 5 average rating, 90 reviews

4.76 out of 5 average rating, 38 reviews

Home in Canton

Luxury lake retreat- pool, fire pit, trails

5.0 out of 5 average rating, 4 reviews

Home in Norwood

4br Near Stadium | Hot Tub + Firepit

4.89 out of 5 average rating, 35 reviews

Apartment in Chelsea

Modern 2BR Retreat Minutes from Boston

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 262 reviews

The living area features two gray sofas positioned around a round wooden coffee table on a vibrant blue area rug. A cozy fireplace is situated against a striking red wall, complemented by a bookshelf filled with books. Natural light enters through a nearby window.

Condo in East Boston

Family Home + Near Downtown + Cool Backyard!

4.83 out of 5 average rating, 101 reviews

A historic clock stands prominently by the waterfront, marking the time against a beautiful sunset. The horizon features vibrant oranges and yellows as the sun descends. An open pavilion structure is visible in the background along the calm beach, reflecting a peaceful atmosphere.

Apartment in Revere

Cozy Apt, minutes from Boston!

4.96 out of 5 average rating, 164 reviews

A spacious bedroom features a large bed dressed in white sheets and a light blue blanket. Nightstands with lamps are positioned on either side of the bed. A subtle area rug adds warmth, while a painting hangs on the wall, complementing the calm color scheme.

Apartment in Revere

Spacious 3 Bedroom Apartment with King Bed

4.91 out of 5 average rating, 128 reviews

An updated kitchen features granite countertops, white cabinetry, and stainless steel appliances. A large island with seating for four is complemented by a dining nook with natural light. Potted plants add a touch of greenery, enhancing the inviting kitchen space.

Apartment in Hull

Coastal Cottage Home

4.98 out of 5 average rating, 106 reviews

A welcoming living area features a marble-topped coffee table surrounded by comfortable seating. A decorative fireplace with a herringbone pattern adds warmth. Natural light filters through the space, highlighting a large mirror and a simple bouquet on the table. The kitchen is visible in the background.

Apartment in Charlestown

Designer 3-BR Apt in Historic Charlestown, Boston

4.95 out of 5 average rating, 143 reviews

A spacious living room features a large gray sectional couch complemented by a sleek wooden coffee table. An accent chair provides additional seating. Striped rug adds a touch of pattern to the hardwood floors. A gallery wall displays various posters, and a flat-screen TV is mounted nearby.

Home in Lynn

Private Cozy Third Floor Space

4.99 out of 5 average rating, 267 reviews

The living area features a mix of comfortable seating, including a floral-patterned sofa and a plaid armchair. A round coffee table sits atop a light blue area rug, and large windows allow natural light to fill the space, enhancing the cozy ambiance.

Condo in Marblehead

Harbor View Suite

4.83 out of 5 average rating, 427 reviews

A spacious bedroom is shown, featuring a black bed with a textured bedding set displaying ocean waves. A cozy armchair sits beside a radiator, and a small folding table is placed nearby. Natural light enters through a window with patterned curtains.

Home in Chelsea

10 minutes to Airport-Boston-Casino (2G)

Family-friendly home rentals with a pool

4.87 out of 5 average rating, 210 reviews

A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.

Guest suite in Revere

Amazing studio

4.99 out of 5 average rating, 169 reviews

Cottage in Marblehead

Steps from Harbor + Walk to Old Town + Restaurants

4.94 out of 5 average rating, 257 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

Guesthouse in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

Country Cottage in the City

4.95 out of 5 average rating, 218 reviews

4.97 out of 5 average rating, 451 reviews

A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.

Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

4.8 out of 5 average rating, 124 reviews

Apartment in Brighton

The Drew : Vibrant • Comfortable • W/D • City View

4.87 out of 5 average rating, 114 reviews

A spacious room features a full-sized bed with light bedding. A euro lounger is positioned in front, decorated with a soft throw. Mirrors on the opposite wall reflect the room's layout, and a window offers natural light, contributing to the overall bright atmosphere.

Guest suite in Rockland

Cozy Private Suite halfway between Cape & Boston