Pet-friendly vacation rentals in Winthrop

4.92 out of 5 average rating, 103 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 Home Walk to Beach

Come have fun at The Coastal Cottage. This newly updated home is only a minute walk to your private beach and is the main floor of the home. Enter into the comfortable living room, with coastal boho vibes and a large sectional couch. One bedroom has a Queen bed, the other has a full and twin bunk bed and a crib. Enjoy the large kitchen with large dining table, breakfast nook and massive granite island. Enjoy grilling, the outdoor shower, or hang in the courtyard to relax with family and friends.

4.92 out of 5 average rating, 1,348 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.

4.92 out of 5 average rating, 353 reviews

A newly remodeled kitchen features modern stainless steel appliances and ample counter space. White cabinetry contrasts with warm wood paneling and flooring. A dining area with a wooden table and chairs is visible, along with soft lighting from pendant fixtures above.

Cabin in Cohasset

Lionsgate at Cohasset

Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

4.92 out of 5 average rating, 110 reviews

The great room is highlighted by 25-foot ceilings and panoramic windows offering views of the ocean. A large sectional sofa surrounds a coffee table, while a flat-screen TV is mounted above the fireplace. Sliding glass doors lead to an outdoor space, enhancing the airy feel.

Home in Swampscott

Ocean Views at Casa de Mar near Salem & Boston

Relax and unwind at Casa de Mar - our 3 bed, 3 full bath seaside home on the North Shore. Close to Salem and Boston, overlooking Swampscott Bay to Nahant. The great room has 25' ceilings, a 70" flat screen TV, a desk, and 2 seating areas. Modern kitchen, new appliances. The master bedroom has a king-sized bed, sitting area, flat screen TV, private balcony, and en suite bath. The first floor bedroom has a queen bed and a private balcony. The third bedroom has a queen bed and en suite bath.

4.94 out of 5 average rating, 155 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.

4.99 out of 5 average rating, 208 reviews

Condo in Winthrop

Truly Ocean-Front!: Spacious Family Home + 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.

4.96 out of 5 average rating, 147 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 Beachmont

Spacious 3 Bedroom Apartment with King Bed

Family friendly, walk-out basement style apartment close to everything! Clean and safe neighborhood. A 10 minute walk to two beaches: Revere Beach - America's first public beach & Short Beach - a neighborhood favorite. 5 minute walk to Beachmont T station and bus lines - 15 minutes to Downtown Boston! 10 minute drive to Logan or 20 minute drive to the Casino. 25 minute drive to Salem. Walkable to an Italian Bakery, Dunkin Donuts and Starbucks as well as a number of restaurants and eateries.

4.89 out of 5 average rating, 127 reviews

The dining area features a wooden table surrounded by six blue chairs, complemented by a cozy couch visible in the background. A full kitchen is equipped with a refrigerator, stove, and ample counter space. Natural light brightens the space through large windows.

Apartment in East Boston

2bd Apt, 3 min walk to train, 7min to airport

Peaceful, private, comfortable and recently renovated 1st floor apartment. Located 3 minutes walk from Suffolk Downs train station and 1 PARKING SPACE. Furnished with all amenities including washer, dryer, wifi, 3 tvs, full kitchen. Conveniently close to downtown Boston. You will love this spacious apartment located in East Boston. 18 minutes by train to Government Center/Downtown Boston. 15 minutes to Faneuil Hall/ Quincy Market and 7 minutes to Revere Beach by public transportation.

4.77 out of 5 average rating, 218 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.

4.93 out of 5 average rating, 219 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!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!

4.9 out of 5 average rating, 116 reviews

A bright bedroom features a spacious bed with soft linens. Nightstands with lamps are positioned on either side. Large windows allow natural light to fill the room, which is adorned with neutral-toned walls and a simple wall art piece above the bed.

Apartment in Malden

Luxe Serene 1BR 15 min from Boston with Gym & More

You will love this beautifully designed 1 Bedroom 1 Bath luxury unit that is in a central location between many great cities! You will be staying in a gorgeous private community with a gym, dog park, kids playground, tennis court, and tons of outdoor space. Have peace of mind knowing you’re in a safe space. Our luxury suite has a Queen Medium Firm bed along with a Queen Air Mattress for any additional guests. Check out more of our amenity spaces below!

4.93 out of 5 average rating, 421 reviews

A spacious living area is furnished with a dark sofa, a decorative wall art piece, and a round coffee table. Bar stools are positioned near the kitchen, which is visible in the background. Natural light enters through windows covered by green curtains.

Apartment in Dorchester

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

Popular amenities for Winthrop pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 281 reviews

A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.

Home in Wakefield

Welcoming 7-room house <15 miles to Boston & Salem

4.85 out of 5 average rating, 320 reviews

The dining area features a wooden table with six chairs, complemented by a striped table runner. A stylish vase with dried stems is placed at the center. A cozy couch, adorned in rich upholstery, is located beside the table, with a cityscape wall art piece above a dark cabinet.

Home in Hyde Park

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

4.89 out of 5 average rating, 207 reviews

A modern living area features a spacious sectional sofa adorned with decorative pillows, positioned in front of a wall-mounted television. A light-colored table with intricate design sits on a soft area rug, while kitchen cabinets and a dining area are visible in the background.

Home in Malden

Beautiful renovated 3 bedroom apt near Boston.

Home in Brookline Village

A spacious living area features a mix of comfortable seating, including a large sofa and a cozy armchair. Natural light streams through multiple windows covered with woven shades. Shelves filled with books and decorative items line one wall, while a light-colored rug adds warmth to the concrete floor.

4.92 out of 5 average rating, 147 reviews

Pretzel Factory Loft w/Peloton

4.86 out of 5 average rating, 122 reviews

A spacious living and dining area features a dark grey sofa complemented by a textured area rug. A modern chandelier hangs above a wooden dining table surrounded by chairs. Natural light enters through sliding glass doors, leading to an outdoor space, while a wall clock and air conditioning unit are visible.

Home in Woburn

Cheerful 1-bedroom New England Ranch

4.98 out of 5 average rating, 267 reviews

A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.

Home in Dedham

Cozy, historic 3 bedroom home close to Boston!

4.86 out of 5 average rating, 244 reviews

A modern living area features a light-colored sectional sofa and two patterned chairs arranged around a small table. A wall-mounted television is positioned above a sleek fireplace, surrounded by built-in shelving displaying decorative items. Natural light filters through sheer curtains.

Home in East Boston

Tribeca chic | 2 BR w/private patio

4.9 out of 5 average rating, 129 reviews

A spacious living area is furnished with a love seat and a sofa, arranged around a decorative coffee table. A patterned rug lies on the tiled floor, while natural light streams in through a nearby window. A wall clock adds a touch of warmth to the space.

Home in Salem

An amazing one bed room level house (No Smoking)

Pet-friendly home rentals with a pool

5 out of 5 average rating, 12 reviews

A spacious living area is highlighted by a large, plush sectional sofa in a soft turquoise hue. Floor-to-ceiling windows offer clear views of the Boston skyline, allowing ample natural light to fill the space. A round coffee table sits in front of the sofa, enhancing the modern design.

Apartment in Boston

Sleek 2BR 2BA in Fenway, High-End Building

Home in Lakeside Marblehead

A cozy living area is highlighted by a light grey sofa adorned with soft pillows in neutral tones. A round, woven coffee table sits at the center, accompanied by decorative accents. Two lamps provide soft lighting, complemented by exposed wooden beams overhead.

4.91 out of 5 average rating, 34 reviews

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

5 out of 5 average rating, 15 reviews

Home in Bedford

Bauhaus Retreat in Nature Preserve

4.95 out of 5 average rating, 44 reviews

The exterior of a two-story house is displayed, featuring white siding and red shutters. A well-maintained front yard is visible, showcasing green grass and shrubs. A brick pathway leads to the front door, framed by two planters with greenery.

Home in Arlington

Beautiful Spacious 4BRM House!

4.97 out of 5 average rating, 62 reviews

An inviting bedroom features wood-paneled ceilings and soft lighting. A spacious bed is situated near a window with light filtering through. A vintage-style chair and a wooden bench add to the room's charm, complemented by a decorative area rug underfoot.

Home in Norwood

the house of id; vintage shop, accessible space

4.88 out of 5 average rating, 98 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

Apartment in Manchester-by-the-Sea

A spacious living area features a large, sectional sofa with neutral upholstery, oriented towards a wooden coffee table. Bright light filters through multiple windows, illuminating the room. A dining area with wooden chairs is visible in the background, along with built-in storage cabinets.

4.9 out of 5 average rating, 177 reviews

Modern Space With Pool Close To Singing Beach

A modern apartment building is illuminated at dusk, showcasing multiple stories with numerous windows. A well-lit parking area is visible in the foreground, filled with vehicles. The surrounding landscape includes greenery and a distant hill, enhancing the suburban setting.

Apartment in Chelsea

4.86 out of 5 average rating, 7 reviews

Entire one bedroom apartment

Private, pet-friendly home rentals

4.96 out of 5 average rating, 72 reviews

The modern two-story home features a blue exterior with white trim and three windows on the ground level, complemented by decorative planters. A bold red front door is centrally positioned, enhancing the welcoming entrance.

Home in Charlestown

Spacious & Pet-Friendly Modern Home in Charlestown

4.93 out of 5 average rating, 60 reviews

A bright living area showcases a navy blue sofa, flanked by two armchairs featuring decorative pillows. A wooden coffee table sits center stage on a patterned rug. Wall art in warm tones adds a pop of color, complemented by two table lamps on either side.

Apartment in Revere

New England Charm - Minutes From Boston

4.89 out of 5 average rating, 100 reviews

A cozy living area features a light-colored rug beneath a dark coffee table, surrounded by a gray sofa. A flat-screen television is mounted above a classic fireplace, while soft lighting from pendant fixtures creates a warm ambiance in the space.

Guest suite in Melrose

Peaceful 2BR near US Route 1 and Boston.

5 out of 5 average rating, 15 reviews

A spacious living area is designed with large windows providing expansive views of the ocean. A comfortable white sofa faces a wooden coffee table, complemented by a cozy throw. Natural light fills the room, accentuating the warm wooden floors and tasteful decor.

Home in Nahant

Sea Forever - Oceanfront Home in Nahant!

4.98 out of 5 average rating, 89 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

5 out of 5 average rating, 17 reviews

A modern dining area is highlighted by a round glass table surrounded by four light-colored chairs. Natural light floods the space through large windows, with a decorative plant positioned on a wooden side table. The open layout connects to a stylish kitchen featuring dark cabinetry.

Apartment in Malden

2 bed | 2 bath | Parking | King beds | Laundry

4.91 out of 5 average rating, 199 reviews

The spacious living area features warm wooden flooring and a central table with seating. Natural light enters through a nearby door, complemented by modern pendant lighting. A kitchenette is visible with a stylish shelf displaying decorative items, creating a functional yet inviting environment.

Apartment in Arlington

Dixie’s House, 1BD in Arlington