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Pet-friendly vacation rentals in Winthrop

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winthrop

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

The living area features a dark blue sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front, surrounded by natural light from nearby windows. The white walls and sleek countertops contribute to a modern, open space. A minisplit unit is visible for climate control.

Home in Lakeside Marblehead

5 out of 5 average rating, 142 reviews

Seaside Cottage

Here you are down the street from some of Marblehead's hidden gems such as Redds Pond, Browns Island & Old Burial Hill Cemetery. One car parking. 5 minute walk to the beach, shops & restaurants. Fully fenced in yard with turf grass. One bedroom with a low profile queen sized bed. In unit washer/dryer. Full bath with tub. Newly renovated kitchen with major appliances: stove, oven, dishwasher, fridge, Nespresso maker & microwave. Sheets & bath linens provided. Minisplit A/C. Home is all one level.

Top guest favorite

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

4.92 out of 5 average rating, 1,330 reviews

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.

Top guest favorite

A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.

Guest suite in Weston

4.99 out of 5 average rating, 172 reviews

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 15-minute drive to Amtrak's "Route 128" station to NYC and points south.

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

4.92 out of 5 average rating, 349 reviews

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.

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

Apartment in Arlington

4.98 out of 5 average rating, 203 reviews

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

Townhouse in Everett

4.89 out of 5 average rating, 315 reviews

#7 Comfortable Spacious Home Near Boston + Parking

Discover comfort & convenience minutes from Boston, Cambridge, & Salem. Whether you're here for work, family, or fun, this stylish 2-story home has everything you need for a relaxing & memorable stay, plus we are experienced Superhosts! 🛏 3 Comfy Bedrooms + 1.5 Baths 🍳 Fully Equipped Kitchen 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🔥 Backyard BBQ + Fire Pit + Outdoor Seating for 6 🌆 Easy Access to Local Attractions 🏡 Perfect for families 5⭐ Reviews

Top guest favorite

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

4.95 out of 5 average rating, 148 reviews

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.

Top guest favorite

The living room features a spacious layout with leather seating and a colorful area rug. A large TV is mounted on the wall, and windows offer an ocean view. A furry dog rests comfortably on the floor, adding to the welcoming ambiance.

Condo in Winthrop

4.99 out of 5 average rating, 201 reviews

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.

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

4.96 out of 5 average rating, 142 reviews

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.

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

4.76 out of 5 average rating, 212 reviews

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 micro studio space features a wall-mounted television positioned near a built-in bookcase. Natural light enters through two large windows, illuminating the minimalist decor and a cozy, spacious bed with crisp white bedding. A small white table and chair enhance the functionality of the room.

Apartment in Fort Hill

4.9 out of 5 average rating, 905 reviews

AKBrownstone: cozy private studio by T

🏠 Live like a local: designed micro studio, in a classic Boston Brownstone 🌳 Your very own cozy 170sqft (15sqm) pied-à-terre on the ground level, overlooking Victorian homes on a tree lined street 🚇 5 mins walk to the T (subway), 3rd stop to Back Bay city center or go on bike & walking path 👣 Walk to Longwood Medical Area (Harvard Medical, etc), Museums (MFA, Gardner), Northeastern, & Fenway Park 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

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

4.91 out of 5 average rating, 112 reviews

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!

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Popular amenities for Winthrop pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

4.85 out of 5 average rating, 313 reviews

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

A modern kitchen features sleek white cabinets and stainless steel appliances. A spacious island with a cooktop is surrounded by red metal stools. Natural light fills the area through a nearby window, complementing the contemporary design and providing a warm, inviting atmosphere.

Home in South Boston

4.92 out of 5 average rating, 409 reviews

3 BR Private Family Home, S. Boston/Seaport/BCEC

A modern kitchen features a central wooden island with a gas stove and a griddle, surrounded by fresh produce. The space includes a dining table with wooden chairs and is adorned with colorful art on the walls, illuminated by natural light from large windows.

Home in Brookline Village

4.92 out of 5 average rating, 140 reviews

Pretzel Factory Loft w/Peloton

The kitchen features white cabinetry and stainless steel appliances, with a spacious layout for cooking. A game table is shown with a pool table in the background. A cozy living area includes a light blue accent wall and comfortable seating. The backyard displays a grassy area with a slide and a playset.

Home in South Boston

4.98 out of 5 average rating, 194 reviews

Family Friendly City Oasis! Free Parking, King Bed

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.

4.85 out of 5 average rating, 116 reviews

Cheerful 1-bedroom New England Ranch

A cozy living room features a traditional fireplace with a decorative mirror above it. A wooden coffee table is placed in front of two patterned chairs. A white media console with a television is positioned against the wall, with light streaming through nearby windows.

Home in Beverly

4.95 out of 5 average rating, 162 reviews

Lovely 2 Bedroom Victorian 1.5 Blocks To Ocean!!!

A cozy sunroom features natural light streaming through multiple wooden windows adorned with blinds. A comfortable couch is complemented by decorative pillows, while a small tray is positioned on a coffee table. A writing desk and a potted plant add to the inviting atmosphere.

Home in Medford

4.85 out of 5 average rating, 150 reviews

Sunny home minutes from Boston. Free parking.

Top guest favorite

A cozy living area is presented with two red couches and a round coffee table at the center. A lamp and wall-mounted shelves enhance the space, which is illuminated by natural light from a nearby window. Artwork and flowers add subtle touches of color.

Home in Cambridge

4.99 out of 5 average rating, 166 reviews

Cozy, Spacious Home in the Heart of Cambridge

Pet-friendly home rentals with a pool

The open-plan living area features a stylish arrangement of a velvet sofa and coffee table, complemented by a large Smart TV. Natural light pours in through expansive windows, revealing a vibrant cityscape. A dining table for four is positioned in the background.

Apartment in Boston

4.85 out of 5 average rating, 27 reviews

Chic 2BR/2BA Retreat in the Heart of Fenway Park

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.

Home in Lakeside Marblehead

4.94 out of 5 average rating, 31 reviews

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

A light-filled living area displays a spacious sectional couch adorned with a soft throw. Two elegant chairs are positioned nearby, while large windows offer expansive city views. A round coffee table sits at the center, showcasing a few decorative items. Lush plants add a touch of nature to the space.

Apartment in South End

5 out of 5 average rating, 3 reviews

Boston Family Suite: Pool, Gym & Paid Parking

Top guest favorite

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

4.95 out of 5 average rating, 40 reviews

Beautiful Spacious 4BRM House!

Top guest favorite

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

4.96 out of 5 average rating, 57 reviews

the house of id; vintage shop, accessible space

The image shows a hot tub situated on a shaded deck, overlooking a calm waterfront. The view includes a distant skyline with industrial buildings, framed by greenery. The clear water of the hot tub reflects the serene outdoor setting.

Home in North Weymouth

4.88 out of 5 average rating, 52 reviews

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

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

4.88 out of 5 average rating, 94 reviews

Cozy Private Suite halfway between Cape & Boston

A spacious outdoor area is showcased with a clear blue pool surrounded by a sun deck. Sun loungers and a wooden deck are visible next to the pool, while lush green trees provide a natural backdrop. A separate structure is positioned to the right.

Apartment in Manchester-by-the-Sea

4.9 out of 5 average rating, 174 reviews

Modern Space With Pool Close To Singing Beach

Private, pet-friendly home rentals

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

4.97 out of 5 average rating, 66 reviews

Spacious & Pet-Friendly Modern Home in Charlestown

An outdoor space is presented, featuring a wooden picnic table surrounded by a sprawling lawn. A slide is integrated into the landscape, complemented by vibrant greenery and a nearby garden area. Outdoor seating is also visible in the background, enhancing the communal atmosphere.

Condo in East Boston

4.93 out of 5 average rating, 213 reviews

Family Home + Near Downtown + Cool Backyard!

A fully equipped kitchen features modern stainless steel appliances, including a gas range and a refrigerator. Sleek white cabinetry complements the granite countertops. A small dining area with four stylish chairs is visible, creating an inviting space for shared meals and gatherings.

Apartment in Salem

4.94 out of 5 average rating, 202 reviews

Close to Salem attractions.

Apartment in South End

4.78 out of 5 average rating, 218 reviews

(T2) Bay Windows, Delicious Pizza, Prime Location!

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.

Home in Winthrop

4.84 out of 5 average rating, 88 reviews

Sunny 3 bedroom on beach

Top guest favorite

A private outdoor patio is shown, featuring a dining table surrounded by four chairs on a patterned rug. Lush greenery is visible in the background alongside a stone wall, with planters adding a touch of color to the setting.

Townhouse in Watertown

5 out of 5 average rating, 136 reviews

Recently Renovated 2 BR Close to Boston w/Parking!

The exterior of a charming barn retreat is displayed, featuring weathered cedar shingles and multiple windows that invite natural light. A gravel path leads to the door, framed by lush greenery, while a small weather vane sits atop the roof, adding a quaint touch.

Barn in Cohasset

4.96 out of 5 average rating, 54 reviews

The Landing at Cohasset Harbor

A modern kitchen displays sleek gray cabinets and stainless steel appliances, complemented by white countertops. A wooden dining table with metal stools provides a dining space. Light hardwood floors enhance the bright atmosphere, while a colorful wall art piece adds a touch of character.

Apartment in Arlington

5 out of 5 average rating, 74 reviews

#2 Completely Renovated 3Br Arlington Height Unit

Quick stats about vacation rentals that are pet-friendly in Winthrop

Total rentals
50 properties
Nightly prices starting at
R1,213 ZAR before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore