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South Boston Holiday Rentals

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    Travellers to Boston are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    35 Matching Rentals in BostonView all 516 rentals
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    High-End Luxury Rental South Boston (5 min walk to beach)1 / 23
    (2)Excellent
    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    South Boston
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Location! Location! Modern 2BD 2 BA w/Parking1 / 8
    (1)Excellent
    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaze at the Boston seaport skyline from this one-bedroom condo, an elegant urban home with a communal roof terrace, a gym inside the building, and a wonderful location close to the T Red and Silver Lines. This condo is located in the Signal Industries Building, a one-time cotton plant that has...
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    Boston, Massachusetts 02127
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Our Andrew Square home is a two family house situated in the active urban neighborhood of South Boston, a section of the City of Boston near the Convention Center, Seaport and Financial Districts, Beaches, Quincy Market/Faneuil Hall and the North End areas of Boston. It is a spacious, sunny and...
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    Boston, Massachusetts 02127
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    South Boston
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated two bedroom apartment available close to Seaport, two blocks from convention center and one subway stop to South Station. Open deck, short walk to grocery store and restaurants, very close to airport and few blocks from major subway line. Minutes to Downtown, the heart of Boston and...
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    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • DVD Player
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you're visiting Washington, D.C. for business or for pleasure, Stay Alfred's vacation rentals at Andover House have all the amenities and comforts that you need for a stress-free stay in our nation's capital. Work on business matters in the community conference room, or go work up a sweat...
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    Boston, Massachusetts 20005
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
    • Washer
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and feel at home in our privately-owned residences featuring spectacular views of the luxurious Seaport District and Boston Harbor. These one bedroom suites include brand new kitchens with stainless steel appliances. Step into the living room and enjoy stylish furniture, hardwood floors, and...
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    Boston, Massachusetts 02210
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Private Garden
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy our newly renovated space! We have a single family home that's two bedrooms two baths, 900sf. There are 3 levels. First level is a modern living room with gleaming large format white tiles. Also on the first floor is the kitchen that has a white marble backsplash wall and skylight with...
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    Boston, Massachusetts 02127
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Created in the nucleus of the neighborhood, Watermark is a marriage between Fort Point Channel and the innovation of the Seaport District. This 17 Story Luxury Tower is situated a few blocks from the Bay and BCEC. Savor skyline views of the Financial District and Boston Harbor from a rooftop sky...
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    Boston, Massachusetts 02210
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    South Boston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Boston Furnished Apartment - 30 West Broadway Street Unit 3011 / 19
    (4)Very good
    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2017
    We loved this place, while waiting for my wife and kids to get ready I drank a beer and people watched out the window which is great entertainment since Starbucks and the train...
    Reviewed 30 June 2016
    After searching for a very long time for reasonable hotels in Boson i settled on this.As i wanted to be in the city...even though it only had share bathroom.I stayed in room...
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    About this property
    The kitchen in this gorgeous 3rd floor unit is fully-equipped with appliances, including refrigerator, range with oven, microwave, pots/pans and cooking utensils. In the living room, there is a 40" flat screen TV with cable and a sofa bed that comfortably sleeps two additional guests. This living...
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This luxury duplex condo boasts two queen size bedrooms, 2 full baths, in unit laundry, a deck with grill and a chef's kitchen with Wolf appliances. The unit is located in the heart of South Boston, a short walk to the new BCEC or the Seaport district. It's also minutes from Castle Island, the...
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    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Boston Harbor View 2 BR Luxury Suite1 / 25
    (1)Terrible
    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and feel at home in our privately-owned residences featuring spectacular views of the luxurious Seaport District and Boston Harbor. These one bedroom suites include brand new kitchens with stainless steel appliances. Step into the living room and enjoy stylish furniture, hardwood floors, and...
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    Location Information
    Boston, Massachusetts 02210
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The apartment is conveniently located right near the Red Line subway. It’s also a short walk or cab ride away from the wildly popular Seaport District, which is known for its restaurants and night life. This rear facing unit is the perfect home away from home for those coming to Boston for a month...
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    Boston, Massachusetts 02127
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Boston Harbor View 1 Bedroom Luxury Suites1 / 9
    (1)Average
    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Central Heating
    • Washer
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2017
    I found this property on my last visit to Boston. During that trip, I was able to stay at the Renaissance Harbor side. This condo hotel is located next door and operated by...
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    About this property
    Conveniently located across from premier shopping, dining, and nightlife establishments. You can walk out your to your front door and you’re in walking distance to some of the city’s premier attractions. Easy access to major highways, adjacent to the Silver Line and airport water shuttle. Suite...
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    Boston, Massachusetts 02210
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Parking
    • Terrace
    • Balcony
    • Washer
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large and comfortable single family home available for short term or vacation rental. It is located in South Boston near Shopping, Dining, Nightlife, Beaches, Boston Convention Center, Seaport District, and Boston Financial District, including Downtown Boston. The third floor loft has a roof deck...
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    Boston, Massachusetts 02127
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Balcony
    • Internet Access
    • Terrace
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Seaport, 315 on A provides one-stop-shop living just steps away from Boston's best dining, nightlife, and entertainment. Boston's most environmentally-friendly community was designed with you in mind, boasting open kitchens, stainless-steel appliances, hardwood floors, and...
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    Boston, Massachusetts 02210
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Internet Access
    • Air Conditioning
    • Patio
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Seaport, 315 on A provides one-stop-shop living just steps away from Boston's best dining, nightlife, and entertainment. Boston's most environmentally-friendly community was designed with you in mind, boasting open kitchens, stainless-steel appliances, hardwood floors, and...
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    Location Information
    Boston, Massachusetts 02210
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    This studio apartment is located in South Boston. Located three blocks from the red line, 4 miles from the airport and minutes to downtown Boston; this apartment is great for visiting tourists and guests going to the convention center. The Space Private guest apartment in historic South Boston....
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South Boston
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Satellite TV
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    • Terrace
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home has updated hardwood flooring, appliances, lighting and more. The main level offers open-concept living and kitchen area with a 1/2 bath and full laundry off the kitchen. The chef's kitchen includes granite counters, stainless steel appliances (refrigerator that includes filtered water...
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    Boston, Massachusetts 02127
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Terrace
    • Washer
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located across from premier shopping, dining, and nightlife establishments. You can walk out your to your front door and you’re in walking distance to some of the city’s premier attractions. Easy access to major highways, adjacent to the Silver Line and airport water shuttle. Suite...
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    Boston, Massachusetts 02210
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious South Boston unit is a sunny and comfortable 2-story Condo located in a duplex home containing 6 rooms, including 3 bedrooms and 2 bathrooms with central air conditioning throughout the home! Situated in a safe, nice, active urban neighborhood, our D street home is located in the...
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    Boston, Massachusetts 02127
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Northern Avenue brings stylish living to the Boston waterfront. With brand new renovated apartments and amenities, you will find everything here to fit your lifestyle. We hope you find your stay relaxing and enjoyable. It is our commitment and passion to meet and exceed your expectations. Located...
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    Boston, Massachusetts 02210
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Conveniently located across from premier shopping, dining, and nightlife establishments. You can walk out to your front door and you’re in for some of the city’s premier attractions. It brings stylish living to the Boston waterfront. With brand new renovated apartments and amenities, you will find...
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    Boston, Massachusetts 02210
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Boston
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    South Boston
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This spacious duplex apartment is spread out over 2 floors and offers 3 queen beds and 1.5 baths. In addition there is an eat in kitchen with washer and dryer in unit. There is a deck out back for relaxing during the nicer weather or snuggle up in the living room on the comfortable couch to catch a...
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    Boston, Massachusetts 02127
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    South Boston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Terrace
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
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    Location Information
    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Wonderful Private 3 floor condo. Bedrooms on top and bottom floors. Living room, kitchen, dining on the middle floor. Minutes to downtown Boston, Airport and all historical sites. Walking distance to beach and seaport district and convention center. Quiet Park across the street. Coffee and...
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    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Boston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Satellite TV
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Boston, Massachusetts 02127
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Satellite TV
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    • Grill
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    Smoking allowed
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    Boston, Massachusetts 02210
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    South Boston
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
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    Smoking allowed
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    Boston, Massachusetts 02127
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    South Boston
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Boston, Massachusetts 02127
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South Boston
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Boston, Massachusetts 02127
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Boston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Boston, Massachusetts 02127
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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