Vacation rentals in South Boston, MA

200 available vacation rental offers

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Best Vacation rentals and Airbnb offers in South Boston, MA

1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena. - South Boston, MA

1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena.

Apartment, South Boston

1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena. is a apartment in South Boston, with easy beach access and room for a group. This stay gives travelers a…

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About 1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena.

1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena. is a apartment in South Boston, with easy beach access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, internet, non smoking, and shower.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,226.

From$111/night
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Quarters on DOT by Short Term Rentals Boston - South Boston, MA

Quarters on DOT by Short Term Rentals Boston

Apartment, South Boston

Quarters on DOT by Short Term Rentals Boston is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Quarters on DOT by Short Term Rentals Boston

Quarters on DOT by Short Term Rentals Boston is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $964.

From$112/night
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Quarters on DOT by Thatch - South Boston, MA

Quarters on DOT by Thatch

Apartment, South Boston

Quarters on DOT by Thatch is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Quarters on DOT by Thatch

Quarters on DOT by Thatch is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $964.

From$112/night
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Airport room 1 - South Boston, MA

Airport room 1

Homestay, South Boston

Airport room 1 is a homestay in South Boston, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Airport room 1

Airport room 1 is a homestay in South Boston, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,031.

From$122/night
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Browse Vacation Rentals with a Pool in South Boston, MA

Add a pool to the search when you want an easy place to cool off between outings.

Cody's Place Winthrop Boston Logan Airport Beaches - South Boston, MA

Cody's Place Winthrop Boston Logan Airport Beaches

Apartment, South Boston

Cody's Place Winthrop Boston Logan Airport Beaches is a apartment in South Boston, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Cody's Place Winthrop Boston Logan Airport Beaches

Cody's Place Winthrop Boston Logan Airport Beaches is a apartment in South Boston, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,308.

From$251/night
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Elegant Oasis with Pool and Gym - South Boston, MA

Elegant Oasis with Pool and Gym

Apartment, South Boston

Elegant Oasis with Pool and Gym is a apartment in South Boston, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Elegant Oasis with Pool and Gym

Elegant Oasis with Pool and Gym is a apartment in South Boston, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,578.

From$318/night
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Elegant 2BR - 2BA Oasis with Pool & Gym - South Boston, MA

Elegant 2BR - 2BA Oasis with Pool & Gym

Apartment, South Boston

Elegant 2BR - 2BA Oasis with Pool & Gym is a apartment in South Boston, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About Elegant 2BR - 2BA Oasis with Pool & Gym

Elegant 2BR - 2BA Oasis with Pool & Gym is a apartment in South Boston, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,350.

From$417/night
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Southie Condo - Near Subway - Bring Pets - Pool Table - South Boston, MA

Southie Condo - Near Subway - Bring Pets - Pool Table

Condo, South Boston

Southie Condo - Near Subway - Bring Pets - Pool Table is a condo in South Boston, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Southie Condo - Near Subway - Bring Pets - Pool Table

Southie Condo - Near Subway - Bring Pets - Pool Table is a condo in South Boston, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,612.

From$600/night
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Best South Boston, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Suite at House of L: Near Boston, Hospitals & Casino – Fast WiFi, Driveway - South Boston, MA

Suite at House of L: Near Boston, Hospitals & Casino – Fast WiFi, Driveway

Condo, South Boston

Suite at House of L: Near Boston, Hospitals & Casino – Fast WiFi, Driveway is a condo in South Boston, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Suite at House of L: Near Boston, Hospitals & Casino – Fast WiFi, Driveway

Suite at House of L: Near Boston, Hospitals & Casino – Fast WiFi, Driveway is a condo in South Boston, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,710.

From$166/night
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Boston Historic Lower Mills - South Boston, MA

Boston Historic Lower Mills

Homestay, South Boston

Boston Historic Lower Mills is a homestay in South Boston, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Boston Historic Lower Mills

Boston Historic Lower Mills is a homestay in South Boston, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,420.

From$166/night
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Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches - South Boston, MA

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Apartment, South Boston

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches is a apartment in South Boston, with easy beach access, parking, and kitchen access. This stay gives…

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About Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches is a apartment in South Boston, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,604.

From$172/night
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Boston's Finest New Renovated Apartment - South Boston, MA

Boston's Finest New Renovated Apartment

Apartment, South Boston

Boston's Finest New Renovated Apartment is a apartment in South Boston, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Boston's Finest New Renovated Apartment

Boston's Finest New Renovated Apartment is a apartment in South Boston, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,156.

From$204/night
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Best Pet-Friendly Vacation Rentals in South Boston, MA

Bring your pet along with stays that welcome four-legged travelers.

Unit 34 Stylish 1BR Apartment Long-term stays - South Boston, MA

Unit 34 Stylish 1BR Apartment Long-term stays

Apartment, South Boston

Unit 34 Stylish 1BR Apartment Long-term stays is a apartment in South Boston, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Unit 34 Stylish 1BR Apartment Long-term stays

Unit 34 Stylish 1BR Apartment Long-term stays is a apartment in South Boston, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,907.

From$193/night
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Downtown Studio | Students Welcome | W/D in unit - South Boston, MA

Downtown Studio | Students Welcome | W/D in unit

Apartment, South Boston

Downtown Studio · Students Welcome · W/D in unit is a apartment in South Boston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Downtown Studio | Students Welcome | W/D in unit

Downtown Studio · Students Welcome · W/D in unit is a apartment in South Boston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,662.

From$245/night
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Airy 1BR Walkable to Everywhere in Boston | W+D - South Boston, MA

Airy 1BR Walkable to Everywhere in Boston | W+D

Apartment, South Boston

Airy 1BR Walkable to Everywhere in Boston · W+D is a apartment in South Boston, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Airy 1BR Walkable to Everywhere in Boston | W+D

Airy 1BR Walkable to Everywhere in Boston · W+D is a apartment in South Boston, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,741.

From$252/night
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Walking distance to Beacon Hill, Back Bay + all tourist spots. Great for work trip too, MBTA nearby - South Boston, MA

Walking distance to Beacon Hill, Back Bay + all tourist spots. Great for work trip too, MBTA nearby

Apartment, South Boston

Walking distance to Beacon Hill, Back Bay + all tourist spots. Great for work trip too, MBTA nearby is a apartment in South Boston, with pet-friendly space, easy beach access, and parking.…

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About Walking distance to Beacon Hill, Back Bay + all tourist spots. Great for work trip too, MBTA nearby

Walking distance to Beacon Hill, Back Bay + all tourist spots. Great for work trip too, MBTA nearby is a apartment in South Boston, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,779.

From$256/night
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Best South Boston, MA vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Luxury Studio Next to Broadway rm2a - South Boston, MA

Luxury Studio Next to Broadway rm2a

Apartment, South Boston

Luxury Studio Next to Broadway rm2a is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Luxury Studio Next to Broadway rm2a

Luxury Studio Next to Broadway rm2a is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,571.

From$261/night
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Luxury Studio Next to Broadway 8svt - South Boston, MA

Luxury Studio Next to Broadway 8svt

Apartment, South Boston

Luxury Studio Next to Broadway 8svt is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Luxury Studio Next to Broadway 8svt

Luxury Studio Next to Broadway 8svt is a apartment in South Boston, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,689.

From$274/night
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Luxury 1BR Next to Broadway f2f6 - South Boston, MA

Luxury 1BR Next to Broadway f2f6

Apartment, South Boston

Luxury 1BR Next to Broadway f2f6 is a apartment in South Boston, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Luxury 1BR Next to Broadway f2f6

Luxury 1BR Next to Broadway f2f6 is a apartment in South Boston, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,832.

From$290/night
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New 3 beds in Southie! W/D in unit. - South Boston, MA

New 3 beds in Southie! W/D in unit.

Holiday Home, South Boston

New 3 beds in Southie! W/D in unit. is a holiday home in South Boston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About New 3 beds in Southie! W/D in unit.

New 3 beds in Southie! W/D in unit. is a holiday home in South Boston, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,758.

From$294/night
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Our Favorite Family-Friendly Vacation Rentals in South Boston, MA

Plan a trip with stays that give families more room to spread out.

Charming Colonial Two Bedroom Basement Apartment - South Boston, MA

Charming Colonial Two Bedroom Basement Apartment

Holiday Home, South Boston

Charming Colonial Two Bedroom Basement Apartment is a holiday home in South Boston, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Charming Colonial Two Bedroom Basement Apartment

Charming Colonial Two Bedroom Basement Apartment is a holiday home in South Boston, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,910.

From$209/night
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1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts - South Boston, MA

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts

Holiday Home, South Boston

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts is a holiday home in South Boston, with parking, kitchen access, and room for a group. This stay gives…

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About 1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts is a holiday home in South Boston, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,390.

From$241/night
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Cozy Cambridge Cottage Retreat Near Harvard - South Boston, MA

Cozy Cambridge Cottage Retreat Near Harvard

Apartment, South Boston

Cozy Cambridge Cottage Retreat Near Harvard is a apartment in South Boston, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Cozy Cambridge Cottage Retreat Near Harvard

Cozy Cambridge Cottage Retreat Near Harvard is a apartment in South Boston, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,746.

From$279/night
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Newly Renovated Open-Concept living space, close to Boston, plenty of parking - South Boston, MA

Newly Renovated Open-Concept living space, close to Boston, plenty of parking

Holiday Home, South Boston

Newly Renovated Open-Concept living space, close to Boston, plenty of parking is a holiday home in South Boston, with parking and kitchen access. This stay gives travelers a comfortable…

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About Newly Renovated Open-Concept living space, close to Boston, plenty of parking

Newly Renovated Open-Concept living space, close to Boston, plenty of parking is a holiday home in South Boston, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,630.

From$302/night
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