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South Boston vacation rentals

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Top-rated vacation rentals in South Boston

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Apartment in Boston

4.89 out of 5 average rating, 251 reviews

🎖The Boiler Room | Close to Subway + Downtown🎖

This unique private suite is brand new & comes w/ its own private entrance. Including a queen size bed, ensuite bathroom, & a wine/craft beer minibar! The unit is extremely clean and very nicely decorated. A quick 5 minute walk to Ashmont Station (Red Line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. Great restaurants nearby - Molinari's & Tavolo Ristorante - as well as a local coffee shop + a Dunkin just across the Ashmont metro station.

Feb 23 – Mar 2

Guest suite in Boston

4.96 out of 5 average rating, 203 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

Apr 8 – 15

Guest suite in Winchester

5.0 out of 5 average rating, 104 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Mar 19 – 26

Guest suite in Boston

4.91 out of 5 average rating, 196 reviews

Cozy Private Garden Studio near the Heart of JP

Best of both worlds: this airy and light, newly renovated private studio is set in a beautiful, secluded backyard/garden. Easy walk to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is a microwave, fridge, counter and and sink but no stove or cooking options.

Oct 13 – 20

Home in Boston

4.92 out of 5 average rating, 205 reviews

Sunny Duplex Condo + Private Parking

Welcome to your cozy urban retreat! This 2-bedroom condo, spread over two floors, offers a warm and inviting atmosphere, along with a roof deck offering views of the Boston Harbor waterfront and downtown skyline. And, enjoy the convenience of your very own private parking space! Located just a mile from the vibrant Seaport District, the Boston Convention & Exhibition Center, and major highways, exploring the city couldn't be easier. Experience the warmth and charm of Boston living like a local!

Nov 12 – 19

Home in Boston

4.92 out of 5 average rating, 333 reviews

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

A beautiful, newly renovated home all to yourself with a private entrance AND GARAGE PARKING in bustling South Boston! Equipped with 3 private bedrooms as well as two bathrooms and outdoor deck space that opens to a small park, this home features luxurious amenities in an unbeatable location with access to a plethora of shops and restaurants. One mile exactly to the Convention Center (BCEC).This is the perfect place for large groups and companies who seek a quiet comfortable Boston experience.

Oct 27 – Nov 3

Apartment in Boston

4.98 out of 5 average rating, 114 reviews

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Feb 6 – 13

Condo in Boston

4.95 out of 5 average rating, 173 reviews

CITY APARTMENT NEAR AIRPORT

CITY APARTMENT NEAR AIRPORT STATION NEW LISTING!!! LUXURY private One bed apartment located in a superb location. You will have the opportunity to stay one block away from Airpor T station, tree blocks away from public Library amazing green way paths, Bremen's park, near shoping center, threndy restaurants, water taxy, one stop from aquarium station and North end of Boston, and so much more to explore. This is the place to stay for your Vacation or Bussiness trip.

Jun 6 – 13

Guest suite in Boston

4.96 out of 5 average rating, 348 reviews

Paul Revere Suite PVT Entry/BATH QN Bed Sparkling

*5 STAR ★★★★★ **No Chores! No To-Do List!** Yes, Private Bathroom! Cleaned and Sanitized *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *National Historic Sites *Dedicated Luxury Suites *Key-less Coded Access *Queen Pillow Top Bed *Private bath with shower *Great Bath Amenities *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking.

Sep 26 – Oct 3

Home in Boston

4.91 out of 5 average rating, 967 reviews

Sanitized Modern 3BD private home-near BCEC

Sanitized and enhanced cleaning implemented using proper cleaning measures and space between guests (per Airbnb requirements)! Updated 3BD in South Boston (near convention center) with chef's kitchen, keyless entry, central AC, deck and amenities. You will have the entire first and 2nd floor space to yourself, minutes to Seaport, subway stop half mile from house (Broadway on the redline) and downtown. (City of Boston registration #: STR383708)

Nov 26 – Dec 3

Apartment in Boston

4.92 out of 5 average rating, 267 reviews

Apartment 1BR mins from JFK/UMASS on Red Line

Airbnb Superhost offering meticulous and specious 1 bedroom 1 bath, 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.

Dec 12 – 19

Home in Boston

4.89 out of 5 average rating, 295 reviews

Treetop Haven in the City

Our space is unique in that it's completely private, affordable, quiet, clean, and with all the amenities you would find in a regular home. It is also cozy, not fancy, but homey. Think of a place you would find in a relative's home. The deck is special - it looks over our neighbor's backyards with plenty of sun and flowers in the Spring and summer. The neighborhood is quiet and safe. No animals are permitted.

Dec 28 – Jan 4

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Popular amenities for South Boston vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near South Boston's top sights

South Bay Center67 locals recommend

Castle Island187 locals recommend

The Lawn On D49 locals recommend

Carson Beach73 locals recommend

Beehive Restaurant229 locals recommend

Olive Garden Italian Restaurant13 locals recommend

Other great vacation rentals in South Boston

Condo in Boston

4.95 out of 5 average rating, 232 reviews

Beautiful, spacious South Boston Condo, Near T

Oct 13 – 20

Guest suite in Watertown

4.91 out of 5 average rating, 265 reviews

Private 1BR Pied-a-terre

Jan 5 – 12

Apartment in Boston

4.99 out of 5 average rating, 212 reviews

Astonishing 1 Bed South End Boston's Best Location

Dec 2 – 9

Guest suite in Revere

4.92 out of 5 average rating, 199 reviews

Private Studio 10 min from airport

Feb 6 – 13

Guest suite in Newton

4.97 out of 5 average rating, 556 reviews

Spacious suite with private entrance, parking spot

Oct 3 – 10

Condo in Boston

4.96 out of 5 average rating, 124 reviews

Downtown Loft Boston - Close to everything

Jun 30 – Jul 7

Home in Revere

4.79 out of 5 average rating, 139 reviews

Renovated Cozy City Getaway

Jan 20 – 27

Guest suite in Boston

4.93 out of 5 average rating, 285 reviews

Washer+Dryer+Parking!*Private suite*Cul de sac*

Jun 24 – Jul 1

Other great vacation rentals in South Boston

Condo in Boston

4.97 out of 5 average rating, 240 reviews

Gorgeous Beacon Hill 1BR | 1BA

Jan 22 – 29

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Aug 9 – 16

Home in Quincy

4.96 out of 5 average rating, 124 reviews

Artist's Haven (2)

Jun 20 – 27

Guest suite in Medford

4.92 out of 5 average rating, 125 reviews

Beautiful 1 Bedroom, 1 Bathroom in Medford

Jul 22 – 29

Apartment in Boston

4.84 out of 5 average rating, 307 reviews

Beacon Hills Studio next to State house

Mar 8 – 15

Guest suite in Salem

4.99 out of 5 average rating, 692 reviews

The Mason Suite of Salem

Mar 2 – 9

Apartment in Boston

4.99 out of 5 average rating, 260 reviews

S End/B Bay border! Copley Location- Perfect 1 Br

Oct 16 – 23

Apartment in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Dec 8 – 15

Quick stats about vacation rentals in South Boston

Total rentals
320 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
120 properties are a good fit for families
Total number of reviews
14K reviews
Nightly prices starting at
$20 before taxes and fees

Destinations to explore