Vacation rentals in South Boston Waterfront

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Top-rated vacation rentals in South Boston Waterfront

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Guest favorite

Apartment in Boston

4.99 out of 5 average rating, 212 reviews

Astonishing 1 Bed South End Boston's Best Location

Clean, unique, bright, inviting, 1-bedroom on the 1st floor. Newly renovated with astonishing ceilings, new tall custom windows, new appliances. The best of Boston outside your door Located half a block to Restaurant Row, where you’ll find some of the best dining in the city. Famous bakeries, coffee shops are all near, a super effortless walk to the very BEST Boston has to offer. Complimentary Netflix, movie channels, high speed internet, Keurig coffee, snacks. It doesn't get better than this!

Nov 3 – 10

G$85,355 GYD per night

Guest favorite

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

Jan 14 – 21

G$21,002 GYD per night

Guest favorite

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.

Jan 24 – 31

G$26,759 GYD per night

Superhost

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 24 – Mar 3

G$25,477 GYD per night

Guest favorite

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

G$22,474 GYD per night

Guest favorite

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.

Jan 9 – 16

G$64,897 GYD per night

Guest favorite

Guest suite in Boston

4.97 out of 5 average rating, 442 reviews

Boston’s Hidden Gem: One by Land Suite

*5 STAR ★★★★★ **No Chores! No To-Do List!** *Sparkling Clean and Sanitized *Yes a Private Bathroom *Historic and charming home. *South Boston trendy neighborhood *Beach two blocks *Dedicated Luxury Suites *Key-less Coded Access *King EuroTop Bed *Private bath with shower *Workstation Free WIFI *Minutes to Airport/Downtown/Convention Center *Netflix Limited street parking. Check the photos for free overnight street parking. Paid parking located at: 12 Drydock Ave, Boston, MA 02210

Oct 15 – 22

G$40,389 GYD per night

Guest favorite

Home in Boston

4.91 out of 5 average rating, 971 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

G$61,443 GYD per night

Superhost

Condo in Boston

4.82 out of 5 average rating, 178 reviews

Stylish garden level studio with a private patio

Enjoy your stay in this stylish East Boston garden level studio with a private back patio. It is centrally located near restaurants, the waterfront, a running & biking trail, the airport, public transportation, and it is 1 metro stop away from downtown Boston. The metro stop, Maverick, is a 4 minute walk! The studio is equipped with a king bed that has a memory foam mattress, a queen pull out sofa, and a fully equipped kitchen.

Jan 24 – 31

G$27,137 GYD per night

Guest favorite

Home in Boston

4.89 out of 5 average rating, 296 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

G$26,041 GYD per night

Superhost

Apartment in Boston

4.84 out of 5 average rating, 307 reviews

Beacon Hills Studio next to State house

Come stay at our lovely studio in the heart of Boston's most desirable neighborhood, Beacon Hill! Whether you want to walk the Freedom Trail, or shop on Newbury St, Surrounded by brownstones, coffee shops, and locals, you’ll feel right at home in this community. Steps away from the State House, MGH, and the Boston Common, You could not be more centrally located to take in all the city has to offer.

Dec 21 – 28

G$33,329 GYD per night

Guest favorite

Condo in Boston

4.96 out of 5 average rating, 124 reviews

Downtown Loft Boston - Close to everything

Spacious loft in Downtown Boston, Historic District, with high ceilings, large windows, original wooden floors, private bedroom area, updated bathroom with shower and tub, complete kitchen, and laundry room. The unit also offers the highest speed available in the area -1 gig internet access and 55" smart TV.

Jun 30 – Jul 7

G$64,423 GYD per night