
Holiday rentals in South Boston
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Top-rated holiday rentals in South Boston
Guests agree: these stays are highly rated for location, cleanliness and more.

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry
The home is a short 7 minute walk to Ashmont T Stop. A unique master bedroom and a cozy 2nd bedroom adjacent to a marble spa bathroom (with heated floor and a large shower & built-in bench). With a clean, glass-tiled kitchen & granite-top counters, you’ll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood. Enjoy the feel of a downtown hotel without the high price. Note: There’s no separate living room, but comfortable seating is available in the 2nd bedroom & kitchen

One by Land BCEC History-Cruise- PVT Bath/Entry
*5 STAR ★★★★★ *Distinctive Suites **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 *Edloe Finch Sofa *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

Extraordinary 1-Bedroom Apartment in South Boston!
Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

2 BDR/2b- walk to Seaport & BCEC
We welcome you to stay at our stylish apartment in South Boston (Southie)! Located next to West Broadway, South Boston’s main road with plenty of restaurants, coffee shops, groceries, and boutique stores. Located walking distance to the Seaport District, Convention Center (BCEC), and our local Southie beaches. The space is ideal for travelling professionals, small families, couples, and those looking for a true neighborhood experience, tucked away just minutes from all the big city attractions.

Penthouse 2 Beds /2 Baths luxury in South Boston
Kick back and relax in this calm, stylish space. You won’t even feel like you are in the center of the city . Everything you need is within a walking distance , bars , coffee shops and many restaurants to choose from. Top floor unit, private balcony with 2 full bedrooms & 2 full bathrooms on opposite sides of the house makes traveling in groups much more comfortable. Brand new build 2023 , this is a hotel like stay professionally managed but with the comfort of a home away from home

3 BR Private Family Home, S. Boston/Seaport/BCEC
A beautiful single 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 plenty of 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.

A King Bed | Apartment | Middle of Boston
Located in the geographical middle of Boston you can get to anywhere in the city within 20 minutes including Harvard/MIT, Downtown, Fenway, Hynes Convention Center, Seaport and more. This pseudo apartment on the first floor is separate from the rest of the house and has its own private entrance, a private bathroom and a dedicated off street parking spot. The full kitchen with oversized counter is great for eating; comfy living room for relaxing and an office nook for working.

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

Private Suite-Free Parking,near Boston Airp-Train
--> 7 miles N of Boston & a near subway, beaches, & airport (93, 95 & Rte 1), you’ll find the quaint city of Melrose. During 11/25 - 3/26 longer stay are possible. Please inquire. The Melrosian Suite is nestled behind other houses. Wake up to the chirping birds instead of Boston’s noise. 225 acres of ponds, trails & conservation lands are at top of street w/ distant views of Boston & the ocean. Before booking, check out info required when you book & house rules.

Cozy suite in the city!
Enjoy a stylish experience at this centrally-located place in an extremely vibrant neighborhood of Boston. While staying at the AIRBNB, you will be in close proximity to the BCEC if you are in town for work. If you are in town for a pleasure, you will be very close to Downtown Boston, Fenway Park, the Seaport District, Faneuil Hall and the historic North End. You’ll be pleasantly surprised of how easy public transportation is to navigate around the city from the AIRBNB.

Cozy studio in Bay Village near Public Garden
This newly renovated private studio is ready to welcome you! This unit has 1 queen bed and 1 sleeper sofa, a desk, a kitchenette, a full bathroom, and a washer/dryer. It is the lower level of a historic 1800s Bostonian house, recently renovated. It has its own separate entrance. Great location! Conveniently located in Bay Village next to the Boston Public Garden, the studio is close to Downtown, Theater district, Chinatown, Beacon Hill, Back Bay, and South End!

Sterling 1BR at Everett | Pool & Gym
Enjoy contemporary comfort in this bright and inviting 1BR/1BA apartment in Everett. The home features a modern kitchen with stainless steel appliances, convenient in-unit laundry, and a naturally lit living space designed for relaxation. Make the most of the community’s outdoor courtyard pool, 24/7 fitness center, and cozy lounge areas with fire pits. Located minutes from Encore, Assembly Row, and key highways, it offers easy access to all of Greater Boston.
Popular amenities for South Boston holiday rentals
Other great holiday rentals in South Boston

Boston Charm 5: Private Room Near Downtown

Steps from MGM Music Hall + Free Breakfast & Pool

Clean room with Free parking

Single Private Room B

The Gold Room

Small Penthouse Suite by Longwood & Train

Cozy Somerville Room (Near MBTA/Bike Path)

Modern Brownstone - walk to Longwood Medical Area!
When is the best time to visit South Boston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $216 SGD | $225 SGD | $193 SGD | $225 SGD | $257 SGD | $264 SGD | $234 SGD | $251 SGD | $257 SGD | $257 SGD | $186 SGD | $172 SGD |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Quick stats about holiday rentals in South Boston

Total holiday rentals
Explore 310 holiday rentals in South Boston

Nightly prices starting at
South Boston holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 15,580 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wifi availability
300 of South Boston holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across South Boston rentals

4.7 Average rating
South Boston stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
South Boston’s top spots include Castle Island, Andrew Station and Broadway Station
Destinations to explore
- Rentals with a patio South Boston
- Rentals with a fireplace South Boston
- Family-friendly rentals South Boston
- House rentals South Boston
- Flat rentals South Boston
- Apartment rentals South Boston
- Pet-friendly rentals South Boston
- Rentals with outdoor seating South Boston
- Rentals with pools South Boston
- Fitness-friendly rentals South Boston
- Rentals with a washing machine and dryer South Boston
- Rentals with beach access South Boston
- Hampton Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- MIT Museum
- New England Aquarium
- Freedom Trail
- Good Harbor Beach
- Canobie Lake Park
- Duxbury Beach
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Quincy Market
- Onset Beach
- Rye North Beach
- Prudential Center
- North Hampton Beach
- Oakland Beach
- White Horse Beach




