South End Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in South End, Boston, Massachusetts, USA

New NEW Ultra-Luxury 4 bedroom Boston Designer Brownstone
New
4 Bedrooms 10 Guests
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10.0 (2 Reviews)
1 Bedroom 4 Guests
From US $505 per night
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9.2 (245 Reviews)
1 Bedroom 2 Guests
From US $344 per night
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10.0 (2 Reviews)
3 Bedrooms 10 Guests
From US $220 per night
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9.0 (2167 Reviews)
1 Bedroom 2 Guests
From US $345 per night
10.0 (99 Reviews)
1 Bedroom 2 Guests
From US $210 per night
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10.0 (1 Review)
4 Bedrooms 11 Guests
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8.8 (1019 Reviews)
1 Bedroom 2 Guests
10.0 (96 Reviews)
1 Bedroom 2 Guests
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9.6 (9 Reviews)
1 Bedroom 4 Guests
10.0 (91 Reviews)
2 Bedrooms 4 Guests
From US $860 per night
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9.5 (2 Reviews)
2 Bedrooms 8 Guests
From US $540 per night
10.0 (80 Reviews)
2 Bedrooms 4 Guests
From US $697 per night
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9.0 (1 Review)
1 Bedroom 7 Guests
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8.7 (42 Reviews)
1 Bedroom 2 Guests
From US $546 per night
10.0 (2 Reviews)
1 Bedroom 4 Guests
From US $362 per night
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8.6 (23 Reviews)
1 Bedroom 2 Guests
From US $543 per night
10.0 (2 Reviews)
2 Bedrooms 4 Guests
From US $334 per night
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8.5 (24 Reviews)
1 Bedroom 2 Guests
From US $334 per night
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8.2 (37 Reviews)
1 Bedroom 2 Guests
Bed & Breakfast
From US $1,663 per night
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8.2 (25 Reviews)
5 Bedrooms 4 Guests
9.8 (51 Reviews)
1 Bedroom 4 Guests
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8.2 (22 Reviews)
2 Bedrooms 4 Guests
9.6 (48 Reviews)
1 Bedroom 4 Guests
From US $334 per night
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8.0 (63 Reviews)
1 Bedroom 2 Guests
From US $507 per night
9.2 (20 Reviews)
2 Bedrooms 4 Guests
From US $223 per night
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8.0 (43 Reviews)
1 Bedroom 2 Guests
9.0 (2 Reviews)
1 Bedroom 4 Guests
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8.0 (35 Reviews)
1 Bedroom 2 Guests
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8.0 (18 Reviews)
10 Bedrooms 26 Guests
6.0 (1 Review)
1 Bedroom 2 Guests
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8.0 (1 Review)
2 Bedrooms 4 Guests
3.4 (3 Reviews)
2 Bedrooms 8 Guests
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7.9 (20 Reviews)
1 Bedroom 2 Guests
From US $898 per night
3.0 (2 Reviews)
2 Bedrooms 5 Guests
New
2 Bedrooms 4 Guests
New
1 Bedroom 4 Guests
New
2 Bedrooms 4 Guests
New
1 Bedroom 4 Guests
From US $140 per night
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7.8 (11 Reviews)
9 Bedrooms 11 Guests
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8.8 (1008 Reviews)
1 Bedroom 2 Guests
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7.7 (3 Reviews)
1 Bedroom 1 Guest
From US $257 per night
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8.8 (1004 Reviews)
1 Bedroom 2 Guests
From US $334 per night
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7.4 (8 Reviews)
1 Bedroom 2 Guests
From US $406 per night
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8.8 (22 Reviews)
1 Bedroom 2 Guests
New
1 Bedroom 2 Guests
From US $93 per night
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7.2 (35 Reviews)
2 Bedrooms 5 Guests
New
2 Bedrooms 4 Guests
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7.2 (21 Reviews)
1 Bedroom 2 Guests
From US $218 per night
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7.0 (17 Reviews)
1 Bedroom 2 Guests
From US $245 per night
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7.0 (11 Reviews)
1 Bedroom 2 Guests
From US $129 per night
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6.5 (13 Reviews)
7 Bedrooms 15 Guests
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6.5 (10 Reviews)
6 Bedrooms 12 Guests
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3.3 (14 Reviews)
6 Bedrooms 12 Guests
From US $1,760 per night
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New
2 Bedrooms 7 Guests
From US $880 per night
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New
2 Bedrooms 7 Guests

About South End Vacation Rentals

With more than 258 South End vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in South End.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner South End, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in South End. Places to stay near South End are 590.79 ft² on average, with prices averaging US $361 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in South End with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

South End Vacation Rental Frequently Asked Questions

What are the top vacation rentals in South End?

How many Rentbyowner vacation rentals are available in South End?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 258 in the South End area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in South End. 

Nearby Neighborhood (9)

Neighborhood Property Count
Back Bay Vacation Rentals in Boston, Massachusetts 306
Fenway–Kenmore Vacation Rentals in Boston, Massachusetts 200
Back Bay East Vacation Rentals in Boston, Massachusetts 144
Prudential - St. Botolph Vacation Rentals in Boston, Massachusetts 137
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Shawmut Vacation Rentals in Boston, Massachusetts 74
Columbus Park - Andrew Square Vacation Rentals in Boston, Massachusetts 2926
Harrison Lenox Vacation Rentals in Boston, Massachusetts 645
South of Washington Vacation Rentals in Boston, Massachusetts 643