Find Vacation Rentals in Jamaica Plain

We have 1,994 properties to choose from
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Popular Jamaica Plain Vacation Rentals

Find the perfect Jamaica Plain vacation rental

House Jamaica Plain
from $348 per night
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

Jamaica Plain, Boston, Massachusetts, United States
Agoda
Details
House Jamaica Plain
from $79 per night
2 guests ∙ 2 bedrooms

House

Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
Condo Jamaica Plain
from $278 per night
9 guests ∙ 5 bedrooms

Condo

4.8
Outstanding(19 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
Apartment Jamaica Plain
from $153 per night
3 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(15 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
Apartment Jamaica Plain
from $255 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

116 m² Apartment

4.8
Outstanding(159 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
Apartment Jamaica Plain
from $376 per night
11 guests ∙ 4 bedrooms

Apartment

4.9
Outstanding(67 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
Apartment Jamaica Plain
from $63 per night
2 guests ∙ 4 bedrooms

Apartment

Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
House Jamaica Plain
from $397 per night
House ∙ 10 guests ∙ 4 bedrooms

214 m² House

5.0
Outstanding(62 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
Apartment Jamaica Plain
from $264 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

149 m² Apartment

4.7
Excellent(76 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Vrbo
Details
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Vacation rentals with a balcony

Condo  Jamaica Plain
from $277 per night
9 guests ∙ 5 bedrooms

Condo

4.8
Outstanding(16 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
Vrbo
Details
Condo  Jamaica Plain
from $235 per night
3 guests ∙ 2 bedrooms

Condo

Jamaica Plain, Boston, Massachusetts, United States
Balcony
Vrbo
Details
Condo  Jamaica Plain
from $222 per night
6 guests ∙ 3 bedrooms

Condo

5.0
Outstanding(4 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
Vrbo
Details
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Cabins and Homes With Fireplaces

Apartment  Jamaica Plain
from $488 per night
Apartment ∙ 8 guests ∙ 4 bedrooms

260 m² Apartment

5.0
Outstanding(88 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Fireplace
Vrbo
Details
Apartment  Jamaica Plain
from $254 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

116 m² Apartment

4.8
Outstanding(151 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Fireplace
Vrbo
Details
House  Jamaica Plain
from $306 per night
House ∙ 6 guests ∙ 3 bedrooms

134 m² House

4.9
Outstanding(78 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Fireplace
Vrbo
Details
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Vacation rentals with Wi-Fi

House  Jamaica Plain
from $1,151 per night
House ∙ 14 guests ∙ 7 bedrooms

372 m² House

5.0
Outstanding(88 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Internet
Vrbo
Details
Apartment  Jamaica Plain
from $375 per night
11 guests ∙ 4 bedrooms

Apartment

4.9
Outstanding(70 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Internet
Vrbo
Details
House  Jamaica Plain
from $307 per night
10 guests ∙ 4 bedrooms

House

Jamaica Plain, Boston, Massachusetts, United States
Internet
Vrbo
Details
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Frequently Asked Questions

What is the price of vacation rentals in Jamaica Plain?

Usually, a stay in Jamaica Plain starts at $61 per night.

Is it possible to find vacation rentals in Jamaica Plain?

Currently, there are 1,994 vacation rentals available for you to compare and book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Jamaica Plain

Looking for the perfect vacation rental for your Jamaica Plain getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Jamaica Plain offers 203 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 170 properties with high-speed WiFi Internet, 19 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget. For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $8116 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Jamaica Plain has 203 gorgeous homes with 58 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com. Search properties from 8 vacation rental sites in Jamaica Plain where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 115 HomeAway rentals, 31 Booking.com short term rentals and 23 TripAdvisor vacation rentals.

Popular Day Trips Near Jamaica Plain

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