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Jamaica Plain Vacation Rentals

Find 1,507 available offers from 5 partners
Jamaica Plain
Anytime
Guests
Jamaica Plain
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Apartment
House
Pension
Rating
4.5+
4+

Uncover an alternative Boston with a Jamaica Plain vacation rental

Vacation rentals in Boston's Jamaica Plain district are characterized by green spaces forming part of the Emerald Necklace and a diverse community. Experience another side of Boston in this verdant retreat, where you'll discover heritage around every leaf-dappled corner.

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Vacation Houses With Pools

Make a splash on your next vacation! Over 24% of in Jamaica Plain vacation rentals have a swimming pool.

Apartment  Jamaica Plain
Dec 14 - Dec 21
-83%
$2,283
$392 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Prudential / St. Botolph with Pool

Jamaica Plain, Boston, Massachusetts, United States
Free cancellation
Pool
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Apartment  Jamaica Plain
Dec 14 - Dec 21
-83%
$3,055
$529 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Prudential / St. Botolph with Pool

Jamaica Plain, Boston, Massachusetts, United States
Free cancellation
Pool
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Apartment  Jamaica Plain
Apr 5 - Apr 12
-40%
$1,187
$712 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Prudential / St. Botolph with Pool

Jamaica Plain, Boston, Massachusetts, United States
Free cancellation
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Jamaica Plain!

Apartment  Jamaica Plain
Apr 6 - Apr 13
-19%
$335
$271 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental Apartment in Brookline with Electric Fireplace

Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
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House  Jamaica Plain
Mar 5 - Mar 12
$144 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Fenway/Kenmore

Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
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Apartment  Jamaica Plain
Mar 22 - Mar 29
$132 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental Apartment in Brookline

4.7
Excellent (55 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Pet-friendly
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Jamaica Plain with their own private patios and balconies.

Condo  Jamaica Plain
May 25 - Jun 1
$399 per night
Condo ∙ 8 guests ∙ 4 bedrooms

Entire Condo in Egleston Square with Patio & Yard

5.0
Outstanding (21 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
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Apartment  Jamaica Plain
Apr 20 - Apr 27
$404 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Washington Park

5.0
Outstanding (22 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
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Apartment  Jamaica Plain
Jul 19 - Jul 26
$308 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment in St. Elizabeth\'s

5.0
Outstanding (4 ratings)
Jamaica Plain, Boston, Massachusetts, United States
Balcony
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Best Vacation Home Deals in Jamaica Plain

Save up to 46%

Condo Jamaica Plain
Nov 16 - Nov 23
-40%
$444
$265 per night
Condo ∙ 12 guests ∙ 4 bedrooms

Condo in Stonybrook with Patio

4.6
Excellent (5 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Condo Jamaica Plain
Nov 16 - Nov 23
-38%
$415
$259 per night
Condo ∙ 9 guests ∙ 4 bedrooms

Condo in Egleston Square with Patio

5.0
Outstanding (1 rating)
Jamaica Plain, Boston, Massachusetts, United States
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Condo Jamaica Plain
Nov 16 - Nov 23
-46%
$490
$265 per night
Condo ∙ 12 guests ∙ 4 bedrooms

Condo in Stonybrook with Patio

Jamaica Plain, Boston, Massachusetts, United States
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Find the ideal property from $95 per night by searching among the 1,507 options being offered in Jamaica Plain. Every one of the accommodations from our partner websites are instantaneously compared by our algorithm so you can save up to 64%.

Recommended Vacation Rentals in Jamaica Plain

Find your perfect vacation rental in Jamaica Plain: from $95 per night

Apartment Jamaica Plain
Mar 9 - Mar 16
$100 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Wonderful Apartment in Fenway/Kenmore

Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Mar 30 - Apr 6
$148 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Salisbury Road - Corey Farm

Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Mar 7 - Mar 14
$383 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Codman Square

5.0
Outstanding (4 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Condo Jamaica Plain
Feb 22 - Mar 1
-46%
$644
$350 per night
Condo ∙ 12 guests ∙ 5 bedrooms

Condo in Forest Hills / Woodbourne with Patio

5.0
Outstanding (3 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Aug 17 - Aug 24
$427 per night
Apartment ∙ 11 guests ∙ 4 bedrooms

Apartment in Franklin Field South

5.0
Outstanding (58 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Mar 30 - Apr 6
-45%
$446
$245 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment in Jamaica Hills / Pond with Patio

4.6
Excellent (41 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Nov 23 - Nov 30
$225 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Family Friendly Pleasant Rental Apartment in Lower Washington / Mount Hope with Patio & Yard

5.0
Outstanding (110 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Jun 22 - Jun 29
$119 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Lovely Apartment in Moreland Street Historic District with Yard

Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Sep 21 - Sep 28
$340 per night
Apartment ∙ 14 guests ∙ 4 bedrooms

Apartment in Dudley / Brunswick King

4.8
Outstanding (16 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Budget-friendly Vacation Rentals in Jamaica Plain

Find Fantastic yet Inexpensive Offers

Condo Jamaica Plain
Nov 30 - Dec 7
$487 per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo in Jamaica Hills / Pond with Free Parking

4.9
Outstanding (168 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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House Jamaica Plain
Apr 20 - Apr 27
-36%
$397
$253 per night
House ∙ 6 guests ∙ 3 bedrooms

Pleasant Vacation Home in Centre-South

4.9
Outstanding (18 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Apartment Jamaica Plain
Aug 17 - Aug 24
$270 per night
Apartment ∙ 7 guests ∙ 3 bedrooms

Rental Apartment in Centre-South with Free Parking

4.8
Outstanding (11 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Top-Rated Rentals and Accommodations in Jamaica Plain

Book Vacation Rental Offers with the Highest User Rating

Apartment Jamaica Plain
Nov 23 - Nov 30
$235 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Nice Rental Apartment in Brook Farm

4.8
Outstanding (136 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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House Jamaica Plain
Apr 20 - Apr 27
$627 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Jamaica Plain with Exclusive Patio

5.0
Outstanding (112 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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House Jamaica Plain
Aug 2 - Aug 9
$1,171 per night
House ∙ 11 guests ∙ 3 bedrooms

Private Vacation Home in Brookline with Patio & Grill

4.6
Excellent (29 ratings)
Jamaica Plain, Boston, Massachusetts, United States
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Popular Rental Amenities in Jamaica Plain

  • Pet-friendly (344)
  • Parking (173)
  • WiFi (1,467)
  • Washing machine (961)
  • Microwave (923)
  • Pool (409)
  • Fireplace (111)
  • Balcony/patio (315)
  • Dishwasher (597)
  • No smoking (1,399)
  • TV (1,430)
  • Kitchen (1,167)

Our search page's filters will help you find the ideal property in Jamaica Plain. In Jamaica Plain, 348 properties provide "Pets allowed". Consequently, if you travel with your pet, use the Pets allowed filter to compare these accommodations. You can also look for a vacation rental in Jamaica Plain if you enjoy soaking in the hot tub as 17 of the listed properties there provide "Hot tub."

Price and Availability Index in Jamaica Plain

Click on any bar to see price and availability information

Vacation Rental Price Information in Jamaica Plain

This graph displays the average prices for the next twelve months in Jamaica Plain. The week with the highest average prices is in September (9/21 – 9/28). During this week, a night will cost on average $522. The week with the lowest average prices is in March (3/2 – 3/9).

Rental availability information in Jamaica Plain

This graph shows the vacation rental availability rate for the next twelve months. It is harder to find an accommodation during a week of January (1/25 – 2/1), as 81% of the rentals are booked. On the other hand, the week with the most available offers is in June (6/15 – 6/22).

The Weather in Jamaica Plain

max.
Min.
37°
25°
15 days 15
max.
Min.
39°
23°
15 days 15
max.
Min.
46°
30°
14 days 14
max.
Min.
57°
41°
13 days 13
max.
Min.
66°
52°
14 days 14
max.
Min.
75°
59°
13 days 13
max.
Min.
82°
66°
12 days 12
max.
Min.
82°
66°
9 days 9
max.
Min.
73°
59°
9 days 9
max.
Min.
63°
48°
13 days 13
max.
Min.
52°
37°
10 days 10
max.
Min.
45°
32°
17 days 17
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Jamaica Plain. On average, the warmest month is July. On the other hand, you could have temperatures dropping under 23° in February. The rainiest month is December while the driest month is August.

7-Day Weather Forecast in Jamaica Plain

Mon, 4 Mar
41°
37°

30%

0 h

9 mi/h

Tue, 5 Mar
39°
39°

65%

0 h

7 mi/h

Wed, 6 Mar
55°
50°

85%

0 h

8 mi/h

Thu, 7 Mar
39°
37°

90%

0 h

21 mi/h

Fri, 8 Mar
41°
39°

0%

2 h

14 mi/h

Sat, 9 Mar
46°
42°

0%

1 h

10 mi/h

Sat, 9 Mar
42°
41°

0%

0 h

14 mi/h

Accommodations for your vacation in Jamaica Plain

Vacationers who are searching for apartment rental in Jamaica Plain have many alternatives, as they are the most typical accommodation type in this destination. Additionally, the standard size of apartment rental in Jamaica Plain is 126 m² with a median price of $367 a night. Furthermore, if you are going in a group of 4, apartment rental are a great accommodation type in Jamaica Plain, as they usually welcome this exact group size. You can also consider other property types in Jamaica Plain. House rental are, for example, another typical property type in this destination, with 76 offers to compare. The average size of house rental in Jamaica Plain is 86 m², and the average price is $691 a night.
What are the best places to discover the arts and culture of Jamaica Plain?

Gardens with history

In addition to major attractions, Boston offers more tranquil places to explore. At Forest Hills Cemetery, you can wander through a stunning sculpture garden and visit the graves of world-famous personalities such as E.E. Cummings, Anne Sexton, and suffragette Alice Stone Blackwell. Don't miss the Firemen's Memorial by celebrated sculptor John Wilson.

Where are the unique attractions in Jamaica Plain?

Relax in the city center's natural habitat

Jamaica Pond forms the center of Jamaica Plain. Part of a thousand-acre string of parks, the spot is a serene environment in which to pass the time. Go boating on the water and grill your catch on the banks as the sun sets. You'll never be far from the culture and conveniences of Boston.

Information about vacation rentals in Jamaica Plain

🏡 Vacation rentals available 1,507 rentals
💳 Possible discounts up to 64%
🌙 Nightly prices starting at $95
⭐ Popular amenities Pets allowed, Parking and Internet
🐾 Pet friendly homes 345 homes
🏊 Vacation rentals with pools 369 homes

Frequently Asked Questions

What is the average price per night for a vacation home in Jamaica Plain?

The price of a night's stay in Jamaica Plain starts at $95. If you’re interested in a apartment rental, the average price is $367 per night. A house rental Jamaica Plain will cost on average $691 per night.

How many vacation rentals are available for booking in Jamaica Plain?

Currently there are 1,507 rentals to choose from for your upcoming trip.

What amenities are most popular for vacation homes in Jamaica Plain?

Three most popular amenities for home rentals in Jamaica Plain include accommodations that have: Pets allowed, Parking, and Internet.

How many vacation rentals with pools are there in Jamaica Plain?

There are 369 vacation rentals from 5 providers in Jamaica Plain.

Are dogs allowed in vacation rentals in Jamaica Plain?

Finding a rental in Jamaica Plain that allows dogs is definitely possible, with 345 pet-friendly available.

What's the best time to travel to Jamaica Plain?

When looking for a vacation rental in Jamaica Plain, keep in mind that rainy season is typically in December or January, with August often being the driest.

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