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Jamaica Plain Vacation Rentals & NearbyHoliday Homes

Find Vacation Rentals in or near Jamaica Plain. Find vacation rentals in Jamaica Plain, Boston.

From US $288

Roslindale village condos

8.9 (185 Reviews) Apartment

Apartments • Free on-site parking • Pet friendly

Winthrop Town Boston Logan International Airport • In Jamaica Plain · 2.8km to center

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From US $575

Comfort Stay

8.8 (24 Reviews) Apartment

The entire place is yours • 111 m² size • Free on-site parking

Boston Dorchester • In Jamaica Plain · 4.2km to center

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From US $555

Victorian Condo

9.2 (15 Reviews) Apartment

The entire place is yours • 130 m² size • Free parking

Boston Jamaica Plain • In Jamaica Plain · 1.0km to center

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From US $723

NEW! Boston Entire House Near MBTA, 3 Mi to Fenway!

7.8 (6 Reviews) Apartment

The entire place is yours • 307 m² size • Balcony

Boston Roxbury • In Jamaica Plain · 3.7km to center

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From US $81

Homestay in Boston Fields Corner Area - 30 days M

8.4 (233 Reviews) Homestay

Breakfast • Free parking • Free WiFi

Boston Dorchester • In Jamaica Plain · 4.5km to center

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From US $365

Unique & Peaceful Boston Home, Ideal for 2026 World Cup Visitor, Free Parking

9.4 (73 Reviews) Apartment

The entire place is yours • 88 m² size • Kitchen

Boston West Roxbury • In Jamaica Plain · 5.0km to center

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From US $142

Boston Monadnock Properties

8.6 (315 Reviews) Homestay

Free WiFi • Non-smoking rooms • Family rooms

Boston Dorchester • In Jamaica Plain · 4.2km to center

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From US $269

Cozy Boston Getaway Apartment Perfect for 2026 World Cup Visit, Free Parking

9.1 (57 Reviews) Apartment

The entire place is yours • 11 m² size • Kitchen

Boston West Roxbury • In Jamaica Plain · 5.0km to center

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From US $231

Stylish Studio the Fenway Neighborhood - Unit #106

8.2 (62 Reviews) Apartment

The entire place is yours • 14 m² size • Kitchen

Boston Fenway • In Jamaica Plain · 4.4km to center

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From US $473

Brand New 4BR House 20Min Downtown Boston

9.9 (34 Reviews) Holiday_home

The entire place is yours • 186 m² size • Free on-site parking

Boston Roxbury • In Jamaica Plain · 3.0km to center

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From US $337

Spacious 4BR Near Subway, Sleeps 8per Easy Access to Downtown Boston

8.7 (55 Reviews) Apartment

The entire place is yours • 139 m² size • Balcony

Boston Jamaica Plain • In Jamaica Plain · 1.8km to center

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From US $225

Modern Studio in Historic Boston - Unit #401

8.3 (57 Reviews) Apartment

The entire place is yours • 14 m² size • City view

Boston Fenway • In Jamaica Plain · 4.2km to center

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From US $397

Perrin Place Unit 1

8.7 (39 Reviews) Apartment

Apartments • Kitchen • City view

Boston Roxbury • In Jamaica Plain · 3.4km to center

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From US $233

Stylish Studio in Fenway Neighborhood - Unit #306

9.1 (37 Reviews) Apartment

The entire place is yours • 14 m² size • Free WiFi

Boston Fenway • In Jamaica Plain · 3.7km to center

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From US $246

A Stylish Stay w/ a Queen Bed, Heated Floors.. #26

8.2 (47 Reviews) Apartment

The entire place is yours • 23 m² size • Free WiFi

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.2km to center

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From US $516

Beautiful 2Bedroom in the South End Boston - Ground Level Unit

8.6 (39 Reviews) Apartment

The entire place is yours • 33 m² size • Free WiFi

Boston South End • In Jamaica Plain · 5.0km to center

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From US $246

A Stylish Stay w/ a Queen Bed, Heated Floors.. #36

7.9 (45 Reviews) Apartment

The entire place is yours • 23 m² size • Free WiFi

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.2km to center

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From US $309

A Stylish Stay w/ a Queen Bed, Heated Floors.. #21

7.8 (45 Reviews) Apartment

The entire place is yours • 28 m² size • Free WiFi

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.4km to center

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From US $217

Large Studio w/ Queen AND Sofa Bed..#38

8.9 (31 Reviews) Apartment

The entire place is yours • 33 m² size • Free WiFi

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.4km to center

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From US $231

Stylish Studio in Historic Boston - Unit #406

9.4 (27 Reviews) Apartment

The entire place is yours • 15 m² size • Free WiFi

Boston Fenway • In Jamaica Plain · 3.7km to center

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From US $217

A Stylish Stay w/ a Queen Bed, Heated Floors.. #24

7.9 (43 Reviews) Apartment

The entire place is yours • 28 m² size • Balcony

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.4km to center

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From US $528

Perrin Place Unit 3

8.8 (29 Reviews) Apartment

The entire place is yours • 11 m² size • Balcony

Boston Roxbury • In Jamaica Plain · 3.4km to center

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From US $367

Symphony Suites by Thatch

8.7 (30 Reviews) Apartment

Apartments • Balcony • Free WiFi

Boston Fenway • In Jamaica Plain · 4.3km to center

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From US $259

Stylish Studio in Historic Boston - Unit #204

8.4 (32 Reviews) Apartment

The entire place is yours • 24 m² size • Free WiFi

Boston Fenway • In Jamaica Plain · 3.7km to center

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From US $356

Forest Hill condos -Boston

9.4 (21 Reviews) Apartment

Apartments • Private parking • Pet friendly

Boston Franklin Park Zoo • In Jamaica Plain · 1.5km to center

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From US $950

Parking - Private Entrance - King Beds

9.9 (16 Reviews) Apartment

The entire place is yours • 84 m² size • Free on-site parking

Boston Back Bay • In Jamaica Plain · 4.8km to center

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From US $321

Luxurious Studio in the Heart of Boston

8.6 (24 Reviews) Apartment

The entire place is yours • 28 m² size • City view

Boston Fenway • In Jamaica Plain · 3.7km to center

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From US $217

A Stylish Stay w/ a Queen Bed, Heated Floors.. #14

8.0 (27 Reviews) Apartment

The entire place is yours • 28 m² size • Balcony

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.4km to center

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From US $201

A Stylish Stay w/ a Queen Bed, Heated Floors.. #35

8.1 (25 Reviews) Apartment

The entire place is yours • 28 m² size • Free WiFi

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.2km to center

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From US $116

Peaceful 1BR easy commute, urban suburban mix feel in Boston

8.8 (70 Reviews) Homestay

Free on-site parking • Free WiFi • View

Boston Hyde Park • In Jamaica Plain · 4.4km to center

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From US $267

NEW! Boston Condo Near MBTA, 3 Mi to Fenway! (U2)

8.6 (17 Reviews) Apartment

The entire place is yours • 102 m² size • Free on-site parking

Boston Roxbury • In Jamaica Plain · 3.7km to center

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From US $735

Spacious Apartment in Boston

8.6 (10 Reviews) Apartment

The entire place is yours • 81 m² size • Free WiFi

Boston Allston • In Jamaica Plain · 4.5km to center

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From US $309

A Stylish Stay w/ a Queen Bed, Heated Floors.. #11

8.5 (9 Reviews) Apartment

The entire place is yours • 28 m² size • Free WiFi

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.2km to center

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From US $78

Boston Queen Bedroom

8.4 (274 Reviews) Apartment

Apartments • View • Free WiFi

Boston Dorchester • In Jamaica Plain · 4.5km to center

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From US $217

A Stylish Stay w/ a Queen Bed, Heated Floors.. #32

7.9 (8 Reviews) Apartment

The entire place is yours • 23 m² size • Free WiFi

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.2km to center

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From US $227

Newly Renovated 2bed, 2bath private apartment, minutes from Boston.

7.5 (8 Reviews) Apartment

The entire place is yours • 250 m² size • Kitchen

Boston Isabella Stewart Gardner Museum • In Jamaica Plain · 3.2km to center

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About Jamaica Plain Vacation Rentals on NearbyHoliday

Looking for vacation rentals in Jamaica Plain? Compare top options in Boston.

Find a Vacation Rental and Holiday Home in Jamaica Plain. Compare 185 family vacation homes, private villas, cottages, cabins, and condos in Jamaica Plain.

NearbyHoliday makes it easy to discover vacation rentals in Jamaica Plain that work well for families, groups, and longer stays when you want more room than a standard hotel setup.

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Frequently Asked Questions About Jamaica Plain Vacation Rentals

There are a lot of vacation rentals in Jamaica Plain. If you plan on staying in the Jamaica Plain area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Jamaica Plain: