Holiday rentals in Jamaica Pond

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Top-rated holiday rentals in Jamaica Pond

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Top guest favourite
A spacious studio features a comfortable bed with a decorative pillow against the warm wood headboard. Soft, natural light fills the room, highlighting the wooden floors and cozy seating area. A kitchenette is visible in the background with cabinets and a small coffee setup.
Guest suite in Boston
4.92 out of 5 average rating, 244 reviews

Ann and Esther's Cozy Studio near the Heart of JP

This airy and light private studio is set in a beautiful, secluded backyard/garden. Close to restaurants, shops and acres of green space. Your reservation confirms that you have read "Other Things to Note" in The Space section below and "House Rules" before booking. Guests can only book for themselves. We are 5-7 minutes from the 39 bus and 15 from the Orange line. There is microwave, fridge, counter w/ sink. No stove or cooking. DO NOT request >6 mos ahead. Insta-Book when calendar opens

Top guest favourite
A cozy living room features a dark sofa adorned with decorative pillows, positioned beside a glass coffee table. Light fixtures cast a warm glow, while elegant artwork and a decorative chest add character. Natural light filters in through large windows, enhancing the tranquil ambiance.
Home in Jamaica Plain
4.93 out of 5 average rating, 183 reviews

Fully-Equipped, Private 1st Floor 1-Bed/1-Bath Apt

This is a 1st floor private unit nestled in a serene urban enclave. Conveniently surrounded by public transit, shops, and dining options within a 0.6-mile radius. Originally a charming Victorian abode, meticulously renovated in 2016 to seamlessly blend historic elegance with contemporary comforts. Revel in a fully-equipped kitchen, private rear porch, and a tranquil bedroom boasting a plush queen-size bed. Tailored for your short or extended stay needs, with central air for optimal comfort.

Top guest favourite
A micro studio space features a wall-mounted television positioned near a built-in bookcase. Natural light enters through two large windows, illuminating the minimalist decor and a cozy, spacious bed with crisp white bedding. A small white table and chair enhance the functionality of the room.
Flat in Boston
4.9 out of 5 average rating, 924 reviews

AKBrownstone: cozy private studio by T

🏠 Live like a local: designed micro studio, in a classic Boston Brownstone 🌳 Your very own cozy 170sqft (15sqm) pied-à-terre on the ground level, overlooking Victorian homes on a tree lined street 🚇 5 mins walk to the T (subway), 3rd stop to Back Bay city center or go on bike & walking path 👣 Walk to Longwood Medical Area (Harvard Medical, etc), Museums (MFA, Gardner), Northeastern, & Fenway Park 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

Guest favourite
The front of a Victorian farmhouse is framed by lush greenery and colorful flowers. Stone steps lead to a welcoming porch adorned with potted plants and decorative furnishings. A sunny atmosphere highlights the charming details of the home's exterior and surrounding landscaping.
Guest suite in Boston
4.88 out of 5 average rating, 395 reviews

Light and airy separate apt in funky Jamaica Plain

The apt. has 4 twin beds in our quirky 1880 Victorian farmhouse in central Jamaica Plain. Fast transportation to downtown Boston, Cambridge, and LMA. Separate entrance, kitchen and bathroom, shared deck. PLEASE NOTE: there are STEEP STAIRS to the unit, and a NARROW SPIRAL STAIRCASE inside the unit. Ceiling in the bathroom is LOW. People with mobility issues may find these difficult. Bulky luggage may have to stay on the main floor. PLEASE read description carefully before booking.

Top guest favourite
The private rooftop deck features a shaded seating area with sectional sofas adorned with cushions. Potted plants add greenery, while views of neighboring buildings and trees are visible in the background under a partially cloudy sky.
Apartment in Boston
4.94 out of 5 average rating, 341 reviews

Boston Rooftop Retreat

A beautiful, fully renovated historic brownstone with a private rooftop deck overlooking the city. Come be inspired by this colorful and romantic artist studio filled with books, records, art and all the comforts of home in a quiet neighborhood with lovely views. Conveniently located a short walk from public transportation, world class universities, medical institutions and museums. About a 22 minute walk to Fenway Park, MGM Music Hall and other great attractions!

Top guest favourite
A spacious living area is highlighted by a large leather sectional sofa adorned with colorful cushions. An upholstered ottoman sits in the center, surrounded by vibrant artworks on the walls. Natural light filters through the windows, illuminating the warm wooden flooring.
Townhouse in Boston
4.95 out of 5 average rating, 110 reviews

Modern JP Townhouse w Parking - quiet & convenient

Hi! Welcome to my beautiful place in the coolest part of Boston! Mine is a well-appointed two-story townhome on a quiet street in fabulous JP. My place has its own off-street parking spot, beautiful windows and light, central heat and air conditioning, and all modern appliances including dishwasher, garbage disposal, gas stove and oven, microwave, and even instant hot water! (Please note that my house is not child-friendly and is available for two people maximum.)

Top guest favourite
A modern living area features a comfortable sectional sofa and a large flat-screen TV mounted above a stylish stone wall. A Peloton bike is positioned nearby, with light filtering through two windows adorned with sheer curtains.
Flat in Boston
4.87 out of 5 average rating, 230 reviews

1st Flr 2BR unit with parking + steps from train

Modern ground floor apartment with all updated interior and furnishings. 2 blocks from Stony Brook Orange Line stop. Close to all Boston Universities (Northeastern, Boston University, Boston College, Emerson, Suffolk University, Simmons, etc) as well as all major Boston hospitals (Brigham & Womens, Beth Israel, Dana Farber, Mass General, Boston Medical, etc). Home is also close to Fenway Park, Boston Common, TD Garden, Downtown Boston and the Financial district.

Guest favourite
A cozy corner is visible, featuring an upholstered chair beside a vintage table lamp. Two skylights allow natural light to fill the space. A small table holds plants, and colorful rugs create a warm atmosphere while leading to an inviting bedroom beyond.
Guest suite in Boston
4.96 out of 5 average rating, 311 reviews

Private & serene getaway in beautiful JP

Quiet, private & serene walk-up 3rd floor apt. Separate entrance, full bath & kitchenette. Bright and spacious. 3 blocks from the center of JP with great restaurants and shopping. 5 min. walk to the 39 bus to Longwood Area and Back Bay. 15 min. walk to the Orange Line T (subway); 1/2 block from Jamaica Pond. 5 min. walk to the Arboretum. Our space is NOT good for people with large luggage! Tons (truly) of street parking, no permit or restrictions.

Top guest favourite
A spacious living area is furnished with a dark sofa, a decorative wall art piece, and a round coffee table. Bar stools are positioned near the kitchen, which is visible in the background. Natural light enters through windows covered by green curtains.
Flat in Boston
4.93 out of 5 average rating, 430 reviews

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

Top guest favourite
The exterior of a charming green house is showcased, featuring multiple gabled roofs and a porch with decorative railings. Large windows on the first floor allow ample light, while a balcony extends from the second floor, surrounded by lush trees in warm autumn colors.
Guest suite in Boston
4.96 out of 5 average rating, 212 reviews

Light-filled Private Suite on Beautiful Street

In the heart of hip JPVillage. Peaceful - and private - 3rd floor suite - in our home. This is a great place to be based for visiting Boston: attending conferences, seeing your kids, the various hospital complexes and the sights. Two minute walk to Jamaica Pond and five minute walk to one of Boston's park gems, the Arnold Arboretum. Plenty of Hubway bicycle kiosks as well as bus and "T" access close by.

Guest favourite
An airy living space features high ceilings with slanted angles and large windows allowing natural light to filter in. Wooden floors are complemented by simple furnishings, including a dining table with chairs and a bright arrangement of flowers. Nearby, cabinets provide ample storage.
Home in Jamaica Plain, Boston
4.91 out of 5 average rating, 169 reviews

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Guest favourite
A spacious living area features a comfortable brown leather sofa and a blue armchair. A wooden coffee table sits in the center, and a 55-inch television is positioned on a console against a light blue wall. Large windows allow natural light to fill the space.
Apartment in Boston
4.97 out of 5 average rating, 113 reviews

2 Bedroom by Longwood Medical Hospitals

Perfect location for those visiting Longwood Medical area hospitals. Walkable area with a train that goes anywhere in the city, directly across from tons of green space. Enjoy a restful night sleep on a king sized memory foam mattress or full memory foam in second bedroom. You will be entertained with Roku & streaming (55in TV). Updated kitchen stocked with coffee.

Popular amenities for Jamaica Pond holiday rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Boston
  6. Jamaica Pond