Jamaica Plain holiday rentals

We found 75 holiday rentals — enter your dates for availability

Discover a selection of 11 homes, 21 apartments and other holiday rentals in Jamaica Plain that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a garden. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Jamaica Plain?
Houses are the most popular style of holiday home in Jamaica Plain, according to our data. Even if you have a different idea in mind, Stayz has holiday homes in loads of shapes and sizes. Explore our options to find your perfect Jamaica Plain pad.
How much does it cost to rent a holiday home in Jamaica Plain?
Length of stay, property type and time of year are some of the things that can influence the price of a holiday home. Simply add your travel dates to find your perfect match. From quaint country cottages to expansive luxury villas, all Stayz holiday homes provide incredible value.
How much does it cost to rent a beach house in Jamaica Plain?
Prices for beach houses in Jamaica Plain differ depending on the type and size of the property and when you plan to travel. All you need to do is enter your travel dates into Stayz and the number of guests to view your options and prices. From there you can use the filters to refine your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Jamaica Plain?
Good news. There are. You’ll find 27 holiday homes that welcome pets in Jamaica Plain on Stayz. Our furry kids deserve a break too, so simply use our search function for pet-friendly holiday homes to book a property where your pooch can join the fun.
Can I rent a house with a pool in Jamaica Plain?
Mark the “pool” box in our filter tool and take your pick of four houses with private pools in Jamaica Plain on Stayz. Lazy soak or races and ball games? Leisure time is up to you when your holiday property has a swimming pool.
What are popular home amenities in Jamaica Plain?
A swimming pool, tennis and a nearby river top the list of most popular home amenities in Jamaica Plain. Whether you’re taking to the road as a party of one, with your better half or as a family group, Stayz will help you find a holiday home that fits your style with all the features you need.
Are there large group holiday homes in Jamaica Plain?
Yes, you can pick from one of 12 holiday properties in Jamaica Plain that can host five or more guests. From family getaways to special occasions like birthday parties, these stays have enough space to spend time with the people you love.
Are there holiday homes in Jamaica Plain that welcome kids?
Bring the entire group together for an unforgettable adventure in Jamaica Plain at one of our 27 family-friendly holiday properties. These stays provide conveniences that are just perfect for getaways with youngsters, including laundries, multiple bedrooms and entertainment units. Just click on the “Properties good for families” filter box and decide on your favourite.
What are the top attractions for families in Jamaica Plain?
Keep the kids amused at these fabulous family-friendly attractions in Jamaica Plain:

  • New England Aquarium
  • Museum of Science
  • Boston Tea Party Ship

Are there one-bedroom holiday homes in Jamaica Plain?
There are four one-bedroom properties in Jamaica Plain to choose from. A one-bedroom holiday home is a wonderful option if it’s just the two of you or if you’re holidaying alone. Add in more space, privacy and convenience compared to a standard hotel, and you’ll be sure to have a memorable trip.
Can I find two-bedroom holiday homes in Jamaica Plain?
Take off with your besties and experience complete comfort and privacy in one of the 11 two-bedroom holiday homes Jamaica Plain has to offer.
Are there holiday homes with WiFi in Jamaica Plain?
Whether you want to stay in touch with the news, write a few emails or post a pic to social media, there are 10 holiday homes with WiFi in Jamaica Plain. Check the “WiFi” box when searching on Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Jamaica Plain?
Jamaica Plain has 24 holiday homes where you’ll be able to wind down in air-conditioned comfort. To book a property on Stayz with this perk, choose your travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Jamaica Plain?
You should check with the Jamaica Plain holiday home you want on Stayz as the age limit differs. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in Jamaica Plain for?
How long you can book a holiday home in Jamaica Plain differs according to the property. Just enter your selected dates to view a list of options offering extended stays. With lots of features like washing machines and kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to discover the perfect place to call your home away from home in Jamaica Plain.

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