Skip to content
Sign up
Log in
Vacation rentals in Jamaica Island

Vacation rentals in Jamaica Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Jamaica Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Kittery Cottage - Newly built 2020
    SUPERHOSTEntire guesthouse · 6 guests · 3 beds · 1.5 baths
    Kittery Cottage - Newly built 2020

    Kittery Cottage is a private, newly built property located 1.5 miles from the charming city of Portsmouth and minutes from many of the seacoast beaches. With a ten minute walk to Kittery Foreside you have access to many restaurants and shops. The Kittery outlets are less than 2 miles away.

    What guests are saying:

    “Anyone who stays at Simone’s lovely cottage will be sad to leave. Everything is perfect and reveals how thoughtfully she and her husband Tim have put the whole place together. As other reviewers have mentioned, everything is in the details: comfortable beds and pillows, beautiful linens, fully-equipped kitchen, and the kind of amenities you’d expect to see in a boutique hotel. But on top of all this wonderfulness, Simone and Tim really stand out as exceptional hosts who could not be more helpful or kind in every respect. Couldn’t recommend more.”

  • water view property   "The Little House"
    SUPERHOSTEntire house · 2 guests · 1 bed · 1 bath
    water view property "The Little House"

    Water view cottage, very close to downtown Portsmouth. Easy 20 minute walk to Kittery's Foreside and downtown Portsmouth, NH. Perfect for a couple who wants peace and quiet or a night out in town.

    What guests are saying:

    “This place is really great! I had such a great time and it was so lovely to sit outside with my dog and enjoy the quiet and look at the water across the way. Every morning I would have my coffee and breakfast outside and toss the ball for my pup. I already wish I was back there! The attention to details from the hosts and their quick response made the whole experience that much more amazing. I will definitely be back! It is super close to Portsmouth, which is an absolutely beautiful town. It is also close to some really nice places near the cost of Maine and other parts of New Hampshire, where I went for a drive and saw some quaint neighborhoods by the water.”

  • Seacoast Suite
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bath
    Seacoast Suite

    Welcome to our traditional Maine Gambrel where you will have a private entrance, bedroom, bathroom and sitting area. The 250 sq ft suite has a queen bed, tv, cable, Wi-Fi, hot drinks, fridge, microwave, and private space. We are located just over an hour from Boston MA or Portland ME. Just 5 min to Kittery shopping outlets, half mile to a boat launch and 5-15 min drive to a number of Maine beaches. We are located in a quiet residential neighborhood. There's a cat that lives in private portion of home.

    What guests are saying:

    “Lisa's place is immaculately clean, and furnished with amenities like coffee, shampoo, soap, clear instructions for the TV, small refrigerator and microwave. Directions and arrival instructions were spot on. We only used this place to sleep, we were on the go throughout the day. It's ample space for 2 people for that. It's not a place to spend much time in during the day, if that's what you need. For our travels, the location worked well. One would need a car to get out and about here. Lisa is very responsive via email, the suite connected to her home is warm and welcoming, check-in was a code on the door~super easy and convenient for a very late arrival. Kittery is a nice community on the coast with an outlet shopping mall, which we enjoyed between travels.”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Jamaica Island vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Jamaica Island

Portsmouth Historic District top floor
SUPERHOSTPrivate room
Portsmouth Historic District top floor
Price:$135 CAD/night
Quaint, Sunny & Private - Walk to downtown
SUPERHOSTPrivate room
Quaint, Sunny & Private - Walk to downtown
Price:$107 CAD/night
Downtown Studio - Unit 1
SUPERHOSTEntire apartment
Downtown Studio - Unit 1
Price:$120 CAD/night
Family Friendly 2BR Coastal Kittery Home for 6
SUPERHOSTEntire house
Family Friendly 2BR Coastal Kittery Home for 6
Price:$338 CAD/night
Downtown Kittery Townhouse Apartment
SUPERHOSTEntire apartment
Downtown Kittery Townhouse Apartment
Price:$290 CAD/night
Downtown Gem | Group Getaway 
A+ Locale | Backyard
SUPERHOSTEntire condominium
Downtown Gem | Group Getaway A+ Locale | Backyard
Price:$310 CAD/night
Kittery Inn & Suites - Boutique 1950s Maine Motel
SUPERHOSTRoom in boutique hotel
Kittery Inn & Suites - Boutique 1950s Maine Motel
Price:$203 CAD/night
King Bed in Downtown Portsmouth | Private Suite
Entire apartment
King Bed in Downtown Portsmouth | Private Suite
Price:$171 CAD/night
Classic Cape by the Sea
SUPERHOSTEntire guest suite
Classic Cape by the Sea
Price:$269 CAD/night
Unbeatable condo/host in the heart of Portsmouth
SUPERHOSTEntire condominium
Unbeatable condo/host in the heart of Portsmouth
Price:$232 CAD/night
Charming Southern Maine Water View Coastal Home
SUPERHOSTEntire house
Charming Southern Maine Water View Coastal Home
Price:$233 CAD/night
Great Island Inn - King Studio Apartment - Garden View
SUPERHOSTApartment room
Great Island Inn - King Studio Apartment - Garden View
Price:$476 CAD/night
Show all