Vacation rentals in Jamaica Island

4.97 out of 5 average rating, 147 reviews

Guest suite in Kittery

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.

4.99 out of 5 average rating, 264 reviews

The Tugboat - KingBed, Waterfront! Parking!

Location Location! Welcome to the Tugboat! A Tastefully decorated 1 Bedroom w/King Bd located on the Historic Waterfront of Portsmouth. All the shops, restaurants, rich history, festivities, and nightlife are right here a few steps away! Enjoy the sunsets over the river while sipping a glass of wine on the front steps before going out. Open the Dutch Door to watch the Tugboats and get all the smells from the restaurants surrounding you. It will be hard not to eat out every night.

4.97 out of 5 average rating, 275 reviews

Guest suite in Kittery

Coastal home on the water

A nautical look and feel is what this coastal home away from home offers. A detached from the main house in-law apartment is the perfect get away. Located directly on the water, on an estuary called Spinney Creek, part of the Piscataqua River. Bring your kayak, fishing rod, or sit back enjoy a cold beverage and watch the sunsets by the fire pit. Best water views ever. It is 1.5 miles to downtown Portsmouth, NH and less then 1 mile to the beautiful rejuvenated downtown Kittery.

4.99 out of 5 average rating, 215 reviews

Fresh + Modern Garden Level Kittery Studio

This stylish garden level modern apartment is well located in Kittery and provides local recommendations from the hosts that live in the upper unit. The kitchen is fully stocked with all your cooking and coffee needs, and includes an under-counter fridge, under-counter freezer, and microwave. The house is less than a mile to downtown Kittery and the shipyard gates, and less than two miles to Portsmouth. (All very walkable with sidewalks) Kittery STR License Number: ABNB-24-67

Guest suite in Kittery Point

4.95 out of 5 average rating, 294 reviews

Coastal Maine & 10 Min to Portsmouth+ Hot Tub Too!

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

5 out of 5 average rating, 134 reviews

Home in Kittery Point

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

5 out of 5 average rating, 209 reviews

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

4.98 out of 5 average rating, 132 reviews

Apartment in Eliot

Peaceful Studio Farmstay with Scenic Views

Welcome to our charming studio apartment overlooking a picturesque dairy farm and flower gardens. Nestled in the peaceful countryside of Eliot, this spacious yet affordable retreat offers rustic elegance without compromising comfort. Our farm is home to chickens, ducks, and geese, adding to your authentic rural experience. Guests are welcome to feed the animals, watch the cows graze, and unwind in the beauty of nature—all just 20 minutes from the beach.

4.98 out of 5 average rating, 294 reviews

Home in Kittery

Family Friendly 2BR 1 BA Coastal Kittery Home

Welcome to our cozy family guest home in beautiful Kittery, just 2 miles from downtown Portsmouth. Nearby are beaches, great restaurants, historic sites, boutique shopping, shopping outlets and Portsmouth Naval Shipyard. This home has 2 bedrooms, 1 bathroom, a fenced in yard for up to 4 adults with their children. This house is set up nicely for families of all ages. Dogs welcomed with permission from the owner. STR License # ABNB-22-50

4.97 out of 5 average rating, 223 reviews

Guest suite in Eliot

The Rafters

The Rafters is a finished studio space above our late 1800s barn. It has beautiful light and feels like a getaway as soon as you open the door. With the proximity to Portsmouth, NH and local attractions in Maine, you can escape to the Rafters, but with the ease of being so close to everything. Our neighborhood is beautiful and you can walk down to many spots that overlook the Piscataqua River. Or Uber home from a fun night in Portsmouth!

Superhost

4.81 out of 5 average rating, 358 reviews

Studio w Parking in Portsmouth Historic District

Sunny private studio in historic townhouse, with private entrance, kitchenette, and PARKING INCLUDED in the heart of the Historic Downtown District. Perfect for a couple's getaway, week+ work stay, or local family 'guest room'. One block from Market Square, amidst restaurants and shopping. 2 blocks to Prescott Park, Strawbery Banke, Portsmouth Harbor, and public parks. *Site of Daniel Webster's home. Operator license #100004

4.98 out of 5 average rating, 234 reviews

Goose Point Getaway (a boutique AirBnB experience)

Our Goose Point Getaway is a one bedroom apartment located in the lower level of our home. Completely private with its own entrance and no shared space with the owners. You can see a peek of Spruce Creek (a tidal inlet) from the bedroom window and deck. The space has been designed to offer a relaxed, comfortable get away experience. Our home is located in a quiet neighborhood which loops around Spruce Creek.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Jamaica Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Jamaica Island

5 out of 5 average rating, 14 reviews

New Beautiful Studio above a two car garage

AlexRating, 5 stars4 months ago

Vergie, was a great host. She was easy to communicate with, the place was clean and matched the description. We stayed during the winter months so walking to downtown Portland wasn’t in the cards for us but definitely doable during warmer weather. The morning our stay was ending there was a snowstorm over night, 6-7” of snow fell. Vergie proactively coordinated for the driveway to be cleared including our car so getting out at our convenience was unencumbered. Would recommend, would stay again.

4.84 out of 5 average rating, 81 reviews

Heart of Kittery Foreside, Waterfront Apartment

SamuelRating, 5 stars1 week ago

I would highly recommend staying here to anyone visiting Kittery or Portsmouth. Perfect location right in the middle of everything that Kittery has to offer with a nice view of the water. Easy, scenic walk over the bridge into Portsmouth for an excursion. Danny and Linn had amazing recommendations for where to eat, I could eat Lil's crullers every morning and it's right across the street! The space was ideal for myself and would also be perfect for a couple. Clean, tidy, and had everything that you could need. Hope to get the chance to come back someday soon.

4.86 out of 5 average rating, 66 reviews

Cottage in Portsmouth

Portsmouth Waterfront Cottage

KarenRating, 5 stars1 month ago

Larry's place was beautiful. There was a great view of the inlet from both downstairs and upstairs. It's within walking distance to downtown Portsmouth, which is great because parking can be tricky in town. But we had a long day driving so we just enjoyed sitting out on the balcony and relaxing. Having a bedroom with living room upstairs AND downstairs was perfect as it afforded my daughter and I each our own space. The only problem was we didn't have more than one night to stay!

4.98 out of 5 average rating, 49 reviews

Guesthouse in York

The Tree Haus in York Heights

SarahRating, 5 stars3 days ago

Meredith and Matt’s guest house was the perfect spot for a weekend getaway in York! They were kind, communicative, and made check in and check out seamless. We loved the neighborhood and exploring the restaurants and beaches in York.

4.97 out of 5 average rating, 64 reviews

Guesthouse in Portsmouth

Heron's Nest on North Mill Pond

KiahRating, 5 stars2 weeks ago

We had a great stay at the Heron's Nest—the location is walkable to downtown and peaceful with views of the water. Mary Ellen and Walter were very welcoming when we met them. We would stay here again, and I've already recommended it to others!

4.97 out of 5 average rating, 141 reviews

Cabin in Kennebunk

HotTub/5min to K-port, Pet friendly, @anchorunwind

MinjiRating, 5 stars1 week ago

Such a beautiful and peaceful place! Definitely one of the cleanest places I’ve ever stayed. I’d love to come back!

5 out of 5 average rating, 81 reviews

Historic Portsmouth at Your Doorstep

LisaRating, 5 stars2 weeks ago

Simply delightful! Laurie’s place was clean, comfortable and well equipped. The neighborhood and garden views are beautiful and the off street parking was readily available. The sheets and pillows were high quality and the bed was comfortable (is a firm mattress). We generally prefer a soft mattress, but this one was still adequate. The kitchen was well equipped, and we were able to easily cook breakfast every day. We didn’t arrive until 10 PM on the night of check-in and it was a wonderful surprise to find soft drinks, water, beer and wine in the fridge! Highly recommend 😍