Holiday rentals in Jamaica Island

4.97 out of 5 average rating, 146 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.

4.95 out of 5 average rating, 158 reviews

Cottage in Kittery

Cozy Maine Cottage by the Sea

Cozy one bedroom beach cottage for rent in picturesque Kittery Point, ME. The cottage is located in a quiet coastal community over looking Chauncey Creek, but is just minutes to all the seacoast has to offer. Short drive to many area beaches (Hampton, NH; York, Ogunquit, Wells, ME). Better yet, walk to Kittery's own quiet Seapoint Beach, paddle at the bottom of the hill in the two kayaks provided or just relax on the peaceful deck with a book, a beverage and the gas fire pit for ambience...

4.97 out of 5 average rating, 228 reviews

Home in Kittery

#1 Home in Kittery Foreside - PVT Harbor View Deck

Escape to Kittery, Maine for a peaceful getaway! Our 3-bedroom, 3-bathroom home sleeps up to 10 and is just a short walk from the popular Kittery Foreside, offering a range of shopping and dining options. Perfect for those seeking a quiet vacation, our home is equipped with modern amenities and comfortable furnishings. Enjoy a fully stocked kitchen, comfortable living room, and 3rd floor deck for relaxation. Book now for a stress-free vacation filled with delicious dining and retail therapy!

Superhost

4.8 out of 5 average rating, 647 reviews

Unit 3 Studio - Historical Building Market Square

Under new ownership and recently updated, spacious studio located in the heart of downtown Portsmouth in one of the original historic buildings. With great natural light on 4th floor, we are a walk to everything Portsmouth has to offer. Kitchen includes all customary amenities plus Keurig coffee maker with k-cups. Enjoy your coffee or morning treat at the kitchen bar. NOTE: AC units during summer months (June - September); this unit is located on the third floor, few flights of stairs

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

Flat in Kittery

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, 133 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!

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, 222 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!

4.96 out of 5 average rating, 151 reviews

Flat in Rye

Rye Studio with 4 min walk to Wallis Sands Beach .

We offer a one bath cozy studio-efficiency apartment equipped with a kitchenette. It is only a 4-5 minute walk or a quicker bike ride to beautiful Wallis Sands State Beach. After you enjoy a day at the beach, come back and relax with a cold drink on your circular patio and gaze out over a sea of ferns in the state forest at the rear of our property. You can cook out on your grill or take a short drive to downtown Portsmouth.

Superhost

4.81 out of 5 average rating, 357 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

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Popular amenities for Jamaica Island holiday rentals

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Other great holiday 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.

4.86 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!

4.99 out of 5 average rating, 82 reviews

Tugboat Vista | 2 Bedroom | Downtown Portsmouth

JulieRating, 5 stars5 days ago

Cute little place right in the heart of town! It was a perfect stop off for us in the way to Acadia. Pictures are accurate. Place is very cozy but it worked for a short trip for 5 of us.

4.85 out of 5 average rating, 54 reviews

Flat in Greenland

The Silver Fox Den

JosephRating, 5 starstoday

Very clean and comfy place. Great for our weekend getaway.

Flat in Dover

4.86 out of 5 average rating, 7 reviews

Small apt with a fenced yard

JessicaRating, 5 stars3 weeks ago

We were looking for a place close to Hampton Beach and this airbnb exceeded our expectations. It was about a 25 minute ride from the boardwalk and it was perfect for us, especially because we were just there for a show over night. The place was clean, comfortable, quiet and felt homey. We will definitely be staying again when visiting the area.

4.93 out of 5 average rating, 213 reviews

Flat in Kittery

Private Studio Apartment, Water Views & Walkable

GigiRating, 5 stars9 months ago

absolutely perfect spot! great parking and you can walk so easily over the bridge to Portsmouth. which is a good thing because there's no parking in portsmouth. an Eclectic town and also Kittery is right down the street so you have two towns you can walk to. so many great restaurants to choose from. Jill was responsive and very helpful. she went above and beyond with this sweet little apartment. it was just wonderful! everything was so comfortable. I would highly recommend it. we'll be back

4.96 out of 5 average rating, 92 reviews

Home in Kittery

Newly renovated cottage

CristinaRating, 5 stars2 weeks ago

Camille’s place was a home away from home. Very centrally located to shopping, dining and sightseeing with quick access to several beaches. Beautifully renovated with nice touches like extra pillows on beds and fluffy towels in the bathroom. Perfect for a couple or a small family; with a nice outdoor area for a fire, grilling or just relaxing. We enjoyed the proximity to all of the spots we wanted to see and the bright and airy feel of the space overall. Definitely looking forward to returning.☀️