Vacation rentals in Jamaica Island

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Top-rated vacation rentals in Jamaica Island

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Guest favorite

Guest suite in Kittery

4.96 out of 5 average rating, 126 reviews

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.

Sep 29 – Oct 6

G$20,767 GYD per night

Guest favorite

Guest suite in Kittery Point

4.94 out of 5 average rating, 231 reviews

Hot Tub & Spa-Like! Pamper Yourself This Spring!

Seaside Romance just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub outside 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; catch views of the lighthouse, spectacular sunsets, historical sites, Bistro 1838, 5-minute drive to the beach, world-class restaurants in Kittery or Portsmouth, 10-min to the famous Kittery Outlets

Mar 2 – 9

G$36,124 GYD per night

Guest favorite

Cottage in Kittery

4.95 out of 5 average rating, 139 reviews

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...

Oct 27 – Nov 3

G$35,244 GYD per night

Guest favorite

Guest suite in York

4.96 out of 5 average rating, 497 reviews

Ogunquit Tranquil Setting near Perkins Cove

Private entrance with patio. Two night weekends. A nicely appointed suite with a luxury queen bed. 1/2 mile walk to Perkins Cove and 1 mile to Ogunquit Center and Maine's # 1 beach, where you can savor the outstanding restaurants and gift shops. Walk to scenic Perkins Cove and Marginal Way for breathtaking views of the Atlantic. New England's most treasured scenic coastal walk. On site - Acupuncture - Facial rejuvenation - Red-light Therapy - Reiki Master treatments. (additional fee).

Mar 4 – 11

G$30,929 GYD per night

Guest favorite

Apartment in Newmarket

4.96 out of 5 average rating, 198 reviews

Spacious private Studio & Experienced SuperHosts!

Move-in ready, furnished & fully equipped apartment near downtown & river in working class, generally quiet pocket neighborhood. Separate entrance, spacious sleeping/living room, lots of windows, DOUBLE bed, couch, AC, TV, cable & WiFi. We disinfect spaces with UVC lamp & hospital-grade cleaning products as part of our deep cleaning & disinfection protocols, often closing between guests. Distance check-in. WALK to local fresh market, restaurants, cafes & bars for takeout or eat in.

G$19,806 GYD per night

Guest favorite

Apartment in Kittery

4.99 out of 5 average rating, 141 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-23-70

Aug 2 – 9

G$43,379 GYD per night

Guest favorite

Apartment in Kittery

4.99 out of 5 average rating, 174 reviews

Goose Point Getaway (a boutique AirBnB experience)

Our Goose Point Getaway is a newly constructed, 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 on Goose Point which loops around Spruce Creek.

Aug 27 – Sep 3

G$62,301 GYD per night

Guest favorite

Guest suite in Eliot

4.97 out of 5 average rating, 145 reviews

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!

Oct 2 – 9

G$25,209 GYD per night

Guest favorite

Home in Kittery

4.99 out of 5 average rating, 253 reviews

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

Feb 5 – 12

G$75,195 GYD per night

Guest favorite

Apartment in Rye

4.96 out of 5 average rating, 135 reviews

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.

Sep 10 – 17

G$26,660 GYD per night

Guest favorite

Cottage in Rye

4.91 out of 5 average rating, 120 reviews

Seacoast Solo

Location? You got it. Quiet, rural spot, 5-15 min to beaches, towns, restaurants, arts, historical sites, and outdoor explore options. Easily enroute to MA, ME, and VT for more. Here is a small cozy room for one traveler. Guest room with separate entrance, bath, forest facing semi private deck, and parking. This weathered home has been in the family since built in 1908. Style, original eclectic shabby chic :)

Mar 3 – 10

G$21,644 GYD per night

Guest favorite

Guest suite in Kittery

4.9 out of 5 average rating, 745 reviews

Seacoast Oasis (NH & ME)

The perfect gateway to the NH and ME Seacoast! We are located a few minutes from the highway, ten minutes from the beach and 60 minutes from Logan Airport. Break up your drive to Baxter State Park, or Acadia. Visit nearby Portsmouth, NH (10 min.), Mt. Aggie (10 min) or the Kittery Outlets (5 min.) We are minutes from everything, and yet in a tranquil, wooded setting!

Jun 14 – 19

G$25,813 GYD per night