Vacation rentals in Southport Island

A comfortable outdoor seating area is arranged on a wooden deck, featuring a rectangular table surrounded by cushioned chairs. The space offers views of the surrounding trees and water, providing a serene setting for relaxation.

4.95 out of 5 average rating, 19 reviews

Southport, views of Christmas cove (Boothbay area)

Set on a hill above Christmas cove, enjoy water views from the deck or launch kayaks from the cove. Inside is a refreshed kitchen and full bath. Bedroom 1 has a Queen bed and half bath, bedroom 2 has a bunk and a twin bed and the loft has a king bed with half bath. Nearby are the Southport general store, Hendricks head beach, and Cozy’s dockside/Robinson’s wharf restaurants. Tour the Alpaca farm or drive to nearby Boothbay for a boat tour or the botanical gardens. Great for families and friends!

LocationFamilyQuiet

4.99 out of 5 average rating, 138 reviews

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

Home in Georgetown

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

LocationFamilyLaundry

A three-story cottage is nestled on a hillside, showcasing large bay windows and a charming balcony adorned with decorative elements. Lush greenery surrounds the home, complementing its gentle color scheme against a clear blue sky.

4.92 out of 5 average rating, 106 reviews

Maine Cottage/Your Year-Round Destination

The Stowaway sits on 5.5 private acres atop a hill with breathtaking waterviews from every level. This pet-friendly, 3 story home offers 4 bedrooms, 3 baths & sleeps 8. Perfect for family getaways, milestone celebrations or relaxing escapes, the cottage combines comfort & style! The carriage house sleeps 4 more & together the property can host events of 50-150 guests (event fee $9000). Explore Maine's beauty year-round from summer by the sea, to colorful fall foliage, to snowy winter holidays.

FamilyValueComfort

The exterior of a historic two-story home is showcased, featuring a white façade and a black metal roof. Large windows allow for ample natural light, and a manicured lawn with small shrubs complements the entrance. A pathway leads to the welcoming front door.

4.89 out of 5 average rating, 44 reviews

Cozy Harbor Waterfront

This historic home was once the lightkeeper’s house and has been beautifully renovated with four bedrooms and three bathrooms. Located on idyllic Southport Island, the home feels peaceful and tucked away while still being easily accessible by a swing bridge, so you are never truly isolated. It is a short walk down to Cozy’s Dockside Restaurant where you have a perfect view of all the boats in the harbor. It’s a 10-minute walk to the Southport General Store which has great coffee and food.

LocationFamilyAmenities

Superhost

A cozy living area is viewed through large glass sliding doors. A wooden coffee table is placed in front of a dark seating area, complemented by two plush pillows. A colorful piece of wall art adds vibrancy to the light-toned walls, enhanced by natural light from the outdoors.

Cabin in Georgetown

4.99 out of 5 average rating, 228 reviews

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

ValueFamilyGrill

5.0 out of 5 average rating, 30 reviews

An outdoor deck is furnished with a patterned tablecloth covering a dining table accompanied by six wooden chairs. Two lounge chairs are positioned nearby, offering views of the calm water, boats, and greenery. A flowering centerpiece adds a touch of color to the table.

Home in Georgetown

Five Islands Waterfront Retreat

Your ultimate Maine vacation home: Five Islands charm, modern comfort & ocean views. Escape to Five Islands, in our newly renovated home. Designed for relaxation, this property boasts a custom kitchen, expansive deck, air conditioning, and panoramic views of Five Islands. Enjoy unparalleled convenience: 30 second stroll puts you at Maine's iconic Lobster Shack, a public dock, kayak rentals, and a general store. Perfect for families, couples, or anyone seeking a Maine coastal experience.

LocationValueKitchen

5.0 out of 5 average rating, 17 reviews

Waterfront cottage with private dock Southport, ME

Enjoy an island getaway on a private island off Southport, ME yet only 10 minutes to Boothbay Harbor. The house sits on an acre of waterfront property with views of cozy harbor. House comes with a private dock (seasonal) and 2 kayaks. Master on first floor with King bed. Two additional bedrooms have a bunk and 2 twin beds. Enjoy a fully stocked kitchen so you can feel at home. Close to everything - Hendricks Head Beach, The Southport General store, restaurants, and Botanical Gardens.

FamilyLocationBeach

5.0 out of 5 average rating, 150 reviews

The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.

Cabin in Freeport

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

FamilyLocationComfort

4.98 out of 5 average rating, 466 reviews

The tree dwelling is elevated among sturdy trees, featuring a wraparound balcony surrounded by foliage. Large windows invite natural light, offering views of the lush surroundings. A rope bridge connects to another elevated structure, enhancing the unique treehouse experience.

Treehouse in Georgetown

Modern Treehouse w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

FamilyValueKitchen

5.0 out of 5 average rating, 106 reviews

A modern kitchen is illuminated by a rustic light fixture with exposed bulbs, enhancing the open layout. Quartz countertops extend through the space, complemented by stainless steel appliances. A vase of mixed flowers sits on the counter, with a scenic view of the ocean visible through large windows.

Home in Boothbay Harbor

Pinkham Cove - Water Front Cottage

Authentic oceanfront Maine home, with stunning views and amazing sunsets. Located on Pinkham Cove at the mouth of Boothbay Harbor. Experience the village of BBH , hiking trails, Botanical Gardens and explore the tranquility of Maine. This is the perfect getaway cottage. Enjoy the deck and beach access. The home was recently remodeled. The kitchen is a gem with quartz countertops and Bosch appliances. Curl up by the cozy fireplace, enjoy the amazing harbor view!!

FamilyLocationBeach

5.0 out of 5 average rating, 128 reviews

The rocky coast is lined with spruce trees, showcasing natural contours along the shoreline. Calm blue waters gently lap against the rocks, while a clear sky enhances the scenic view. A few homes are nestled among the trees, blending harmoniously with the coastal landscape.

Home in Georgetown

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

FamilyLocationView

The exterior of a modern house is depicted, featuring a unique architectural design with asymmetrical angles and a combination of white and dark elements. Surrounding trees provide a natural setting, and large windows reflect the surroundings, enhancing the house's connection to nature.