Vacation rentals in Southport Island

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

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.

Private Sauna+Near Beach+FirePit+Forest View+Pond

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat & Backup Automatic Generator * 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.

Cozy log cabin on private pond, near Reid St Park!

Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Sebasco Sprucewold Cabin@ the Beach

This quaint and cozy log cabin built in the 1940's is located in the summer colony of Sprucewold. It is just about 1 mile from downtown Boothbay Harbor. At 750 square feet, this adorable cabin is suited for no more than 4 people. You will have access to a small, private, sandy beach; a rare find on the rocky coast of Maine. There is so much to see and do in the Boothbay area. Life slows down and there is no better place to experience that "Maine, the way life should be" feeling.

Modern Treehouse with hottub + Water Views

Experience the airiness of life up among the pines. This unique tree dwelling, with its own private attached wood-fired cedar hot tub, is perched atop a 21-acre wooded hillside sloping to beautiful water views. Enjoy the view from the wood-fired cedar hot-tub or the king size bed--through a wall of windows. This treehouse is cozy all year round, especially in winter. Located in a classic coastal Maine village with Reid State Park's beaches and the famed Five Islands Lobster Co.

Cottage in the woods on Ocean Point

Secluded getaway in the woods close enough to see and hear the ocean and catch amazing sunsets. Charming 1BR + Loft, 1BA cottage situated among an acre of Ocean Point fir trees providing privacy and a quiet get away. Less than 100yd walk to the shore, beach and path at Grimes Cove, Ocean Point Inn Restaurant & Bar, and daily activities at the community "casino" building with playground, tennis, pickle ball, basketball, and Sunday softball. Harbor is 20 mins away for exploring.

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

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!!

The Rowe House

We love our little coastal house. It's in Boothbay Harbor within walking distance of Spruce Point and Downtown. The entire house is yours! 2 bedrooms, full bathroom, washer/dryer, a fully furnished living room, kitchen and dining room. Hardwood floors downstairs and carpet upstairs. Perfect for couples, solo adventurers, business travelers, small families and pets. NOTE: WE DO CHARGE $40 NON REFUNDABLE PET FEE PER PET DURING YOUR STAY.

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.