Family-friendly holiday rentals in Southport

Rosie's Hideaway By the Sea

Rosie's Hideaway By The Sea is in a lovely turn of the century Victorian farm house filled with paintings by Maine artists and beautiful hardwood floors. The front yard has gorgeous shade trees and a stone wall. Fabulous views of the harbor is a short walk away. . Follow the road along the harbor and you'll end up downtown Boothbay Harbor where all the shops and restaurants are. While we love children and animals, the space is not appropriate / safe for children under 8 or pets of any kind.

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.

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.

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.

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.

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!!

Chic 1-Bedroom at the Heart of Boothbay Harbor

Come and Stay in Oak Ledge! Oak Ledge is a beautifully-renovated 2-storey 1-bedroom apartment in the heart of Boothbay Harbor. Bedroom and Bathroom on the upper level. 2-night minimum 5-night maximum This is an adults only listing. Sorry, no pets. Our friendly rescue dog "Oscar" roams freely on the property. Off-street parking for one car. Self check-in. Smart TV with streaming - remember to have your log-ins.

Battersea Cottage - quintessential Maine! ALL new!

Everything about this cottage is brand new! This quaint Boothbay Harbor cottage has been completely renovated. Fresh and new without sacrificing the charm of a Maine coastal village home. Located in the area of West Harbor, this cottage is within walking distance of the rocky shore of Mill Cove as well as the village center. Nestled in the trees on an ample lot, Battersea has everything you could need for a perfect getaway!

Sail Loft: Oceanfront Apartment on a Pier.

Experience a one-of-a-kind waterfront escape at the Sail Loft in Boothbay Harbor! This unique 1-bedroom apartment is located directly over the water in a working marina, offering stunning panoramic views from every window. It feels like being on a private yacht. Perfect for a couple's getaway, you're just a short walk from all the downtown shops and restaurants. Enjoy a truly memorable stay with free parking included.

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

The Rowe House

Charming Coastal Cottage Walk to Harbor – Perfect Couples Escape w/ Private Setting 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.