Fitness-friendly holiday rentals in South Portland

Coastal Dream · Firepit · Hot Tub · Chef's Kitchen

Escape to Portland’s Coastal Maine ‘s Seaside Sanctuary—a brand-new, custom-built luxury retreat just built. Nestled in heart of Portland, this award-winning design offers sleek open-concept elegance with high ceilings, floor-to-ceiling windows, and a gourmet kitchen. Unwind in the 8 person hot tub under a gazebo, cozy up to large linear fireplace, or explore nearby beaches, trails, ski, and dining. Perfectly blending luxury with adventure, this retreat promises an unforgettable Maine getaway.

Lakefront | Dock + Fire Pit Near Sebago & Portland

Experience the charm of Forest Lake just 28 mins from Sebago & Portland! Swim, kayak, paddleboard, or unwind on your private beach. Enjoy BBQs & bonfires in the spacious yard under the stars. Sleeps 6. Fully stocked home with 72" OLED TV, PS5, surround sound, and fast Wi-Fi. New heat pumps ensure comfort year-round. Whether you're after lakeside peace or easy access to southern Maine's best spots, your perfect escape awaits. Explore local trails, beaches, breweries, & classic Maine lake towns.

Home on Historical Island and Saco River (+ Gym)

This four bedroom 1.5 bath home on historic Springs Island in Saco has both the charm and amenities that you need for your next vacation. Stay in this restored new englander on the Saco River in Biddeford where you can enjoy the water at home or you are just a short drive to the many of the most traversed beaches in Maine. You are also within walking distance to thriving downtown Biddeford, its mill district, and all of its restaurants and shops. Guests get access to a private gym as well.

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront

Peaceful lakeside getaway, 2 hrs from Boston. Lake views from living area w/ spectacular screened-in porch. Lake freezes in winter- great for ice fishing, x-country skis, snowmobiles, etc. Morning coffee while sitting by the lake, calm afternoons in a lake-side hammock. Private lake access on property, w/ a dock, swimming area, canoes, kayaks! Lake is deep enough off the dock for swimming! New 6-person hot tub with a view! 1 hour to Conway, NH & White Mtns. 45 min to ocean beaches.

Local Landmark! Gorgeous Downtown Historic Home

This exceptional landmark property is your home away from home while visiting the Port City! The home is #46 on Greater Portland Landmarks coveted tour of Portland, but it's your first stop and your portal for exploration, relaxation, and authenticity. Built in 1865 and made available to you now, this meticulously maintained and locally celebrated property in the heart of Portland's historic downtown is your cornerstone for a truly incomparable and unforgettable Portland, Maine experience.

The Hill's on Buttonwood

We are out of the baby stage and ready to share our home while away. Our home is a great house for entertaining or just relaxing without feeling cramped. There are places for everyone, from the heated pool, the patio, or outdoor activities, to the many living/sitting rooms, gym or theater/game room. Located just minutes from the airport and minutes from downtown in the historic Stroudwater district or Portland. Sitting on nearly an acre on a small cul-de-sac of similar stately homes.

A Commanding View of Town of Old Orchard Beach

Enjoy Atlantic Ocean views from the lawn, deck, porch, or airy loft of this charming Old Orchard Beach rental. Perfectly located across from Walgreens for easy access to essentials. Each bedroom features a private exterior door, inviting the refreshing ocean breeze. Enjoy exclusive use of the entire property, complete with four parking spaces and two showers. Explore “The Pier,” an iconic boardwalk, brimming with dining, and scenic charm. Your perfect coastal getaway awaits.

Family Friendly Kennebunk Pond Lakefront Retreat

This family-friendly vacation rental in coastal Maine is perfect for 6 guests. Located on Kennebunk Pond, the 3-bedroom, 2-bath house features a fire pit area and hammock, by the lake. Nothing is more relaxing than listening to loon calls and enjoying stunning sunsets from your private dock. With two paddle boards available, swimming and fishing are a breeze. Explore the charming towns of Kennebunk and Kennebunkport and their lovely beaches. Also, Portland is just 25 miles away!

Captain Vacation House by beach, shopping, pets EV

Ahoy Mate! Welcome to Captain Vacation House, a nautical home inspired by a lifetime of a travel on the seven seas. Located in Scarborough, Maine accessible easily to the beaches, the Maine Mall shopping area, downtown Portland restaurants and activities and an easy jump onto all major highways. There is a sunny office that can be used as a fifth bedroom and a dedicated work space. With 4 Bedrooms, ten people can sleep comfortably. Cots and crib are available.