Fitness-friendly holiday rentals in South Portland

Beach Home w/ Exclusive privacy in Southern Maine

Modern with current renovations, custom built home. Walk to Drakes Island beach and Laudholm Farm. This house is comfortable for a range of people and needs. In the 6000 square foot house you'll find many great features like 30 foot ceilings in the great room w/ plenty of space for each person. The house features spacious bedrooms along with split duct air conditioning and heating units. The deck overlooking Laudholm Farms comes with new patio furniture for relaxing. House Only sleeps 16 ppl

Entire Home 5 mins from Downtown

5 minute walk to downtown. 5 beds (2 queens, 2 doubles, one large daybed) 3 bedrooms, 2.5 baths, home theater with blackout shades, built in bar, large yard and driveway, detached home gym with full weight sets and built in audio, and laundry room. This 3 story home is a 5 minute walk to downtown and local beaches and has air conditioning and heat in every room. Comes with a beach cart filled with chairs, umbrella, towels and all you’ll need for your trip to the sandy shores of OOB. Pet Friendly

Wells Maine Home with a View

Our Contemporary Cottages, at Seagull, gracefully sits on a grassy 11 acre bluff with panoramic views of the Rachel Carson Refuge and the Atlantic Ocean. This tastefully decorated cottages offer air conditioning, heat, ceiling fans, fully equipped kitchen with dishwasher, gas grill, cable TV, skylights, and a large screened in porch with sliding glass doors opening into the livingroom and master bedroom. Cottage has a great pool/hot tub. WIth ocean view and comfortably accommodates six guests.

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 8. 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.

1 Bedroom Suite steps to the Beach!

Tastefully decorated and furnished. Recently remodeled, one bedroom unit located just across the street from Old Orchard Beach. The unit has a fully equipped kitchenette, microwave, toaster, coffee maker and all the basic necessities for your stay. First floor unit, sleeps 4 people with one queen size bed and a queen size pull out couch. Perfect location, close to the Pier, downtown and Palace Playland Adventure. Please note that our unit is located near the train tracks that run thru OOB.

Family Friendly Kennebunk Pond Lakefront Retreat

Time of Wonder is a family-friendly vacation rental in coastal Maine, ideal for up to 6 guests. Nestled on Kennebunk Pond, this 3-bedroom, 2-bath home features a fire pit and hammock by the lake. Relax by your private dock while listening to loons and enjoying breathtaking sunsets. With two paddle boards available, lake fun is at your fingertips. Discover the charming towns of Kennebunk and Kennebunkport, along with their beautiful beaches. Plus, Kennebunk Pond is great for ice fishing too!!!

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.

Sweet 2-story 1910 Bungalow near Portland, Beaches

This lovely, 2-story Sears-Roebuck 1910 bungalow with its own entrance has sea breezes in summer and fireside coziness in winter. Borrow bikes to explore nearby Town Landing beach, Audubon, and forest trails. Walk three blocks to a local bakery for coffee. The upstairs bedroom with a king bed looks out on white pines. Furnishings have been updated, but the original woodwork is untouched. Just 4 miles up the coast from Portland, it's a wonderful base for exploring Maine's towns and beaches.

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

NEW Luxe Coastal Retreat | Hot Tub & Fire Pit

Brand-new luxury coastal home minutes from Portland’s Old Port. Relax in the 8-person hot tub, gather around the fire pit, and enjoy a beautifully appointed chef’s kitchen designed for memorable group getaways. A private deck overlooks the garden with a play area, play kitchen, crib, pak n play and fire pit, while a covered gazebo shelters the year-round spa. Perfect for families, friends, or remote work, with easy access to beaches, Portland’s dining scene, and waterfront attractions.

Lake Arrowhead, Maine Waterfront House

Amazing 4 bedroom/4 bathroom lakefront house! Lake Arrowhead is a perfect family destination for all seasons. In the summer, lake life has great swimming, boating, fishing, and ATV trails. The fall season is amazing for hiking, biking and ATV'ing, fishing, and leaf peeping. Winter months offer great snowmobiling, skating and fishing, and cross-country skiing. Perfectly located for day trips into Portland, Kennebunk, Freeport, Kittery, and Old Orchard Beach.

Captain Vacation House by beach, shopping, pets

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.