Fitness-friendly holiday rentals in South Portland

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.

Designers Dream Home with Pool!

Discover this brand-new, beautifully appointed 2-bedroom home nestled within a secure, private community surrounded by 200 acres of preserved natural beauty. Enjoy full access to outdoor heated pools, a clubhouse featuring a game room (with ping pong, foosball, shuffleboard, and a poker room), and a fully equipped fitness center to keep you on routine. Mingle with fellow guests at the clubhouse or relax in your peaceful, private backyard, and enjoy the perfect balance of activity and serenity.

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.

Modern condo steps to the beach

Great location! 6 minute walk to the Pier, across the street from the beach! Ground floor 1 bedroom condo has 2 full size beds in the bedroom, a sofa bed in the living room and sleeps 6. The unit has a kitchenette with Keurig, refrigerator, cooktop, toaster oven, toaster, coffee pot and microwave. Please note this unit does not have an oven. Guests have access to an indoor lounge/recreation room with games, including air hockey and foosball, an on-site fitness area and laundry room.

2BR Condo across from the beach (108)

Fully furnished and clean 2 bedroom condo. 2-3 min walk to the beach. Part of the Saco Bay Condominium complex of 15 units. The unit has a kitchenette with fridge, microwave, cook top, coffee maker, toaster, etc. One full bed in each bedroom with a full sleeper sofa in the LR. Sleeps 6! Guests have access to the rec room with games, a lounge to relax; on site gym and laundry facility. Perfect location, close to the beach and downtown so you can enjoy all OOB has to offer!

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.