Fitness-friendly holiday rentals in South Portland

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

Well Stocked House Private Yard Hot Tub Near All

Close to Beach, Shopping and Highways! Colonial on wooded lot w/ new hot tub with a nod to the U-Maine fans! Fun, well stocked 4 bedroom, 3 bath, work area and gym on dead end street. A nod to the Black Bear fans and friends throughout. Designed for comfort the friends and family gathering for any occasion. Whether arriving by car or plane, we are very easy to access. When here the house is easy to get to beaches (<15 min.), Maine Mall and all major shopping (< 10 min.) and Portland (<12 min.)

Seaside Winter Retreat | Chef Kitchen•Hot Tub•Fire

Welcome to your modern brand new custom built Coastal Escape! Relax in the private hot tub, gather at the fire pit, and cook like a pro in the fully equipped chef’s kitchen. Bedrooms: Four restful rooms with fresh linens and blackout shades. Outdoor perks: Spacious yard, grill, and Adirondack seating. SuperFast Fiber Optics Wi-Fi & Smart TVs Home Theater Washer/dryer Self-check-in Minutes to Portland’s Old Port, beaches, breweries, and hiking trails. Book now for year-round Maine adventure!

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 in the w

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 7. 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.

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.

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.