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

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.

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.

This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!

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.

The Ogunquit House Downtown | Walk 2 beach HotTub

ULTIMATE OGUNQUIT BEACH HOUSE! Renovated & fully equipped private oasis located in the heart of beautiful downtown Ogunquit, ME Park on site & walk to the beach, restaurants/bars & village shops all in under 5 minutes! Ideal for families, friends or couples looking for a perfect beach getaway. Our goal is to provide you with everything you need so there’s less time spent on essentials & renting equipment. Queen, double bunk bed, & 2 pull out couches can sleep 6 comfortably!

Serenity on the Cove Non Smoking Property

Spacious comfortable apartment on Mill Cove in West Bath, Maine. Sit outside or on the dock, kayak or boat, swim when the tide is in. Mill Cove leads to the ocean. Walking trails and coastal towns nearby. This non-smoking property comes with all appliances, washer- dryer, and private entrance. In addition to the King Bed, there is a queen sofa bed. There is an outdoor grill; and a water filtration system for drinking water. Quiet privacy. Well behaved dog with owners approval.