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

Captain's Quarters

This rental is off the beaten path on a private road minutes from Wells' famed beaches, local attractions, and dining hotspots. Enjoy easy access to outdoor recreational activities like kayaking, fishing, or simply strolling along the trails at Rachel Carson Preserve. This spacious rental features three bedrooms, three bathrooms, and ample living space totaling 1,536 square feet. The interior exudes a cozy ambiance, with tasteful furnishings, hardwood floors, and large windows allowing for natu

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.

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.

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.

Ogunquit Beach Cottage | Pools & Resort Amenities

Escape to a coastal cottage in Wells, Maine near Ogunquit Beach, located in the sought after Summer Village resort. Perfect for families, couples, and small groups, this Maine vacation rental with three pools and resort-style amenities offers a peaceful retreat minutes from Ogunquit and Wells Beach. Enjoy easy access to shops, dining, and beaches, then relax in a tranquil coastal setting, ideal for a New England getaway!

Secluded Rustic Log Cabin on Beautiful Frye Island

Welcome to our cozy pet-friendly log cabin on beautiful Frye Island! Relax with the whole family in this peaceful private retreat featuring 3 bedrooms and 1 full bath. Enjoy morning coffee in rocking chairs on the covered front porch, grill dinner on the back deck, and experience Maine “the way life should be.” Perfect for families, couples, and anyone looking to unwind away from the crowds.