Fitness-friendly holiday rentals in Kennebunk

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

Captains 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 scenic riverbank. This spacious rental features three bedrooms, three bathrooms, and ample living space spread across 1536 square feet. The interior exudes a cozy ambiance, with tasteful furnishings, hardwood floors, and large windows allowing for natural light. Thi

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

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.

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!!!

2 BR house, close to Ogunquit, w/ AC + golf cart!

One of the largest air-conditioned, 2 bedroom houses at the luxury Seaglass Village. Our cottage is located at the end of a quiet cul de sac, a short walk to the pools, hot tub, clubhouse, gym, and tennis court. We offer parking for 2 cars, a gas grill, in-unit washer and dryer, cable, wifi, desks, and a dining room table for 6 people. Beach and bath towels, pool noodles, and toiletries provided. We also offer a golf cart for free - which many other places charge an extra $400/week to use.

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.

Paradise Found Minutes from Ogunquit | Heated Pool

Your Year-Round Oasis in Seaglass Village close to Ogunquit Maine! Nestled within a picturesque resort community in the heart of Maine, "Paradise Found" is more than just a cottage; it's your ultimate year round retreat. Immerse yourself in comfort and convenience with newly updated furniture, a modern kitchen featuring granite countertops, central AC and heating throughout the home, an in unit washer and dryer, wifi, cable and a delightful golf cart to explore this coastal haven.

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!

Entire Home in Sunny Saco + Gym

This 3 bed 2 bath restored stone ranch in Saco awaits your next vacation to Coastal Maine. Here you will enjoy the best of both worlds, staying in a quiet community making memories in the private back yard while being just a short drive to Maine's most sought after beaches including OOB, Ferry Beach, and Hills Beach, to name a few. Also walkable to Saco's Historic downtown and just a short drive to thriving Biddeford. Kennebunkport and Portland are just a short 20 min drive too.

Spectacular 3 Bed Resort Cottage

This newly built cottage features a modern design with all the cozy features and amenities of home. There’s plenty of room for the family in this 3 bedroom, 2 bath home nestled on a more private lot and just a short walk to the resort pools and clubhouse. Explore the history of a beautiful coastal Maine community that's known for its spectacular rocky coast, soft sandy beaches, and renowned boutique stores and restaurants just down the street.

*New 4BR Beach House|Sleeps 9|York| Cape Neddick

Enjoy a cozy coastal winter retreat! This beautifully updated 4-bedroom, 3-bath home on Shore Road combines comfort and charm, just minutes from Ogunquit, Marginal Way, Perkins Cove, and Harbor Beach, ideal for a relaxing getaway with family and friends! 🏖️ Cape Neddick Beach - 7-10 min walk 🏖️ Short Sands Beach - 5 min drive 🏙️ Downtown York - 7-10 min drive 🎢 York’s Wild Kingdom Zoo & Amusement Park - 6 min drive