Holiday rentals in Naples

Kayak to the Causeway-50s cottage with modern vibe

Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.

Lakeside Story - Log Cabin, Fire Pit, Beach!

Built in 1963, this classic Maine Log Cabin is a real charmer! You'll love the warmth of the natural wood interior and exposed beams throughout, which all add to character that could never be recreated in this one-of-a-kind property. Steps to a spacious semi-private beach on Long Lake, and an easy walk to the Naples Causeway, the cabin is a perfect home base for a family vacation, or a group getaway. Fully updated amenities including super-comfy beds, streaming media, and a cook's kitchen.

Long Lake Leisure Chalet

This Leisurely Chalet is ready for 6 guests. Located 2.5 hours from Boston, 45 mins from Portland and 20 mins from Shawnee Peak/Pleasant Mountain. This house can accommodate many different types of groups. It's furnished for fun no matter what your age. TVs, games, 2 min walk to the lake and a 5 min walk to the bar. You are guaranteed to have a good time at this vacation house. Send us an inquiry if you have any questions. We are happy to answer any questions about the house or the area.

Cabin at Sunshine on Long Lake

You can't get any closer to Long Lake! The Cabin at Sunshine is a few short steps to the sandy bottom of this crystal clear lake. The Cabin at Sunshine was recently remodeled to give the home a relaxed, lake feeling with unobstructed views of Long Lake. All new mattresses and appliances throughout the cabin. A new Webber grill is outside for those days when you want to spend every second outside. Walk into Naples for ice cream, cocktails, shopping, entertainment, boat rentals, and dinner.

Newly Built Studio Apartment

This studio apartment is a part of a newly constructed Carolina Barn home. Located on the first level adjacent to the 2-bay garage, the apartment has it's own private patio entrance which bestows a designated gas grill for your use. The secluded property is adjoining miles of walking paths for hiking and mountain biking. A grocery store, pharmacy, restaurants and the Naples Causeway and Boardwalk are only a half mile away. The apartment is completely furnished with utilities included.

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Private Sebago Cove Escape – Dock, Kayak & Firepit

NEW for 2026- Waterfront Sebago Cove Retreat- close to Naples Causeway and wedding venues! Enjoy 125 ft of private lake access for swimming, fishing, kayaking & canoeing. This 2-bed, 2.5-bath home blends modern comfort with retro charm, featuring AC, a fully equipped kitchen, and a cozy living room with a fireplace. Relax on the deck, at the fire-pit, or at the end of our private dock. Minutes from beaches, hiking, dining, and family adventures—perfect for a peaceful Maine getaway!

Trickey Moose Family Retreat | Fire Pit Kayaks

Enjoy 4 seasons of fun with shared access to Trickey Pond and use of 2 kayaks, large deck, fire pit, gas grille, backyard, wood stove, air hockey, ping pong table, close to skiing, snowmobile trails, boating, hiking & much more. *** Last Minute Special: 7/13-7/15 (3 nights) *** Beautiful open concept house with loft and cathedral ceilings is perfect for large families with a well appointed kitchen, fast Wi-Fi, laptop friendly workspace, central AC, jacuzzi, free parking.

The Birches on Long Lake at Rickers Resort

BRAND NEW PICKLEBALL. COURTS The Birches on Long Lake sits beside the woods with a large private campfire with a "peek a boo" view of the lake. The Birches is just 1 of our 4 Airbnb units here at: Rickers Resort. Surrounded by the beauty of nature. The Birches is a large spacious unit an Our Beaches have long been considered the best private beach on this 11 mile pristine lake. you would have the house all to yourself. see also The PINES, THE FERNS AND RICKERS RIDGE.

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Paradise in the Lakes Region

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Summer fun (beaches & watersports galore), winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make every moment a memory!

The "Bay of Naples Cupola Inn"

It's rare to find a place that's both historic and one-of-a-kind! Welcome to the original Cupola from the Bay of Naples Hotel which was built in 1899. This Cupola is the only remaining piece of history left from the majestic Hotel which overlooked the Naples causeway up until 1960 when it was demolished. The Cupola has been fully renovated to accommodate luxury and rich history. It is 620 square feet and has been constructed with post and beam to have 2 levels.