House holiday rentals in Naples

Family & Friends Retreat*Hot Tub*Game Room*King Be

MAKE MEMORIES together in the school's large classroom which is an impressive gathering spot for the whole group with the modern kitchen, massive dining table and comfy living room. Endless entertainment in the brand new barn game room! This lovingly restored schoolhouse is a unique mixture of historic charm, warmth, character and modern ease. Gather outside on the 7 acre property for a cookout, chat by the fire or relax in the sauna and hot tub after hiking, swimming, boating, skiing, dining or

Waterfront Sebago Cove Camp- pet & kid friendly!

Looking for the perfect lakeside escape? Just 7 minutes from the Naples Causeway, this family-friendly, waterfront retreat in Sebago Cove offers all the charm and convenience of a Maine camp vacation. With its private dock, stunning lake views, and a plethora of indoor and outdoor activities, this home is the ideal spot for relaxation and memory-making. Whether you’re kayaking, fishing, swimming, enjoying the fire pit, or competing in air hockey matches, this home has something for every guest!

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Perched at the summit with complete privacy and sweeping views of Mount Washington, the White Mountains, and Woods Pond, Mainely Mountain Views is a 4-bedroom Maine retreat that earns its name the moment you step onto the deck. Perfect for large groups with easy access to Pleasant Mountain, Long Lake, Sebago Lake, and the Saco River - plus hiking, mountain biking, and snowmobile trails. Watch the sun set over the mountains from the hot tub. The kind of place you come to relax, unwind, and enjoy.

Cabin Fever Reliever

Have fun with the family at this waterfront property. Placed on 1.5 acres on the Songo River with 500' of private shoreline. Laze in shade, take a swim, fish off the dock, or bring your boat and explore Long Lake, Brandy Pond, & Sebago Lake all from this one central location. This picturesque log cabin has a massive front porch, perfect for relaxing in an Adirondack chair with a cool drink. Located moments away from the amenities of the Naples Causeway & Bridgeton, but still secluded and quiet.

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.

Lake Region Comfort, Close to Everything!

Come enjoy the Highland Lake area known for its clear water, boating and fishing! Just a few miles away from Shawnee Peak which offers both day/night skiing. Also a few miles away is downtown Bridgton where there is the Magic Lantern movie theater and the drive-in theatre. Downtown also offers shopping and many options for superb dining. This single-family residence will provide you with 3 bedrooms, a newly renovated kitchen, sliders to deck, bathroom, living room with large panel tv and WiFi.

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.

Best Views on Long Lake - 4 Season Home

Limited Summer 2026 Friday-Friday weeks remaining! Landscaping upgrade photos coming soon! Enjoy lakefront views from the deck + swim, kayak, paddle board, fish or boat from the private dock. Catch amazing sunsets around the campfire or visit the nearby Naples Causeway. In winter, curl up by the fire or enjoy snowshoeing, ice fishing + ski at Pleasant Mountain. Sleep peacefully in two spacious bedrooms upstairs + one on the ground floor (+ bonus basement space with 2 full futons for teens.)

*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!

Bridgton Getaway

Come enjoy the peace, quiet, and comfort of this lovingly renovated 4 bedroom home. Located on 13 acres with views of Pleasant mountain. Close to lakes, downtown Bridgton, 10 minutes from Shawnee Peak, and 20 min from the White Mountains. Sit in the hot tub and take in the sounds of nature. Curl up in front of the fire or watch a movie on the big screen TV. Perfect for large groups. Sprawling property with space for outdoor games, picnicking, and bonfires. This place is a true getaway!

Beautiful Views, Bridgton Maine

Vacation getaway for all seasons. Enjoy mountain and golf course views from this 3,800 square foot home. Pleasant Mountain Ski Area beckons from 10 minutes away. Sunday River Ski Area is 40 minutes away. Or bring your clubs and test your skills on the challenging 18 holes at Bridgton Highlands Golf located steps away. At the end of the day, sip on an adult beverage in the spacious timber frame great room and marvel at the field-stone fireplace that stretches from floor to the ceiling.

Tri-Lake Escape: Brandy Pond

Tri-Lake Escape offers the ultimate waterfront getaway with direct access to Brandy Pond, Long Lake, and Sebago Lake. This charming retreat is perfect for families, couples, and outdoor enthusiasts looking to relax and explore. Enjoy stunning lake views, a private dock, and endless activities, including swimming, boating, fishing, and kayaking. Unwind on the spacious deck, gather around the fire pit, or take a short drive to downtown Naples for dining, shopping, and local attractions.