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Villa holiday rentals in Cumberland County

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Top-rated villa rentals in Cumberland County

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Villa in Sebago

New! Northwest Eagle Nest Limit 9

368 - 3 Bedrooms, 3.0 Baths (Sleeps 9) OCCUPANCY LIMIT 9 - Waterfront home has 3-bedroom 3 bath. This stunning waterfront property offers the perfect blend of serenity and modern living. Prime waterfront location on Northwest River Road with direct access to Sebago Lake. Open concept living and dining area with breathtaking views of the water. Expansive deck overlooking the lake. Easy access to boating, fishing, and swimming right from your backyard. Waterfront/Lot Description: Flat Lot.

A cottage exterior is shown, featuring wooden shingles and large windows that provide natural light. Two blue adirondack chairs are positioned on the lawn, alongside a picnic table on a flat grassy area, surrounded by trees and under a clear blue sky.
Villa in Windham

Boomfish Limit 5

518 - 2 Bedrooms, 1.0 Baths (Sleeps 5) OCCUPANCY LIMIT 5 - A waterfront 2 Bedroom 1 Bath on Highland Lake in Windham. Enjoy lake living while being less than 30 minutes from Portland. The cottage has an open living space with views of the lake from the living room and kitchen. Both bedrooms are on the main floor with full beds. There is also a loft with 2 twin beds. A nice-sized flat lot with a fire pit near the water. Shallow entry is great for swimming. Also enjoy the 2 kayaks provide.

The cottage exterior features a single-story design with large windows allowing for ample natural light. A well-maintained lawn surrounds the structure, and a patio area is visible with comfortable seating set against a backdrop of tall trees.
Villa in Sebago

Mary's Lakeview - Limit 10

MARY'S LAKEVIEW 4 Bedrooms,1 Bathrooms OCCUPANCY LIMIT 10 guests - This 4 bedroom 1 bath cottage has a large yard, views of Sebago Lake, and just 0.2 miles from Nason's Beach. Your rental comes with a free walk on pass to Nason's Beach. All the living area is on the 1st floor. A open floor plan combines the living room, dining room, and kitchen. 2 bedrooms with king beds. The 3rd bedroom has a futon. The 4th bedroom has 1 twin bed and 1 full. There is also a sleeper sofa in the foyer.

A view of the charming house situated among tall trees, accessible by a set of stairs leading up from the sandy beach. A wooden dock extends into the water, with a small boat nearby. Outdoor seating areas are present on the beach, enhancing the inviting setting.
Villa in Standish

Sandy Cove Escape Limit 8

335 - 3 Bedrooms, 2.0 Baths (Sleeps 8) OCCUPANCY- LIMIT 8 - 3-bedroom 2 bathroom with a large sandy beach. One bedroom on the main floor with a Queen and twin bed. There are 2 bedrooms on the 2nd floor. One bedroom with a full bed. The other bedroom upstairs has a Queen bed and 2 twins. There is a full bathroom on the 1st and 2nd floor. The very large lot with plenty of sitting areas to enjoy the views of the lake. The large sandy beach is one of the biggest we have in our inventory.

An expansive view of Sebago Lake is captured at sunset, featuring warm shades of orange and yellow reflecting off the calm water surface. The horizon is lined with distant mountains, creating a serene backdrop against the sky filled with soft clouds.
Villa in Sebago

Grandview Lakefront Limit 9

331 - 4 Bedrooms, 2.5 Baths (Sleeps 9) OCCUPANCY LIMIT 9 - This 4-bedroom 2.5 bath home on Sebago Lake has space for everyone. Expansive lake views and sandy bottom frontage. There is 1 bedroom and 1.5 bath on the 1st floor. The upstairs has a separate living area and kitchen plus 3 bedrooms. 2 separate entrances for both the upstairs and downstairs areas. The 2nd level has a deck directly off the living area. There is a large yard area for plenty of room for gathering outside.

Villa in Sebago
4.8 out of 5 average rating, 5 reviews

Lily of the Valley Limit 8

LILY OF THE VALLEY 2 BEDROOM 1 BATH WITH AC OCCUPANCY LIMIT 6 2-bedroom 1 bath remodeled cottage with a bunkroom. It's just a short walk to an association beach. The cottage is very nicely updated. A great option for guests who want the comforts of home but still can walk to the beach. 2 AC units will keep the house nice and cool. Also, a backup generator in case the power goes out. 2 kayaks and 2 paddle boards will be available for guest. A washer and dryer is a great plus.

A firepit made of large stones is situated near the water, with remnants of wood and ash visible. The tranquil lake reflects greenery from trees along the edge. A dock is seen in the distance, leading out over the calm water.
Villa in Sebago
5 out of 5 average rating, 4 reviews

Eva's Place Limit 7

578 - 4 Bedrooms, 3.0 Baths (Sleeps 7) OCCUPANCY LIMIT 7 Waterfront home has 4-bedroom 2 bath. The home has great finishes with a dock on the Northwest River. Direct access to Sebago Lake. Sit around the firepit with views of the water. 3 heat pumps provide AC for the home. Views of the water from the kitchen and living room. 2 bedrooms and 1 bath downstairs. 2 bedrooms upstairs with a Jack and Jill bathroom. 2 kayaks and 1 canoe provided. Fishing poles also provided.

The lakefront property is set against a backdrop of tall pine trees, featuring a grassy yard that gently slopes to the waterโ€™s edge. Colorful adirondack chairs are arranged along the shore, complementing the clear water with a sandy bottom.
Villa in Bridgton

Tremont Limit 10

TREMONT LIMIT 4 Bedrooms,2 Bathrooms (sleeps10) OCCUPANCY LIMT 10 - - WOODS POND SHOREFRONT. Lovely lakefront contemporary with all the conveniences of home. Absolutely NO PETS in or on the property due to serious owner allegies. Well equipped and nicely appointed open concept living for vacation gathering. Four bedrooms, 2 1/2 baths. Spacious open living/kitchen/dining area. Great open lake views from the living areas and the master bedroom. Dishwasher. Washer/Dryer.

Villa in Standish
New place to stay

New! Beachside on Sebago Limit 6

186 - 2 Bedrooms, 1.0 Baths (Sleeps 6) OCCUPANCY LIMIT 6 - NO PETS - SEBAGO LAKE SHOREFRONT. MONDAY - FRIDAY RENTAL. 11AM check in. 1PM check out. This Guest Cottage on an Estate Property sits on 330 ft and over 3 acres of privately owned sandy beachfront on the renowned 'Gold Coast of Sebago Lake', which prides itself for the rocky coastline-like shore fronts combined with gorgeous, clean sandy beaches and crystal clear, aqua like, warm waters.

The exterior of the house showcases a striking red facade with large windows that allow natural light to flood the interior. A spacious deck is featured at the front, furnished with seating for relaxation. A pathway leads to a well-maintained yard surrounded by lush greenery.
Villa in Frye Island

Unusual Latitude Limit 7

342 - 3 Bedrooms, 2.0 Baths (Sleeps 7) OCCUPANCY LIMIT 7 This centrally located 3 bedrooms, 2 bath home on Frye Island is close to all the wonderful amenities that Frye Island has to offer. 9-hole golf course, tennis courts, pickle ball courts, ballfields, cafe and general store. Best of all there are 14 wonderful community beaches to enjoy on Sebago. The large sandy beach 6 is the closest to the house and is less than a 3-minute walk away.

A row of cabins with yellow accents is positioned along a reflective pond. A walkway connects the cabins to the waterfront, while greenery and a firepit are visible in the foreground. The setting showcases a harmonious blend of nature and cabin architecture.
Villa in Sebago

Cardinal Limit 3

701 - 1 Bedrooms, 1.0 Baths (Sleeps 3) OCCUPANCY LIMIT 3. The cabin includes a private bedroom and bath, plus a common room with kitchenette. This one-bedroom cabin has a direct walk out onto the pond side floating boardwalk. A queen bed and a small futon in the common room. This allows for up to 3 guests. Guests will also have access to the natural pond. You can also enjoy Sebago Lake with private access for guests staying at the estate.

Villa in Sebago

New! Barker Pond Escape Limit 8

367 - 4 Bedrooms, 2.0 Baths (Sleeps 8) OCCUPANCY LIMIT 8 - Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago. This property offers great outside area with a dock, sandy beach, and a nice deck to take in the views. The enclosed porch is another great spot to enjoy the views. 2 separate sitting areas downstairs is a nice plus. Both bathrooms are downstairs. The 4 bedrooms are upstairs. Enjoy the 3 kayaks, 2 for adults and 1 for children.

Popular amenities for Cumberland County villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

The chalet-style cottage is positioned on a sandy and rocky shorefront. It features a two-story design with a balcony on the upper level. Surrounding trees provide shade, and a small area is visible for outdoor seating.
Villa in Sebago

Little Sandy-Limit 8

A rustic cottage is nestled among trees at the water's edge, surrounded by colorful foliage. Sunlight shines through the leaves, casting reflections on the clear water. A wooden dock extends into the tranquil lake, enhancing the serene atmosphere.
Villa in Sebago

Whip Poor Will Limit 5

An outdoor deck features a seating area with colorful chairs and a glass-top table, surrounded by greenery. A large umbrella provides shade for a nearby dining set, and a patterned rug adds comfort to the space, inviting relaxation in the natural surroundings.
Villa in Sebago

Daybreak Limit 8

The exterior of the cottage showcases a two-story structure with a classic design, featuring multiple windows that emit a warm glow. A wooden staircase leads to the front entrance, bordered by flower beds with vibrant blooms.
Villa in Standish

Cozy Cove Cottage Limit 6

The exterior of a three-bedroom cottage is shown, featuring a white wooden facade with a black roof. A tall tree with autumn foliage stands nearby, and the ground is covered in fallen leaves. Windows allow natural light to enter, enhancing the home's serene appearance.
Villa in Standish

Hate to Leave It Limit 6

A rustic shorefront cottage is positioned on a sandy beach, with a wooden walkway leading to the entrance. Surrounding trees offer gentle shade, while clouds drift across a bright sky overhead. The peaceful waters of Sebago Lake are visible in the background.
Villa in Standish

Limberlost Limit 6

A rustic cottage is set among trees, featuring a wooden exterior and a wheelchair-accessible ramp. The scene captures a grassy area leading to the sandy beach, where lakefront seating can be seen in the background. Natural light brightens the surroundings.
Villa in Standish

Harmon's Beach Limit 5

Luxury villa rentals

The exterior of a two-story house is shown, surrounded by greenery and trees. A wooden deck with railings can be seen in the foreground. The driveway and road are visible, leading to the property, with the house situated on slightly elevated ground.
Villa in Standish

Loon Lodge Limit 8

A charming cottage with a classic design features a large screened porch, framed by an American flag. The exterior showcases light blue shingle siding and is surrounded by trees, with a sandy yard leading to a tranquil waterfront.
Villa in Sebago

Friendly Inn Limit 5

The exterior of the cottage features a wooden deck leading to a gravel pathway. Sunlight filters through the trees, creating patterns on the ground. In the background, the serene blue waters of the lake are visible, enhancing the peaceful setting.
Villa in Sebago

Placyd Pines Limit 8

A charming cottage is visible from the dock, surrounded by trees and located on a sandy beach. A pathway leads from the dock to the front of the cottage, where outdoor seating is arranged on a patio. The sky is partly cloudy.
Villa in Sebago

Clearview Limit 6

Villa in Sebago

Crystal Oasis- Limit 8

Villa in Standish

New! Cove Overlook Limit 6

Two lounge chairs are positioned on a wooden dock, facing an expansive view of the lake. Clear blue skies with fluffy clouds reflect on the water's surface, creating a serene atmosphere. The surrounding area offers a peaceful and open waterfront space.
Villa in Sebago

A Sense of Place Limit 17

A spacious deck featuring a round glass table surrounded by six cushioned chairs is seen against a backdrop of lush trees. A gas grill is positioned in the corner, with views of the serene lake visible through the greenery.
Villa in Naples

Joyfull Camp Limit 10

Villa rentals with a pool

A group of cabins is situated along a calm pond, connected by a raised boardwalk. Each cabin features a distinct black and yellow exterior. Surrounding greenery and a stone patio with a fire pit enhance the outdoor space, reflecting the tranquil setting.
Villa in Sebago

Phoebe Limit 3

A row of black cabins with distinct yellow trim is set against a backdrop of greenery. Each cabin is positioned along a pebbled pathway, surrounded by trees and natural terrain, providing a serene environment. The cabins feature sloped roofs and front porches, inviting outdoor relaxation.
Villa in Sebago

Nuthatch Limit 4

A row of modern cabins with dark exteriors and contrasting yellow accents is set among a natural landscape. Gravel paths connect the cabins, which are surrounded by greenery and trees, providing a serene and spacious outdoor environment.
Villa in Sebago

Titmouse Limit 4

Villa in Sebago

Couples Cottage Limit 4

Aerial view of a row of cabins set in a natural landscape, featuring a gravel path lined with trees. Each cabin has a dark exterior with contrasting yellow trim, and a small porch. The surrounding greenery adds to the serene atmosphere.
Villa in Sebago

Finch Limit 4

A collection of cabins is arranged along a gravel path, surrounded by trees and natural landscaping. Each cabin features a black facade with yellow trim and a small porch. The setting conveys a serene and rustic atmosphere, ideal for a peaceful getaway.
Villa in Sebago

Chickadee Limit 4

A series of quaint cabins with bold yellow trim are arranged along a floating boardwalk, reflecting their vibrant colors in the calm water of the pond. Stone pathways and greenery frame the scene, enhancing the natural outdoor setting.
Villa in Sebago

Hummingbird Limit 3

A row of modern cabins is nestled among trees, each featuring a dark exterior with bright trim. A gravel path leads through the property, providing access to the cabins. Surrounding greenery offers a natural setting, enhancing the quiet ambiance of the area.
Villa in Sebago

Junco Limit 4

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