Villa holiday rentals in Portland

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.

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.

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.

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.

Whip Poor Will Limit 5

WHIP POOR WILL 1 Bedrooms,1 Bathrooms sleeps 5 OCCUPANCY LIMIT 5 - ONE PET OK with $125 fee - PEABODY POND SHOREFRONT. What a spot! Loads of privacy at this cottage that sits literally at the water's edge. A perfect getaway spot. Listen to the cry of the Loons and watch beautiful sun and moon rises. Screen porch, large stone fireplace, open living/dining area, well equipped kitchen. Lovely view, relax and listen to the brook that borders the property. Nice dock and swim float.

New place to stay

New! Cove Overlook Limit 6

538 - 3 Bedrooms, 2.5 Baths (Sleeps 6) OCCUPANCY LIMIT 6 - 3-bedroom 2.5 bath. Just steps away from shared waterfront access with a swim float and a shared dock. You also have access to a larger sandy beach a short walk away. Enjoy spectacular views of Sebago Lake from most of the rooms in the house including all the bedrooms. This new home was built in 2019 and has a lot of very nice finishes. The three bedrooms are on the 2nd floor. The main suite has an attached bath.

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.

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 water’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.

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.

Limberlost Limit 6

LIMBERLOST 2 Bedrooms,1 Bathrooms (sleeps6) OCCUPANCY LIMIT 5- STRICT LIMIT OF 4 OCCASIONAL DAY GUESTS - SEBAGO LAKE BEACHFRONT. Pleasant, yet rustic, shorefront cottage on absolutely beautiful beach on the west shore of Sebago Lake. Picnic table on the screen porch overlooking the water, Nice quiet location. Pretty view of Sebago. WiFi, High speed internet and basic cable. Great spot! DOG CONSIDERED WITH $125 PET FEE Waterfront/Lot Description: beautiful sandy beach.

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 East Sebago

A Sense of Place Limit 17

376 - 6 Bedrooms, 3.0 Baths (Sleeps 17) OCCUPANCY LIMIT 17 Take a step back in time at this turn of the century lakeside cottage. Loads of charm from the fieldstone fireplace in the livingroom to the big wraparound porch overlooking the lake. Plenty of room for the whole family and then some - with 6 bedrooms plus a bunk house with 4 twin beds and a half bath. Wonderful, private lot with big lawn on lake side. Nice L shaped dock plus a mooring. Sandy bottom swimming.

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.

Placyd Pines Limit 8

108 - 4 Bedrooms, 1.0 Baths (Sleeps 8) OCCUPANCY LIMIT 8 - PETS OK WITH $125 FEE - SEBAGO LAKE SHOREFRONT. This lakefront cottage is located at the end of a road on a pretty wooded lot making it nice and private. A very large, shared beach is just a short walk away. Screen porch with open lake and island views from the large rock frontage. Flat rocks allow access into the water for swimming. With four bedrooms, there is plenty of room for everyone. Bath with shower.

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

399 - 4 Bedrooms, 2.5 Baths (Sleeps 10) OCCUPANCY LIMIT 10 - Newly remodeled 4 bedrooms and 2.5 baths. The house has 3 levels. 3 bedrooms on the top level and 1 bedroom on the bottom level. A full bathroom on the main floor and 3rd floor, plus a half bath on the bottom level. 118' of frontage for easy access for swimming. A large deck to enjoy the views of the lake or tie your boat up to. The large deck is a great place to hang out with views of the lake.

An outdoor seating area features several black Adirondack chairs arranged around a circular fire pit. Gravel flooring surrounds the fire pit, while a backdrop of lush green hills and a clear blue sky extends into the distance.

Sebago Sunrise Limit 8

513 - 3 Bedrooms, 2.5 Baths (Sleeps 8) OCCUPANCY LIMIT 8- A 3-bedroom 2.5 bath house with stunning views. This property has 180 degrees of unbeatable mountain, lake, and pond views! Enjoy sunrise views over Sebago Lake. The property has great sitting areas outside to take in the views. The large lot offers plenty of room for kids to enjoy. There are also disc golf baskets and a basketball hoop. The automatic generator and Telsa charger are great pluses.

Popular amenities for villa rentals in Portland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

Eva's Place Limit 7

New! Northwest Eagle Nest Limit 9

A wooden walkway leads to the entrance of the cabin, with sunlight casting shadows across the planks. The entryway features a small set of steps and is surrounded by trees. In the background, the lake can be seen through the foliage.

Dockside Retreat Limit 14

Villa in Windham

Boomfish Limit 5

Villa in Bridgton

Tremont Limit 10

Sebago Sunrise Limit 8

Limberlost Limit 6

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.

Cardinal Limit 3

Luxury villa rentals

New place to stay

New! Barker Pond Escape 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.

Clearview Limit 6

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.

Grandview Lakefront Limit 9

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.

Friendly Inn Limit 5

A charming two-story cottage is set amidst tall pine trees, featuring a welcoming front porch with green door and steps leading to the entrance. The surrounding area has natural gravel pathways and a shaded, serene atmosphere created by the tree canopy.

Fletcher Limit 8

The image captures a sandy beach leading to Sebago Lake, with gentle waves lapping against the shore. A wooden dock extends into the clear water, providing access for boats. Multiple boats are anchored in the distance under a bright blue sky with scattered clouds.

Camp Lindy Limit 7

Villa rentals with a pool

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.

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.

Titmouse Limit 4

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.

Phoebe Limit 3

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.

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.

Chickadee Limit 4

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.

Junco 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.

Hummingbird Limit 3

A series of black and yellow cabins line a floating boardwalk that extends over a calm pond. The scene is complemented by manicured landscaping and a stone patio area with a fire pit, inviting relaxation by the water.