Villa holiday rentals in Portland

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Top-rated villa rentals in Portland

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Villa in Fryeburg

4.97 out of 5 average rating, 78 reviews

R&R White Mountain Retreat (Mtn Views!)

Enjoy a fully-stocked Mountain Retreat! Breathtaking sunsets, modern amenities, full kitchen - PLUS popcorn maker, lobster pot, blender, waffle maker, coffee maker, etc! Open floor plan for gatherings that spills out onto the covered patio with grill & fire pit (split wood provided). Beaches and kayak/canoe rentals just minutes away. North Conway Outlets are 12 mi away. Ski slopes galore and snowmobile trails accessible from the house! More adventurous, message me for hikes or family walks.

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.

Villa in Wells

5 out of 5 average rating, 6 reviews

Beach Villa w/Ocean Views 2 Blocks from Shore

6 bedrooms, 5 baths; sleeps 12. 3,200 sq. feet. Property features eat-in kitchen w/ gas range; screened-in porch; 2 master suites on 2nd floor; huge 2nd-floor deck with ocean views; 3 bedrooms on main level; lower level w/bedroom, full bathroom, family room, game room, and access to yard. There is plenty to do, including ping pong, foosball, and air hockey, piano, 4 TVs, and whole-house sound system. The huge backyard has a badminton/volleyball net, horseshoes, and a putting green.

Villa in Standish

New! 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.

Villa in Bridgton

New! Highland Lake Cottage Limit 8

486 - 4 Bedrooms, 2.0 Baths (Sleeps 8) OCCUPANCY- LIMIT 8 - This 2-bedroom 1.5 bath with two bunkrooms, is just steps away from Highland Lake. The home also has a bunk area upstairs and one in the basement. The main floor has a bedroom with a queen bed and a bedroom with 2 sets of bunk beds. The full bath is located on the main floor. Upstairs is another sitting area along with a Queen bed. There is also a half bath upstairs. The basement bunk room has a sitting area, and games.

Villa in Sebago

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.

Villa in Sebago

5 out of 5 average rating, 3 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.

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 Windham

Shuriken Shores Limit 5

375 - 2 Bedrooms, 1.0 Baths (Sleeps 5) OCCUPANCY LIMIT 5 2-bedroom 1 bath cottage on Pettengill Pond. Enjoy 50 feet of water frontage, dock and amazing water views. The main floor has an open concept Kitchen/Living area. The couch in the living room is a pull out. Both bedrooms and the full bath are also on the main floor. The walkout basement level gives up some extra space during your stay and direct access to the water. The laundry area is in the basement as well.

Villa in Raymond

New! Thomas Pond Cottage Limit 8

312 - 3 Bedrooms, 1.5 Baths (Sleeps 8) OCCUPANCY- LIMIT 8 - This 3-bedroom 1.5 bath with family room in the daylight basement, is just steps away from Thomas Pond. Large flat lot with plenty of frontage and a sandy beach. The open concept first floor has great views of the water. The main floor has a bedroom with a king bed. The full bath is located on the main floor. Upstairs has 2 bedrooms. One with a Queen and Twin. The other has a Twin over Full bunk bed.

Villa in Naples

New! 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.

Villa in Sebago

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.