Villa holiday rentals in Portland

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Top-rated villa rentals in Portland

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A charming cottage exterior is surrounded by lush green grass. Two wooden lounge chairs and a small table are placed under a large green umbrella, inviting relaxation. Flower boxes adorned with colorful plants are positioned beneath the windows, enhancing the cottage's welcoming appearance.
Villa in Wells

Sea Rose

Welcome to Sea Rose! This cozy one-bedroom cottage is nestled in the charming Holiday House resort, conveniently located just outside the Ogunquit town line in beautiful Moody, Maine. It's the perfect spot to unwind and experience everything southern Maine has to offer. You’ll love the tasteful decor throughout, plus a full kitchen and an inviting living space. The spacious bathroom features a stand-up shower, while the cozy bedroom comes with a comfortable Queen-size bed. The resort also has a

Top guest favourite
A spacious kitchen features modern appliances, including a stainless steel stove and overhead lighting. Wooden cabinets and an island with bar seating complement the open layout, which flows into the dining and living areas. Large windows allow natural light and views of the outdoors.
Villa in Fryeburg
4.98 out of 5 average rating, 80 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.

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 exterior of a two-story house is presented, showcasing a gray siding and a peaked roof. A prominent front entrance features white railings leading to a covered porch. Large windows and a balcony enhance the design. Neatly trimmed shrubs frame the walkway and driveway.
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.

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 North 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

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.

Guest favourite
A well-maintained putting green is featured in the foreground, with two flags positioned on the artificial turf. In the background, a spacious deck with outdoor seating is visible, shaded by two blue umbrellas. Lush greenery and flowers surround the area, enhancing the outdoor space.
Villa in Ogunquit
4.93 out of 5 average rating, 99 reviews

The Ogunquit House Downtown | Walk 2 beach HotTub

ULTIMATE OGUNQUIT BEACH HOUSE! Renovated & fully equipped private oasis located in the heart of beautiful downtown Ogunquit, ME Park on site & walk to the beach, restaurants/bars & village shops all in under 5 minutes! Ideal for families, friends or couples looking for a perfect beach getaway. Our goal is to provide you with everything you need so there’s less time spent on essentials & renting equipment. Queen, double bunk bed, & 2 pull out couches can sleep 6 comfortably!

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

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.

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, 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.

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.
Villa in Sebago
5 out of 5 average rating, 3 reviews

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.

A wooden dock extends into calm waters, providing access to Annabessacook Lake. Lush greenery frames the walkway leading down to the dock. A clear blue sky reflects on the surface of the lake, enhancing the serene lakeside setting.
Villa in Winthrop

Annabessacook Retreat Limit 8

ANNABESSACOOK RETREAT 3 Bedrooms,2 Bathrooms sleeps 8 OCCUPANCY- LIMIT 8 - Waterfront on Annabessacook Lake in Winthrop. This 3-bedroom 1.5 bath is located just steps away from the water. You will have a great view from this well-maintained and equipped home overlooking the private waterfront and dock. There is a bunkroom downstairs with 2 twin beds and a futon. There is also a half bath and washer/dryer on the first floor. The 2nd floor has 2 bedrooms.

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.

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