Villa holiday rentals in Kennebunkport

4.96 out of 5 average rating, 127 reviews

A bright living area features a stone fireplace as the focal point, surrounded by large windows that allow natural light to fill the space. A comfortable sectional sofa and two leather armchairs are arranged around a coffee table on a textured rug, creating a welcoming atmosphere.

Villa in Conway

Luxurious Retreat with Hot Tub & Walk to Echo Lake

Welcome to the most luxurious home in the Valley. We designed, built and equipped this home for the most comfortable rental experience possible. From Boll & Branch Sheets to a DeLonghi espresso machine, we have cut no corners and thought of everything. Our goal when we built and designed this house was to create a cozy & upscale spot to escape to in North Conway. With Echo lake only a 5 minute walk & multiple ski mountains only minutes away, our villa is the perfect jumping point for any season!

A spacious lake house is visible among tall trees, presenting a welcoming facade with multiple windows and a broad deck. A gazebo and dock with seating are situated along the water's edge, while an American flag is seen fluttering in the breeze.

Villa in Wolfeboro

4.64 out of 5 average rating, 55 reviews

6 Night Min Lake Winnipesaukee Lakefront Villa

Once the largest house on the lake. My place is close to great views, family-friendly activities, and restaurants. You’ll love my place because of the coziness, the views, and the location (desirable Winter Harbor). The dock can house two boats (one small and one standard boat up to 22 ft long). The grassy area next to the house is fabulous for playing games with your kids/grandchildren. While there is no beach it is shallow enough for young children. Fabulous for a getaway or a family reunion.

4.98 out of 5 average rating, 85 reviews

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

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.

4.94 out of 5 average rating, 113 reviews

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

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.

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.

4.65 out of 5 average rating, 34 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 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.

Villa in Madison

Indoor Saltwater Pool | Sauna | Sleeps 12+

Welcome to the crown jewel of Eidelweiss! Offering breathtaking views of the White Mountains. Your very own indoor oasis, complete with an indoor saltwater pool and sauna. Savor your morning coffee on the top-floor deck, where you can gaze at the majestic Mount Washington. Create culinary delights in the kitchen and gather around the fire pit in the backyard for cozy evening conversations. With 11 beds in the property, there's space for all of your family and friends!

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

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.

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 Kennebunkport villa rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

Eva's Place Limit 7

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.

4.91 out of 5 average rating, 33 reviews

Dockside Retreat Limit 14

Villa in Windham

Boomfish Limit 5

Guest favourite

Villa in Bartlett

Alpenglow Estate | Hot Tub, Sauna & Euro-Inspired

4.65 out of 5 average rating, 34 reviews

Sebago Sunrise Limit 8

Villa in Madison

Indoor Saltwater Pool | Sauna | Sleeps 12+

Villa in Wolfeboro

4.64 out of 5 average rating, 55 reviews

6 Night Min Lake Winnipesaukee Lakefront Villa

4.98 out of 5 average rating, 85 reviews

Villa in Fryeburg

R&R White Mountain Retreat (Mtn Views!)

Luxury villa rentals

New place to stay

New! Barker Pond Escape Limit 8

A large waterfront lot features green grass and shaded areas, complemented by several outdoor chairs arranged for seating. The serene lake is visible, reflecting the blue sky and surrounding trees, enhancing the natural landscape.

Villa in Naples

Lakeview Bliss Limit 8

New! Northwest Eagle Nest Limit 9

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

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

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

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

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 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

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.