Villa vacation rentals in Montauk

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Popular amenities for Montauk villa rentals

Private villa rentals

Guest favorite
An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.
Villa in East Hampton
4.97 out of 5 average rating, 30 reviews

Luxe| Pool|BeachCar Beach Pass|GameRm|Movie|HotTub

Albertina M.Rating, 5 stars5 days ago
This home was beautiful and exactly as described. The hostess was wonderful and very responsive. The location in east hampton in a quiet and peaceful street was close to all our favorite restaurants, shops and beaches. The hot tub was so great to have in the cold and rainy days. The home is chic, comfortable and clean. We loved it and recommend it.
Superhost
A modern outdoor space features a rectangular pool with crystal clear water, framed by a wooden deck. Comfortable seating arrangements, including two chairs with cushions and a dining table set for six, are complemented by an umbrella for shade.
Villa in North Fork
4.86 out of 5 average rating, 57 reviews

Year-Round Heated Pool Villa - 3 blocks from town

JaimieRating, 5 stars2 months ago
George was an excellent Air BnB host!!!! His responses were prompt and answered any questions we had. The location was ideal in Greenport as everything was walking distance. We had an amazing time!
Top guest favorite
An open-concept living space displays high ceilings with exposed beams. A modern kitchen features wooden cabinetry and stainless steel appliances. Two stylish cream-colored chairs are positioned on a light wood floor, with large windows allowing natural light to illuminate the room.
Villa in Hampton Bays
5 out of 5 average rating, 17 reviews

Hamptons Bungalow With Pool

RalphRating, 5 stars1 month ago
My family and I were lucky enough to stay at Jenna’s over Memorial Day Weekend. The house was even better than the pictures, if that’s possible. Very clean, and beautifully presentable. Everything was clean and ready for us, and Jenna had genuinely everything we could have possibly needed. Jenna was extremely communicative even leading up to our stay. Hope to stay again sometime soon!
Superhost
A clear view of the outdoor pool highlights a serene setting with two large umbrellas shading lounge chairs. Green lawn and bushes surround the pool, with a backdrop of coastal landscape and gentle waters visible in the distance.
Villa in Guilford
4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

VirginiaRating, 5 stars23 months ago
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.
Guest favorite
A heated salt water pool is surrounded by a stone patio, reflecting sunlight on its clear surface. A Japanese Maple tree provides shade along one edge, enhancing the serene outdoor space. Lush green grass and a white fence enclose the area, creating a private setting.
Villa in Southampton
4.95 out of 5 average rating, 60 reviews

Just renovated Southampton retreat w/ heated pool

KathrynRating, 5 stars2 weeks ago
Beautiful home, impeccably clean and modern. Exactly as described! Alessandro was quick to respond and made check in very easy. Heated pool was a delight, even on a cooler day. Great location, close drive to beach and center of town. We will definitely return!
An inviting backyard features a sparkling inground pool with steps leading down into the water. Bright red lounge chairs line the poolside, offering vibrant seating options. A gazebo and well-maintained grass area create a serene setting for relaxation and gatherings.
Villa in Medford
4.68 out of 5 average rating, 28 reviews

Oasis Event Venue

ChakraRating, 5 stars5 months ago
It was perfect for the holidays it made everything better for me and my family
Guest favorite
A spacious two-story house features a light-colored exterior with large windows and a welcoming front porch. Well-maintained green grass surrounds the property, complemented by neatly trimmed shrubs. A gravel driveway leads to the home, providing easy access.
Villa in Hampton Bays
4.94 out of 5 average rating, 18 reviews

Picturesque 5-bedroom Hamptons villa with pool

AlbertRating, 5 stars1 month ago
Tony’s place was wonderful. Looks just like the pictures and was a great time for our time away. The place was clean and Tony was also very responsive and accommodating. Highly recommend Tony as a host!
Superhost
Expansive green lawn extends towards the horizon, bordered by white fencing and mature trees. A serene landscape is visible with grazing horses in the background. Bright blue sky complements the lush surroundings, creating a peaceful outdoor environment.
Villa in East Quogue
4.74 out of 5 average rating, 27 reviews

Farm reserve sunset views

ArielRating, 5 stars1 month ago
Josh's Villa is beautiful! Views were spectacular the grounds are very peaceful and well kept. The place was perfectly clean and close to anything we needed. Photos are accurate. Josh was responsive, polite, and flexible. Had plenty of recommendations and was very attentive. Worth the cost. I would stay here again in a heart beat. Highly recommend!

Luxury villa rentals

Guest favorite
An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.
Villa in East Hampton
4.97 out of 5 average rating, 30 reviews

Luxe| Pool|BeachCar Beach Pass|GameRm|Movie|HotTub

Albertina M.Rating, 5 stars5 days ago
This home was beautiful and exactly as described. The hostess was wonderful and very responsive. The location in east hampton in a quiet and peaceful street was close to all our favorite restaurants, shops and beaches. The hot tub was so great to have in the cold and rainy days. The home is chic, comfortable and clean. We loved it and recommend it.
Superhost
A modern outdoor space features a rectangular pool with crystal clear water, framed by a wooden deck. Comfortable seating arrangements, including two chairs with cushions and a dining table set for six, are complemented by an umbrella for shade.
Villa in North Fork
4.86 out of 5 average rating, 57 reviews

Year-Round Heated Pool Villa - 3 blocks from town

JaimieRating, 5 stars2 months ago
George was an excellent Air BnB host!!!! His responses were prompt and answered any questions we had. The location was ideal in Greenport as everything was walking distance. We had an amazing time!
A sandy beach stretches along a tranquil shoreline, framed by lush green trees. The calm blue waters extend to the horizon under a clear blue sky, creating a serene coastal environment.
Private room in North Fork

spend the weekend on the beach in my grd fl studio

ConorRating, 5 stars34 months ago
We had a great stay, would definitely recommend staying here
A sandy beach stretches along the coastline, bordered by lush greenery and scattered rock formations. The calm waters reflect the clear blue sky, creating a serene view. Nearby trees provide shade, contributing to the peaceful setting of the oceanfront escape.
Private room in North Fork
4.89 out of 5 average rating, 9 reviews

Spend the weekend at the beach in my studio grd fl

JohnRating, 5 stars34 months ago
The place was great! Perfect if you are looking for a quiet, serene place to relax. Just steps from a beautiful, secluded pebble beach where we had a picturesque sunset stroll. Check in was seamless and everything was just as described. We are looking forward to going back!
Top guest favorite
An open-concept living space displays high ceilings with exposed beams. A modern kitchen features wooden cabinetry and stainless steel appliances. Two stylish cream-colored chairs are positioned on a light wood floor, with large windows allowing natural light to illuminate the room.
Villa in Hampton Bays
5 out of 5 average rating, 17 reviews

Hamptons Bungalow With Pool

RalphRating, 5 stars1 month ago
My family and I were lucky enough to stay at Jenna’s over Memorial Day Weekend. The house was even better than the pictures, if that’s possible. Very clean, and beautifully presentable. Everything was clean and ready for us, and Jenna had genuinely everything we could have possibly needed. Jenna was extremely communicative even leading up to our stay. Hope to stay again sometime soon!
Superhost
A clear view of the outdoor pool highlights a serene setting with two large umbrellas shading lounge chairs. Green lawn and bushes surround the pool, with a backdrop of coastal landscape and gentle waters visible in the distance.
Villa in Guilford
4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

VirginiaRating, 5 stars23 months ago
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.
Guest favorite
A heated salt water pool is surrounded by a stone patio, reflecting sunlight on its clear surface. A Japanese Maple tree provides shade along one edge, enhancing the serene outdoor space. Lush green grass and a white fence enclose the area, creating a private setting.
Villa in Southampton
4.95 out of 5 average rating, 60 reviews

Just renovated Southampton retreat w/ heated pool

KathrynRating, 5 stars2 weeks ago
Beautiful home, impeccably clean and modern. Exactly as described! Alessandro was quick to respond and made check in very easy. Heated pool was a delight, even on a cooler day. Great location, close drive to beach and center of town. We will definitely return!
Guest favorite
A spacious two-story house features a light-colored exterior with large windows and a welcoming front porch. Well-maintained green grass surrounds the property, complemented by neatly trimmed shrubs. A gravel driveway leads to the home, providing easy access.
Villa in Hampton Bays
4.94 out of 5 average rating, 18 reviews

Picturesque 5-bedroom Hamptons villa with pool

AlbertRating, 5 stars1 month ago
Tony’s place was wonderful. Looks just like the pictures and was a great time for our time away. The place was clean and Tony was also very responsive and accommodating. Highly recommend Tony as a host!

Villa rentals with a pool

Guest favorite
A spacious backyard is highlighted, featuring a beautifully landscaped lawn, a heated pool, and a fire pit area with unique wooden seating. The modern home with large windows presents a stylish facade, surrounded by lush greenery under a clear blue sky.
Villa in East Hampton
4.97 out of 5 average rating, 30 reviews

Luxe| Pool|BeachCar Beach Pass|GameRm|Movie|HotTub

Albertina M.Rating, 5 stars5 days ago
This home was beautiful and exactly as described. The hostess was wonderful and very responsive. The location in east hampton in a quiet and peaceful street was close to all our favorite restaurants, shops and beaches. The hot tub was so great to have in the cold and rainy days. The home is chic, comfortable and clean. We loved it and recommend it.
Superhost
A backyard area features a heated pool with an adjoining hot tub section, surrounded by wooden decking. Sun loungers and an umbrella-covered dining table are positioned nearby, while well-maintained greenery provides privacy. The house with a light exterior stands in the background, complementing the outdoor space.
Villa in North Fork
4.86 out of 5 average rating, 57 reviews

Year-Round Heated Pool Villa - 3 blocks from town

JaimieRating, 5 stars2 months ago
George was an excellent Air BnB host!!!! His responses were prompt and answered any questions we had. The location was ideal in Greenport as everything was walking distance. We had an amazing time!
Superhost
A clear view of the outdoor pool highlights a serene setting with two large umbrellas shading lounge chairs. Green lawn and bushes surround the pool, with a backdrop of coastal landscape and gentle waters visible in the distance.
Villa in Guilford
4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

VirginiaRating, 5 stars23 months ago
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.
Guest favorite
A heated salt water pool is surrounded by a stone patio, reflecting sunlight on its clear surface. A Japanese Maple tree provides shade along one edge, enhancing the serene outdoor space. Lush green grass and a white fence enclose the area, creating a private setting.
Villa in Southampton
4.95 out of 5 average rating, 60 reviews

Just renovated Southampton retreat w/ heated pool

KathrynRating, 5 stars2 weeks ago
Beautiful home, impeccably clean and modern. Exactly as described! Alessandro was quick to respond and made check in very easy. Heated pool was a delight, even on a cooler day. Great location, close drive to beach and center of town. We will definitely return!
Guest favorite
Villa in Hampton Bays
4.94 out of 5 average rating, 18 reviews

Picturesque 5-bedroom Hamptons villa with pool

AlbertRating, 5 stars1 month ago
Tony’s place was wonderful. Looks just like the pictures and was a great time for our time away. The place was clean and Tony was also very responsive and accommodating. Highly recommend Tony as a host!
Guest favorite
Villa in Guilford
5 out of 5 average rating, 31 reviews

TREETOPS! An upscale, unique 5 bdrm home with POOL

NikkiRating, 5 stars3 days ago
We all loved our stay at Treetops! The pictures really cannot capture how beautifully unique this place is. The pool is lovely. The location is serene and private, yet close to many great restaurants and beaches. Dan was extremely friendly and accommodating. I recommend this place to anyone with eclectic taste looking for a peaceful getaway!
Top guest favorite
A serene outdoor space features a clear swimming pool surrounded by a brick patio. Soft lounge chairs are positioned nearby, and lush greenery lines the perimeter, providing a sense of privacy. Sunlight reflects off the water's surface under a bright blue sky.
Villa in Hampton Bays
5 out of 5 average rating, 17 reviews

Hamptons Bungalow With Pool

RalphRating, 5 stars1 month ago
My family and I were lucky enough to stay at Jenna’s over Memorial Day Weekend. The house was even better than the pictures, if that’s possible. Very clean, and beautifully presentable. Everything was clean and ready for us, and Jenna had genuinely everything we could have possibly needed. Jenna was extremely communicative even leading up to our stay. Hope to stay again sometime soon!
An outdoor heated pool is surrounded by lush greenery, featuring built-in loungers along the pool's edge. A spill-over pool spa adds tranquility, while several white poolside loungers offer ample space for relaxation under the sun.
Villa in North Fork

Villa Emilio -pool/beach retreat

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