Vacation rentals with a pool in Lake Montauk

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Top-rated rentals with a pool in Lake Montauk

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A serene outdoor space features a heated pool surrounded by a brick patio, bordered by lush greenery. The modern home, visible in the background, displays multiple windows and a chimney, contributing to the inviting outdoor atmosphere.

Home in Southampton

4.92 out of 5 average rating, 111 reviews

Village Charmer, 5 bedrooms with pool

This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Superhost

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

Home in East Hampton

4.87 out of 5 average rating, 212 reviews

HeatedPool, Walk2Beach, FencedYard4Pup, Spotless

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Guest favorite

The outdoor space features a rectangular heated pool surrounded by a wooden deck. Sun loungers are placed on one side, while a seating area with armchairs and umbrellas provides shade. Lush greenery surrounds the property, enhancing the tranquil setting.

Home in Sagaponack

4.94 out of 5 average rating, 310 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

Top guest favorite

A large outdoor swimming pool is surrounded by lounge chairs and several umbrellas. The water is clear and appears inviting, reflecting sunlight. A portion of the condo building with multiple levels is visible in the background, framed by trees.

Condo in Montauk

5 out of 5 average rating, 234 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Superhost

A modern home is set in a lush green environment, showcasing a spacious heated saltwater pool surrounded by a stone patio. Relaxing lounge chairs are placed alongside the pool, and the house features large windows that reflect the tranquility of the yard.

Home in East Hampton

4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe deck and huge yard. The house also features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 24-656

Top guest favorite

A light blue house features a welcoming front porch with bright blue chairs. The well-maintained lawn is surrounded by a white picket fence and shaded by a leafy tree. A gravel driveway leads to the garage, creating an inviting outdoor space.

Cottage in Montauk

4.93 out of 5 average rating, 164 reviews

Montauk Cottage Escape

EH Town Rental Registry #: 23-483 MINIMUM STAYS REQUIRED Updated, spacious and comfortably furnished home in Montauk. Well situated to get you most places on foot or bike. Less than 10 minute walk to town, beaches, restaurants, nightlife. Walk to Sole East where you can enjoy use of pool and have lunch or a cocktail. Great place to enjoy your time in Montauk. Additional nightly fees apply for 5th guest. Pets considered with prior owner approval (Dogs ONLY). Additional Pet Fee applies.

Guest favorite

A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.

Home in East Hampton

4.93 out of 5 average rating, 158 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Top guest favorite

Home in Stonington

4.99 out of 5 average rating, 113 reviews

4BR Private Indoor Heated Pool - Lux Mystic Home

Experience Mystic in style at this spacious retreat featuring a private heated indoor pool (additional fee applies). Relax poolside, cook in the gourmet kitchen, or explore the charming town center. Designed for comfort and convenience, this home is perfect for groups with four king beds, an open-concept living area, and a cozy outdoor patio for evening relaxation. Whether you're seeking adventure or relaxation, this coastal getaway is your perfect escape! Min. Age 25. Govt ID required.

Superhost

Home in Sag Harbor

4.87 out of 5 average rating, 119 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Superhost

The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.

Condo in Montauk

4.82 out of 5 average rating, 185 reviews

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

Guest favorite

An indoor pool is centrally located within a spacious area, surrounded by light-colored stone flooring. The pool features a rounded shape, with lounge chairs arranged around its perimeter. Skylights allow natural light to illuminate the space.

Apartment in Montauk

4.87 out of 5 average rating, 120 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Guest favorite

A serene backyard setting is showcased, featuring a solar heated pool surrounded by manicured grass. Two lounge chairs face the pool, with an umbrella providing shade. Mature landscaping and a stone patio create a tranquil atmosphere, ideal for relaxation.

Home in Southampton

4.97 out of 5 average rating, 184 reviews

Dream Home with a wonderful heated pool in SH

Situated on a half-acre of land, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 4 wonderful bedrooms 3 modern bathrooms and a solar heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –