Compare Vacation Rentals with Pools in Montauk, NY

Just half a mile from Montauk's beaches and town, this apartment offers a secluded, mountain-like feel with the sounds of ocean waves audible on windy days.
This 4-bedroom, 3-bathroom apartment accommodates 8 guests and features a private 20'x40' swimming pool with a newly renovated deck, a hammock, and indoor entertainment including a pool/ping pong table and karaoke machine.

Oceanfront condo in Montauk offers direct access to the Atlantic Ocean, perfect for beach lovers seeking a getaway with a pool.
Enjoy spectacular ocean views from your private deck, complete with a heated swimming pool and beach bonfire opportunities, as well as an onsite food truck.

Just 500 feet from Duryea's and Navy Beach, this waterfront apartment offers direct access to a private beach and serene sunset views over Fort Pond Bay.
This Montauk apartment, accommodating up to 4 guests, features a spacious 450 sq ft balcony, a fully equipped kitchen, and access to a swimming pool, jacuzzi, and 5 tennis courts within the complex, perfect for a getaway with a pool.

Experience Montauk from this exclusive condo, offering panoramic views within a premier resort setting.
This loft-style apartment with 18ft ceilings accommodates up to 4 guests and features a full kitchen, air conditioning, and access to multiple swimming pools, including an indoor pool, a heated pool, and a jacuzzi, making it an ideal getaway with a pool.

Directly on the oceanfront in Montauk, this apartment offers unparalleled ocean vistas and beach access, with sandy beaches only steps away.
This pet-friendly apartment with a pool features a full kitchen, air conditioning, and a fireplace, perfect for a cozy stay for up to two guests.

Experience waterfront living in Montauk with this unique boat accommodation, docked for immediate access to restaurants and bars.
This boat offers a romantic sleeping escape with full swimming pool access, ideal for enjoying Montauk's waterfront lifestyle right from the dock.

Just 50 yards from the beach, this Montauk apartment offers unbeatable proximity to the Atlantic Ocean in a family-friendly community.
Enjoy modern comforts in this newly renovated 1-bedroom apartment with a private patio, a communal swimming pool, and convenient walking or biking access to Montauk town.

Directly on Fort Pond Bay, this beachfront apartment offers private beach access and panoramic views of Gardiners Island, Plum Island, and Little Gull Island, just a short distance from Montauk's dining, nightlife, and the Montauk Train Station.
This apartment sleeps five and features a heated swimming pool, a hot tub, and a luxurious interior with a king-size bed, bunk beds, and a high-tech entertainment system, perfect for a memorable getaway.

Directly on 200 feet of ocean frontage with a private walkway to the beach, this Napeague oceanfront mansion in Amagansett offers unparalleled beachfront access and is located approximately 1.5 miles from local dining options like Lobster Roll and grocery stores.
This 8,000 square foot, three-story custom-designed residence accommodates 18 guests with 7 bedrooms and 8 bathrooms, featuring world-class amenities including a heated ionized-water gunite swimming pool with jacuzzi, a tennis court, and expansive wrap-around decks with spectacular ocean panoramas.

Directly on 8.5 acres with a 550-foot private beach in Montauk, this resort is a 5-minute drive from Hither Woods and 4 miles from Suffolk County Parkland.
This family-friendly resort offers spacious 1-bedroom apartments with fully equipped kitchens and balconies, featuring a seasonal outdoor swimming pool, tennis courts, and a sauna for a complete getaway with a pool.

This resort on Star Island, directly on Lake Montauk, offers a prime waterfront location within the renowned East End of Montauk.
Enjoy the resort's expansive 16-acre property, featuring multiple swimming pools including an indoor pool, tennis courts, and a private beach, perfect for a getaway with a pool.

Directly on the Montauk Downs golf course, this classic Tudor house is just minutes from world-famous ocean beaches and the village of Montauk.
This spacious house accommodates 10 guests and features a private in-ground swimming pool, a separate studio with a full bathroom, and a finished basement, offering an excellent getaway with a pool.

Just 500 feet from Ditch Plains beach, this Montauk apartment offers a prime location for surfers and sunset enthusiasts, with the Montauk Downs Golf Course also nearby.
This pet-friendly apartment accommodates up to 7 guests and features air conditioning, a full kitchen with a fridge and freezer, and access to a swimming pool and garden for a complete Montauk getaway with a pool.

Villa Mist Manor in East Hampton is conveniently located 7.6 miles from Montauk Point Lighthouse and 13 miles from Second House Museum.
This spacious 3500 square foot house features 5 bedrooms and accommodates up to 19 guests, offering a private swimming pool for exclusive relaxation and free WiFi.

Offering direct beachfront access in Montauk, this resort is located 8.3 miles from Montauk Point Lighthouse and 2.3 miles from Hither Hills State Park.
Gurney's Montauk Resort & Seawater Spa provides a luxurious escape with an ocean-fed swimming pool, a full-service spa, and five on-site dining options, perfect for travelers seeking a getaway with a pool.

Enjoy a waterfront getaway on Montauk Lake, just a 5-minute drive or 10-minute bike ride from town and the beach, with this newly-renovated apartment featuring a salt water swimming pool.
This family-friendly apartment accommodates up to 11 guests and offers luxurious sleeping arrangements with five bedrooms, including two master king suites, alongside provided bicycles and an EV charger.

Rare ocean view Montauk apartment on 1 acre, located just one mile from the beach and within walking distance of Rushmeyer's.
This spacious 3-bedroom apartment accommodates up to 7 guests and features a brand new 50ft swimming pool, jacuzzi spa, sauna, and a children's playground, perfect for a getaway with a pool.

Summerlight Estate, a Rove Travel Home in Montauk, offers a luxurious hotel-like experience with 5-star quality and care, perfect for those seeking premium accommodations with a pool.
This spacious 2680 sq ft house accommodates up to 8 guests and features 4 bedrooms, a full kitchen with a dishwasher, air conditioning, a garden, and a swimming pool, ideal for family getaways.

Offering panoramic water views and stunning sunsets, this Montauk apartment is located on a quiet cul-de-sac, just 500 feet from a bay beach with provided kayaks and a 5-minute drive to Montauk attractions.
This family-friendly apartment boasts a huge, heated saltwater swimming pool with a slide, a spacious 3000 square feet interior, and accommodates up to 10 guests.

Directly on the oceanfront in Napeague, this resort is a 7-minute drive from Montauk and 15 minutes from East Hampton.
Enjoy an outdoor swimming pool at this family-friendly resort, offering kitchenettes, balconies, and a tennis court for your stay.

Enjoy waterfront access in Montauk's city center, just 1 mile from The Hamptons Beaches and Montauk Point.
This 930 sq ft loft-style apartment offers a queen sleeper sofa, a full kitchen, and access to Montauk Manor's amenities including a heated swimming pool, indoor pool, and fitness center, perfect for up to 4 guests.

This renovated lakefront apartment in Montauk offers direct waterfront access, with a private yacht club next door featuring a heated pool and private beach, just 1.5 miles from Montauk Point.
Enjoy 2400 square feet of luxurious living space with 4 bedrooms accommodating up to 8 guests, complete with a modern kitchen, smart TVs, spa-like bathrooms, a waterfront hot tub, and complimentary watersports.

Just 0.3 miles from Ditch Plains Beach and Montauk Downs State Park Golf Course, this Montauk apartment offers a serene location with a private heated pool perfect for a pool getaway.
This spacious 4-bedroom apartment accommodates up to 8 guests and features a fully equipped outdoor entertainment area with a gas BBQ, kayaks, paddleboards, and a sauna for a luxurious stay.

Enjoy a private heated swimming pool at this spacious 3-bedroom apartment in Montauk, located just half a mile from the town center, the Atlantic Ocean, and the Long Island Sound.
This family-friendly apartment accommodates up to 6 guests and features a full kitchen, air conditioning, and four outdoor decks perfect for dining and sunbathing.

This charter yacht offers direct waterfront access, docked at Star Island Yacht Club, directly across from the renowned Montauk Yacht Club, providing a prime Montauk location.
Enjoy a unique getaway with this boat, featuring 2 bedrooms for 4 guests, private beach access, and a swimming pool at the marina yacht club amenities, perfect for fishing and cruising.

This luxurious 10,000 sq ft glass house in East Hampton is located 6.9 miles from Montauk Point Lighthouse and 12 miles from Second House Museum.
Enjoy a unique architectural experience with a private swimming pool, fully equipped kitchen, and air conditioning, perfect for a relaxing getaway with a capacity for 29 guests.

Directly on the ocean in Montauk, this apartment offers stunning, unobstructed ocean vistas and sounds, with private access just steps from the sandy beaches.
This pet-friendly apartment with a pool features a working fireplace, a private sun-drenched porch, and modern amenities for a comfortable stay, accommodating up to 2 guests.

Directly within the Montauk Downs Golf Club, this five-bedroom apartment offers prime access for golf enthusiasts on Long Island's eastern tip, just 500 feet from the greens.
This luxurious apartment features an oversized heated gunite salt-water swimming pool, a chef's kitchen, and provides ample space for 11 guests, making it an ideal Montauk getaway with a pool.

Enjoy a prime Montauk location, just steps from town, shops, beaches, and the harbor, offering easy walkability and a classic outdoor shower amenity.
This spacious 4-bedroom apartment accommodates up to 8 guests and features a private swimming pool, hot tub, and a rooftop deck with water views, perfect for a pool getaway.