Compare Vacation Rentals with Pools in Montauk, NY

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.

Direct private walk to the ocean in Montauk makes this apartment an ideal choice for beach lovers.
This one-bedroom apartment with a luxurious bathroom and a Leesa mattress accommodates two guests and features a swimming pool, complimentary Wi-Fi, and an on-site restaurant.

Enjoy exclusive access to a private bay beach with lifeguard service, a rarity in Montauk, and a communal swimming pool with a water slide, all within the Culloden Shores community, offering proximity to the restaurant scene at the docks.
This apartment features two bedrooms, a queen-sized pull-out sofa, and a fenced backyard with a deck, BBQ grill, outdoor dining, firepit, and outdoor shower, plus central air, laundry, and Wi-Fi for up to 4 guests.

Directly on the beach, this resort is located 1640 feet from Montauk village and offers easy access to Shadmoor State Park, with Montauk Lighthouse 5.7 miles away.
Enjoy a refreshing dip in the outdoor oceanside swimming pool at this family-friendly resort, which also provides free Wi-Fi and air-conditioned rooms with private terraces or balconies.

Located at The Plum in Montauk, NY, this one-bedroom apartment offers convenient access to the town's renowned beaches and surf spots, just a short distance away.
This apartment sleeps up to 6 guests and features a swimming pool, making it an ideal choice for a getaway with a pool.

Enjoy a spacious 3-bedroom apartment in Montauk, offering convenient access to both ocean and sound beaches, with nature trails just a short walk away.
This family-friendly Montauk apartment features a swimming pool, a garden, and parking, perfect for a getaway with a guest capacity of 6.

Just 50 yards from the beach, this Montauk apartment offers unbeatable proximity for your coastal getaway.
Enjoy modern comforts in this newly renovated one-bedroom apartment, featuring a full kitchen, a private patio, and access to a communal swimming pool, all within walking distance to Montauk town.

Within the Historic Montauk Manor, this newly renovated simplex condo offers spectacular views of Fort Pond and the Ocean, located just 2 miles from The Hamptons Beaches and Montauk Point.
This 1-bedroom apartment accommodates up to 4 guests and features access to an indoor swimming pool, hot tub, and gym, making it a perfect getaway with a pool.

Just 500 feet from Montauk town and ocean beaches, this apartment offers a peaceful Hamptons getaway on a tranquil 1-acre lot.
This spacious 3,000 sq ft residence features four bedrooms, three bathrooms, hardwood floors, and a wraparound balcony with a 30-foot swimming pool, perfect for those seeking a pool getaway near golf courses and sunset water views.

Centrally located in Montauk, this apartment is just a short walk to town, Atlantic Ocean beaches, and Fort Pond Bay.
This private lower-level unit offers modern comforts, including a recently renovated kitchen and bathroom, laundry facilities, and access to an off-site swimming pool, perfect for a getaway with a pool.

Directly on the Atlantic coastline, this Montauk apartment offers immediate beachfront access, perfect for an immersive coastal experience and a rejuvenating escape.
This one-bedroom apartment, accommodating up to four guests, features air conditioning, a kitchen with a fridge, and an outdoor swimming pool with a garden and parking, ideal for beach lovers and nature enthusiasts.

Just 500 feet from the beach, this first-floor studio in Plum, Montauk, offers direct private access and is a short walk to Downtown Montauk.
This studio accommodation with a pool sleeps up to three guests and features air conditioning, a kitchen, and community heated outdoor pool access for year-round enjoyment.

Directly on the beach in Montauk's city center, this renovated 1940s cottage offers exclusive private ocean beach access just steps from your door.
This cottage, accommodating up to eight guests, features a newly renovated kitchen, a spacious ocean-view deck, and access to Wavecrest Resort amenities, including an indoor heated pool for a perfect getaway with a pool.

Located in a historic 1920s Tudor landmark in rural Montauk, this studio offers unique historical charm and is just minutes from The Hamptons Beaches and Montauk Point.
This studio accommodation, perfect for up to 4 guests, features 480 square feet of living space and comes with a fully equipped kitchenette, air conditioning, and an indoor swimming pool for a refreshing getaway.

Directly on the beachfront in Montauk, this resort is located less than 1 mile from the town center and Fort Pond, with Montauk Point Lighthouse a 10-minute drive away.
Enjoy a refreshing dip in the outdoor swimming pool with towel service at this family-friendly resort, which also offers free WiFi throughout the property and daily room cleaning.

Located in Montauk, this apartment offers stunning water views of Long Island Sound and is just a short ride to The Hamptons Beaches, with Gosmans Restaurant and the Viking Ferry to Block Island conveniently nearby.
Enjoy this spacious 3000 square foot apartment with a heated swimming pool, perfect for relaxation and water sports like jet skiing, accommodating up to 8 guests with 4 bedrooms and 2 bathrooms.

Just a short walk or bike ride from Hither Hills beach and Gurney's Resort, this newly-renovated 3-bedroom apartment in Montauk offers a prime location for beach lovers.
Enjoy a spacious, family-friendly retreat with a heated Gunite saltwater swimming pool, a large deck with outdoor dining, and a newly designed open floorplan, perfect for accommodating up to 8 guests with excellent ratings for location and cleanliness.

Centrally located in Montauk, this apartment is less than 0.5 miles from Montauk Downs State Park and a 5-minute drive from the village, harbor, and Ditch Plains beach.
This spacious 5-bedroom apartment accommodates up to 10 guests and features a fenced-in swimming pool area with a grill, perfect for enjoying your getaway with a pool.

Directly on the Atlantic Ocean in Montauk, this resort is 3.8 miles from Montauk Point Lighthouse and 3.6 miles from Hither Woods Preserve.
Experience a fantastic beach getaway with this resort's beachfront access, offering both indoor and outdoor swimming pool options, plus complimentary WiFi and parking.

Located on Old Montauk Highway, this apartment offers magnificent ocean views and is just a short walk to the beach and Montauk town.
This family-friendly apartment accommodates up to 6 guests and features a swimming pool, a large lawn, and an outdoor shower, perfect for enjoying a getaway with a pool.

Just 500 feet from Gurneys, this Montauk apartment offers a prime location with the soothing sound of waves audible at night.
This expansive private home features a heated inground swimming pool, a fully fenced yard, and two master suites, perfect for families and groups of up to 10 guests.

Directly on the Montauk coast, this apartment offers unparalleled ocean vistas and immediate access to sandy beaches, just steps from the soothing sounds of the waves.
This ocean view apartment features a working fireplace, a sun-drenched porch, and modern amenities including air conditioning and internet, all complemented by a swimming pool perfect for your getaway.

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.

Directly on the oceanfront in Montauk, this apartment offers unobstructed ocean views and immediate access to sandy beaches, just steps from the water's edge.
This pet-friendly apartment with a pool also features a private porch, a working fireplace, and modern amenities for a comfortable stay, perfect for a capacity of 2 guests.

Directly on the oceanfront in Montauk, this apartment offers unobstructed ocean views and immediate sandy beach access, perfect for enjoying the soothing ocean sounds and sea breeze.
This apartment sleeps up to 4 guests and features a working fireplace, air conditioning, and a kitchen with a fridge, microwave, and dishwasher, all complemented by a swimming pool on the property.

Located in a tranquil area of Montauk, this house offers a peaceful escape with responsive hosts nearby.
This family-friendly house, perfect for up to 9 guests, features 4 bedrooms, 3 bathrooms, and a fully stocked chef's kitchen, complete with a swimming pool for ultimate relaxation.

Just 500 feet from Ditch Plains Beach, this modern Montauk apartment offers a private block location minutes from Montauk town and Montauk Point Lighthouse.
This spacious 4-bedroom apartment accommodates 8 guests and features a private heated outdoor swimming pool, an expansive patio with a gas BBQ, and a gourmet kitchen, providing an ideal pool getaway.

Located in Montauk, Summerlight Estate is a 19-minute walk from Hither Hills State Park and 2.2 miles from the Second House Museum.
This spacious 2680 square foot house offers accommodations for up to 9 guests, featuring 4 bedrooms, 5 bathrooms, and a kitchen equipped with a fridge, microwave, and dishwasher, all complete with a swimming pool for your enjoyment.