Compare Vacation Rentals with Pools in Montauk, NY

This deluxe studio apartment is located in the historic Tudor-style Montauk Manor, a registered landmark, just a short walk from Montauk's renowned beaches.
Guests can enjoy access to an indoor swimming pool, jacuzzi, and sauna, along with an outdoor pool, exercise room, and tennis courts, all part of this exceptional pool getaway.

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.

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.

Just 500 feet from Navy Beach and Duryea's, this modern 1-bedroom condo in Montauk's desirable Rough Riders gated community offers waterfront living with stunning sunset views from a large sun deck.
This apartment, accommodating up to 4 guests, features a full kitchen, air conditioning, and access to a community swimming pool, jacuzzi, and tennis courts, all within a short 5-minute drive to Montauk town.

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.

Experience a peaceful off-season retreat in Montauk's quiet district, conveniently located just 1 mile from town, beaches, and scenic trails.
This spacious 1000+ square foot apartment, perfect for up to 5 guests, features a fully equipped kitchen, Wi-Fi, and outdoor patios, offering a comfortable stay with a swimming pool for ultimate relaxation.

Directly on the oceanfront in Montauk, this apartment offers unparalleled ocean vistas and immediate sandy beach access, perfect for enjoying the soothing sounds of waves and a gentle sea breeze.
This pet-friendly apartment with a pool features a sun-drenched porch, a working fireplace, and modern amenities for a comfortable stay, ideal for unwinding with the horizon as a backdrop.

Offering panoramic rooftop views from the ocean to the Long Island Sound, this modern, architect-designed apartment is situated hilltop behind Fort Pond, just a 15-minute walk or short drive to Montauk town and ocean beaches, with convenient proximity to Surf Lodge and Navy Beach.
This family-friendly apartment with a swimming pool features 4 bedrooms, 3.5 bathrooms, accommodates 6 guests, and boasts a private gunnite pool and multi-level wooden decks, perfect for enjoying the Montauk surroundings.

Just 50 yards from the beach, this Montauk apartment offers a prime location with ocean views and convenient access to Montauk town.
This family-friendly apartment, perfect for up to 4 guests, features 2 bedrooms, 1 bathroom, a fully equipped kitchen, and a private patio, all complemented by access to a shared swimming pool.

Steps from Kirk Park Beach, this apartment in Montauk offers excellent access to the shore and is a 12-minute walk to the historic Second House Museum.
This 900-square-foot apartment features a terrace with sea views and includes a swimming pool, complimentary bikes, and on-site dining for a complete 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.

Located in Montauk's Soundview section, this apartment is just steps from Block Island Sound with private sound beaches within walking distance and a short walk to Gosman's Dock, the harbor area, and numerous restaurants and shops.
This family-friendly apartment offers 3000 square feet of living space, sleeps 10, and features a heated saltwater swimming pool, a chef's kitchen, and a large screened-in porch perfect for outdoor dining.

Directly across from Montauk Downs State Park, this apartment offers a prime Montauk location, just a short walk or bike ride to local attractions and beaches.
Enjoy 1800 square feet of living space with accommodation for up to 8 guests, featuring 3 bedrooms, 2.5 bathrooms, a well-stocked kitchen, and a private backyard with a gas grill and fire pit, all complemented by access to a swimming pool.

Just half a mile from Kirk Park Beach, this Montauk resort offers ocean views and easy access to Montauk Point Lighthouse Museum, located a 10-minute drive away.
Enjoy a family-friendly stay at this resort with a pool, featuring 650 square feet of living space, air conditioning, internet, and gardens with barbecue facilities.

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.

Enjoy spectacular hilltop views and majestic sunsets in this Montauk apartment, just a short distance from The Hamptons Beaches and Montauk Point.
This 860 sq ft apartment offers a duplex layout with a queen-size sofa bed, accommodating up to 6 guests and featuring a fully equipped kitchen, air conditioning, and access to a heated swimming pool, indoor pool, and spa.

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.

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.