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Condo vacation rentals in Amagansett

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Top-rated condo rentals in Amagansett

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A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

Condo in North Fork

4.85 out of 5 average rating, 146 reviews

2 BR Waterfront Autumn Escape in Wine Country

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

A spacious studio is shown, featuring a king-size bed with crisp white linens. Natural light floods the room through large sliding doors that open to a private balcony with views of the waterfront. A ceiling fan hangs above, and a sitting area with a green sofa is present.

Condo in Montauk

4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

Look no further for your perfect holiday in Montauk! This stylishly renovated large waterfront studio condo has everything you need for a truly amazing stay because there’s no place like home, except for the beach. This gated waterfront complex includes tennis courts, a heated swimming pool, hot tub, fishing pier with a gazebo, BBQ by the beach waiting for you to have a lobster bake, walking trails, an on-site laundry room and parking. Get sand on your toes and let the Mtk sun kiss your nose!

Top guest favorite

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

Condo in Montauk

5 out of 5 average rating, 237 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)

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

Condo in North Fork

4.91 out of 5 average rating, 148 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Top guest favorite

A cozy bedroom features a queen-sized bed adorned with decorative pillows and a soft blanket. Two bedside tables with lamps flank the bed. A wall art piece above the bed depicts a figure against stripes, accentuating the refreshing green walls.

Condo in Montauk

5 out of 5 average rating, 65 reviews

Montauk Retreat - Steps from Beach and Town

This 2nd floor two room suite across the street from the beach is steps to shops, restaurants & more! The bedroom and living room are divided by a galley kitchen. Perfect for your for family’s fall escape! Includes toiletries, beach towels & chairs, a fully stocked kitchen with a Keurig and tea kettle, and board games! Features a queen-sized bed and pull-out sofabed, a large smart TV, fast WiFi, dining table and a terrace overlooking a heated pool (Memorial Day to Columbus Day).

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

4.83 out of 5 average rating, 189 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).

The image captures a sunset over the water, with silhouettes of people in the foreground. Soft, warm light is reflected on the water's surface, while clouds create a serene backdrop. String lights are visible above, adding a festive atmosphere.

Condo in Montauk

4.81 out of 5 average rating, 36 reviews

Montauk Sunsets

This is a gated condo on the stunning Fort Pond Bay. Enjoy access to pool, jacuzzi, and tennis courts. Catch nightly sunsets on your own deck! Fish off of a private pier. Grill and dine right on Navy Beach. You’re walking distance to the LIRR, Navy Beach, The Surf Lodge, Duryeas, and The Montauket. About a 1/2 mile walk to ocean and main street. Shuttles take you to the harbor, town,& beaches. New flooring, appliances,new QN bed, and new sliding doors.

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

Condo in North Fork

4.89 out of 5 average rating, 164 reviews

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.

Condo in Montauk

4.92 out of 5 average rating, 38 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

This is our 5th season as the owners of Unit #126, which is of the nicest units at Montauk Manor. We are hosting our 925 sq. ft. one BR loft corner unit with a cathedral high ceiling, brand new kitchen and bathrooms plus with a sleeper sofa and TVs on both floors. Montauk Manor is an amazing property that features 3 tennis courts, indoor & outdoor pools, a nice sized fitness center, an on-site restaurant/bar and much more!

A spacious green lawn extends towards the ocean, with gentle waves visible in the distance. A multi-story building with defined balconies is situated to the left, surrounded by well-maintained bushes and trees, contributing to a serene coastal atmosphere.

Condo in Montauk

4.83 out of 5 average rating, 101 reviews

Beautiful Condo on the Ocean Bluffs

Located just outside of town on Old Montauk Highway that runs along the ocean. Just a 10 minute walk to town, enjoy a private beach, beautiful grounds and stunning pool. Located at the Atlantic Bluffs Club, one of the nicest private condo facilities in Montauk, you get to enjoy the peace and tranquility of Montauk yet you’re just a short walk to the village with its restaurants, shops and nightlife.

A sunlit corner of the room features a tall plant stand made of natural materials, adorned with various plants. Sheer curtains are gracefully draped over a glass door, leading to a balcony overlooking a pool area, creating an open and airy feel.

Condo in Montauk

4.83 out of 5 average rating, 35 reviews

Condo on the ocean in Montauk

This centrally located spot is ideal for your perfect beach getaway. Only steps away from the Atlantic Ocean, family owned shops, restaurants, bars, and beautiful hiking trails. Located a short few miles away from the Montauk Lighthouse, Camp Hero and Shadmoor State parks, there are plenty of adventures here to discover.

The exterior of a historic Tudor-style building is framed by large, blooming cherry blossom trees. The soft pink flowers create a vibrant contrast against the architecture. A paved pathway leads to the entrance, where benches are positioned for seating.

Condo in Montauk

4.95 out of 5 average rating, 122 reviews

Deluxe Studio Apt@The Montauk Manor

Beautiful, deluxe studio apartment with every amenity. Registered historical landmark. Magnificent lobby with fireplace, restaurant. Cable TV with HBO, DVD and WI FI. Great news the in-door pool, jacuzzi and sauna are now open! The restaurant is now open! Don’t miss out on the fabulous beaches.

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Popular amenities for Amagansett condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

Condo in North Fork

4.85 out of 5 average rating, 146 reviews

2 BR Waterfront Autumn Escape in Wine Country

Top guest favorite

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

Condo in Montauk

5 out of 5 average rating, 237 reviews

Montauk Waterfront Condo w/ Sunset Views

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

Condo in North Fork

4.89 out of 5 average rating, 164 reviews

Beautiful Waterview Condo on the North Fork of LI

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in North Fork

4.88 out of 5 average rating, 146 reviews

Waterfront Autumn Escape in Wine Country: 2BR

A spacious living area features a modern sectional sofa with decorative pillows and a cozy rug. A wall-mounted television is positioned opposite the seating, and natural light filters in from a window, highlighting the room's neutral color palette.

Condo in Sag Harbor

4.87 out of 5 average rating, 90 reviews

Cute cottage apartment upstairs in Sag

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

Condo in North Fork

4.91 out of 5 average rating, 148 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

The exterior of a historic Tudor-style building is framed by large, blooming cherry blossom trees. The soft pink flowers create a vibrant contrast against the architecture. A paved pathway leads to the entrance, where benches are positioned for seating.

Condo in Montauk

4.95 out of 5 average rating, 122 reviews

Deluxe Studio Apt@The Montauk Manor

A spacious private deck overlooks the ocean, featuring wooden railings and loungers positioned for relaxation. The sea and sandy beach are visible beyond the deck, with light clouds scattered across a bright blue sky.

Condo in Montauk

5 out of 5 average rating, 10 reviews

Montauk Oceanfront Condo

Condo rentals with a pool

A spacious deck offers a clear view of Fort Pond Bay, with distant boats visible on the water. The landscaped grounds feature neatly arranged shrubbery and open space. Nearby, a multi-story building provides a backdrop to the serene outdoor setting.

Condo in Montauk

5 out of 5 average rating, 5 reviews

Serene Montauk Condo with Stunning Bay View & Pool

Condo in Montauk

4.89 out of 5 average rating, 44 reviews

Romantic and unique treat in Historic Montauk.

Lounge chairs are arranged around a patio area, each shaded by a large umbrella. A potted plant adds a touch of greenery, and a serene body of water is visible in the background, bordered by lush vegetation and a wooden fence.

Condo in Amagansett

4.67 out of 5 average rating, 3 reviews

One Bedroom Apartment Nestled in the Dunes

A clear blue swimming pool is framed by a well-maintained grassy area. A single orange umbrella provides shade for a lounge chair beside the pool. The two-story building in the background features multiple balconies and white railings, set against a bright, sunny sky.

Condo in Montauk

4.8 out of 5 average rating, 241 reviews

Montauk Royal Atlantic Beach Resort North

A bright and airy living space is highlighted by skylights and white wooden beams. A spacious kitchenette is situated behind a dining table surrounded by light chairs. Large windows invite natural light, and a television sits on a white console between soothing tones of gray and cream.

Condo in Hampton Bays

4.79 out of 5 average rating, 24 reviews

Waterfront Elevated Bungalow - Spectacular Views

A spacious swimming pool is surrounded by lounge chairs and umbrellas, situated on a paved area. Lush greenery can be seen in the background, providing a serene environment for relaxation.

Condo in Southampton

5 out of 5 average rating, 13 reviews

Newly Renovated Modern Townhouse w/Pool & Tennis

A spacious outdoor pool area is framed by lush greenery and vibrant flowers. The rectangular pool is surrounded by a paved deck, with several lounge chairs positioned around it. A corner of the property includes a poolside storage shed, providing functional space.

Condo in Bridgehampton

4.89 out of 5 average rating, 18 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

A clear swimming pool is seen with a shimmering blue surface, reflecting the sky above. Loungers are arranged around the pool area, offering views of Shinnecock Bay beyond the pool, framed by a protective fence and grassy landscaping.

Condo in Hampton Bays

4.95 out of 5 average rating, 43 reviews

A Unique Piece of Paradise, Water Front pool

Private condo rentals

A heated swimming pool is surrounded by lounge chairs and umbrellas, with multiple access steps leading into the inviting, clear blue water. In the background, a two-story building features private balconies overlooking the pool area.

Condo in North Fork

4.94 out of 5 average rating, 17 reviews

Cliffside Resort Poolside Condo A204

A modern living space is shown, featuring a charcoal gray sofa adorned with a yellow pillow. A foldable drying rack is visible alongside a small wooden side table. The dining area is equipped with gray chairs and a vibrant green serving tray on a textured area rug.

Condo in Amagansett

Modern Two Bedroom Apartment. Beach Ready!

A private outdoor patio features a wooden deck with two lounge chairs and a dining table with four chairs, set against a backdrop of green grass. Sliding glass doors provide access to the interior space.

Condo in Montauk

4.77 out of 5 average rating, 31 reviews

Newly Renovated One Bedroom One Bathroom Suite

A bright bedroom features a spacious bed with a light-colored plaid duvet cover. Two bedside tables with lamps are positioned on either side. A wall art piece of a tree adds a touch of nature, while natural light streams through a door leading to another room.

Condo in Amagansett

Bright and Airy One Bedroom Apartment in the Dunes

A bright and colorful room features bold stripes in green, orange, and purple on the walls. A spacious bed with white linens and pink accent pillows is positioned near a window. A spiral staircase leads to an upper level, complementing the room's playful design.

Condo in Amagansett

Charming 2 Bedroom Apartment with Beach Amenities!

A modern kitchen area features a dark granite island with seating for four. White cabinetry provides ample storage space, and an array of stainless steel appliances is neatly arranged. A colorful wall art piece adds a touch of vibrancy to the neutral color scheme.

Condo in East Hampton

4.61 out of 5 average rating, 28 reviews

Private 3 Bedroom Amagansett on the Ocean with WiF

A bright bedroom features two twin beds with light bedding. A small nightstand with a lamp sits between the beds. Large windows allow natural light to fill the room, while blinds provide privacy and control over light exposure.

Condo in North Fork

Seaside Escape I The Cliffside Resort Exclusive

A spacious studio unit is presented with a queen bed dressed in neutral linens. Light-colored walls reflect natural light from large windows, and a cozy seating area features a small table. A calming ceiling fan and modern decor enhance the tranquil atmosphere.

Condo in Montauk

Step Into the Sand from this Full Service Unit!

Destinations to explore