Condo holiday rentals in Shelter Island Heights

4.92 out of 5 average rating, 36 reviews

Sun N Sound Resort, Montauk, NY

The location of this 1 bedroom condo at Sun N Sound is, without a doubt, one of our prime assets. It offers the perfect blend of privacy and convenience. Situated on the waterfront of beautiful Block Island Sound, you'll relish in its tranquil surroundings and enjoy the soothing sounds of the waves. It's the ideal balance for a vacation – a peaceful retreat with easy access to everything you'll need. This hideaway is the perfect vacation destination for you! Summer fills up fast, don't wait!

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Top Guest favourite

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.

5 out of 5 average rating, 256 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)

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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.

4.9 out of 5 average rating, 153 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

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A view from the balcony overlooks the pool area, featuring a clear blue pool surrounded by lounge chairs. Colorful umbrellas provide shade for several tables, while the surrounding buildings reflect a simple, two-story design.

4.8 out of 5 average rating, 243 reviews

Montauk Royal Atlantic Beach Resort North

My cute one-bedroom suite is at Royal Atlantic Beach Resort North, with the beach just across the street! The resort features two pools—one just outside the room and another oceanfront with a tiki bar. Other amenities include a game room, a BBQ area (just bring charcoal and fluid), and poolside bed loungers. It's all about location, with the village just a block away. You are steps away from restaurants, shopping, bars, and lots of family activities. Location, location, location!

FamilyValuePool

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.

4.83 out of 5 average rating, 200 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).

LocationFamilyQuiet

4.87 out of 5 average rating, 15 reviews

Greenport Getaway at Cliffside Condos

Welcome to our Cliffside condo in Greenport, a comfortable 2-bedroom retreat perfect for families and friends. The home features a queen bed in the primary bedroom, two twin beds in the second bedroom. Enjoy easy access to the private beach, seasonal pool, BBQ on the great lawn and the most beautiful sunsets over the Long Island Sound. You’re just minutes from Greenport’s shops, restaurants, and vineyards, an ideal North Fork getaway to relax and unwind.

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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.

4.9 out of 5 average rating, 184 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.

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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.

4.93 out of 5 average rating, 42 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!

LocationFamilyOutdoor spaces

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.

4.88 out of 5 average rating, 162 reviews

Waterfront Escape | Private Beach, Pool & Views

Overlooking the Long Island Sound, this beautiful waterfront condo is the perfect North Fork coastal escape. Enjoy peaceful mornings with panoramic water views, spend your days soaking up the sun on the private beach, and unwind on the waterfront deck as the sun sets over the Sound. Located just minutes from Greenport Village, you’ll be close to charming boutiques, local farms, award-winning wineries, and gourmet dining.

FamilyValueAmenities

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

4.86 out of 5 average rating, 130 reviews

Beautiful condo on Long Islands Northfork

This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.

FamilyValueCondition

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.

4.84 out of 5 average rating, 105 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.

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Top Guest favourite

5 out of 5 average rating, 82 reviews

Montauk Poolside Suite, Steps to Beach

Escape to our stylish, second-floor coastal suite in Montauk, just steps from the sand! This bright, railroad-style retreat comfortably fits 4 guests. Enjoy a private terrace with pool views, fast WiFi, and easy access to the beach and town. Perfect for a sun-soaked vacation or a quiet getaway, with two pools available seasonally. Your ideal Montauk adventure starts here!

LocationFamilyHospitality

Popular amenities for Shelter Island Heights condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

Cliffside Resort - Water View 2 Bed Condo

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.

4.94 out of 5 average rating, 17 reviews

Cliffside Resort Poolside Condo A204

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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.

Modern Two Bedroom Apartment. Beach Ready!

LocationBeachWalkability

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.

4.77 out of 5 average rating, 31 reviews

Newly Renovated One Bedroom One Bathroom Suite

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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.

Bright and Airy One Bedroom Apartment in the Dunes

Location

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.

Charming 2 Bedroom Apartment with Beach Amenities!

New place to stay

Mead to be Montauk - Long Island Coastal Escape

A spacious heated pool is framed by lounge chairs, providing ample seating for relaxation. The pool reflects clear blue waters under a bright sky, with shaded areas offered by nearby umbrellas. The resort's balconies overlook the pool area, enhancing the inviting atmosphere.

5 out of 5 average rating, 3 reviews

Cliffside Resort Poolside Condo A106

AmenitiesHospitalityCleanliness

Condo rentals with a pool

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.

4.67 out of 5 average rating, 3 reviews

One Bedroom Apartment Nestled in the Dunes

LocationViewBeach

An aerial view captures a sandy beach bordered by lush dunes and shrubs. In the distance, the resort's accommodations are visible, nestled among greenery. The sky is clear with scattered clouds, creating a serene coastal atmosphere.

4.9 out of 5 average rating, 30 reviews

Second Floor Corner Unit Overlooking the Ocean

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The kitchen features modern appliances, including a stove and refrigerator, complemented by open shelving displaying dishware. A dining area with a spacious table is visible, along with large glass doors that provide a view of the waterfront. Natural light enhances the warm atmosphere.

5 out of 5 average rating, 7 reviews

Water front, sunsets, sail boats, 30 day minimum

LocationFamilyGetting around

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.

4.9 out of 5 average rating, 10 reviews

Endless Summer Montauk Studio w/Bayview Balcony

LocationGetting aroundWalkability

4.8 out of 5 average rating, 25 reviews

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

Waterfront Elevated Bungalow - Spectacular Views

LocationValueKitchen

A modern kitchen space features stainless steel appliances and white cabinetry. A spacious island with a sink provides a functional area for meal preparation. Natural light floods the room, highlighting the dining area with a view of the water through sliding glass doors.

4.86 out of 5 average rating, 14 reviews

Condo on the Sound - Navy Beach

ValueLocationAmenities

4.95 out of 5 average rating, 44 reviews

A well-maintained garden area is visible, featuring a circular pathway adorned with colorful flower beds. Various blooming flowers such as lavender and pink blossoms are admired among lush greenery. Benches are placed strategically for relaxation, surrounded by neatly trimmed hedges.

Condo in Hampton Bays

A Unique Piece of Paradise, Water Front pool

LocationFamilyCondition

Top Guest favourite

The living area showcases a comfortable sofa adorned with decorative cushions, complemented by a coffee table. A kitchen area with modern appliances is visible, alongside a dining cart. Art pieces frame the walls, and natural light enters through sliding glass doors.

Condo in North Fork

4.89 out of 5 average rating, 105 reviews

Waterfront Condo C-204 at The Cliffside Resort

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Private condo rentals

A serene twilight scene features a calm waterfront with soft hues of orange and blue in the sky, reflecting over the still water. A winding boardwalk leads towards the horizon, illuminated by subtle lights. A pier stands in the distance, enhancing the tranquil ambiance.

5 out of 5 average rating, 5 reviews

Montauk Sunset at your fingertip!

LocationHospitalityComfort

The image captures a serene waterfront at sunset, with vibrant hues of purple, orange, and pink reflected in the calm water. A wooden pier extends into the bay, leading towards a small gazebo at the end, framed by distant clouds.

5 out of 5 average rating, 5 reviews

Serene Montauk Condo with Stunning Bay View & Pool

LocationViewLong stay

4.89 out of 5 average rating, 9 reviews

Montauk co-op on Fort Pond Bay

LocationBarbecueComfort

A grand entrance is framed by lush trees, with vibrant foliage surrounding a charming brick building. The pathway leads to large double doors, inviting guests inside. Sunlight filters through the leaves, casting playful shadows on the walkway.

4.89 out of 5 average rating, 44 reviews

Romantic and unique treat in Historic Montauk.

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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

4.63 out of 5 average rating, 30 reviews

Private 3 Bedroom Amagansett on the Ocean with WiF

ValueFamilyLayout

A vivid sunset is captured over the water, with orange and yellow hues radiating across the sky. A calm sea reflects the colors, while a small blue structure stands near the shore, overlooking the scene. A wooden boardwalk leads toward the gentle waves.

4.54 out of 5 average rating, 24 reviews

Immersed in Montauk's Mesmerizing Waterfront Bliss

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A serene sunset illuminates the horizon over calm waters, with soft golden reflections stretching across the surface. The sky displays subtle gradients of orange and blue, creating a tranquil atmosphere as the day transitions to night.