Holiday rentals with outdoor seating in Montauk

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 252 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 495 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

4.85 out of 5 average rating, 140 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

4.93 out of 5 average rating, 169 reviews

A light blue house features a welcoming front porch with bright blue chairs. The well-maintained lawn is surrounded by a white picket fence and shaded by a leafy tree. A gravel driveway leads to the garage, creating an inviting outdoor space.

Cottage in The Hamptons

Montauk Cottage Escape

EH Town Rental Registry: 23-483 Escape to Montauk’s Quiet Side- Enjoy the peaceful beauty of Montauk in the off-season from this updated, spacious, comfortable home - close to town, beaches, and scenic trails. Between cozy nights in and crisp coastal walks, this is the perfect retreat for a weekend getaway or a work-from-home reset. Reliable Wi-Fi and a fully equipped kitchen make it easy to settle in for a few days—or weeks. Dogs are welcome with prior approval (Additional pet fee applies.)

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, 252 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)

Guest suite in The Hamptons

A sandy beach extends toward calm waters in the distance, framed by a clear blue sky. Gentle waves ripple towards the shore, while tire tracks are visible in the smooth sand, indicating recent use. The scene offers an unobstructed view of the serene coastline.

4.97 out of 5 average rating, 118 reviews

Twin Pond Ocean View Studio 3

Semi-private path to one of the best beaches in Montauk. Imagine not having to deal with Ditch parking but beach passes included! Twin Pond is a compound on 2.5 acres on Old Montauk Highway. Studio is one of 7 units—galley kitchen (no cooktop) with 180 degree views (1) Qn Size Bed. Walk to Town & restaurants. Modern chic with flat screen TV and WiFi. Ideal for couples/single. Outdoor furniture and a gas grill. Dog fee is $250 per dog. Only small to medium size dogs. No cats or other animals.

4.92 out of 5 average rating, 103 reviews

An outdoor seating area features a round table surrounded by four wooden chairs under a vibrant red umbrella. The grassy ground extends towards a clear view of the ocean, framed by trees and shrubs, with a gravel path leading away from the space.

Bungalow in The Hamptons

Montauk Beach Bungalow East Apt.

Charming, clean, private, quiet, 2 bed 1 bath ocean view apartment across from ocean beach via through dunes path. Check the surf from the living room window. Dine in or out with the moon rising over the ocean. Includes BBQ and fire pit, outside table. Private entrance, lawn, outdoor shower, storage space for bikes, etc. Perfect vacation rental. Full kitchen with stove oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc - monthly discounts. Small bathrm & shower

Guesthouse in The Hamptons

A well-maintained outdoor space features a large swimming pool surrounded by a wooden deck. Lounge chairs are placed around the pool, with red umbrellas providing shade. Adjacently, a patio area includes a dining table. Lush greenery frames the area, contributing to a serene ambiance.

5 out of 5 average rating, 109 reviews

The Quail’s Nest

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

An open living area features a comfortable sectional sofa and a large area rug, with natural light streaming through multiple windows. A dining table is visible, accompanied by stools, and the kitchen area includes modern appliances and a view into the outdoor patio space.

4.95 out of 5 average rating, 122 reviews

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway with open-plan interior & large, private fenced yard. • 950 sq ft, 2 BRs (compact but comfy), 1 Ba, full high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens & furnishings/decor • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private studio w/ own entrance in the house. No shared spaces! • Ask about dogs & flexible rental periods CLICK MORE for IMPORTANT INFO!

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

4.99 out of 5 average rating, 112 reviews

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Holiday home in The Hamptons

An inviting living area is presented, featuring a white brick fireplace as a focal point. Comfortable seating includes light-colored sofas adorned with varying throw pillows. Large windows allow natural light to fill the space, and double doors lead to the outdoor area.

4.98 out of 5 average rating, 121 reviews

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a 3 block walk to one of the most beautiful ocean beaches in the Hamptons! This apartment is located in a beautiful, wooded, quiet neighborhood. Town is 1.5 miles away. This apartment has an open concept living space with a fully equipped kitchen. There are 2 cozy bedrooms and one bath with a walk in shower. We prefer families and mature adults. We supply beach towels, chairs, umbrella and beach wagon.

An expansive view of the ocean stretches across the horizon, framed by wooden sliding doors. Gentle waves wash onto a sandy beach, with greenery in the foreground. A potted plant rests on the railing, adding a natural touch to the serene scene.

4.88 out of 5 average rating, 129 reviews

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

Popular amenities for Montauk outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

The living room features a cozy seating arrangement, including a spacious sofa and armchairs. A round coffee table centers the room, and large windows allow natural light to brighten the space. A textured area rug adds warmth, while a chandelier complements the high ceiling.

4.96 out of 5 average rating, 102 reviews

Casa Amagansett

A spacious living area is showcased, featuring a contemporary sofa adorned with decorative cushions. A flat-screen TV is positioned on a stand, complemented by a large, dark rug. Natural light streams in through sliding glass doors that lead to an outdoor deck, with a dining area visible in the background.

4.98 out of 5 average rating, 47 reviews

Culloden Beach House|Private Beach|Sleeps 6 + Pup

A wooden dock extends into calm waters, bordered by lush greenery and sandy paths. Small boats can be seen moored at the end of the dock, while the serene landscape features gentle grasses along the shoreline, offering a peaceful view of the bay.

4.95 out of 5 average rating, 228 reviews

Rex- East Hampton Cottage- 5 stars

4.92 out of 5 average rating, 12 reviews

Sunlit cozy cottage by the bay.

4.94 out of 5 average rating, 177 reviews

1800 Historical EH Home, 1 Mile to Town!

A sunset scene is captured over a sandy landscape, where vibrant shades of orange and pink fill the sky. Silhouettes of beach fencing and grassy dunes are visible in the foreground, complemented by a wooden structure to the right.

4.99 out of 5 average rating, 129 reviews

Charming Retreat Near Ocean Beaches

4.93 out of 5 average rating, 126 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in North Fork

Modern farmhouse w/ pool, beach, horses and winery

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

4.87 out of 5 average rating, 284 reviews

Exclusive Sag Harbor Compound

Apartment rentals with outdoor seating

A charming two-story house is nestled among lush greenery, with large windows reflecting sunlight. The wooden exterior features shingle siding, and a gentle slope of grass leads up to the entrance. Surrounding trees create a serene, private atmosphere.

4.96 out of 5 average rating, 163 reviews

Hamptons Hills Escape

A spacious outdoor deck is shown with a round table and four chairs shaded by a purple umbrella. Nearby, a cozy seating area is arranged with cushions. Lush green trees provide privacy along the perimeter, enhancing the tranquil atmosphere.

4.96 out of 5 average rating, 306 reviews

The House of the Mermaid aka La Casa della Sirena

4.96 out of 5 average rating, 167 reviews

A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.

Apartment in North Fork

Upscale Newly Constructed Apartment

Apartment in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.9 out of 5 average rating, 260 reviews

Squire Chase House

An open layout features a cozy living area with a patterned rug and a glass coffee table. A small dining space with two stools is positioned near a kitchenette, which includes a refrigerator. A private sleeping area with a bed is visible in the background.

4.94 out of 5 average rating, 226 reviews

Private paradise 3 min from town ice skating pond!

A well-lit living area is highlighted by a cream-colored sofa with nautical-themed pillows. A wooden coffee table features shells and a vase of flowers. Display shelves in the background hold decorative items, with natural light streaming through large windows.

4.84 out of 5 average rating, 141 reviews

Vacation at the Beach: Entire Home

Apartment in Center Moriches

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

4.82 out of 5 average rating, 114 reviews

Cozy Studio 15 Min From Hampton Beaches

A bright living area is depicted, featuring a sleek sofa, a wooden coffee table, and a round dining table surrounded by red chairs. The space incorporates a large potted plant, and light streams through a nearby window, illuminating the whitewashed wood floors.

4.97 out of 5 average rating, 129 reviews

Renovated Guest Cottage close to E.Hampton Village

Condo rentals with outdoor seating

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, 41 reviews

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

An aerial view displays the condo complex adjacent to the waterfront, featuring a central pool surrounded by a landscaped patio. The blue ocean extends beyond the property, with boats visible in the distance under a clear sky, enhancing the serene coastal environment.

4.94 out of 5 average rating, 34 reviews

Sun N Sound Resort, Montauk, NY

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

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, 242 reviews

Montauk Royal Atlantic Beach Resort North

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.

4.84 out of 5 average rating, 160 reviews

Waterfront Escape | Private Beach, Pool & 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.

4.9 out of 5 average rating, 180 reviews

Beautiful Waterview Condo on the North Fork of LI

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.

4.78 out of 5 average rating, 37 reviews

Condo on the ocean in Montauk

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.