Vacation rentals with a pool in Montauk

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

4.77 out of 5 average rating, 142 reviews

Sprawling Hamptons Estate with Hot Tub & Amenities

Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches

4.91 out of 5 average rating, 128 reviews

Serenity + privacy; 1 block to waterfront dining

Serene, chic, vibes await you at your Hamptons oasis! Enjoy the privacy of your own home located just minutes to the water + Main St. Hang poolside or on the porch + enjoy the bucolic views. Spark up the firepit + BBQ under the starry sky! Soak up the nature and calm vibes here. Stream on your 80' TV. Walk 1 block to waterfront cafe + dining for coffee on the sea + dinner/cocktails while watching the sunset over the harbor. You'll be 8 mins to Main St. shopping, beaches, bays + so much more.

4.93 out of 5 average rating, 170 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 Montauk

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, 254 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)

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 137 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway. (No AI used in these photos!)

4.91 out of 5 average rating, 653 reviews

A serene beach view captures gentle waves lapping at the shore under a soft light. The smooth sand stretches into the distance, with subtle textures and footprints creating a sense of tranquility. A distant silhouette of a bird can be seen against the sky.

Cottage in Montauk

Montauk Oceanview

Wake up to ocean vistas every morning in a charming cottage. There are stunning views of the waves, soothing ocean sounds, and a gentle sea breeze. Sip coffee on a sun-drenched porch, enjoy a sunset stroll along sandy beaches, or simply unwind with the mesmerizing horizon as your backdrop, this cottage provides the perfect blend of comfort and charm. The cottage features a cozy interior with a working fireplace, modern amenities, and large windows that showcase the stunning seaside scenery.

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

4.87 out of 5 average rating, 228 reviews

Walk2Beach, HeatedPool, Yard4Pup, NewGasBBQ

Meticulous easy home.Tranquil family neighborhood in historic artist's beach community.Lush private yard! Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

4.99 out of 5 average rating, 111 reviews

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.

Guesthouse in Springs

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.

Guest suite in East Hampton

A spacious living area is presented with a cozy blue sofa and an accent chair, complemented by a decorative rug. A dining table for four is positioned nearby, and a large TV center is visible. The room is well-lit with natural light streaming through skylights.

4.98 out of 5 average rating, 147 reviews

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also a TV and blue Ray player in the bedroom.

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

4.92 out of 5 average rating, 128 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

4.99 out of 5 average rating, 117 reviews

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.

Home in Montauk

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.

A private balcony is shown with a wooden table and two matching chairs. The view includes a glimpse of a swimming pool with umbrellas and the resort building in the background, all set against a sunny sky.

4.83 out of 5 average rating, 198 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).

Popular amenities for Montauk rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 17 reviews

A modern home is set against a twilight sky, accessible via a well-lit stone pathway lined with greenery. The landscaped garden features low shrubs and ornamental grasses, while the house is designed with large windows that provide a glimpse of the inviting interior.

Home in Montauk

Modern beach getaway ocean views

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

4.89 out of 5 average rating, 116 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

4.8 out of 5 average rating, 10 reviews

A charming exterior view of a home is featured, surrounded by lush greenery and colorful landscaping. A tranquil swimming pool is positioned in the foreground, with a well-maintained lawn leading up to the house, which includes multiple large windows and a spacious patio area.

Home in Amagansett

Beautiful Cozy Home in East Hampton

An in-ground salt-water pool is surrounded by natural stone, set amidst lush greenery. Sun loungers are positioned alongside the pool, and a shaded seating area is visible to the right. A wooden structure stands in the background, blending with the tranquil landscape.

4.89 out of 5 average rating, 56 reviews

East Hampton Secluded Escape with Gunite Pool

4.94 out of 5 average rating, 178 reviews

1800 Historical EH Home, 1 Mile to Town!

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

4.95 out of 5 average rating, 96 reviews

Oasis backyard, Pool, Gym, and Sunroom!

4.92 out of 5 average rating, 132 reviews

A serene pool area is surrounded by lush greenery and colorful hydrangea flowers. Lounge chairs offer relaxation under large umbrellas, while the inviting pool reflects the clear blue sky. A charming home stands in the background, adding to the peaceful setting.

Home in Southampton

Southampton Charmer, 5 bedrooms w pool - Location

4.89 out of 5 average rating, 37 reviews

Home in Sag Harbor

Sag Harbor Chic 4 Bedroom Saltwater Pool

Condo rentals with a pool

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!

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

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, 183 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

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

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.

4.89 out of 5 average rating, 151 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

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.

5 out of 5 average rating, 11 reviews

Montauk Oceanfront Condo

Home rentals with a private pool

An inviting heated pool is surrounded by lush greenery and flowering landscaping. Comfortable loungers are positioned along the wooden deck, accompanied by a shaded umbrella. Steps lead from the poolside to a charming surrounding garden, offering a serene environment for relaxation.

4.84 out of 5 average rating, 49 reviews

Enchanting Home with Large Decks and Heated Pool

Villa in Springs

4.91 out of 5 average rating, 112 reviews

East Hampton Villa | Heated Saltwater Pool & Beach

4.96 out of 5 average rating, 24 reviews

A spacious backyard is highlighted by a bright blue swimming pool, featuring a whimsical white swan float. Surrounding the pool are several lounge chairs and umbrellas, set against lush green hedges and trees that provide privacy.

Home in Southampton

Perfect Getaway at Sunny Modern Shampton LakeHouse