Vacation rentals with a pool in North Sea

4.9 out of 5 average rating, 144 reviews

Home in Springs

Serene, chic private house near best attractions!

Escape to your serene, chic, Hamptons oasis! Cuddle up at the wood-burning fireplace with nature views all around the house. Enjoy your cozy bedrooms, fully stocked Chef's kitchen + 80' streaming TV. You may see deer and bunnies around the property! Toast marshmallows around the firepit + spark up the BBQ under the starry sky. A perfect escape for you to reset! You will be 8 minutes to Main St of East Hampton + Amagansett. Near coffee shops, restaurants, beaches, pumpkin/apple picking + more!

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.

4.78 out of 5 average rating, 146 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

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.

4.93 out of 5 average rating, 139 reviews

Southampton Charmer, 5 bedrooms w pool - Location

This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

4.98 out of 5 average rating, 160 reviews

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

Stylish + Modern Cozy Cape - 5 min to beach

Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully-fenced, tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

Guesthouse in Southampton

A serene outdoor space showcases a heated saltwater pool framed by neatly trimmed hedges. Comfortable lounge chairs are arranged beside the water, while a large umbrella provides shade. A two-story house is visible in the background, surrounded by greenery.

3 Bedroom Guest House in Southampton

This magical getaway delivers peace and relaxation. Curl up to the wood burning fireplace. Wake up to coffee on the porch with a view of the pool. Play in your heated, saltwater pool, (Open April 17-October 23) and relax under the stars in your hot tub. Get a workout in on the Peloton bike or the Cybex Arc Trainer. The gym is equipped with REP Fitness weights and squat rack. You can also drive 12 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

4.96 out of 5 average rating, 23 reviews

4.96 out of 5 average rating, 189 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

4.87 out of 5 average rating, 144 reviews

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.

4.97 out of 5 average rating, 218 reviews

A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Home in Westhampton Beach

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

4.98 out of 5 average rating, 179 reviews

4.84 out of 5 average rating, 131 reviews

Home in Hampton Bays

Luxury Hamptons Getaway w/ Private pool- sleeps 14

Escape to this private Hamptons retreat in the exclusive Bay-Woods enclave of Hampton Bays. Set on a beautifully landscaped acre, the home is just 10 minutes to ocean beaches, 5 minutes to the bay, and 10–15 minutes to Southampton Village for dining, shopping, nightlife, and Cooper’s Beach. Enjoy peaceful luxury, outdoor living, and the perfect location for a relaxing Hamptons getaway. Shinnecock Hills Golf Club is also just minutes away.

4.96 out of 5 average rating, 110 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool wIth Fire Pit /Coffee Bar

Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit.. We are just minutes from the beach. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

4.98 out of 5 average rating, 97 reviews

Southampton Estate w Heated Pool

****POOL HEATED AND OPEN UNTIL OCTOBER 6TH******** Escape to a private Hamptons sanctuary in North Sea! This stylish 3-bed, 3-bath home on nearly an acre is perfect for families or groups of up to 6. Enjoy a heated pool (seasonal), cozy fireplace, and dedicated workspace. Just one mile from the bay, this light-filled retreat offers a perfect year-round getaway with modern decor and premium amenities.

Popular amenities for North Sea rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 222 reviews

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

4.93 out of 5 average rating, 109 reviews

A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.

Home in Bridgehampton

Central Private Bridgehampton Home

4.89 out of 5 average rating, 159 reviews

A modern, sleek structure is surrounded by lush greenery, featuring a private pool and spacious patio area. Chaise lounges are positioned beside the clear water, while large glass doors provide a view of the interior, inviting natural light into the space.

Home in Water Mill

Modern House close to the beach

5.0 out of 5 average rating, 20 reviews

Home in Water Mill

Luxury Southampton Home/outdoor Sauna/hottub

4.98 out of 5 average rating, 41 reviews

A modern two-story home stands illuminated at dusk, showcasing a welcoming porch with wooden steps. The facade features a combination of white metal and black trim. Lush landscaping with lighted pathways guides visitors toward the entrance, enhancing the exterior's contemporary appeal.

Home in Water Mill

Hamptons Modern Retreat NEW CONS

4.89 out of 5 average rating, 9 reviews

Private Home in Southhampton

An open-plan living area features a spacious dining table surrounded by black chairs. Natural light floods in through several windows and skylights, illuminating the modern kitchen equipped with sleek cabinets and stainless-steel appliances.

4.97 out of 5 average rating, 61 reviews

Renovated Southampton Home+Pool

4.95 out of 5 average rating, 62 reviews

A large outdoor pool is surrounded by lounge chairs and umbrellas, inviting relaxation. Well-maintained gardens and trees frame the area, with a spacious deck along one side. The bright blue sky enhances the tranquil atmosphere of this inviting outdoor retreat.

Home in Shinnecock Hills

Spectacular Southampton Retreat!

Condo rentals with a pool

An expansive view of the ocean under a bright blue sky, featuring wispy clouds. The shoreline is lined with gentle waves, and a grassy area is visible in the foreground, leading down to the water.

4.89 out of 5 average rating, 284 reviews

Sound Front Condominium

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, 200 reviews

Beautiful Waterview Condo on the North Fork of LI

Superhost

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, 173 reviews

Waterfront Escape | Private Beach, Pool & Views

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, 136 reviews

Beautiful condo on Long Islands Northfork

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.

5.0 out of 5 average rating, 262 reviews

Montauk Waterfront Condo w/ Sunset Views

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.

4.84 out of 5 average rating, 221 reviews

Coastline View Studio

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.

4.85 out of 5 average rating, 113 reviews

Beautiful Condo on the Ocean Bluffs

Superhost

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, 248 reviews

Montauk Royal Atlantic Beach Resort North

Home rentals with a private pool

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, 148 reviews

Explore the Water & Woods at a Relaxing Retreat

Superhost

4.91 out of 5 average rating, 74 reviews

Southampton Private House with Pool / Peaceful

4.91 out of 5 average rating, 116 reviews

Villa in Springs

East Hampton Villa | Heated Saltwater Pool & Beach

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.

4.96 out of 5 average rating, 25 reviews

Perfect Getaway at Sunny Modern Shampton LakeHouse

4.85 out of 5 average rating, 52 reviews

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.

Home in Springs

Enchanting Home with Large Decks and Heated Pool

A spacious living area is highlighted by a modern fireplace and large skylight windows that allow natural light to fill the room. Chic furnishings, including a light-colored couch with textured throw blankets, complement the soft color palette. A dining area is visible in the background.

4.89 out of 5 average rating, 38 reviews

Chic Poolside Hideaway in East Hampton

A spacious deck is shown surrounding a large pool, with wooden flooring and colorful umbrellas providing shade. Comfortable outdoor couches with striped throws are positioned to face the pool, creating an inviting space for relaxation amid lush greenery.