Holiday rentals with a patio in Bridgehampton

4.76 out of 5 average rating, 50 reviews

A two-story beach house features wooden shingle siding and large windows. A sparkling blue pool is positioned in the foreground, surrounded by a wooden deck. Comfortable lounge chairs are placed nearby, offering options for relaxation outdoors.

Home in Bridgehampton

Cheerful 3 bed-3bath beach cottage home with pool

Heart of the Hamptons is situated this bright, beach house 5 min from the ocean, BH/Sag Harbor town, & Wolfer vineyards. 2 master suites w/ ensuite bathrooms and an additional guest room with adjacent bathroom that comfortably sleeps 6 -1 King, 1 queen, 2 twin. Open kitchen that adjoins the dining area and the double height living room w/ fireplace. Sparkling heated (add charge) pool (MD-mid Sept) and palatial lawns with room to roam. Keep it simple at this peaceful and centrally located getaway

4.92 out of 5 average rating, 123 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

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.

4.86 out of 5 average rating, 128 reviews

Home in Hampton Bays

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!

4.95 out of 5 average rating, 101 reviews

An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.

Cottage in Bridgehampton

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

A heated pool is framed by a spacious deck and surrounded by trees, providing a tranquil outdoor space. The pool reflects the clear blue sky above, while a diving board stands at the edge, inviting refreshing summer activities.

4.91 out of 5 average rating, 54 reviews

The Hamptons Casita: Summer Meets the Perfect Pool

NOTE: the Hamptons Casita accommodates 6 guests from December 2 to March 31, with 3 bedrooms and 2.5 bathrooms. One bedroom with a private bathroom is winterized and unavailable during colder months. Our newly-renovated home is available for month-long summer stays. Designed by award-winning firm Sommet, it offers modern comforts, two floors, 3 decks, a pool, cozy firepit, and a rooftop deck. Close to Foster Memorial Beach, popular wineries, and Sag Harbor's amazing dining and shopping.

A spacious backyard is showcased, featuring a large saltwater pool surrounded by six lounge chairs. Lush green grass is complemented by a flowerbed, while tall trees provide shade. The house, with a wooden deck, is visible in the background.

4.92 out of 5 average rating, 12 reviews

Hamptons Home w/ Salt Water Pool

3 Bed/ 2 Bath Sag Harbor Retreat w/ Salt Water Pool. Nestled close to both Sag Harbor Village and Sagaponack, this charming home offers the perfect blend of comfort and convenience. With 3 bedrooms, 2 baths, and situated on a generous .66-acre lot. Outdoors, the expansive yard features a 35x17 saltwater pool. Located just moments from Sag Harbor Village, you'll enjoy easy access to boutique shops, acclaimed restaurants, Wolffer Estate Vineyards, and picturesque waterfront views.

4.97 out of 5 average rating, 176 reviews

A spacious living area features high ceilings and natural light streaming through large windows. A white sofa is paired with wooden chairs, while a glass coffee table sits on a woven rug. An elegant dining area is visible in the background with a large table.

Cottage in North Sea

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

4.97 out of 5 average rating, 39 reviews

BeachCottage|Steps To Water|Firepit|Top10%

Kick back and relax in this calm, stylish beach cottage in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, BBQ and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in August/September/October stays). Firepit area is shared with Bouy Cottage.

4.92 out of 5 average rating, 158 reviews

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in Mattituck

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

4.99 out of 5 average rating, 125 reviews

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.

Home in Hampton Bays

Winter Getaway 2 miles from Ocean Beaches

Entire House! Large fenced in yard, great for pets. Two bedrooms, one song ride away from Ponquogue Beach. Have the beach to yourself for walks and exercise! Perfect place to get away and Unwind. The house is located on a quiet residential street close to the hamlet of Hampton Bays. Enjoy the patio and fire pit (use non-windy days) on 1/4 acre property. Still plenty to do here, we are 20 minutes from Wine Country and Tanger Outlets.

4.94 out of 5 average rating, 34 reviews

A charming house is presented, featuring a blend of shingled and brick exterior. The porch is outlined by neatly trimmed hedges, and a gravel pathway leads to the entrance. Lush greenery surrounds the home, accentuating its inviting curb appeal.

Home in East Hampton

East hampton 3 bedroom home w/ pool great location

Welcome to your hamptons summer home! Amazing location 5 minutes from both Sag Harbor and East Hampton towns and 10 minutes to Bridge Hampton. Beautifully landscaped backyard with heated pool and bbq. The primary bedroom includes a king bed, the 2 secondary bedrooms have queen beds. Open floor plan with kitchen and dining room flowing to the backyard is perfect for indoor/outdoor lunch and dinners. 2 full bathrooms and central air.

A living area features striped sofas and wooden furniture arranged for comfort. Shelves lined with books are visible in the background. Natural light fills the space through windows with shades, while a fireplace adds a classic touch to this welcoming space.

5 out of 5 average rating, 18 reviews

Charming Village Cottage

Charming cottage in historic Sag Harbor village. Peaceful respite centrally located. Five minute stroll to Main Street shops, restaurants, theater, cinema, marina, Long Wharf, local bay beach, and Hampton Jitney stop. Quiet local street steps away from all the action in town. Short easy drives to East Hampton, Bridgehampton, Southampton, Watermill, Shelter Island and ocean beaches.

Popular amenities for Bridgehampton Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.92 out of 5 average rating, 105 reviews

An expansive ocean view is showcased from the studio, featuring calm waters that reflect the sunlight. Soft waves gently lap at the sandy shore, while lush greenery lines the foreground, contrasting with the clear blue sky above.

Apartment in Montauk

Ocean View Studio with King Bed

5 out of 5 average rating, 10 reviews

Apartment in Mastic

South Shore Studio

Apartment in Hampton Bays

4.84 out of 5 average rating, 31 reviews

2Br Hampton Family Escape: Beaches, kayaks, BBQ

5 out of 5 average rating, 16 reviews

The exterior of a spacious two-story home is shown, featuring a light beige façade and large windows. A set of white steps leads to the front door, flanked by neatly maintained shrubs. The property includes a two-car garage and a paved driveway.

Apartment in Springs

The Hamptons

4.79 out of 5 average rating, 34 reviews

Apartment in Sag Harbor

Peaceful getaway in the Hamptons

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.

4.84 out of 5 average rating, 109 reviews

Quiet and comfy studio near the Hamptons

Apartment in East Hampton

A serene sleeping area features a spacious bed dressed in crisp white linens and accented by a dark throw pillow. Framed artwork adorns the walls, while stylish side tables complement the modern aesthetic. Floor-to-ceiling curtains in a neutral tone add a touch of elegance.

4.85 out of 5 average rating, 86 reviews

Private Newly built Modern East Hampton Apartment!

4.92 out of 5 average rating, 121 reviews

A cozy living area features a comfortable gray sofa adorned with patterned pillows. A light-colored side table and an illuminated lamp create a soft glow. A decorative coffee table sits in front, accompanied by a potted plant in the corner, adding a touch of greenery.

Apartment in Greenport

Private 1st flr apt w/ patio 3 blocks from beach

Holiday House Rentals with a Verandah

4.99 out of 5 average rating, 112 reviews

A vibrant orange car is parked on a gravel driveway in front of a navy blue house. Lush greenery surrounds the property, and a neatly manicured lawn extends beside a stone walkway leading to the entrance.

Home in North Fork

Beach House in L.I. Wine Country

4.96 out of 5 average rating, 53 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!

5 out of 5 average rating, 8 reviews

Home in Water Mill

Luxury Southampton Home/outdoor Sauna/hottub

4.98 out of 5 average rating, 52 reviews

A cedar shingle home is framed by lush greenery and well-maintained landscaping. A stone pathway leads to a bright blue front door, framed by symmetrical shrubs. The clear sky adds a light ambiance to the inviting entrance.

Home in East Hampton

Perfect getaway in Heart of East Hampton

5 out of 5 average rating, 27 reviews

A bright living area features a spacious sectional sofa and an armchair, arranged around a rustic coffee table. Sunlight streams through multiple skylights and large windows, providing views of the lush greenery outside. A flat-screen TV is mounted above a brick fireplace.

Home in Springs

Enchanted Story Book Home

5 out of 5 average rating, 50 reviews

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.

Home in Shinnecock Hills

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Home in Westhampton Beach

A spacious saltwater pool is surrounded by a well-manicured yard, featuring lounge chairs and large umbrellas. Water features create gentle splashes, enhancing the serene environment. The area is framed by trees, providing a natural backdrop for relaxation.

4.98 out of 5 average rating, 100 reviews

Brand new house with an all year round hot tub.

Home in Westhampton Beach

A spacious beach house is seen from the exterior, featuring a modern design with large windows and a wrap-around deck. The surrounding landscape includes gentle sand dunes and a grass area, highlighting the proximity to the ocean. Warm sunlight brightens the scene.

5 out of 5 average rating, 20 reviews

Dune Road Steps to the Beach - 4 Bedroom Home

Holiday condos with a patio

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

5 out of 5 average rating, 3 reviews

Condo in Greenport

Greenport Getaway at Cliffside Condos

A bright living area is furnished with a light-colored sofa, floral-patterned chairs, and a coffee table with decorative items. A large television is positioned on a dark wooden console. Natural light filters in through windows, illuminating the space with a cozy ambiance.

Condo in North Sea

Charming Bayfront Condo

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