Holiday rentals with outdoor seating in Hampton Bays

The Hamptons Surf Cottage!

Newly renovated and professionally decorated Hamptons home. Located in Hampton Bays just a 5 min drive to beaches, catering venues, waterfront restaurants, wineries & golf. Open floor plan w/ modern flair. 2 bedrooms, 1 full bath, spacious living room with games and arcade. Comfortably fits a group of 8! Enjoy amenities including our classic arcade games, smart TVs/appliances, WiFi, a large deck and patio w/ string lights, BBQ, and a fire-pit! Brand new arcade games like Miss PacMan and more

Designer Home w/ Heated, Salt-Water Pool

Charming and modern Hamptons retreat. This home is perfect for a getaway, business trip, staycation, work-from-home alternative, or cozy home base while exploring everything the Hamptons has to offer. Enjoy the expansive private yard including an 18x36 salt-water heated pool, outdoor lounge area, alfresco dining, grill, fire-pit, and outdoor shower. Comfort and convenience as you and your guests will only be 5 minutes from ocean beaches when you stay at this centrally-located Hampton Bays home.

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!

Stylish+Modern Cape w/Saltwater Pool-5min 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.

The House of the Mermaid aka La Casa della Sirena

Welcome to The House of the Mermaid! Come stay in this newly renovated and decorated basement apartment in my house in a quiet and residential area of Hampton Bays. Close to all that you could ever want; restaurants, bars, shopping, and beaches. Perfect getaway for any season. The Hamptons are known for their amazing Summers at the beach, but don't forget about all that Long Island has to offer throughout the seasons. Shopping at Tanger Outlets, apple/pumpkin picking, and the N.F. vineyards!

Hamptons "Get Away" Near Beach/Wineries/Golf

Located in Hampton Bays-the heart of The Hamptons surrounded by water! Close to beaches, waterfront restaurants, wineries, golf & wedding venues. Open floor plan w/ modern flair. 4 bedrooms, 2 full baths, eat-in kitchen, spacious living room and lower level recreation area/ foosball. Enjoy amenities including smart TVs/appliances, EV Charger, 2 fireplaces, 1Gb WiFi, large deck w/ string lites, BBQ, firepit, & outdoor shower. Great for families, couples, coworkers and friends!

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.

Living the Dream

Cozy cottage in a peaceful neighborhood, walking distance to local restaurants and bars. 1.5 mile from the beach & local town. Newly renovated individual suite in separate building with private entrance. Outdoor shower, outdoor fire pit, eating and lounging area. Includes mini refrigerator, coffee, beach towels, chairs and umbrella, boogie boards, two bikes, Brita, and microwave -- all you need to enjoy a getaway! Shared outdoor space.

Peaceful Retreat in Immaculate Architect’s House

This "like new" contemporary home features 4 bedrooms, 3.5 baths, open living spaces, soaring ceilings, abundant natural light, and a modern kitchen. Nestled in tranquil West Tiana Shores, minutes from bay & ocean beaches, and charming Hampton villages (Southampton, Westhampton, Quogue). The living room directly faces your private pool, cedar deck, and lush garden—a perfect getaway for vibrant summers and relaxing winters