Vacation rentals in Shinnecock Hills

4.96 out of 5 average rating, 46 reviews

Spectacular Southampton Retreat!

Experience a lifestyle of relaxation and create lifelong memories with loved ones. Imagine yourself lounging by the pool with your favorite drink, surrounded by beautifully manicured gardens that help you unwind and calm your mind and body. Located just beyond Southampton Village, south of the highway, our 1-acre estate features a spacious 4-bedroom, 2.5-bathroom home This property is perfect for a relaxing Hamptons getaway offering a large pool, comfy beds, sunroom, BBQ, fire pit + much more

Superhost

Home in Hampton Bays

4.86 out of 5 average rating, 87 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!

Vacation home in Southampton

4.74 out of 5 average rating, 38 reviews

Southampton Duplex with private Hotub + backyard

inside this thoughtfully renovated 2 bedroom duplexed cottage you will find hardwood floors, high ceilings, brand new furniture and fixtures and a gorgeous kitchen. Outside you will find a beautiful patio, garden, and deck equally perfect for enjoying your morning coffee or a cocktail after a long day in the private hot tub. while there are two other guest cottages on the property this unit is completely private and sectioned off from the rest of the world. Built for friends and families alike

Superhost

4.89 out of 5 average rating, 55 reviews

Summer Getaway in the Hamptons. Mins from Beaches

Welcome to your perfect Hamptons getaway! This sun-filled, architecturally unique home is ideal for a summer retreat or a cozy weekend escape. Offering modern furnishings, and an open floor plan, this space is perfect for small groups. Whether you're enjoying the crisp evenings of early spring, sun-drenched summer days, or the vibrant fall season, this home is a serene escape year-round. Cozy up by the fire, relax on the sun-soaked balconies, or unwind in the beautifully renovated pool house.

4.94 out of 5 average rating, 69 reviews

Villa in Southampton

Just renovated Southampton retreat w/ heated pool

JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooper’s Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32’ heated salt water pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.

5 out of 5 average rating, 20 reviews

Dream Colonial with Heated Pool Southampton, NY

This picturesque abode boasts classic cedar shingle siding, exuding timeless elegance and charm. Conveniently situated south of the highway, this residence offers easy access to all the amenities of Southampton. Dive into relaxation and soak up the sun in your private pool oasis. Embrace the comfort of generous living spaces designed for relaxation and entertainment. Host unforgettable gatherings in the beautifully landscaped outdoor space, perfect for summer barbecues and al fresco dining.

4.96 out of 5 average rating, 196 reviews

Cottage in Southampton

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

4.89 out of 5 average rating, 44 reviews

Amazing Hamptons Home with 6 BR w saltwater Pool

POOL OPENS May 31, 2025 Situated on an acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 6 wonderful bedrooms 4 modern bathrooms and a heated pool with landscaping offers a relaxing escape. The house has 3 decks and is very private and quiet. The home is kid friendly. The house is 5 minutes away from town and best beaches in Hamptons . Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

4.98 out of 5 average rating, 168 reviews

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

4.85 out of 5 average rating, 34 reviews

Cottage in Southampton

Enchanting Cottage in the Heart of Southampton Vil

Enchanting Cottage in the Heart of Southampton Village Escape to this delightful cottage nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, restaurants, and entertainment, this retreat boasts private gardens and access to a refreshing pool. 🛏️ Bedrooms: Studio 🛁 Bathrooms: 1 🌳 Outdoor Space: Private gardens 🏊 Pool Access: Available (open MDW -LDW) 🚘 Two Parking Spaces

4.92 out of 5 average rating, 38 reviews

Southampton-Perfect escape anytime

Beautiful beach house perfect for couples, friends & families. Only minutes from area beaches including Coopers Beach and the Bay. Less than 10 minutes from Main Street, Jobs Lane and great area restaurants plus wineries and golf courses. Set in a calm and serene area, it is the perfect house for couples or a family. Brand new renovation of entire house and fenced backyard. Private walks are common within the area with a wonderful community of friendly neighbors.