Pet-friendly holiday rentals in Shinnecock Hills

4.85 out of 5 average rating, 147 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!

Outdoor spacesWalkabilityKitchen

4.91 out of 5 average rating, 172 reviews

A classic two-story house with a wooden exterior is framed by neatly trimmed greenery. The front porch features a white gate, inviting guests. Views of the water and trees are visible in the background, suggesting a serene location.

Apartment in Sag Harbor

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Outdoor spacesWalkabilityIndoor spaces

Guesthouse in Hampton Bays

A private outdoor space is showcased with a wooden deck, featuring two lounge chairs and a dining table shaded by an umbrella. Potted flowers add color, while a path leads through the well-maintained garden, enhancing the serene atmosphere of the yard.

4.97 out of 5 average rating, 220 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

PetsWalkabilityValue

Apartment in Hampton Bays

A calm waterfront scene shows a serene body of water reflecting the sky. A sandy beach is visible, framed by natural vegetation, with a wooden barrier along the shoreline. The peaceful setting invites relaxation and enjoyment of the outdoors.

4.97 out of 5 average rating, 419 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

PetsOutdoor spacesParking

4.97 out of 5 average rating, 187 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 Southampton

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!

WalkabilityPetsLaundry

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.

4.86 out of 5 average rating, 132 reviews

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 open May 23, 2026 and close on Labor Day.

Outdoor spacesPetsLocation

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

4.93 out of 5 average rating, 106 reviews

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

Outdoor spacesWalkabilityCondition

4.92 out of 5 average rating, 170 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.

PetsWalkabilityQuiet

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.

4.99 out of 5 average rating, 133 reviews

Charming Retreat Near 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.

Outdoor spacesWalkabilityLaundry

4.97 out of 5 average rating, 192 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

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Outdoor spacesWalkabilityBeach

Guest suite in North Fork

The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.

4.88 out of 5 average rating, 725 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Outdoor spacesPetsBackyard

4.92 out of 5 average rating, 143 reviews

The living room features a bright and airy arrangement with a large white sectional sofa and a coffee table at the center. Natural light streams through the wide windows, creating a welcoming environment. A front door and a lamp add to the cozy feel of the space.

Cottage in Hampton Bays

Hamptons Cottage 3-minute walk to breezy bay beach

Bright, airy 3 bedroom classic Hamptons cottage less than a block from bay beach which is perfect temp and temperament for swimming, wading, paddleboarding and kayaking. Sunsets over the Peconic Bay are amazing especially when you do it with a cold beverage at Tiki Joe’s which has food, drink and fun bands every summer night—only a short stroll away.

PetsWalkabilityDecor

Popular amenities for Shinnecock Hills pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An outdoor space featuring a saltwater pool with a jacuzzi positioned nearby. A patio area includes an umbrella and ample seating options. Lush green grass surrounds the pool, while two white decorative swan floats are visible on the water, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 59 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

WalkabilityOutdoor spacesLong stay

A bright living room features a light-colored sectional sofa accompanied by dark accent chairs. A glass coffee table sits in the center, showcasing various books. Natural light streams through large windows, revealing a view of the outdoors. Decorative elements include a wall-mounted TV and an ornate cabinet.

4.96 out of 5 average rating, 57 reviews

Sophisticated and Sweet

PetsOutdoor spacesHeating

4.95 out of 5 average rating, 256 reviews

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in Springs

Private beach, fully updated house, on 2 acres.

PetsWalkabilityLong stay

4.91 out of 5 average rating, 129 reviews

Home in Springs

Serene with large pool ~ 1 block to water + dining

Outdoor spacesWalkabilityTV

4.94 out of 5 average rating, 330 reviews

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Bridgehampton

Amazing Home close to Everything -

Outdoor spacesPetsCheck-in

4.96 out of 5 average rating, 54 reviews

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.

Home in Southampton

Renovated Southampton Home+Pool

Outdoor spacesWalkabilityGetting around

4.95 out of 5 average rating, 75 reviews

The exterior of the Scandinavian cottage features a modern design with wooden paneling and a metal roof. Lush green grass surrounds the building, with mature trees providing shade. Outdoor seating is positioned beside the structure, contributing to a serene outdoor atmosphere.

Home in Southampton

Scandinavian Cottage

Outdoor spacesWalkabilityCleanliness

4.89 out of 5 average rating, 66 reviews

Home in Shinnecock Hills

Walk to US Golf Open! Southampton Lux Stay

Outdoor spacesWalkabilityBeach

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 120 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!

Outdoor spacesPetsAir conditioning

Luxe

Villa in East Hampton

4.98 out of 5 average rating, 59 reviews

Outdoor spacesSleep qualityCleanliness

5 out of 5 average rating, 13 reviews

The image captures a spacious backyard featuring a heated swimming pool with a gentle waterfall. Surrounding the pool, lounge chairs are neatly arranged. A charming house with multiple windows and outdoor seating is visible in the background, complemented by mature trees and colorful flower beds.

Home in Sag Harbor

Sag Harbor Hamptons hideaway

Outdoor spacesHospitalityCleanliness

5 out of 5 average rating, 11 reviews

Home in Water Mill

Luxury Southampton Home/outdoor Sauna/hottub

Outdoor spacesHospitalitySleep quality

4.82 out of 5 average rating, 131 reviews

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

Home in Springs

East Hampton Oasis - Pool and Hot Tub

PetsOutdoor spacesBarbecue

4.83 out of 5 average rating, 42 reviews

Bright Hamptons Getaway ☀️ Pool▪︎ Beach▪︎FamilyFun

PetsOutdoor spacesCheck-in

4.99 out of 5 average rating, 178 reviews

Home in Commack

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

WalkabilityOutdoor spacesTV

4.97 out of 5 average rating, 76 reviews

A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.

Cottage in Water Mill

Head of Pond House - Waterfront Cottage

PetsWalkabilitySleep quality

Private, pet-friendly home rentals

4.79 out of 5 average rating, 28 reviews

A cottage is nestled among a lush garden with blooming flowers and manicured grass. The exterior features a combination of green siding and gray shingles. Pathways made of stones lead to the entrance, embracing a serene and inviting environment.

Cottage in Hampton Bays

Seabreeze 4 Charming Cottage footsteps to beach

PetsOutdoor spacesCheckout

A bright living area features a comfortable white sofa and two accent chairs. A coffee table sits in front, accompanied by a floral centerpiece. Natural light filters through a window, and a wall-mounted TV is positioned across from the seating. Steps lead to the kitchen area.

5 out of 5 average rating, 72 reviews

The Hamptons Surf Cottage!

PetsOutdoor spacesBackyard

4.89 out of 5 average rating, 73 reviews

A well-equipped kitchen features light wood paneling and open shelves displaying dishware and plants. A stainless-steel oven and microwave are visible, along with a sleek sink and a wooden countertop. Natural light flows in through a nearby window, enhancing the space's functionality.

Cottage in Southampton

Bay View Cottage - Steps to Bay Private Beach

PetsWalkabilityLong stay

5 out of 5 average rating, 27 reviews

A cozy living area features a comfortable sofa adorned with neutral-toned cushions. A large television is mounted on the wall. Natural light filters through multiple windows, brightening the space. A small side table and an armchair complement the seating arrangement, creating an inviting atmosphere.

Apartment in Southampton

Southampton apt walk to village

WalkabilityPetsValue

4.94 out of 5 average rating, 16 reviews

A warm living room features a large stone fireplace as a focal point, surrounded by vaulted wooden ceilings. A comfortable sofa and wooden coffee table are complemented by two chairs, enhancing the inviting atmosphere. Large windows provide views of the lush greenery outside.

Home in Shinnecock Hills

Lakay-Porte Rouge-The Hamptons cottage

Outdoor spacesBikingSleep quality

4.95 out of 5 average rating, 77 reviews

A bright sleeping area is furnished with a queen bed, complemented by soft bedding and decorative pillows. Natural light fills the space through two small windows, with an antique mirror and a lamp providing additional lighting. A small seating area is visible to the side.

Cottage in North Fork

Beach Cottage 3 | New Suffolk | Northfork

Outdoor spacesWalkabilityValue

4.88 out of 5 average rating, 16 reviews

A historic hillside home with a unique Shingle Style design is set amid lush greenery. The structure features multiple levels, large windows, and a spacious front yard. A broad porch extends along the side, allowing for outdoor relaxation, while trees frame the inviting exterior.

Home in Shinnecock Hills

Sugarloaf House

Outdoor spacesWalkabilityCondition