Pet-friendly vacation rentals in Greenport

4.91 out of 5 average rating, 140 reviews

Chic w/ large pool ~ 1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block from waterfront dining + 8 mins to beaches + Main St. Enjoy your large private home nestled in nature, perched back on a quiet tree lined street. Swim in your pool, spark up the BBQ + firepit under the starry sky! Cook in your Chef's kitchen + stream on the 80' TV. Walk 1 block to waterfront dinner + cocktails watching the best sunsets. Enjoy morning coffee on the sea. Walk back home in 4 minutes. You'll be 8 minutes to Main St., beaches + more!

WalkabilityPetsCheckout

The exterior of the farmhouse is framed by well-maintained hedges, with a simple wooden staircase leading to the front door. Brightly lit windows are positioned symmetrically, highlighting the home's classic architecture. The surrounding greenery complements the inviting entrance.

4.92 out of 5 average rating, 132 reviews

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

Outdoor spacesWalkabilityBathroom

4.85 out of 5 average rating, 158 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!

WalkabilityOutdoor spacesHeating

4.93 out of 5 average rating, 134 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Outdoor spacesPetsCleanliness

4.98 out of 5 average rating, 181 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

PetsWalkabilityDecor

4.92 out of 5 average rating, 142 reviews

Apartment in Greenport

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

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

Outdoor spacesPetsLocation

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, 434 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.

Outdoor spacesWalkabilityGetting around

Guest suite in North Fork

A spacious two-story apartment building is surrounded by well-kept greenery and manicured lawns. A paved pathway leads to the entrance, with colorful landscaping enhancing the inviting exterior. Two bright orange lounge chairs are positioned under trees on the side, offering a peaceful outdoor seating area.

4.93 out of 5 average rating, 171 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

4-6 GUEST MAXIMUM PLEASE. Cozy 2 BR and 1 BTHRM apartment in private home in Greenport NY. Total privacy and separation of unit!! Perfectly situated on 1.75 acres. 3 minute drive, or easy walk, to the center of Greenport village, 2 minute ferry ride to quaint Shelter Island, and a 6 minute drive to tip of Orient. So right in the middle of the action with the peace and serenity of living outside the village. Private beach a short walk/ride down the street.

PetsOutdoor spacesDecor

4.95 out of 5 average rating, 203 reviews

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Outdoor spacesWalkabilityAccuracy

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

4.95 out of 5 average rating, 394 reviews

The Sandpiper

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

WalkabilityOutdoor spacesIndoor spaces

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.

4.96 out of 5 average rating, 213 reviews

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.

PetsOutdoor spacesAmenities

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, 738 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!

PetsOutdoor spacesNearby

Popular amenities for Greenport pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly home rentals with a pool

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

4.93 out of 5 average rating, 138 reviews

Private & Pristine with Pool and Kid’s Playard

PetsWalkabilityHospitality

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

4.89 out of 5 average rating, 133 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

WalkabilityOutdoor spacesDecor

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

4.89 out of 5 average rating, 117 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

Outdoor spacesWalkabilityNearby

4.97 out of 5 average rating, 152 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 Cape w/Saltwater Pool-5min to Beach

WalkabilityPetsDecor

4.92 out of 5 average rating, 106 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

Pool Central Private Bridgehampton Home

WalkabilityOutdoor spacesCleanliness

4.96 out of 5 average rating, 131 reviews

A comfortable sleeping area features a spacious bed with a blue quilt and decorative pillows. Two side tables with lamps are placed beside the bed. A small arrangement of flowers adds a touch of color. Blinds cover the window, allowing for adjustable natural light.

Guesthouse in Shirley

La casita J place

Outdoor spacesPetsBackyard

4.89 out of 5 average rating, 149 reviews

A bright living area features a white sofa adorned with patterned blue pillows, positioned beside a rustic wooden coffee table. Large glass doors open to reveal a glimmering pool and lush outdoor landscaping, enhanced by vibrant potted plants and a shaded seating area.

Home in Southampton

Serene 3 Bed 2.5 Bath House w/Heated Pool

WalkabilityPetsWifi

4.94 out of 5 average rating, 116 reviews

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.

Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

WalkabilityOutdoor spacesAccess

Pet-friendly house rentals

An outdoor seating area is presented with woven furniture featuring bright red cushions. A rectangular table is centered on a striped rug, surrounded by several chairs and ottomans. A grill is positioned in the corner, with a fire pit adjacent, enhancing the space's functionality.

5 out of 5 average rating, 31 reviews

Newly renovated farmhouse - steps to Village

Outdoor spacesPetsParking

4.89 out of 5 average rating, 309 reviews

The airy living space features white shiplap walls and a high ceiling, accented by natural light from multiple windows. A gray sofa is paired with a glass coffee table, while a decorative fireplace adds charm. A ceiling fan provides airflow, enhancing the inviting atmosphere.

Home in Southampton

PICTURE PERFECT SOUTHAMPTON HOME-

WalkabilityPetsBackyard

The two-story home features a classic design with a white exterior and covered porches on both levels. A well-maintained front yard showcases manicured grass and colorful flower beds, while a paved walkway leads up to the entrance.

4.99 out of 5 average rating, 86 reviews

The Big Easy... A gentle, slow and easy going stay

Outdoor spacesWalkabilityWifi

A modern kitchen showcases stainless steel appliances and white cabinetry. A spacious island is accented with a decorative vase of flowers. Wooden chairs provide seating at the island, and natural light floods the space through a nearby window.

4.92 out of 5 average rating, 50 reviews

Walk to town, Marina Views, Greenport Village

Outdoor spacesPetsParking

A well-lit living area features a large window and a glass door leading to the outdoor space. A modern fireplace is centered in the room, complemented by stylish furniture, including a curved sofa and a standing lamp. Art decor adds visual interest to the wall.

4.81 out of 5 average rating, 42 reviews

Stylish Getaway in Greenport

PetsWalkabilityLocation

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.

4.95 out of 5 average rating, 263 reviews

Private beach, fully updated house, on 2 acres.

PetsWalkabilityComfort

4.9 out of 5 average rating, 84 reviews

Home in Southold

Southold waterfront 4 bed, pool open til October

Outdoor spacesWalkabilityLocation

A spacious balcony extends along the side of the house, offering unobstructed views of the shimmering water. Weathered wooden benches provide seating, while the gentle waves can be observed lapping against the shore in the distance.

4.89 out of 5 average rating, 44 reviews

North Fork Sound Front Home with Pool

WalkabilityOutdoor spacesCleanliness

Private, pet-friendly home rentals

4.99 out of 5 average rating, 85 reviews

The exterior of a meticulously restored Victorian house is showcased, featuring a light grey façade with white trim and a welcoming front porch. A decorative railing borders the yard, which includes neatly maintained landscaping, and the entrance is highlighted by a brown front door.

Apartment in Greenport

Victorian Pearl

Outdoor spacesPetsGetting around

4.91 out of 5 average rating, 43 reviews

Lakefront NoFo Cottage, walkable to public beach

Outdoor spacesPetsCleanliness

A spacious kitchen features light grey cabinetry and a large white farmhouse sink. Stainless steel appliances, including a gas stove and refrigerator, complement the wood-like flooring. Natural light enters through the window above the sink, highlighting the organized counter space.

4.89 out of 5 average rating, 9 reviews

Greenport Village Farmhouse

Outdoor spacesWalkabilityNearby

An inviting outdoor space with a spacious patio features a barbecue grill, seating area, and a dining table shaded by umbrellas. Lush greenery surrounds the area, and a glistening pool is visible in the background, enhancing the relaxing atmosphere.

5 out of 5 average rating, 13 reviews

Charming North Fork escape by the beach

Outdoor spacesWalkabilityKitchen

4.88 out of 5 average rating, 24 reviews

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

Home in Southold

Stylish Beach Getaway: pool & walking location

WalkabilityOutdoor spacesPool

4.93 out of 5 average rating, 14 reviews

Apartment in Southold

Kenney's Beach Loft - Vineyards, Horton Lighthouse

PetsWalkabilityNearby

4.91 out of 5 average rating, 88 reviews

A sunlit living area features a light-colored sofa accented with blue pillows. A coffee table sits in front, and a ceiling fan adds comfort. Large windows provide views of greenery outside, while a side table with a lamp enhances the cozy ambiance.

Guesthouse in Southold

Southold- Adorable 1 Bedroom Cottage

Outdoor spacesWalkabilityComfort

The outdoor area features a modern pool reflecting the house's warm glow at dusk. A spacious patio with seating is visible under a shaded overhang, surrounded by trees. The tranquil scene is enhanced by the illumination from the windows.