Pet-friendly vacation rentals in Jamesport

4.88 out of 5 average rating, 104 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!

4.93 out of 5 average rating, 122 reviews

Walk to Vineyards, Beach, Restaurants • Sleeps 8

• Spacious 3 BR house in heart of Jamesport - includes King, Queen & 2 twin beds. Queen air mattress also available. • Great for family vacations, weekend getaways & local weddings. • Clean sheets, pillows, fresh towels & toiletries. • Backyard complete w/ outdoor bbq, fire pit, hammock & patio seating. • Cook in open kitchen fully equipped w/ dishes, utensils, spices, pots & pans; eat local ingredients from nearby farms & markets. • Indoor & outdoor dining tables seat up to 8 guests.

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.

4.94 out of 5 average rating, 316 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

4.96 out of 5 average rating, 321 reviews

An open living space features a bright white interior with large windows allowing natural light. Seating includes a plush sofa and wicker chairs. A modern kitchen with stainless steel appliances is visible. The dining area showcases a table for six, enhancing a communal atmosphere.

Bungalow in Woodmont

Fall Sale! Cozy Bungalow/Pet-friendly/Walk2Beach

Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

4.89 out of 5 average rating, 537 reviews

A serene beach scene illustrates a vast stretch of shoreline, with gentle waves lapping at the sand. The water is a mix of blue and green hues under a clear sky, providing a calming seaside atmosphere.

Cabin in Rocky Point

Great little place just for a couple

The outdoor courtyard is especially nice and private ,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton.

4.98 out of 5 average rating, 167 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 North Fork

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.

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.

4.98 out of 5 average rating, 182 reviews

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!)

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.

4.85 out of 5 average rating, 113 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views 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! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

A spacious living area is illuminated by natural light from large windows. A comfortable sofa and armchair are arranged around a low coffee table. A dining table with six chairs sits adjacent, while the kitchen is visible in the background. A staircase leads to the upper floor.

4.94 out of 5 average rating, 144 reviews

Modern 5BR Getaway • Close to Beaches & Wineries

⭐ Rated 4.95 with 135+ glowing reviews! This modern 5BR, 4BA Hampton Bays retreat sleeps 10 and is just minutes from beaches, dining, and shops. Enjoy open living spaces, Smart TVs, and fast WiFi. The finished basement features ping pong, a gym, and lounge, while the backyard offers a BBQ, patio, and outdoor seating. Beach gear is included, making it easy to explore. Perfect for families or groups seeking the ultimate Hamptons getaway with comfort and style.

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.

4.93 out of 5 average rating, 150 reviews

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.

4.94 out of 5 average rating, 252 reviews

A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.

Cottage in Patchogue

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.

4.94 out of 5 average rating, 145 reviews

Astounding Watermill 5 Bedroom home with Pool

Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Popular amenities for Jamesport pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

4.89 out of 5 average rating, 38 reviews

Waterfront NoFo Cottage w/ public beach access

A landscaped yard features a lush green lawn framed by mature trees and bushes. The expansive bay and ocean views are visible in the background. A colorful sunset paints the sky, creating a serene and tranquil setting.

4.98 out of 5 average rating, 57 reviews

Best View + Putting Green + Private Beach

4.82 out of 5 average rating, 102 reviews

The image captures a serene beach at sunset, where gentle waves lap against the shore. The sky displays a gradient of colors from warm oranges to cool purples, reflected softly on the water's surface. The distant cliffs are outlined against the colorful horizon.

Home in South End

Summer Retreat at the beach , enjoy Wine Country

4.96 out of 5 average rating, 117 reviews

A two-story oceanfront home features a light gray exterior with large windows and a turquoise front door. A spacious ground level is accessible via white railings, leading to an outdoor sitting area. The serene beach and water views are visible in the background.

Home in Milford

Oceanfront Retreat with Hot Tub

The backyard features a large, clear swimming pool complemented by lounge chairs and a shaded dining area under an umbrella. The ranch-style home and surrounding trees create a serene, private space. Soft blue skies and dappled sunlight reflect off the water, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 31 reviews

Renovated Ranch Home wPool & Beach Acces

4.93 out of 5 average rating, 170 reviews

1800 Historical EH Home, 1 Mile to Town!

A comfortable living room features a cozy sofa adorned with plaid pillows. A fireplace is positioned beneath a wall-mounted television. Natural light enters through well-dressed windows, illuminating the space and providing a view of the green yard outside.

5 out of 5 average rating, 25 reviews

Cozy Home Near Beach and Restaurants

4.93 out of 5 average rating, 137 reviews

A dining area is presented featuring a dark wooden table surrounded by four white chairs. A decorative potted plant is centered on the table, complementing the modern decor. A doorway leads to a softly lit bedroom in the background.

Home in Port Jefferson

Port Jefferson Convenient, Cozy and Chic!

Pet-friendly home rentals with a pool

4.99 out of 5 average rating, 109 reviews

An open-concept living space features a dining area with a rectangular wooden table adorned with a decorative bowl. A spacious couch is positioned near a fireplace, with large windows allowing ample natural light. A stylish chandelier hangs above, complementing the high, pitched ceiling.

Villa in The Hamptons

East Hampton Village Fringe, Renovated with Pool

4.93 out of 5 average rating, 136 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

Guesthouse in The Hamptons

A serene view of a spacious barn with a deck illuminated by the golden light of sunset. Surrounded by lush foliage, the barn features large windows and a welcoming porch, providing a glimpse of modern yet comfortable architecture.

4.9 out of 5 average rating, 214 reviews

Beautiful Airy Barn in Springs

4.87 out of 5 average rating, 126 reviews

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

Condo in North Fork

Beautiful condo on Long Islands Northfork

4.89 out of 5 average rating, 102 reviews

Serene + chic Hamptons home, near all attractions

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.

4.84 out of 5 average rating, 122 reviews

East Hampton Oasis - Pool and Hot Tub

4.96 out of 5 average rating, 105 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

4.98 out of 5 average rating, 47 reviews

A spacious outdoor area features a heated gunite pool surrounded by sun loungers and greenery. The villa is visible in the background, showcasing large windows and a blend of natural materials. Shade is provided by overhanging trees scattered around the property.

Villa in The Hamptons

Incredible 9+ Bed Watermill Home Wellness Retreat

Private, pet-friendly home rentals

The exterior of a two-story home displays a welcoming porch with white railings and steps leading to a red front door. The house features light-colored siding under a peaked roof. A manicured lawn and trees surround the property, providing a serene and inviting atmosphere.

4.82 out of 5 average rating, 87 reviews

Hamptons 5BR Stay • Near Bay & Cozy Firepit

4.96 out of 5 average rating, 48 reviews

A serene waterfront scene is presented, showcasing calm blue waters extending towards the horizon under a clear sky sprinkled with a few clouds. The sandy shoreline gently curves along the edge, bordered by sparse greenery for a peaceful coastal ambiance.

Home in Mastic Beach

Mastic Beach Surf House

Cottage in South Jamesport

A charming beach cottage is set against a clear blue sky, featuring a welcoming enclosed front porch. Surrounding gardens are filled with vibrant pink and purple flowers, framing the path leading to the front door and adding to the property’s tranquil ambiance.

5 out of 5 average rating, 8 reviews

Charming Beach Cottage, Vineyards & Sunset Views

5 out of 5 average rating, 25 reviews

A spacious great room is highlighted by a cathedral ceiling with exposed wooden beams. Comfortable sofas frame a central coffee table, while large windows provide natural light, accentuated by sheer white curtains. A cozy reading nook is positioned against the wall, complemented by a variety of books.

Cottage in North Fork

Lovely North Fork Beach Cottage (2 BR/2 bath)!

4.93 out of 5 average rating, 56 reviews

An inviting two-story home is highlighted by a stone facade and a decorative chimney. A spacious deck is furnished with chairs for relaxation, surrounded by a well-kept lawn and a variety of trees, creating a serene outdoor environment.

Home in South End

Gorgeous home with saltwater pool. Steps to beach!

An expansive home is set against a backdrop of lush green trees, featuring a well-maintained lawn. The fenced-in yard showcases a clear, inviting heated pool and a paved pathway leading towards the house, which has a deck with sliding doors that open into the living area.

4.95 out of 5 average rating, 64 reviews

Luxury retreat w/ heated pool, steps to the Beach!

5 out of 5 average rating, 14 reviews

The exterior of the two-story apartment is showcased, featuring grey siding and multiple windows with white trim. A defined driveway leads to the building, bordered by manicured greenery. Sunlight casts soft shadows across the landscape, enhancing the inviting atmosphere.

Apartment in North Fork

Beachside Bliss