Pet-friendly holiday rentals in Sag Harbor

4.91 out of 5 average rating, 141 reviews

Serene + private ~ 1 block to waterfront dining

Enjoy zen living at this serene, chic, Hamptons oasis! Ideally located 1 block to waterfront dining, 8 minutes to beaches + 9 minutes to Main St! Relax poolside w/ tons of greenery + nature views. Spark up the BBQ + firepit under the starry sky. Listen to the crickets + spot a deer on the property. Curl up to the wood burning fireplace, cook in your Chef's kitchen + stream on your 80' TV Enjoy coffee on the sea + dinner w the best sunsets just 1 block away. A perfect escape + place to unwind!

Outdoor spacesWalkabilityCheck-in

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 523 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Outdoor spacesWalkabilityCheckout

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, 266 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

PetsOutdoor spacesNearby

4.94 out of 5 average rating, 334 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 -

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 grounds are smoke-free.

Outdoor spacesWalkabilityCheckout

A flower-filled back deck is highlighted by comfortable seating arrangements and a small dining table. Potted flowers in vibrant colors complement the wooden decking, while a table reflects the surrounding greenery. Various lounge chairs invite relaxation in this serene outdoor space.

4.91 out of 5 average rating, 117 reviews

Walk to Village Sag Harbor Victorian

Charming 2 bedroom 2 bathroom house in the historic Village of Sag Harbor with view of pond and park. Walking distance (not driving) to the quaint village with restaurants, shops, long wharf, gym, yoga. Living room with fireplace, dining room, kitchen and office. Upstairs loft ensuite bedroom and bathroom. Downstairs bedroom and full bath with tub and shower. Flower filled back deck with BBQ. Wireless internet, 2 TV's, air conditioner units, washer dryer. Minutes to ocean and bay beaches.

WalkabilityOutdoor spacesWi-Fi

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

4.98 out of 5 average rating, 144 reviews

Explore the Water & Woods at a Relaxing Retreat

Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway. (No AI used in these photos!)

Outdoor spacesWalkabilityBathroom

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.

PetsWalkabilityGetting around

4.91 out of 5 average rating, 202 reviews

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

Outdoor spacesPetsLayout

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

4.94 out of 5 average rating, 106 reviews

Oasis backyard, Pool, Gym, and Sunroom!

Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back yard. Decks in the back yard with lounge chairs and 2 patio dining tables. Front deck with lounge chairs. Outdoor gym located in the corner of the yard. Paddle boards, boogie boards, beach chairs, and beach towels provided. Walk to EHP Resort (SiSi Restaurant), and Harbor Bistro featured on Delicious Destinations. Paddle Diva paddle board/kayak rentals also nearby.

PetsWalkabilitySleep quality

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, 140 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

WalkabilityPetsLaundry

4.94 out of 5 average rating, 155 reviews

A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.

Apartment in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

WalkabilityPetsAccess

A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.

4.9 out of 5 average rating, 117 reviews

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

Outdoor spacesPetsCheck-in

Popular amenities for Sag Harbor pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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 spacesNearby

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 spacesPetsSleep quality

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 spacesBiking

4.87 out of 5 average rating, 137 reviews

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.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

WalkabilityPetsAmenities

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-

PetsOutdoor spacesBiking

4.85 out of 5 average rating, 172 reviews

Sag Harbor House for rent.

PetsOutdoor spacesAccuracy

4.92 out of 5 average rating, 130 reviews

The exterior of a two-story home is visible, featuring large glass windows that promote natural light. A spacious wooden deck hosts a dining area with a white umbrella. Lush green grass and trees surround the area, creating a serene outdoor setting.

Home in Water Mill

Elegant Modern Artist's Residence

WalkabilityOutdoor spacesFamily

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

PetsOutdoor spacesLayout

Pet-friendly home rentals with a pool

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

4.88 out of 5 average rating, 236 reviews

HeatedPool, Walk2Beach, Yard4Pup, Spotless, GasBBQ

WalkabilityPetsValue

4.96 out of 5 average rating, 215 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

Outdoor spacesWalkabilityCondition

A private swimming pool reflects clear blue skies, surrounded by lounge chairs and umbrellas. Lush greenery frames the scene, while a wooden deck leads to the main house, which features a modern architectural design. A swing set adds an element of leisure to the serene outdoor space.

4.94 out of 5 average rating, 50 reviews

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

Outdoor spacesPetsCleanliness

The exterior of a spacious home is visible, featuring a large pool surrounded by a wooden deck. Comfortable outdoor seating arrangements are present. Lush greenery and trees provide a natural backdrop, with the house showcasing a distinctive lofted roof and multiple large windows.

4.8 out of 5 average rating, 15 reviews

Quintessential Summer Classic

PetsWalkabilityPool

An in-ground salt-water pool is surrounded by natural stone, set amidst lush greenery. Sun loungers are positioned alongside the pool, and a shaded seating area is visible to the right. A wooden structure stands in the background, blending with the tranquil landscape.

4.91 out of 5 average rating, 65 reviews

East Hampton Secluded Escape with Gunite Pool

WalkabilityOutdoor spacesBackyard

A spacious dining area features a large wooden table surrounded by white chairs. Natural light streams through multiple windows, highlighting the warm tones of the decor. Stylish woven pendant lights hang from the ceiling, creating an inviting atmosphere for gatherings.

4.96 out of 5 average rating, 24 reviews

Tasteful Hampton 4 Bedroom w Heated Pool EH / Sag

PetsOutdoor spacesHospitality

4.98 out of 5 average rating, 80 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

PetsOutdoor spacesWi-Fi

A spacious outdoor area features a large swimming pool surrounded by lush green grass. Four lounge chairs are positioned nearby, alongside a parasol offering shade. A quaint shed with red accents is visible in the background, complemented by seating areas. Tall trees provide a natural backdrop.

5.0 out of 5 average rating, 17 reviews

Sag Harbor Dream Home: Heated Pool

Getting aroundLayoutAccuracy

Private, pet-friendly home rentals

5.0 out of 5 average rating, 113 reviews

A spacious backyard is framed by mature trees, featuring a fire pit surrounded by white Adirondack chairs. A children’s playground with swing set is visible nearby, while the home, illuminated by warm lights, stands invitingly in the background.

Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

Outdoor spacesWalkabilitySleep quality

A bright living room features large windows that showcase water views. Comfortable white sofas are arranged around a wooden coffee table, while a dining area is visible in the background. A ceiling fan and a wall-mounted TV add to the room's functionality.

4.92 out of 5 average rating, 48 reviews

Wake up to Stunning Views at a Serene Waterfront Haven

PetsOutdoor spacesCleanliness

5.0 out of 5 average rating, 14 reviews

Light-filled Retreat by the Bay

WalkabilityOutdoor spacesBackyard

4.88 out of 5 average rating, 32 reviews

A bright living room is featured with a large flat-screen television mounted above a modern fireplace. A bay window offers views of greenery, complemented by a cozy seating area. Elegant decor includes a stylish mirror and a decorative table, enhancing the inviting ambiance.

Cottage in Southampton

SPA DEPARTURES NEAR THE SEA

Outdoor spacesLong stayView

5.0 out of 5 average rating, 68 reviews

A spacious studio apartment is presented, featuring a large circular mirror and light-colored furnishings. Two separate sleeping areas are visible, with one prominent bed framed by bamboo-style headboards. Natural light filters in through sliding glass doors, enhancing the welcoming ambiance of the room.

Apartment in Sag Harbor

Spacious apartment in Sag Harbor

Outdoor spacesWalkabilityLayout

The charming exterior of a cedar shingle house is framed by lush greenery. A welcoming entryway features a blue front door, complemented by symmetrical windows on either side. The landscaped front yard includes low shrubs and a gravel pathway leading to the entrance.

4.79 out of 5 average rating, 72 reviews

Beautiful E. Hampton Home w/ Brand New heated pool

PetsOutdoor spacesCheck-in

The exterior of the cottage is presented, showcasing its wooden shingle design and large windows. The surrounding grassy area is well-maintained, with lounge seating visible on a stone patio. Trees provide privacy on the property, enhancing the peaceful environment.

5.0 out of 5 average rating, 10 reviews

Modern Cottage with a View

Outdoor spacesWalkabilityIndoor spaces