Pet-friendly holiday rentals in Sagaponack

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

WalkabilityOutdoor spacesSolo travel

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.

Outdoor spacesWalkabilityAccess

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 spacesWalkabilitySleep quality

4.91 out of 5 average rating, 178 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)

WalkabilityOutdoor spacesCheck-in

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

Peace and serenity in East Hampton and minutes from the Village. This exquisite modern home features high-end finishes such as Sub-Zero and Wolf appliances, quartzite waterfall kitchen island and counters, marble tiled bathrooms, designer mid-century decor and separately zoned air conditioning. The heated saltwater pool is surrounded by a bluestone patio, Ipe lighted deck and huge yard. The house features two wood-burning fireplaces in the living room and den and an outdoor fire-pit. RR# 26-891

PetsOutdoor spacesView

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!)

PetsOutdoor spacesCondition

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 spacesWalkabilityPool

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.

WalkabilityPetsValue

4.88 out of 5 average rating, 105 reviews

An airy living space features exposed wooden beams and large windows allowing natural light to fill the room. A modern yellow sofa and a dining table with elegant chairs create a welcoming atmosphere. Decorative elements include a gold-framed artwork and bronze accent tables on a soft area rug.

Home in Water Mill

Designer's Own, w Pool, 5 min. to Ocean & Village

Our 4BR airy home in a prime Hamptons location--Water Mill South--offers comfort, luxury, and tranquility, all while being just 5 min. away from ocean beaches, restaurants in Bridgehampton Village, and the area's best fields and farm stands. Impeccably renovated, comfortable, family-oriented traditional shingle house is in a quiet, established neighborhood perfect for walks or bike rides. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking

Outdoor spacesPetsTV

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.

Outdoor spacesPetsBeach

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.

PetsWalkabilityBarbecue

A modern kitchen is featured, equipped with sleek stainless steel appliances and an island with seating for four. Pendant lights hang above the counter, illuminating the space, while the white cabinetry provides a clean look. Large windows allow natural light to fill the room.

4.88 out of 5 average rating, 103 reviews

Contemporary East Hampton 4 Bedroom, Pool

Newly Built East Hampton home, a 5-minute drive from the ocean beaches and the Village center. The contemporary interior boasts 4 bedrooms equipped with 5 beds, all thoughtfully furnished, complemented by 2.5 well-designed bathrooms. Prepared to perfection for guests, the home offers a chef's kitchen, matching linens, both interior and beach towels, among other amenities. The outside space is highlighted by meticulous landscaping, a spacious yard, a patio with a a Non heated pool.

PetsWalkabilityLaundry

Popular amenities for Sagaponack pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

PetsOutdoor spacesIndoor spaces

4.95 out of 5 average rating, 204 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

Outdoor spacesPetsKitchen

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

WalkabilityPetsBeach

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

PetsOutdoor spacesBeach

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

Outdoor spacesWalkabilityHospitality

4.98 out of 5 average rating, 115 reviews

A cozy living area features a light-colored sofa adorned with blue and white throw pillows. Woven armchairs flank a wooden coffee table, while a stone fireplace adds warmth. Two large windows allow natural light to fill the space, complemented by greenery and decorative accents.

Home in Montauk

Sea Roost

WalkabilityOutdoor spacesBathroom

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

Outdoor spacesWalkabilityCheck-in

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 ¤¤¤

PetsOutdoor spacesWi-Fi

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 109 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

WalkabilityOutdoor spacesAccuracy

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

Outdoor spacesPetsHospitality

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 spacesQuiet

Luxe

An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.

Villa in East Hampton

Outdoor spacesLayoutBathroom

4.99 out of 5 average rating, 67 reviews

4.89 out of 5 average rating, 18 reviews

A heated pool is surrounded by a spacious wooden deck, providing ample room for relaxation. Sun loungers are positioned neatly nearby, offering comfortable seating options. A colorful inflatable float is visible on the water's surface, with lush greenery framing the tranquil setting.

Cabin in East Hampton

Close to all! Peaceful Heated Pool! *Month

Outdoor spacesBeachAccuracy

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 spacesAccuracy

An aerial view of a backyard features a spacious wood deck surrounding a gunite pool. Comfortable lounge chairs are positioned near the pool, alongside a shaded area with an umbrella. The natural greenery provides a serene backdrop to the outdoor dining area.

5.0 out of 5 average rating, 57 reviews

Secluded Luxury: New Gunite Pool, Walk to Bay

WalkabilityPetsAir conditioning

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 spacesComfort

Private, pet-friendly home rentals

5.0 out of 5 average rating, 21 reviews

Cottage in Bridgehampton

New Bridgehampton Sag Harbor Hamptons Cottage

PetsOutdoor spacesGetting around

A serene waterfront scene captures a vibrant sunset, showcasing a blend of orange, pink, and purple hues reflected on calm water. A wooden dock extends into the water, while silhouettes of people can be seen engaging at the water's edge.

4.92 out of 5 average rating, 12 reviews

Sag Harbor Village Waterfront Cottage

WalkabilityOutdoor spacesIndoor spaces

Apartment in East Hampton

A clean and inviting sleeping area is presented with a spacious bed adorned with white bedding. Two decorative pillows are arranged on the bed, adding a touch of texture. A floor-length mirror and a slender arrangement of decorative branches enhance the modern aesthetic of the space.

NEW Private, modern centrally located Apartment!

WalkabilityComfortLayout

4.92 out of 5 average rating, 36 reviews

5.0 out of 5 average rating, 23 reviews

Cozy East Hampton Getaway

PetsOutdoor spacesNearby

4.91 out of 5 average rating, 68 reviews

Modern Sag Harbor Home

WalkabilityOutdoor spacesCheck-in

Guesthouse in East Hampton

The exterior of the cottage is surrounded by lush, vibrant greenery, with climbing plants and flowering shrubbery. Natural light illuminates the soft colors of the cottage, which features multiple windows and a door framed by greenery, presenting an inviting and tranquil setting.

Enchanting studio cottage, walk everywhere

PetsWalkabilityHospitality

4.95 out of 5 average rating, 19 reviews

Apartment in East Hampton

A serene sleeping area features a spacious bed dressed in crisp white linens and accented by a dark throw pillow. Framed artwork adorns the walls, while stylish side tables complement the modern aesthetic. Floor-to-ceiling curtains in a neutral tone add a touch of elegance.

Private Newly built Modern East Hampton Apartment!

WalkabilityPetsShared spaces

4.85 out of 5 average rating, 95 reviews

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.