Holiday rentals in Sagaponack

A two-story beach house features wooden shingle siding and large windows. A sparkling blue pool is positioned in the foreground, surrounded by a wooden deck. Comfortable lounge chairs are placed nearby, offering options for relaxation outdoors.

4.76 out of 5 average rating, 51 reviews

Cheerful 3 bedrm-4 beds-3 bath -beach home w pool

Heart of the Hamptons is situated this bright, beach house 5 min from the ocean, BH/Sag Harbor town, & Wolfer vineyards. 2 master suites w/ ensuite bathrooms and an additional guest room with adjacent bathroom that comfortably sleeps 6 -1 King, 1 queen, 2 twin. Open kitchen that adjoins the dining area and the double height living room w/ fireplace. Sparkling heated (add charge) pool (MD-mid Sept) and palatial lawns with room to roam. Keep it simple at this peaceful and centrally located getaway

A spacious bedroom is featured with a comfortable king-sized bed, adorned with soft linen and decorative pillows. Nightstands with stylish lamps provide gentle illumination, complementing the calm color scheme of the room.

4.96 out of 5 average rating, 81 reviews

Hamptons Elegant and Comfortable Apartment

Enjoy your stay in this beautifully decorated and completely private basement apartment - with all original artwork- in the center of the Hamptons with the added convenience of being close to major towns and beaches. Large bedroom with comfortable king sized bed and high quality mattress and linen. Large-screen smart TV with many channels. Closet space, well equipped kitchenette, bathroom with glass-enclosed shower. Seating area for 4 and second large-screen smart-TV with comfy oversized couch.

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, 330 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 grounds are smoke-free.

4.85 out of 5 average rating, 144 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!

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.

4.91 out of 5 average rating, 171 reviews

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)

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

4.99 out of 5 average rating, 220 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

A spacious backyard is showcased, featuring a large saltwater pool surrounded by six lounge chairs. Lush green grass is complemented by a flowerbed, while tall trees provide shade. The house, with a wooden deck, is visible in the background.

4.94 out of 5 average rating, 16 reviews

Hamptons Home w/ Salt Water Pool

3 Bed/ 2 Bath Sag Harbor Retreat w/ Salt Water Pool. Nestled close to both Sag Harbor Village and Sagaponack, this charming home offers the perfect blend of comfort and convenience. With 3 bedrooms, 2 baths, and situated on a generous .66-acre lot. Outdoors, the expansive yard features a 35x17 saltwater pool. Located just moments from Sag Harbor Village, you'll enjoy easy access to boutique shops, acclaimed restaurants, Wolffer Estate Vineyards, and picturesque waterfront views.

Guest suite in The Hamptons

A cozy sleeping area is highlighted by a spacious bed with light blue bedding, positioned near a working fireplace. A television is placed on a wooden stand across from the bed. Soft lighting from bedside lamps creates a warm ambiance, complemented by a decorative artwork on the wall.

4.9 out of 5 average rating, 394 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

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.

4.94 out of 5 average rating, 141 reviews

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 .

Luxe

Villa in The Hamptons

4.98 out of 5 average rating, 58 reviews

SERENITY AT SHOREWOOD Pool is Open April 1 - November 1. Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

Guest suite in The Hamptons

4.97 out of 5 average rating, 174 reviews

Super sweet king en-suite prvt access pool central

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

4.95 out of 5 average rating, 317 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Popular amenities for Sagaponack holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sagaponack

The exterior of the artist's beach cottage features a charming facade with wood shingles and well-maintained landscaping. A welcoming front porch is flanked by shrubs and flower beds, while a serene lawn leads toward a lush backyard visible in the distance.

4.91 out of 5 average rating, 55 reviews

Classic Hamptons Cottage - Heart of Amagansett

A welcoming living area features a comfortable sofa adorned with coral-patterned pillows. A rustic coffee table sits at the center, surrounded by natural light from large windows. A view of the open space and kitchen area can be seen in the background.

4.98 out of 5 average rating, 162 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

A modern studio room features a spacious bed beside a seating area with a comfortable sofa and a small coffee table. Large windows with slatted shades allow natural light in, while a round mirror enhances the decor. Soft green and brown tones are present in the furnishings.

5 out of 5 average rating, 41 reviews

A Fall/Winter Escape from the City

A gated patio area is surrounded by lush greenery, featuring tall plant hedges on one side. Two wooden arches frame the entrances, leading to a scenic garden path. A small seating area with a patterned cushion is set in the foreground, inviting relaxation.

5 out of 5 average rating, 5 reviews

Cozy Hamptons Cottage