Family-friendly holiday rentals in Sagaponack

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.

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

Whaling Captain Pierson's Apartment

Whaling Captain Pierson's Apartment 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 TOO and Whaling Captain Pierson's Cottage).

Swimming pool w/Hot tub Fire Pit Coffee Bar

Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit. Heated pool seasonal. We are just minutes from the beach. Spend time in our 6 person jacuzzi. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

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!)

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

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!

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds, 2.5 baths - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond -Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action. NOTE: Due to water leakage issues, the bath in pool house is not available

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.

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 12 minute walk to historic Sag Harbor Village Main Street. Ten minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea maker. Air conditioned. Bedroom and large living area. Strictly 2 person max. Not suitable for infants/children No pets - owner is allergic.

Marvelous 4 Bed East Hampton home w Heated Pool

Beautiful, designer home with new appliances located just a few short minutes to ocean beaches, Wolffer Vineyard, East hampton /Sag Harbor villages. The home has mature landscaping and pristine. Every attention to detail has been met. Please read my disclosures & house manual before you request in order to be on the same page. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Pool Central Private Bridgehampton Home

Longer stay and reduced rate please email 169bridgehamptoncottage@gmail.com. NOTE* Rest assured, as always, even more so now, our housekeeper is aware to put in the extra tedious clean needed for a happy healthy stay! 7 minute drive to Hampton classic or less 20 min bike ride. Restaurants, studio 89 gym, on same rd. Ocean+bay 5-10 min drive. Bike to 1 ocean Yoga/winery. Halfway to Sag Harbor+Bridgehampton. There is pet fee.