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127 Head of Pond Road, Water Mill. (Photo courtesy of Douglas Elliman)

Spring may be the official season on the calendar, but for those eying summer rentals, it’s also the season to find your home away from home. This year, agents say, the market is robust for both long and shorter-term rentals, with pricing stabilized post-Covid, and “a healthy balance of supply and demand” says Joseph Van Asco of Douglas Elliman. 

“The rental market is the strongest and most active it’s been in several years,” he says.

Sarah Keogh of the Atlantic Team at Douglas Elliman, agrees. “The summer rental market is off to a strong start in comparison to last year’s down market,” she says. “We are seeing the more traditional month or full-season renter return to the Hamptons.” 

Judging by the abundance of signed leases agents are noting, it’s shaping up to be a busy summer season on the South Fork.

“Many landlords listed their homes at the reduced rental rates that they ended with last season and have already locked in rentals for the summer,” Keogh notes, adding that despite those deals, inventory still remains strong.

For homeowners looking to rent out their homes, Van Asco advises, “If you are aware of your competition, priced competitively and have created a great rental vibe, then you should have no issue renting this summer. We still have a strong four to six weeks of serious rental activity head of us.” 

No matter which side of the rental equation you’re on, it’s time to get in on the action. For seekers, here are a few to consider:

127 Head of Pond Road, Water Mill

127 Head of Pond Road, Water Mill (Photo courtesy of Douglas Elliman)

If you have a large clan or a lot of friends, this seven-bedroom, eight bathroom home offers lots of room inside and out. Sited on 1.6 acres, it includes a sunken tennis court, oversized gunite pool and fully appointed pool house, and expanses of lush lawn (croquet, anyone?). The first floor has multiple options for gathering — in the double-height, light-filled great room with a fireplace and separate areas for quieter conversation, playing board games or quiet refuge. Ditto the dining areas: There’s a formal dining room, ample seating at the center island in the kitchen, a separate cozy table with banquette and chairs and many options outside on the patio. On the lower level, there’s a home theater, table tennis, foosball and a treadmill. Water Mill’s main drag is less than a mile away and the Southampton beaches are about six miles. 

Rates: June: $100,000; September: $120,000; August through Labor Day: $280,000

27 Ezekills Hollow, Sag Harbor 

27 Ezekills Hollow Road, Sag Harbor. (Photo courtesy of Douglas Elliman)

This five-bedroom, five-bath rental on 1.84 acres near Gleason Point on Genet Creek is a respite among the leafy trees, with natural ornamental grasses creating a backyard haven. The lower level features an open format conducive for entertaining with multiple areas for seating and dining, and extending to the outdoor patio for seamless indoor/outdoor living. Pretty natural wood tones provide a warmth throughout the common rooms, some of which have fireplaces. The lower level includes a comfy home theater, billiards table and wet bar, an equipped gym. The outdoor living room is covered and overlooks the creek and lush plantings, and the swimming pool with a spa. There’s really no reason to leave, but if you have to, the home is near the South Ferry to Shelter Island and less than four miles from Sag Harbor Village. 

Rates: July/August through Labor Day: $300,000; Memorial to Labor day: $350,000 

57 Sammy’s Beach, East Hampton

57 Sammy’s Beach, East Hampton. (Photo courtesy of Douglas Elliman)

This four-bedroom rental is packed with amenities inside and out, including a beach in the front yard. The common areas include numerous spaces for getting together or getting away from it all, including a settee embedded in a cozy reading nook created of bookshelves. The large chef’s kitchen seats at least four at the center island, and there are additional dining areas inside and out. The lower level entertainment area includes a pool table, television and Peloton, and additional space for guests. Outdoors is equipped for recreation and entertaining, with a gas grill (direct gas line, so buh-bye propane tanks!) and a dining table that seats eight, a wrap-around mahogany deck and outdoor shower; kayaks and paddleboards are provided. Flexible time frames, including weekly rentals ($35,000)

Rates: June; $75,000; July: $100,000; August: $125,000; July/August through Labor Day: $250,000; August – Labor Day: $150,000.

7 Old Station Place, Amagansett

7 Old Station Place, Amagansett. (Photo courtesy of Douglas Elliman)

Charming cottage style on the outside and updated, modern furnishings on the inside, this six-bedroom and 6.5 bathroom home on .58 acres south of the highway is a fun house with a quadruple bunk room for kids, a game room with billiards and table tennis, media room and a high-design interior for the grownups. The open format kitchen offers seating at the island for causal eating, and dining for eight at the table. A formal dining room and a covered patio provides expanded dining options. Two plush living rooms—one with a fireplace—offer comfy places for down time. The pool house is equipped with a wet bar and lounge area and enjoys privacy behind a wall of hedges. 

Rates: July/August through Labor Day: $350,000; Memorial to Labor days: $495,000 

29 Monroe Drive, Montauk

29 Monroe Dr., Montauk. (Photo courtesy of Douglas Elliman)

This six-bedroom, five+ bath-home offers a multi-leveled stylish respite in the Hither Hills neighborhood. The chef’s kitchen is located on the ground level with seating at the long marble island and a window-side table. On the mezzanine level is the living room with a fireplace and additional dining, and sliding doors leading to the deck with additional dining and a portable grill area. The bedrooms are equipped with wall-mounted televisions and each has its own ensuite bathroom. Outdoor amenities include heated gunite pool and spa, outdoor shower, hot tub, outdoor firepit and creative landscaping. Gurney’s Montauk Resort & Seawater Spa is just over a mile away, with monthly membership options. 

Rates: July: $110,000 (only availability)