Vacation rentals with a pool in Sag Harbor

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

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.

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Sag Harbor Village Cottage with Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Spacious East Hampton Getaway with Pool

This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Light-filled Sag Harbor village gem

Midcentury style in the heart of Sag Harbor Historic district. Soaring 20-foot floor-to-ceiling windows and skylights throughout offer the ideal indoor-outdoor experience for enjoying all seasons. Featured in Home & Garden, the house is situated on sprawling grounds, one of the largest lots in Sag Harbor. In the winter, enjoy the Scandinavian sauna and lounge in front of the fireplace. Gunite pool open May 25 to Sept 3.

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Serene 3 Bed 2.5 Bath House w/Heated Pool

Situated off a quiet lane on a half-acre, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 3 wonderful bedrooms 2 modern bathroom and a heated saltwater pool ( See Pool heat and Pool Closure Details ) with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Astounding Watermill 5 Bedroom home with Pool

Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!