Fitness-friendly holiday rentals in Wainscott

Spacious Modern 5BR • Close to Town & Beach

⭐ Rated 4.95 with 145+ glowing reviews! Welcome to your modern Hampton Bays retreat, perfect for families and groups. Ideally located just minutes from beaches, town, dining, and shops. Enjoy bright, open living spaces with Smart TVs and fast WiFi throughout. Enjoy a finished basement with ping pong, gym, and tv lounge, plus a backyard with BBQ and outdoor seating. Whether you're here to explore, relax, or reconnect, this home offers the ideal Hamptons getaway with thoughtful touches throughout.

Secluded Oasis Heated salt Pool 5 min ride beach

Kick back and relax in this calm, stylish, Zen appeal home. Brand new newly renovated house, mid century furniture, electric induction stove, Smeg fridge, 400sq ft mahogany deck (for yoga). HEATED POOL extra fee opens May 20x40 ft saltwater .4Bdr/3Bthr, full kitchen, working fireplace, dedicated workspace room, enjoy the outdoors, propane gas grill, sunbathing chairs, umbrella, wifi, TV, DW, W/D. Located in the artsy Springs area, neighborhood to Maidstone Park Beach, and Pollock Krasner house.

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.

North Fork True Beachfront Home

This is New York version of California's Big Sur, with direct beach access and spectacular water views, surrounded by forest. Modern, 3,000 sq feet. Walk down path from house to a fantastic sand beach with lifeguard. Large deck for lounging, BBQ, and sunset views. 4 bedrooms, 3 baths, outdoor shower, 4 person hot tub, 2 person sauna, separate den w/home theater, gym, hammocks, wood burning fireplace. Experience the Long Island Sound without neighbors and the suburbs; a naturalist's haven.

Incredible 9+ Bed Watermill Home Wellness Retreat

Luxury 9000 SF Southampton villa with a heated gunite pool, hot tub, steam shower & sauna, 9-bedroom, 8.5-bathroom, nestled on a quiet cul-de-sac in Watermill. Bright with large windows, e-shades in bedrooms, indoor/outdoor sound system, W/D on every floor (3 sets). Formal dining/living area, chefs' kitchen, TV room, movie room, gym, outdoor kitchen, arcade, pool table, air hockey and foosball. Please read our disclosures & house manual. Not a party house and no events permitted.

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Elegantly designed 7 Bedroom / 7 Bath home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches and the vibrant Easthampton Village. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Kindly 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 are smoke-free.

Beachside Escape from NYC

Topping Rose House has been standing on the same intersection of Montauk Highway in Bridgehampton since 1843. The hotel was renovated and reopened in 2012 and is now the preeminent place to feel like a Hamptonite. In the summer, relax by the pool or bike to the Atlantic. In the winter, enjoy the stunning landscape of the villages of the Northeast. The hotel has 22 rooms, and is only listing on AirBnB for a limited time. The specific room type is assigned on the day of arrival.

Luxury 4-bedroom in East Hampton [w/private beach]

Welcome to Camelot House East End, where Norman Rockwell meets the South of France. Your home away from home in the Hamptons is close to all the action, and yet, located in a tranquil paradise just steps away from a members-only beach. Camelot House is appropriate for individuals and families alike. The home is fully equipped with high end appliances and finishes, and yet, kid-friendly with a pool fence, stair gates, and a pack-n-play available for use.

East Hampton 3 Bed / 3 Bath Charmer w Pool

Situated on a half-acre of land, this classic shingle cottage with designer interiors offers the ideal Hamptons getaway. Located in the picturesque area of East Hampton, less than 5 miles from town, bay 7 Ocean beaches. 3 bedrooms, 3 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Luxe| Pool|Game Room |Outdoor Movie|HotTub|Firepit

SERENITY AT SHOREWOOD 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.