Fitness-friendly vacation rentals in Southampton

Private 1br Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

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 grouds are smoke-free.

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.

AMG- Fall retreat Pool heated thru Oct. Walk2Town

Sleek renovated Amagansett home. Large corner property with Heated Saltwater Pool (May to late October) & separate cottage/pool house w/with Peloton, Sonos surround sound, large screen TV, bar & foosball table. Open kitchen w/marble counters. 2 baths with glass showers & Jacuzzi tub. Master with Queen bed, second bedroom has two twin beds. There is also an oversized sleeping loft with two twin beds. Bluestone patio with BBQ, dining & lounge area. Walk to town & beaches. No Pets.

Stunning North Fork House • Heated Pool/ Wineries

Chic and luxurious farmhouse retreat in North Fork. Set on a private 1-acre lot with a pool, lounge areas, and ocean breeze. Family-friendly and perfect for couples or a friends' getaway. Just 1.5 hours from NYC and close to beaches, wineries, farm stands, hiking, seafood, and golf. Enjoy fast Wi-Fi, a full kitchen, stylish interiors, outdoor pool, and landscaped grounds. Ideal for a peaceful escape, remote work, or wine country retreat near the Hamptons, North Fork and Shelter Island.

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.

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.

Hamptons Lux Retreat

Our modern Hamptons retreat offers not only luxury and comfort but also convenience. We are ideally located less than 5 minutes from incredible bay beaches, less than 10 minutes away from some of the Hamptons' most beautiful ocean beaches, 10 minutes from the charming town of Southampton and the renowned North Fork wineries and farms are less than 20 minutes away. Plan your perfect weekend getaway and enjoy all that both The Hamptons and The North Fork have to offer!

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.