Fitness-friendly holiday rentals in The Hamptons

North Fork Extended-Stay Retreat, Pool, Beaches

Escape to the heart of Long Island's North Fork and enjoy a private farmhouse designed for extended stays. Whether you're working remotely, exploring wine country, spending time with family, or escaping the city for a few weeks, this peaceful retreat offers everything you need to settle in and relax. Surrounded by vineyards and farms, yet minutes from beaches, marinas, Love Lane, and Greenport Village, you'll experience the best of North Fork living from one central location. Rental permit 0925

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 grounds are smoke-free.

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

POOL + Beach Oasis! Winter deals 2+ nights!

Chef kitchen: 2 ovens/lux app's/coffee bar w/ Nespresso/Keurig 2 living rooms Dining room seats 10 1st floor Primary Suite: king bed, gas fireplace, furnished deck overlooking pool, 4 piece bath: huge shower & jacuzzi tub 2 of 4 Guest rooms on 1st fl Gym/yoga rm: bench + weights (no treadmill) TV's in bedrooms inc. Firesticks Fenced backyard oasis w/ heated mineral spring pool, loungers, shaded cabana, outdoor dining, & Weber BBQ, outdoor shower Kitchenette in den/office Central AC/heat/fans

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.

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

Located in Hampton Bays just a 5 min drive to beaches, waterfront restaurants, wineries & golf courses. This vacation property offers an open concept single family home w/ 4 bedrooms, 5 baths, a spacious living room, an outdoor deck and patio with a table and chairs, pool, jacuzzi and a pool house! The pool is opened mid May - second week of October and can be heated at an additional cost. Located just 5min away from Hampton Bays town and 5min drive to one of our lovely beaches.

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.

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.

After Beach Family Retreat

A Newly Renovated 3 Bedroom Post Modern Ranch including new bathrooms, updated kitchen with granite tops, refinished hardwood floors, outdoor deck, new salt water pool an outdoor cedar shower, and a pristine lawn. Location is just a short ride to Ponquogue or Tiana Beach. This house is perfect for family fun. Great restaurants, golf, fishing, wineries, bowling, Tanger Outlets, the Long Island Aquarium, & Splish Splash water park are all nearby!

Modern Oasis in Southampton

INQUIRE ABOUT MONTHLY RENTALS! Renovated house in Southampton beach, fantastic for families or couples looking for relaxing time in the middle of the greenery. 10-15 min drive to towns and beaches. Perfect city escape and ideal, silent WFH refuge. Chefs kitchen fully equipped, washer and dryer in the unit. Balconies on each floor, heated pool and fire pit for extra fun. Newly renovated basement with a gym, Ping Pong and Foosball tables.

*Hamptons Oasis* 4BR Cool Getaway

Can't beat autumn in the Hamptonsl. The beaches, sun, shopping, restaurants & nightlife. Or just stay at the house. It has everything you might need for a family vacation. With a spacious deck and firepit, the backyard might be all you need. And it's walking distance from town (groceries, coffee, train station & more). The neighborhood is super quiet. 55in LG TV, WiFi, X-Box, board games. Pool closes in September. Families only please.

Serene and refined North Fork home with pool

Welcome to your North Fork lifestyle home - tranquil, refined and walking distance to a sandy beach. This fully renovated 4 BDR / 3 BA with European inspired elements offers elegant indoor and outdoor living with a landscaped backyard featuring an in-ground pool (open during peak season). Nearby: Love Lane groceries, Southold shopping, top-tier vineyards like Rose Hill, sandy beaches, Harbes farms, historic Oregon Road and more.