Fitness-friendly holiday rentals in Lake Montauk

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.

Relax and Refresh at the Mill-on-Sill

Discover the history of Old Lyme at this unique estate on the Connecticut Shoreline. Once inspiring artists, this stunningly converted granite mill is perched on a dam. Enjoy the sights and sounds of a waterfall through numerous windows, framing views of Upper Mill Pond. Spanning nearly 2.5 acres, the estate offers bird watching, fishing, canoeing, piano playing, and a home gym. Nearby, enjoy beach relaxation, tennis, or golf. Experience a blend of history, nature, and architecture at the Mill.

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

Your dream Hamptons vacation! Located on the border of Southampton and Hampton Bays, this stunning home is nestled at the end of a private cul de sac, just steps away from the gorgeous Peconic Bay Beach. • In-ground Heated Pool w/lounge chairs • Outdoor Hot Tub • Outdoor Shower • 3-Burner Weber Grill • 1 Acre Yard fully fenced in that is child-friendly • Bay Beach Access • Minutes from the Ocean beach Longer stays (30+ nights) available by request. Please message for custom pricing.

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.

Oasis backyard, Pool, Gym, and Sunroom!

Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back yard. Decks in the back yard with lounge chairs and 2 patio dining tables. Front deck with lounge chairs. Outdoor gym located in the corner of the yard. Paddle boards, boogie boards, beach chairs, and beach towels provided. Walk to EHP Resort (SiSi Restaurant), and Harbor Bistro featured on Delicious Destinations. Paddle Diva paddle board/kayak rentals also nearby.

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.

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

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.

Pool|GOLFSim|HotTub|Movie|Games|Firepit|Dogs

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings and an open floorplan. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool.

Oceanfront Corner Studio Bungalow on the beach

Kick back and relax in this calm, stylish space and listen to the waves. Best rental unit in entire resort. Corner oceanfront studio, 700 sq feet with 1500 sq ft private patio with ocean and dune views, outdoor bbq, with outdoor dining table. Kitchen has a full size fridge and dishwasher. queen bed and queen size pull out sofa accommodates 4. Resort Property includes heated pool, tennis courts, gym, beach with towels, umbrellas and chairs.

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!

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

This is our 5th season as the owners of Unit #126, which is of the nicest units at Montauk Manor. We are hosting our 925 sq. ft. one BR loft corner unit with a cathedral high ceiling, brand new kitchen and bathrooms plus with a sleeper sofa and TVs on both floors. Montauk Manor is an amazing property that features 3 tennis courts, indoor & outdoor pools, a nice sized fitness center, an on-site restaurant/bar and much more!