Fitness-friendly holiday rentals in Hampton Bays

4.9 out of 5 average rating, 48 reviews

A calm beach scene is depicted at sunset, with vibrant colors reflecting off the water's surface. The sandy shore stretches into the distance, bordered by gently lapping waves. Soft clouds create a gradient of hues in the evening sky, enhancing the tranquil atmosphere.

Home in Riverhead

The Perfect Bay House Escape

Escape to the perfect summer rental in the Township of Southampton, just a block away from the community beach and convenient access to the bay for boaters. This beautifully renovated 3-bedroom, 2-bath retreat features a tv room loft with sleeper sofa , enclosed porch, cozy fireplace, state-of-the-art appliances, deck for family gatherings, fire pit, and the added bonus of being only steps away from the beach! Embrace the ultimate summer getaway at this stylish rental, perfect for group trips.

4.86 out of 5 average rating, 267 reviews

A living area features a gray futon adorned with decorative pillows, complemented by a small coffee table. A red accent chair provides additional seating. Soft lighting from the ceiling enhances the space, while wall art depicts blooming flowers, contributing to a welcoming atmosphere.

Flat in East Patchogue

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

4.99 out of 5 average rating, 180 reviews

A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.

Home in Milford

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

5 out of 5 average rating, 110 reviews

A spacious backyard is framed by mature trees, featuring a fire pit surrounded by white Adirondack chairs. A children’s playground with swing set is visible nearby, while the home, illuminated by warm lights, stands invitingly in the background.

Villa in Southampton

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.

An outdoor space featuring a saltwater pool with a jacuzzi positioned nearby. A patio area includes an umbrella and ample seating options. Lush green grass surrounds the pool, while two white decorative swan floats are visible on the water, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 62 reviews

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.

4.98 out of 5 average rating, 55 reviews

A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.

Home in Shinnecock Hills

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.

5 out of 5 average rating, 12 reviews

Hampton Gem: Heated Pool, BBQ, 5 Min to the Beach

Welcome to your ultimate Hamptons summer retreat! This spacious, family-friendly 4-bedroom home sleeps up to 12 and offers everything you need for a memorable getaway, including a heated pool, volleyball court, game room, fully equipped gym, and easy beach access just 5 minutes away. Whether you're planning a family or friends getaway, this home brings comfort, space, and fun together in one beautiful setting. The pool is open and heated from May 1st to October 6th

4.87 out of 5 average rating, 121 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in 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.

Superhost

Home in Fairfield

5 out of 5 average rating, 3 reviews

Longevity Stay | Gym, Sauna, Red Light, Plunge

Welcome to RO House Fairfield, where luxury, wellness, and connection come together. Designed to help you reset, recharge, and optimize your stay, every detail encourages movement, recovery, quality sleep, and meaningful time with family and friends. Enjoy a private gym, sauna, cold plunge, red light therapy, hot tub, movie theater, basketball court, and outdoor living—all just minutes from Fairfield’s beaches, downtown, restaurants, and the NYC train.

4.95 out of 5 average rating, 60 reviews

A spacious salt-water pool is framed by a paved patio and secured by a black fence. White lounge chairs are positioned nearby, with two adirondack chairs visible under trees in the background. String lights are hung along the patio area, enhancing the outdoor setting.

Home in East Quogue

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!

The living area features high ceilings and large windows that fill the space with natural light. A neutral-colored sofa and loveseat provide comfortable seating, complemented by a simple coffee table. A ceiling fan enhances air circulation, while a welcoming rug adds warmth to the wooden floor.

4.88 out of 5 average rating, 108 reviews

*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.

A spacious wooden deck features a large outdoor dining table surrounded by comfortable chairs. A colorful orange umbrella provides shade over the seating area. The deck overlooks a neatly maintained lawn, framed by trees and shrubs, creating a relaxing outdoor environment.