Fitness-friendly holiday rentals in Southampton

4.86 out of 5 average rating, 28 reviews

The exterior of the beach bungalow is illuminated at dusk, showcasing large windows that reflect warm light. Surrounded by mature trees, the spacious lawn contrasts with the building's neutral tones, creating a serene atmosphere. The driveway hints at the inviting interior.

Bungalow in The Hamptons

Civilian Surf Club: a family-friendly beach house

Iconic 70’s beach bungalow & pool nestled in a private 3/4 acre plot surrounded by mature oaks and evergreens. Our home is intentionally appointed by interior designers, filled with collectibles, art & antiques. Embrace the ‘Hamptons Bohemia’ feel, with a vaulted living room, ample seating, a wood burning fireplace and an outdoor area with a sprawling cedar deck & a heated pool. Located within walking distance of the bay beaches and an 8 min drive to Ponquogue beach & The Bowl Spot for surfing.

4.88 out of 5 average rating, 234 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 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

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

4.94 out of 5 average rating, 315 reviews

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.

4.99 out of 5 average rating, 109 reviews

An open-concept living space features a dining area with a rectangular wooden table adorned with a decorative bowl. A spacious couch is positioned near a fireplace, with large windows allowing ample natural light. A stylish chandelier hangs above, complementing the high, pitched ceiling.

Villa in The Hamptons

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.

4.98 out of 5 average rating, 47 reviews

A spacious outdoor area features a heated gunite pool surrounded by sun loungers and greenery. The villa is visible in the background, showcasing large windows and a blend of natural materials. Shade is provided by overhanging trees scattered around the property.

Villa in The Hamptons

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.

5 out of 5 average rating, 104 reviews

A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.

Villa in The Hamptons

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, 49 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.

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.

5 out of 5 average rating, 53 reviews

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.

The exterior of the home features a modern facade with natural wood siding and a green lawn surrounding a heated pool. Two umbrellas provide shade for patio seating, while large windows allow for ample natural light. Trees frame the backdrop for a serene atmosphere.

4.97 out of 5 average rating, 36 reviews

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.

A modern kitchen equipped with wooden cabinetry features a central island topped with dark stone. The space is illuminated by pendant lights, while glass doors offer views of the pool outside. Wall decor includes woven baskets, enhancing the aesthetic of the area.

4.97 out of 5 average rating, 68 reviews

Renovated Southampton Shores pool, tennis, beach

Fully renovated; the house was gutted top to bottom. Heated pool, water views, massive bbq, four bedrooms, three full baths and two pull-out couches. New kitchen, floors, windows, etc. Designed with comfort in view. Everything new! The large master bedroom has two walk in closets and en suite bathroom. Southampton Shores residents and our guests have access to a private bay beach as well as three tennis courts for your use. Heated pool is private to the house.

A spacious living area is illuminated by natural light from large windows. A comfortable sofa and armchair are arranged around a low coffee table. A dining table with six chairs sits adjacent, while the kitchen is visible in the background. A staircase leads to the upper floor.

4.94 out of 5 average rating, 144 reviews

Modern 5BR Getaway • Close to Beaches & Wineries

⭐ Rated 4.95 with 135+ glowing reviews! This modern 5BR, 4BA Hampton Bays retreat sleeps 10 and is just minutes from beaches, dining, and shops. Enjoy open living spaces, Smart TVs, and fast WiFi. The finished basement features ping pong, a gym, and lounge, while the backyard offers a BBQ, patio, and outdoor seating. Beach gear is included, making it easy to explore. Perfect for families or groups seeking the ultimate Hamptons getaway with comfort and style.

A spacious living area is filled with natural light from large windows. A decorative fireplace frames the room, accompanied by comfortable seating options including a beige sofa and patterned armchair. Artwork and decorative items adorn the walls, contributing to a welcoming ambiance.

4.96 out of 5 average rating, 55 reviews

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!

Popular amenities for fitness-friendly rentals in Southampton

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

A bright and airy room features two spacious Queen-size beds adorned with soft linens. Natural light floods the space through large glass doors that open to a private balcony. A neutral color palette and minimal furnishings create a calming environment, complemented by a modern TV mounted on the wall.

Flat in Shelter Island Heights

Offshore Hotel - Ocean View Suite w/ Kitchenette

A serene view of the harbor is captured, showcasing gentle waves and sailboats anchored in the water. Lush green grass and tall trees frame the scene, providing a tranquil backdrop to the picturesque waterfront. The expansive sky is clear, allowing ample sunlight to illuminate the landscape.

5 out of 5 average rating, 7 reviews

CHIC WATER VIEW APT. ON SHELTER ISLAND

A spacious suite is showcased, featuring two comfortable beds and large glass doors leading to a balcony. Natural light floods the room, highlighting neutral tones and wood accents. A clear view of the spa-style bathroom with a walk-in shower is visible through the doorway.

4 out of 5 average rating, 3 reviews

Offshore - Coastal Getaway with Ocean View

An inviting living area showcases a spacious layout with plush seating and natural lighting. A wooden dining table, surrounded by chairs, offers a comfortable space for meals. A staircase leads to an upper level, and a rocking chair is positioned nearby, enhancing the cozy ambiance.

Flat in Mount Sinai

Lovely 1-bedroom basement apartment in Mt. Sinai

A spacious sleeping area features a king-sized bed with crisp white linens. Light wood flooring complements the soft, neutral color palette. Natural light enters the room through a nearby doorway, while wall sconces provide gentle illumination.

Offshore - Suite Steps from the Shore

A spacious bedroom features a large bed dressed in crisp white linens, complemented by soft neutral throw pillows. Natural light floods in through sliding glass doors, which lead to a private balcony. A stylish area rug covers the wooden floor, and ceiling fans add to the comfort.

Offshore - Serene Suite by the Sea

A serene bedroom is featured, showcasing a spacious bed with white linens and two bedside lamps. Natural light filters through the soft, neutral-toned curtains. A piece of coastal artwork decorates the wall above the bed, complementing the calming color scheme.

Offshore - Dune King View Suite

A bright and airy studio space features large glass doors opening to a private patio with views of the dunes and ocean. A seating area with a sofa and coffee table complements the open layout, alongside a dining table and a spacious bed.

4.91 out of 5 average rating, 23 reviews

Oceanfront Corner Studio Bungalow on the beach

Fitness-friendly apartment rentals

A grand entrance is framed by lush trees, with vibrant foliage surrounding a charming brick building. The pathway leads to large double doors, inviting guests inside. Sunlight filters through the leaves, casting playful shadows on the walkway.

4.89 out of 5 average rating, 44 reviews

Romantic and unique treat in Historic Montauk.

A light-filled living space features a large arched window with scenic views. A soft gray couch is positioned near a round dining table, complemented by a cozy area rug. Colorful artwork decorates one wall, enhancing the room's modern design.

4.65 out of 5 average rating, 51 reviews

The Exclusive Resort in Montauk

A compact bathroom features white paneling on the walls and a modern toilet. A small sink is positioned nearby, complemented by a mirror and neatly arranged toiletries on the side. Natural light enhances the bright and clean appearance.

4.3 out of 5 average rating, 10 reviews

2 Bedroom Cottage| Montauk, NY

The exterior of a historic Tudor-style building is framed by large, blooming cherry blossom trees. The soft pink flowers create a vibrant contrast against the architecture. A paved pathway leads to the entrance, where benches are positioned for seating.

4.95 out of 5 average rating, 122 reviews

Deluxe Studio Apt@The Montauk Manor

An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.

4.92 out of 5 average rating, 39 reviews

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

Superhost

A bright and airy living space is highlighted by skylights and white wooden beams. A spacious kitchenette is situated behind a dining table surrounded by light chairs. Large windows invite natural light, and a television sits on a white console between soothing tones of gray and cream.

4.8 out of 5 average rating, 25 reviews

Waterfront Elevated Bungalow - Spectacular Views

Fitness-friendly house rentals

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.

4.99 out of 5 average rating, 75 reviews

Family Fun House by the Bay #chateaustclair

4.95 out of 5 average rating, 39 reviews

Home in North Fork

“Winter Escape – Cozy Farmhouse by the Vineyards”

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.

4.86 out of 5 average rating, 36 reviews

The Perfect Bay House Escape

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

4.95 out of 5 average rating, 95 reviews

Oasis backyard, Pool, Gym, and Sunroom!

An open living area features a large sectional sofa and a sleek dining table surrounded by several chairs. A modern ceiling fan hangs overhead, while natural light floods through skylights and large windows, enhancing the spacious ambiance of the room.

4.88 out of 5 average rating, 26 reviews

Cozy up in the Hamptons

4.94 out of 5 average rating, 16 reviews

A serene backyard retreat features a heated pool surrounded by lush greenery. Lounge chairs with black and white stripes are positioned on the grassy area, complemented by shaded umbrellas. The clear sky and sunlight enhance the outdoor space, creating a refreshing ambiance.

Home in Bellport

Stunning 4 Bedroom Bellport Village House W/Pool

4.85 out of 5 average rating, 41 reviews

An open living area features high ceilings and large windows that bring in natural light. A sectional sofa in deep blue surrounds a vibrant orange rug, while an artwork adorns the wall. A dining area with a wooden table and chairs can be seen in the background.

Home in Riverhead

North Fork True Beachfront Home

A spacious outdoor deck features a hot tub and comfortable seating area, surrounded by lush greenery. The inviting hot tub offers a relaxing retreat, while the seating includes a large sofa and a coffee table, creating an ideal space for outdoor gatherings.