Fitness-friendly vacation rentals in Southampton

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.

Apartment 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

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

This is New York version of California's Big Sur, with direct beach access and spectacular water views, surrounded by forest. Modern, 3,000 sq feet. Walk down path from house to a fantastic sand beach with lifeguard. Large deck for lounging, BBQ, and sunset views. 4 bedrooms, 3 baths, outdoor shower, 4 person hot tub, 2 person sauna, separate den w/home theater, gym, hammocks, wood burning fireplace. Experience the Long Island Sound without neighbors and the suburbs; a naturalist's haven.

A heated saltwater pool is framed by a spacious lawn and wooden lounge chairs. White floating orbs are seen on the water's surface, contributing to a serene atmosphere. In the background, a charming cottage with a garage door is visible, surrounded by lush greenery.

4.75 out of 5 average rating, 36 reviews

AMG-Saltwater Pool heated to November 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.

Guesthouse in The Hamptons

A serene outdoor space showcases a heated saltwater pool framed by neatly trimmed hedges. Comfortable lounge chairs are arranged beside the water, while a large umbrella provides shade. A two-story house is visible in the background, surrounded by greenery.

4.92 out of 5 average rating, 13 reviews

3 Bedroom Guest House in Southampton

This magical getaway delivers peace and relaxation. Curl up to the wood burning fireplace. Wake up to coffee on the porch with a view of the pool. Play in your heated, saltwater pool, (Open May 1-September 30) and relax under the stars in your hot tub. Get a workout in on the Peloton bike or the Cybex Arc Trainer. The gym is equipped with REP Fitness weights and squat rack. You can also drive 12 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

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!

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.

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.

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, 143 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 modern ranch-style home is set among lush greenery, featuring a white exterior with a sloped, dark roof. A spacious front porch is flanked by two chairs, and a well-maintained lawn extends to a gravel driveway leading to a gated entry.

5 out of 5 average rating, 33 reviews

Gated Amagansett Ranch Pool, Hot Tub & Fire Pit

Modern 4BR 3BA ranch in Amagansett with gated entry pool, hot tub, fire pit, and patio. Just a 5 minute drive to the ocean and a short stroll to the Village. Perfect for families or friends with a private gym and studio, central air, WiFi , and generator. Sleeps 8. Pool and hot tub open May to Oct. Guests rave about their stays, check out the amazing reviews and see why this Hamptons getaway is a guest favorite year after year.

A spacious outdoor area features a large swimming pool surrounded by lush green grass. Four lounge chairs are positioned nearby, alongside a parasol offering shade. A quaint shed with red accents is visible in the background, complemented by seating areas. Tall trees provide a natural backdrop.

5 out of 5 average rating, 16 reviews

Sag Harbor Dream Home: Heated Pool

Just minutes from Main Sreet in Sag Harbor, Long Beach, Wolffer Vineyard, and Sagg Main Beach, this home is a perfectly located, brand-new gut remodel, with over 3500sqft interior and an entertainer's dream yard - on a quiet cul-de-sac street. A stylish experience at this centrally-located escape! Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Popular amenities for Southampton fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

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.

Apartment in Shelter Island Heights

5 out of 5 average rating, 7 reviews

CHIC WATER VIEW APT. ON SHELTER ISLAND

Apartment in The Hamptons

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, 22 reviews

Oceanfront Corner Studio Bungalow on the beach

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.

Apartment in Mount Sinai

4 out of 5 average rating, 3 reviews

Lovely 1-bedroom basement apartment in Mt. Sinai

A bright living space features a spacious bed with light bedding, flanked by bedside lamps. A dining table with four chairs is set nearby, accompanied by a decorative centerpiece. Natural light fills the area, enhancing the neutral color palette and inviting ambiance.

Private room in The Hamptons

Luxurious Open Floor Plan - Walk to Village

5 out of 5 average rating, 9 reviews

A serene view of the water is captured under a cloudy sky, with sunlight reflecting off the surface. The horizon features a gentle gradient of blues and silvers, offering a calming atmosphere. Soft waves can be seen in the foreground, enhancing the tranquil scene.

Apartment in Milford

Walk to the beach

Fitness-friendly house rentals

5 out of 5 average rating, 31 reviews

A stylish living area showcases a comfortable sofa and accent chairs arranged around a modern coffee table. Warm wood flooring complements the dark walls, and soft lighting is provided by a chandelier. Large windows are dressed with elegant drapes, inviting natural light into the space.

Home in North Fork

Elegant Greenport Victorian -Winter Harbor House-

A charming home is surrounded by tall trees, showcasing a blend of natural greenery and well-maintained landscaping. The brown exterior is complemented by a welcoming front porch, and steps lead to a bright entrance, creating an inviting presence within the tranquil setting.

4.67 out of 5 average rating, 6 reviews

A Little Slice of Heaven

The kitchen and dining area feature modern cabinetry in muted tones against light wood flooring. A vintage-inspired Smeg fridge stands opposite a sleek kitchen layout with a black stove. Eye-catching circular wall art accents the space, complemented by a wooden dining table surrounded by six chairs.

4.96 out of 5 average rating, 24 reviews

Secluded Oasis Heated salt Pool 5 min ride beach

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

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

5 out of 5 average rating, 70 reviews

A serene poolside scene features a clear blue saltwater pool alongside a comfortable lounge area. An umbrella provides shade over the sunbed, while a rustic outdoor seating arrangement sits nearby, surrounded by lush trees and well-maintained landscaping.

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

4.88 out of 5 average rating, 52 reviews

The exterior of a four-square house is shown, featuring a light green facade and a welcoming front porch. Lush shrubs and neatly trimmed hedges enhance the garden. Large windows allow plenty of natural light, and a gravel driveway leads to the entrance.

Home in Sayville

Sunrise Over The Bay

Other fitness-friendly vacation rentals

The image captures a sparkling saltwater pool surrounded by lush green grass and shaded by large umbrellas. Comfortable lounge chairs are positioned on the pool deck, providing a relaxing outdoor space. The white exterior of the house and deck are visible in the background under a clear blue sky.

5 out of 5 average rating, 47 reviews

Sag Harbor Chic Pool Grill Gym 2Br/2Bth Dogs okay

4.94 out of 5 average rating, 17 reviews

An outdoor space features a large hot tub beside a sunken seating area, surrounded by neatly trimmed hedges. A swimming pool with a slide can be seen in the distance, along with shaded lounge areas under red umbrellas. Trees provide greenery and privacy.

Home in Center Moriches

Hamptons Escape: Pool Hot Tub Grill Firepit

An indoor heated pool is surrounded by elegant wood paneling and framed artwork. Natural light filters through the windows, reflecting off the water's surface. A cozy sitting area is positioned nearby, offering a relaxing space adjacent to the pool.

4.9 out of 5 average rating, 81 reviews

Lovely Year Round Vacation Home in the Hamptons

Guesthouse in Shelter Island

A spacious studio features a cozy queen bed with a light grey duvet and matching pillows, complemented by two ceiling fans. A comfortable seating arrangement includes a modern sofa and armchair. Large windows provide ample natural light, and a soft area rug enhances the warm aesthetic.

4.92 out of 5 average rating, 12 reviews

Stylish Studio Suite on Shelter Island

The entrance features a welcoming porch flanked by lush green shrubs and trees. A double-door entryway is evident, complemented by large windows that allow natural light to enter. The peaked roof adds character to the home's exterior.

4.98 out of 5 average rating, 41 reviews

Get away from it all in Sag Harbor Village w/Pool

A wooden dock extends across calm waters, where various boats are moored. Lush greenery borders the scene, with trees providing shade. Reflections of boats and surrounding nature can be seen in the water, creating a serene atmosphere at the waterfront.

Home in North Fork

4.83 out of 5 average rating, 84 reviews

Brand New Renovation Aug 25 - Waterfront + Hot Tub

4.93 out of 5 average rating, 16 reviews

A clear blue pool reflects sunlight, surrounded by a spacious deck. A stylish outdoor seating area with a cozy, round lounge chair is positioned beside the pool, offering a perfect spot for relaxation. Large windows of the house overlook the tranquil setting.

Home in Shelter Island

Waterfront Haven

A bright living area features a large cream-colored sofa facing a wooden coffee table. Natural light filters through window blinds, illuminating the space. An elegant spiral staircase ascends to the loft, while the adjacent kitchen is visible through an open layout.