Fitness-friendly vacation rentals in Southampton

4.87 out of 5 average rating, 31 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 Hampton Bays

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.

4.94 out of 5 average rating, 326 reviews

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.

Home in Bridgehampton

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.

Apartment in East Patchogue

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.

4.86 out of 5 average rating, 259 reviews

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, 169 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

4.95 out of 5 average rating, 96 reviews

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.

Home in Springs

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.

4.89 out of 5 average rating, 57 reviews

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.

Home in Hampton Bays

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.

5 out of 5 average rating, 51 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.

4.86 out of 5 average rating, 115 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.

4.94 out of 5 average rating, 54 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!

4.99 out of 5 average rating, 83 reviews

A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.

Villa in East Hampton

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.

4.87 out of 5 average rating, 101 reviews

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.

Home in Hampton Bays

*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.

4.86 out of 5 average rating, 7 reviews

Home in Water Mill

Exceptional Water Mill Beach Home

You will be close to everything when you stay at this centrally located home. This 2017, 4 bed and 4.5 bathroom home is 6 minutes from Flying Point Beach, 5 minutes to Southampton Village, 10 minutes to Bridgehampton and Sag Harbor. Be in the middle of it all in the stylish, family friendly home. This new home is wonderful for adults and young children alike. Baby gates and changing table provided upon request.

Popular amenities for Southampton fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

4.91 out of 5 average rating, 23 reviews

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.

Apartment in Montauk

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 small outdoor seating area is presented, featuring two woven chairs positioned around a round metal table. A tower of wooden blocks is neatly stacked on the table, surrounded by a green artificial lawn and a backdrop of lush greenery.

Apartment in Shirley

5 out of 5 average rating, 3 reviews

East end Oasis near outdoor outlet, winery & beach

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 East Hampton

Luxurious Open Floor Plan - Walk to Village

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.

Apartment in Montauk

Offshore - Suite Steps from the Shore

5 out of 5 average rating, 10 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 condo 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 modern living room features large sliding glass doors that open to a spacious balcony. Neutral-colored furniture, including a sectional sofa, a minimalist chair, and a wooden coffee table, is arranged around a rug. A decorative vase and a television are positioned on the wall.

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.

4.94 out of 5 average rating, 124 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.

4.93 out of 5 average rating, 41 reviews

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

4.8 out of 5 average rating, 25 reviews

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.

Condo in Hampton Bays

Waterfront Elevated Bungalow - Spectacular Views

A welcoming living room is featured, with two white sofas facing a wooden coffee table. A decorative brick fireplace serves as the focal point, complemented by light-colored walls and soft natural light filtering through a nearby window. A cozy area rug enhances the space.

Condo in Southampton

5 out of 5 average rating, 14 reviews

Newly Renovated Modern Townhouse w/Pool & Tennis

Fitness-friendly house rentals

4.96 out of 5 average rating, 23 reviews

The landscaped backyard features a heated mineral spring pool with clear blue water. Surrounding the pool are loungers and a shaded cabana with a striped canopy. Lush greenery and colorful foliage add to the serene environment.

Home in East Marion

POOL + Beach Oasis! Winter deals 2+ nights!

4.96 out of 5 average rating, 25 reviews

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.

Home in Springs

Secluded Oasis salt water pool near beach

5 out of 5 average rating, 29 reviews

A two-story white house with blue shutters and a welcoming front porch is surrounded by a well-maintained lawn and landscaping. The entrance features an elegant door with a decorative window, framed by a variety of shrubs and flowers that add to the inviting exterior.

Home in East Quogue

Farmhouse Style Hamptons Beach Home, Quogue

4.89 out of 5 average rating, 45 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 Flanders

The Perfect Bay House Escape

5 out of 5 average rating, 3 reviews

Home in Mattituck

Serene and refined North Fork home with pool

5 out of 5 average rating, 41 reviews

A modern studio room features a spacious bed beside a seating area with a comfortable sofa and a small coffee table. Large windows with slatted shades allow natural light in, while a round mirror enhances the decor. Soft green and brown tones are present in the furnishings.

Home in Bridgehampton

A Fall/Winter Escape from the City

4.89 out of 5 average rating, 18 reviews

The rear view of the house showcases a spacious outdoor area with an expansive saltwater pool set within a landscaped yard. Comfortable outdoor seating is visible under a covered patio, providing shade, while chairs are arranged around the pool area for relaxation.

Home in Shinnecock Hills

Southampton Dream