Fitness-friendly vacation rentals in Wainscott

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

Kick back and relax in this calm, stylish, Zen appeal home. Brand new newly renovated house, mid century furniture, electric induction stove, Smeg fridge, 400sq ft mahogany deck (for yoga). HEATED POOL extra fee opens May 20x40 ft saltwater .4Bdr/3Bthr, full kitchen, working fireplace, dedicated workspace room, enjoy the outdoors, propane gas grill, sunbathing chairs, umbrella, wifi, TV, DW, W/D. Located in the artsy Springs area, neighborhood to Maidstone Park Beach, and Pollock Krasner house.

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.

Superhost

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.

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!

An open-concept living space features a circular marble dining table surrounded by light wooden chairs. A spacious kitchen with modern cabinetry is visible, alongside large glass doors that provide unobstructed views of the harbor and bay. Natural light fills the room through the skylight.

5 out of 5 average rating, 25 reviews

Designer East Hampton with Bay Views + Pool

Direct Harbor & Bay Views- Designer renovated 4 bedroom/3.5 bath East Hampton pool home has the wow factor! Nestled on a half acre in prime East Hampton, the home sits on the highest lot in the neighborhood allowing incredible views of Three Mile Harbor and Gardiners Bay. A short 5 minute drive to Main Street and 8 minutes to East Hampton Beach! Please note: Pool is open from June 1- September 15

Popular amenities for Wainscott 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

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 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.

Offshore - Coastal Getaway with Ocean View

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

A spacious bedroom is highlighted by a plush bed with white linens and natural wood accents. Soft light from a wall-mounted sconce illuminates the room, while a serene coastal artwork hangs above the bed. A bathroom door is visible, leading to a well-appointed spa-style space.

Offshore - Steam Spa + EightSleep Experience

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.

Private room in The Hamptons

Offshore - Suite Steps from the Shore

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.

Luxurious Open Floor Plan - Walk to Village

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 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!

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-

Superhost

An aerial view reveals a private pool surrounded by lush greenery and a spacious outdoor area. A cozy seating arrangement is established around a fire pit, with a well-maintained patio leading to the home. The inviting blue of the pool contrasts with the natural surroundings.

3BR/3BA: Renovated & Modern, Pool, Outdoor Shower

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!

Superhost

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

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

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

A spacious heated in-ground pool is surrounded by a stone patio and vibrant landscaping. Lounge chairs are arranged along the poolside, accompanied by a large umbrella for shade. Lush greenery and blooming flowers frame the area, creating a serene outdoor retreat.

4.97 out of 5 average rating, 72 reviews

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