Fitness-friendly vacation rentals in Montauk

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.

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, 25 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.

4.99 out of 5 average rating, 110 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.

4.96 out of 5 average rating, 49 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, 50 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.

4.96 out of 5 average rating, 106 reviews

A spacious farmhouse is showcased, featuring a welcoming porch with an American flag. The exterior is adorned with dark wooden shingles and large windows. Lush green lawn and well-maintained flower beds enhance the inviting curb appeal under a clear blue sky.

Home in North Fork

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

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, 145 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.

The charming exterior of a two-story home is framed by lush greenery and a manicured lawn. A vintage blue vehicle is parked on a gravel driveway, leading up to the inviting front porch with white railings and a welcoming entryway.

4.93 out of 5 average rating, 40 reviews

Luxury 4-bedroom in East Hampton [w/private beach]

Welcome to Camelot House East End, where Norman Rockwell meets the South of France. Your home away from home in the Hamptons is close to all the action, and yet, located in a tranquil paradise just steps away from a members-only beach. Camelot House is appropriate for individuals and families alike. The home is fully equipped with high end appliances and finishes, and yet, kid-friendly with a pool fence, stair gates, and a pack-n-play available for use.

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

Kick back and relax in this calm, stylish space and listen to the waves. Best rental unit in entire resort. Corner oceanfront studio, 700 sq feet with 1500 sq ft private patio with ocean and dune views, outdoor bbq, with outdoor dining table. Kitchen has a full size fridge and dishwasher. queen bed and queen size pull out sofa accommodates 4. Resort Property includes heated pool, tennis courts, gym, beach with towels, umbrellas and chairs.

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.

Popular amenities for Montauk 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 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 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 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 serene bedroom is presented with a spacious bed featuring soft linens and decorative pillows. Natural light enters through a large window, highlighting the soothing palette. Two bedside tables support elegant lamps, and a mirror reflects the calm ambiance, creating a peaceful retreat.

Offshore - Oceanview Montauk Apartment

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

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

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.

5 out of 5 average rating, 14 reviews

Newly Renovated Modern Townhouse w/Pool & Tennis

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

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, 73 reviews

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

Luxe

A spacious backyard features a heated gunite pool, lined with lounging chairs and surrounded by landscaped greenery. The residence, designed in a classic style, boasts large windows that allow natural light to flow. A covered patio area provides shade and comfort for outdoor gatherings.

4.86 out of 5 average rating, 7 reviews

Oceanstone by Rove | Villa w/ Pool & Beach Access

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

5 out of 5 average rating, 7 reviews

Beachfront Oasis