Fitness-friendly holiday rentals in Montauk

4.87 out of 5 average rating, 30 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.

4.95 out of 5 average rating, 150 reviews

Spacious Modern 5BR • Close to Town & Beach

⭐ Rated 4.95 with 145+ glowing reviews! Welcome to your modern Hampton Bays retreat, perfect for families and groups. Ideally located just minutes from beaches, town, dining, and shops. Enjoy bright, open living spaces with Smart TVs and fast WiFi throughout. Enjoy a finished basement with ping pong, gym, and tv lounge, plus a backyard with BBQ and outdoor seating. Whether you're here to explore, relax, or reconnect, this home offers the ideal Hamptons getaway with thoughtful touches throughout.

4.86 out of 5 average rating, 249 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

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, 74 reviews

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

Your dream Hamptons vacation! Located on the border of Southampton and Hampton Bays, this stunning home is nestled at the end of a private cul de sac, just steps away from the gorgeous Peconic Bay Beach. • In-ground Heated Pool w/lounge chairs • Outdoor Hot Tub • Outdoor Shower • 3-Burner Weber Grill • 1 Acre Yard fully fenced in that is child-friendly • Bay Beach Access • Minutes from the Ocean beach Longer stays (30+ nights) available by request. Please message for custom pricing.

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 North Fork

POOL + Beach Oasis! Winter deals 2+ nights!

Chef kitchen: 2 ovens/lux app's/coffee bar w/ Nespresso/Keurig 2 living rooms Dining room seats 10 1st floor Primary Suite: king bed, gas fireplace, furnished deck overlooking pool, 4 piece bath: huge shower & jacuzzi tub 2 of 4 Guest rooms on 1st fl Gym/yoga rm: bench + weights (no treadmill) TV's in bedrooms inc. Firesticks Fenced backyard oasis w/ heated mineral spring pool, loungers, shaded cabana, outdoor dining, & Weber BBQ, outdoor shower Kitchenette in den/office Central AC/heat/fans

4.96 out of 5 average rating, 51 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.

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, 106 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.

4.87 out of 5 average rating, 113 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.

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, 43 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.

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.

Flat in The Hamptons

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.

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!

This is our 5th season as the owners of Unit #126, which is of the nicest units at Montauk Manor. We are hosting our 925 sq. ft. one BR loft corner unit with a cathedral high ceiling, brand new kitchen and bathrooms plus with a sleeper sofa and TVs on both floors. Montauk Manor is an amazing property that features 3 tennis courts, indoor & outdoor pools, a nice sized fitness center, an on-site restaurant/bar and much more!

Popular amenities for fitness-friendly rentals in Montauk

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

Flat in Shelter Island Heights

5 out of 5 average rating, 7 reviews

CHIC WATER VIEW APT. ON SHELTER ISLAND

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

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

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.

Flat in Shirley

5 out of 5 average rating, 3 reviews

East end Oasis near outdoor outlet, winery & 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

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, 123 reviews

Deluxe Studio Apt@The Montauk Manor

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

4.76 out of 5 average rating, 125 reviews

Villa Luz: Cozy Family Home w/ Jacuzzi year-round

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.

4.88 out of 5 average rating, 52 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

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, 42 reviews

Home in North Fork

“Winter Escape – Cozy Farmhouse by the Vineyards”

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, 56 reviews

East Hampton 3 Bed / 3 Bath Charmer w Pool

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.

5 out of 5 average rating, 29 reviews

Farmhouse Style Hamptons Beach Home, Quogue

5 out of 5 average rating, 3 reviews

Home

Serene and refined North Fork home with pool

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.