Fitness-friendly holiday rentals in Shelter Island

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 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, 324 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.

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 East Marion

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

4.86 out of 5 average rating, 44 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 Baiting Hollow

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.

4.97 out of 5 average rating, 32 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 Greenport

Elegant Greenport Victorian-Winter Harbor House-

Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Village. Absolutely perfect location. Only a few hundred feet from the Mitchell Park/Marina, Waterfront Boardwalk/Beach and the North Ferry to Shelter Island. Enjoy gorgeous marina views and great people watching from the front porch. This 1890's Victorian has all the modern amenities you want while making you feel like you're experiencing a part of Greenport's history.

4.95 out of 5 average rating, 95 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.

5 out of 5 average rating, 108 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 North Sea

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.

5 out of 5 average rating, 39 reviews

The exterior of a spacious home is illuminated by soft twilight, showcasing a private pool with a smooth, blue surface. A shaded dining area beneath a pergola sits next to the inviting outdoor seating area, featuring a fire table. The wooden deck surrounds the house.

Home in East Hampton

Hamptons Retreat: Pool, Hot Tub, Gym, 3.5 Acres

Escape to a rare 3.5-acre private Hamptons estate, a serene retreat just 1 mile Sag Harbor Village. Designed for wellness, privacy, and rejuvenation, this luxury home features a heated pool, year-round hot tub, full Peloton gym, and dedicated workspaces—perfect for remote work, extended stays, or a peaceful Hamptons getaway. The home offers serene indoor-outdoor living, expansive landscaped grounds, and a rare opportunity to experience the Hamptons in complete privacy and calm.

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 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.

4.87 out of 5 average rating, 101 reviews

*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.

Luxe

Villa in East Hampton

4.98 out of 5 average rating, 52 reviews

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

Popular amenities for fitness-friendly rentals in Shelter Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

4.83 out of 5 average rating, 126 reviews

The exterior of a three-story house features light grey siding with turquoise shutters. A welcoming front porch contains multiple windows, and the entrance is accentuated by a small flight of stairs. Lush greenery surrounds the property, enhancing its appeal.

Flat in Greenport

House on First

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 Montauk

Oceanfront Corner Studio Bungalow on the 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 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 house rentals

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.

4.89 out of 5 average rating, 55 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

Superhost

The exterior of a spacious home is showcased against a clear blue sky. Lush green grass and neatly trimmed shrubs surround the house, which features a blend of shingle and clapboard siding. Large windows and a welcoming front porch can be seen on the facade.

Home in Remsenburg - Speonk

Luxury Hampton Home Near Bay 4 beds 4 Baths

4.96 out of 5 average rating, 57 reviews

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.

Home in Springs

East Hampton 3 Bed / 3 Bath Charmer w Pool

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, 72 reviews

Family Fun House by the Bay #chateaustclair

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

Superhost

Home in Springs

Prime location, in East Hampton

4.88 out of 5 average rating, 42 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

Superhost

Home in North Fork

5 out of 5 average rating, 4 reviews

3BR/2.5BA: outdoor shower, close to wineries

Other fitness-friendly holiday rentals

Townhouse in Southampton

Southampton 2 Bedroom 2.5 Bath Townhome

4.95 out of 5 average rating, 21 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

A marina is visible along the calm waters of the Peconic River, featuring numerous boats docked at wooden piers. Lush greenery surrounds the area, while a few decorative flags add color to the scene. The sky shows soft hues of blue and gray, indicating early evening.

Place to stay in Riverhead

4.9 out of 5 average rating, 49 reviews

The Waterfront Suite on the Peconic River 💙

Home in East Hampton

New place to stay

Modern retreat surrounded by nature

A serene outdoor space features a saltwater pool surrounded by a bluestone patio. Sun loungers are arranged for relaxation, with a decorative white umbrella providing shade. Lush greenery and landscaped borders enhance the privacy and tranquility of the backyard area.

4.95 out of 5 average rating, 22 reviews

Hamptons escape: 5 mins from beach, saltwater pool

A charming guest house is framed by a large tree and lush green lawn. The porch features white railings and potted plants, inviting relaxation. A gravel pathway leads to the entrance, while the backdrop showcases a horse paddock and carefully maintained greenery.

Cottage in Westhampton Beach

5 out of 5 average rating, 16 reviews

Bayfield Farms Country Estate Guest House

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.

Apartment in Southampton

5 out of 5 average rating, 14 reviews

Newly Renovated Modern Townhouse w/Pool & Tennis

A spacious living area features light-colored sofas adorned with blue and white pillows, complemented by a round coffee table. Large windows allow natural light to fill the room, while a decorative mirror enhances the sense of space. A contrasting blue accent wall adds visual interest.