Fitness-friendly holiday rentals in Shelter Island

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in Shelter Island

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness and more.

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Superhost

Home in East Hampton

4.93 out of 5 average rating, 60 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 and fire pit. 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.

23–30 Dec

€ 614 per night

Guest favourite

Villa in Southampton

5.0 out of 5 average rating, 76 reviews

NEW Hamptons Water Living: Dock Beach Kayak & Fish

One mile from the beach, this child-friendly waterfront Southampton home is a perfect family destination. Ready for watersports: kayaking, paddleboarding, boating, or jet skiing. Walk down to the beach for a swim in the bay. Return home to a backyard that has it all: a large private dock, fire pit, swing/playset, hammock, Weber grill, and oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village and Sag Harbor.

5–12 Jun

€ 783 per night

Guest favourite

Holiday home in Southampton

4.98 out of 5 average rating, 42 reviews

5BR, Luxury Home, Pool, Yard Close to Beach & Town

Magnificent Renovated 4,416 sq ft. Contemporary on .67 acre has 5 bedrooms 5 full bathrooms Enter into light filled living areas, faulted ceiling , fireplace with stone , white panel wainscoting and eat in kitchen with island seating , stainless steel appliances and door to a wrap around rear deck. A family room has French Doors , Bar , to the pool and expansive backyard. The beautifully appointed master suite features a vaulted ceiling in the bedroom, walk in closets & Luxe bath.

24–31 Jan

€ 876 per night

Guest favourite

Flat in New Haven

4.96 out of 5 average rating, 279 reviews

Luxury Apt with Parking and Gym | Downtown at Yale

Nestled in the vibrant core of New Haven's historic downtown, our stunning luxury apartment promises an unmatched experience in urban living. Immerse yourself in a world where modern comforts meet timeless charm. Highlights: - Steps away from Yale - Rigorous deep-cleaning for each guest - Complimentary coffee, fresh linens, and essentials - State-of-the-art 24/7 fitness center - Expansive rooftop terrace featuring grills and relaxation areas - Spacious 700+ sqft bathed in natural light

4–11 Jan

€ 240 per night

Guest favourite

Home in Mattituck

4.9 out of 5 average rating, 10 reviews

NorthFork FarmHouse, Amazing Pool, Beach, Wineries

Relax with the whole family at this peaceful place to stay. Centrally located surround by best vineyards, farms, great neighborhood, beaches only 10 minutes away, aquarium 15', water park 15' A bustling beach town year-round From boating to wining and dining, it’s all at your fingertips in Mattituck.Locally owned restaurants, bakeries and boutiques on Love Lane; boaters have direct access to Long Island Sound via the Mattituck Inlet; and wine lovers will relish the area’s vineyards.

6–13 Dec

€ 543 per night

Guest favourite

Home in Manorville

4.98 out of 5 average rating, 199 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

2–9 Oct

€ 609 per night

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 16 reviews

Stunning 3 BR / 2.5 New Construction with Pool

Conveniently located equidistant to East Hampton and Sag Habor Villages, this 3 BR / 2.5 Bath ranch home on 1.3 acres is set back behind a buffer of trees. Offering approximately 1,700 sq. ft. of living space this L shaped home's open concept living areas flow among the living room with fireplace, dining area and kitchen. The primary suite includes a walk-in closet and luxe bath. 2 additional rooms share a Jack and Jill bath. Outdoors relax on the deck overlooking the inground pool.

24–31 Oct

€ 1,008 per night

Guest favourite

Home in Southampton

5.0 out of 5 average rating, 34 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.

10–17 Feb

€ 733 per night

Guest favourite

Home in Southampton

4.96 out of 5 average rating, 50 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.

8–15 Dec

€ 908 per night

Guest favourite

Home in Riverhead

5.0 out of 5 average rating, 12 reviews

Luxurious beach house on the Long Island sound

Welcome to the Vista Azul, a true hidden gem in Jamesport! Enjoy the newly renovated corner beach house overlooking the Long Island sound with spectacular sunset views in the heart of wine country. It's only 50 steps from the beach with a fishing pier, a boat ramp and a quick bike ride away from all the local wineries, farms, stores and restaurants that North Fork has to offer! The Vista Azul is the perfect coastal getaway less than 2 hours from NYC.

25 Oct – 1 Nov

€ 1,019 per night

Guest favourite

Home in East Hampton

4.96 out of 5 average rating, 27 reviews

Heated pool open May 1- Luxury 4-bed modern home

*HEATED POOL!* Rental Reg Certificate No.: 23-1352 Situated on a corner half acre lot in the heart of East Hampton Springs is this luxurious 4 bedroom 3.5 bath two-story home LOCATION LOCATION LOCATION! This home is perfectly located in a family-friendly neighborhood and just a short bike ride to the best beaches of East Hampton. Neighboring towns of Amagansett, Sagaponack, and Bridgehampton. 20min drive to Montauk!

3–10 Oct

€ 1,065 per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 6 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!

27 Nov – 4 Dec

€ 831 per night