Fitness-friendly vacation rentals in Shelter Island

Find and book unique fitness-friendly accommodations 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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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.

Jun. 3 – 10

$1,150 CAD per night

Superhost

Home in East Hampton

4.93 out of 5 average rating, 61 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.

Sep. 26 – Oct. 3

$1,145 CAD per night

Superhost

Home in Bridgehampton

4.85 out of 5 average rating, 13 reviews

Bridgehampton Private Rd Fireplace & heated pool

Nestled in the charming town of Bridgehampton this 3BR house offers a luxurious retreat with a heated pool, access to community tennis courts, & a bright and spacious interior. The tastefully furnished living room boasts vaulted ceilings & large windows, creating a welcoming and airy atmosphere. Upon entering the house, you'll be greeted by a generously sized living room that serves as the heart of the home. Its vaulted ceilings and abundance of natural light make it feel open and inviting.

Aug. 17 – 24

$1,582 CAD per night

Guest favourite

Apartment in New Haven

4.96 out of 5 average rating, 281 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

Jan. 9 – 16

$425 CAD per night

Guest favourite

Home in Water Mill

4.92 out of 5 average rating, 91 reviews

Peaceful 1850s barn w/Pool

Family, friends and work-friendly property. Sleeps 8 (+2) in 4 bedrooms with 3 bathrooms. Tranquil 3000 sq ft house w/heated pool (pool season circa May 21 to Sept 20) set in 1.7 quiet acres off private driveway. Large garden and fenced pool area. Fresh in summer, cozy w/log fires in winter. Minutes from beautiful beaches, Water Mill's historic charm and the visual & performing arts. A simple but stylish and very comfortable house! Well-behaved pets with thoughtful owners are welcome.

Apr. 16 – 23

$1,244 CAD per night

Guest favourite

Home in Manorville

4.99 out of 5 average rating, 200 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.

Oct. 13 – 20

$895 CAD per night

Guest favourite

Home in Mattituck

4.9 out of 5 average rating, 10 reviews

NorthFork FarmHouse, Amazing Pool, Beach,Vineyards

Relax with the whole family at this peaceful place to stay. Centrally located surround by best vineyards, farms, great neighborhood, beaches only 5 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.

Oct. 12 – 19

$1,313 CAD 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.

Feb. 10 – 17

$1,076 CAD 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.

Mar. 19 – 26

$1,495 CAD per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 7 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!

Sep. 28 – Oct. 5

$1,514 CAD per night

Guest favourite

Condo in Montauk

4.95 out of 5 average rating, 107 reviews

Deluxe Studio Apt@The Montauk Manor

Beautiful, deluxe studio apartment with every amenity. Registered historical landmark. Magnificent lobby with fireplace, restaurant. Cable TV with HBO, DVD and WI FI. The in-door pool, jacuzzi and sauna are not available due to renovations) The restaurant is open at various dates and times off season. Call the Montauk Manor for more information. Don’t miss out on the fabulous beaches.

Apr. 23 – 30

$463 CAD per night

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 11 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!

Feb. 18 – 25

$1,571 CAD per night