Fitness-friendly vacation rentals in Sag Harbor

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Top-rated fitness-friendly rentals in Sag Harbor

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Guest favourite

Home in Southampton

4.96 out of 5 average rating, 24 reviews

Southampton Estate 5 min to beach, village, tennis

Escape the city & relax in this charming Southampton Estate! Enjoy this spacious 5 bedrooms/4 bathrooms home with a gym, office, billiards room, and space for nanny & crib. The large fenced-in backyard with a pool, hottub, deck, and gas BBQ grill is perfect for lounging with family and friends. Located in a prime spot "south of the highway." 5 mins to ocean beaches & village main street and just a short walk to the neighborhood tennis court. Perfect for enjoying all the Hamptons has to offer!

Sep. 27 – Oct. 4

$1,616 CAD 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.

Jun. 5 – 12

$1,144 CAD per night

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.

Dec. 23 – 30

$888 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

$1,559 CAD per night

Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 14 reviews

Hamptons Oasis, 5bed/4bath, 1 acre w/ Heated Pool

Welcome to your luxurious getaway in East Hampton! Nestled on a serene 1-acre of cleared land, this spacious 5-bedroom, 4-bathroom, home offers the perfect retreat for families or groups. The house is perfectly located on a tranquil cul-du-sac road, with ample amounts of indoor and outdoor entertainment space overlooking a fully fenced-in backyard and 20x40 heated pool. Just 3-mins to neighboring bay beaches, restaurants, & shops and 10-mins to Amagansett, EH Village and Atlantic Beaches.

Nov. 4 – 11

$1,280 CAD per night

Guest favourite

Vacation 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.

Jan. 25 – Feb. 1

$1,268 CAD 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.

Oct. 3 – 10

$882 CAD 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.

Nov. 24 – Dec. 1

$1,458 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

$1,060 CAD 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.

Oct. 30 – Nov. 6

$1,314 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!

Jun. 8 – 15

$1,292 CAD 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!

Oct. 3 – 10

$1,358 CAD per night