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Sag Harbor Vacation Rentals

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    Travelers to Sag Harbor are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 29 Rentals in Sag Harbor
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    Sag Harbor with water views & perfect sunsets1 / 11
    (8)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Sag Harbor with perfect water view and sunset1 / 14
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Grill
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stylishly decorated home is perfectly located near the town of Sag Harbor…close to vineyards, beaches, restaurants, shopping and theaters. You will have all the privacy you want. Outside you have a beautiful pool, huge deck with BBQ grille, fire-pit and outdoor shower. Inside you have a...
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    Sag Harbor, Hamptons 11963
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is nestled in a park like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool & jacuzzi. The home is clean, stylishly decorated, and steps away from a gorgeous North Sea bay beach. Visit Southampton or Sag Harbor town only 3 min...
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    Sag Harbor, Hamptons 11963
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Yard
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful custom built 2 bedroom home offers authentic charm and elegance from the finishing to the furnishings. It is located in a waterfront community just steps to the Peconic Bay with access to launching your boat! Enjoy the view of the heated pool from a spacious deck overlooking a large...
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    Sag Harbor, Hamptons 11963
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation rental cottage in the Sag Harbor area of the Hamptons is a cozy getaway with 3-bedrooms and 2-bathrooms, comfortably accommodating up to 6 guests. Newly renovated throughout, the property upholds the historic beach cottage charm of the Hamptons! Close to North and South Hampton with...
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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chic and Modern Beach retreat with heated Pool1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 4, 2016
    This house has everything you need and is perfectly located. It is not far from Sag Harbour in a quiet area. Close to marina for kayaking and stand up paddle boarding. With...
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    About this property
    Privately situated on a park-like landscaped grounds, this classic 2 story French cottage was completely renovated for modern comfort and indoor/outdoor summer entertainment. This delightful house features an open-plan living room with fireplace, dining room, a gourmet kitchen with stainless...
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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Put up your feet and relax in this idyllic home just minutes from Long Beach and the rest of the luxuries the Hamptons have to offer. The open concept kitchen is a chef's dream, with a six burner Viking stove, Subzero refrigerator, Bosch dishwasher, and plenty counter space; perfect for...
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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a newly renovated bungalow with 2 bedrooms, full living room, eat-in kitchen, closed in and sunny porch, roomie deck with outdoor furniture (in season). It is a 5-10 minute walk to the village, fine restaurants, museums, shops, churches and temple and beach.This is a prime location. The...
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    Sag Harbor, Hamptons 11963
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning, spacious three bedroom home, with water views from every room, and a heated gunite pool, will be your dream-come-true vacation rental. You will be minutes away from several gorgeous beaches as well as 1 mile from the lively and historic village of Sag Harbor. Decorated to a high...
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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cottage in the historic district1 / 11
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2017
    Great location. Very convenient to town, beaches and attractions. Claudie and Andrew were great hosts
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    About this property
    Perfect get away in the heart of the village. Newly renovated carriage house in the historic district. 2 bedrooms, kitchen, dining room, living room, full bathroom, private yard. Located in the Historic District of Sag Harbor Village. Only 10 minutes walk to the center and 15 minutes to the...
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    Sag Harbor, Hamptons 11963
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Central Heating
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home sits on 2.2 private and gated acres surrounded by nature. Viking kitchen, double sinks, double dishwashers and wine cooler. Six well appointed bedrooms, 3 en-suite. Three fireplaces. Formal living room, den, outdoor den, outdoor living room, formal dining room, covered porch with dining...
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    Sag Harbor, Hamptons 11937
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, new space is nicely appointed with modern fixtures and finishes. High ceilings, clean and bright. Walk to the bay beach for stunning sunsets. New furniture, linens, towels, etc. Contact us for weekly, monthly or seasonal pricing. This beautiful, new space is nicely appointed...
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    Sag Harbor, Hamptons 11963
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths, two additional bedrooms one...
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    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Resort style living in this fantastic private beachfront oasis in Sag Harbor Village. Enjoy fabulous views and amazing sunsets over Sag Harbor Bay from this wonderful 3 bedroom, 2.5 bath house with hot tub and sandy beach right in your backyard. Great family rental. Kids have their own private...
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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 10 Quick View
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    • Waterfront
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take 4 hour day trips with this boat and captain. It is the perfect size to entertain 10 of your closest friends. This family boat has a kitchen, bath & front deck to dive off the boat. Seen the Hamptons before? See it from a new perspective! Take the boat to Sunset Beach! Take cruising to Sag...
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    Sag Harbor, Hamptons 11963
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy acre beautiful parcel sits this updated light filled home in a Development with wide street for walking. With 4 Master Ensuite bedrooms, spacious with 2 masters with king beds and private baths, one with queen bed and private baths and the other with two twin beds and private bath...
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    Sag Harbor, Hamptons 11963
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water and sandybeach. Grill,...
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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2017
    We loved everything about this place. From the outdoor fire pit to my elderly parents having the time of their lives. Everything was impeccable. We look forward to returning...
    Reviewed March 23, 2017
    Our family enjoyed a great week in Sag Harbor and wonderful accommodations. The house is as advertised, nicely and warmly decorated with beautiful pool and outdoor grounds. The...
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    About this property
    For a truly authentic experience of Sag Harbor, stay at this delightful 5-bedroom, 2-bathroom designer's home with oversized heated pool and ideally situated just 2 blocks from Long Beach . With 2,800-square feet of living space and enough sleeping accommodations for up to 10 guests, this residence...
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    Sag Harbor, Hamptons 11963
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    OPEN HOUSE!! Sunday May 18 One of the last houses in the area with pool AND tennis! MD-LD $60,000 Please call first. Welcome to my paradise! My home has everything you need for a fantastic summer. 6 bedroom/4 bath contemporary home on 10 secluded acres. Heated in ground 20x40 pool, all weather...
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    Sag Harbor, Hamptons 11963
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Housekeeping Included
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4...
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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Patio
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has just gone through a hi-end renovation. It has a beautiful updated Viking kitchen, amazing yard with a 50 ft gunite pool with shallow end 'tanning bed', great for kids and adults alike! There are four bedrooms, 3 full baths in the main house, plus an additional full bath in the...
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    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Patio
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured totally private lawns with...
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    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Hot Tub
    • Ocean Views
    • Balcony
    • Grill
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello, This is a wonderful beach house to stay over the summer. It has everything you want in it (Salt Water Pool, Wreck Room, Jacuzzi, Home Theater, Alarm Systems, etc...)! For those who want the best, come here. It has wonderful views of beaches. In under 100 yards, you can be at the best...
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    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Village traditional on a quiet village street perfect for family gatherings. Magnificent backyard including a stone patio with fridge, grill, heated gunite pool and beautiful gardens. The park is accessible from our backyard allowing children to enjoy fields and playground and adults to have...
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    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house is light filled and open. We are a 15 min. walk to town and a 10 min walk to the bay. The neighborhood is quiet yet close to all. We are also a short distance (5 min walk) to the Harbor Market where they have really great coffee and yummy healthy food to eat in or take out. We use...
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    Sag Harbor, Hamptons 11963
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Parking
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located just steps from the only private beach in the Hampton. You can walk or bike to town. Watch the sunset from the front porch, enjoy the evening sea breeze. The Sea Breeze House is a chic, modern, yet...
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    Sag Harbor, Hamptons
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Parking
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW CENTRAL AIR CONDITION WITH NEST THAT KEEPS HOUSE KOOL AT ALL TIME .PRICELESS!! All room have the own TV's. All Beds are memory form and super comfortable .house is very clean wit all new linens. 2 ned bathrooms.great home feeling in a family neighborhood. you can walk or walk into town main st...
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    Location Information
    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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