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Holiday Rentals with Pools in Sag Harbor

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    Travellers to Sag Harbor are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    14 Matching Rentals in Sag HarborView all 31 rentals
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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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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1940 and carefully restored, this bright, sunny, happy and very comfortable house is perfect for a summer getaway. Four equally attractive bedrooms with king/queen size beds ensure you can comfortably accommodate everyone, heated pool and spa will provide necessary relief during hot summer...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • 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
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Washer
    • 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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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Shared Garden
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the quaint historic whaling Village of Sag Harbor, 12 minute walking distance to the center of town, with close proximity to the bay and ocean beaches. This European designer's home totals 5000 sq.ft., the lower level just shy of 1000, sq ft and is the designer's private lower level...
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    Location Information
    Sag Harbor, Hamptons 11963
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    • 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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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • 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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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    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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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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