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Sag Harbor Holiday Vacation with Pools

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    $1,518 Average
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    Travellers to Sag Harbor are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    22 Matching Rentals in Sag HarborView all 62 rentals
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (4)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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Parking
    • Satellite TV
    • Hot Tub
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    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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    • 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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (1)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It's like getting a free house! Generous lot bordering golf course has room for a substantial house, pool and tennis court. Presently improved with an easygoing modern home bordering Noyac Golf Club, with updated kitchen and baths, boasting a free-flowing floor plan, opening onto a large deck...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • 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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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    • 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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    Sag Harbor, Hamptons 11963
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Spacious Contemporary home is great for entertaining and play. The interior kitchen/dining is open and light filled. There are 2 living rooms and 2 dining areas as well as a breakfast bar. There are sliding glass doors to the large deck which affords flow between interior and exterior....
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designer's own home boasts every detail. This stylish home has stainless steel chef's kitchen with wine room, breakfast bar and butler's pantry. Dining room with venetian palster walls and modern crystal chandelier. Living room w fireplace and 50" tv. All marble and travertine baths. Master is en...
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    Sag Harbor, Hamptons
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    10 Bedrooms, 13 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular 13,000 square foot estate, on 30 acres of open reserve with water views, boasts 11 bedrooms, 13 full bathroom, heated gunite pool, large outside patio area, Grill, perfect for entertaining, weddings, large family gatherings, etc. Located in Bridgehampton neighborhood in Sag Harbor....
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 10 Bedrooms, 13 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two bed, two bath first floor apartment that is seconds away from Long Beach, Bridge Golf Club, Sag Harbor Village and Bridgehampton. Be close to all the opportunities that the Hamptons have to offer without all the...
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    Sag Harbor, Hamptons 11963
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
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    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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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Suite available for your Summer Enjoyment. This is an Apartment Within a Larger Home. Perfect as a weekend Getaway for 2. Five minutes to Sag harbor, Five Minutes to Bridgehampton. Eight minutes to the Ocean.Hamptons Classic 5 Minutes away. Crisp and clean with your own bedroom and bath,...
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    Location Information
    Sag Harbor, Hamptons 11963
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated chrisp and clean Sag Harbor charming home. Everything you would need for an Excellent Summer!!! Just a little over a mile from the center of the Village and just a skip to Long Beach to boot. Come home from a day at the Ocean 8 minutes away and relax by the pool. Don't Wait, it...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Sag Harbor Village home. Located on quite tree lined street this home features heated gunite pool and tranquil gardens. Three bedrooms located on the second floor with a third floor featuring specious bedroom with private bath. The main floor offers completely updated kitchen. Great room...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This three bedroom rental is located just minutes from the bay beaches of Noyac and the village of Sag Harbor. Recently renovated, it boasts a modern kitchen, light filled dining area, large living room as well as three large bedrooms. The private backyard has a heated pool for your...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated four bedroom, three bath traditional house is located close to Sag Harbor Village. The home is tucked away in a quiet neighborhood within close proximity to Sag Harbor bay beaches and village. It features new kitchen, wide plank floors, and large back yard...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this Beautifully Renovated 5 Bedroom, 2.5 Bath Home with Open Living/Dining Area, Finished Basement and Heated Pool. Finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This villa features 5,600 +/- sq. ft. of living space with five bedrooms, four and one-half baths, plus a gourmet kitchen, living room with fireplace, media room, office, large master, and a finished lower level, on 1.87 +/- beautifully landscaped ac. Located in The Hamptons neighborhood in Sag...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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