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Holiday Rentals with Pools in Nantucket

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    Travellers to Nantucket are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    39 Matching Rentals in NantucketView all 1,062 rentals
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright, sunny home with multiple living areas on a quiet cul-de-sac in Naushop. Community pool and tennis available. Additional amenities include: beach towels, ipod dock, outdoor shower, winter, cd players: 1, a/c units: 4, disposal, 1/2 bath: 1, DVDs: 2, ironboard, lobster pot, area: naushop,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Hot Tub
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the privacy and ocean views of Madequecham Valley on the South Shore in this new 2006 luxurious vacation home with all the amenities. Upside down house with a gourmet kitchen with granite and marble counter tops. Fine appointments. Privacy, and two large living spaces with satellite TVs and...
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    Siasconset, Nantucket 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Luxury 8br 7ba Home, Pool,guest House1 / 44
    (6)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
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    • Grill
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    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2017
    Our extended family of 16 stayed at "Pilgrims Bliss" over July 4th week, and blissful it was. Only minutes away from the beach and town, we had endless options of how to...
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    About this property
    'Pilgrim's Bliss' is located off of Cliff Road, which starts from the center of town and runs parallel to the cliffside beaches, beach clubs and restaurants. The Cliff Road residential section is one of the most desirable areas on the island. 'Pilgrim's Bliss' has consistently garnered...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Hot Tub
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1st floor: Large open foyer. Living room with fireplace and antique restored parquet floors; dining room with French doors to large covered deck; large kitchen/family room with state of the art appliances and fireplace. Large guest suite with fireplace, jacuzzi and separate shower. 2nd floor: Large...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Five bedroom home on a culdesac in Naushop. Central AC and Wifi. Three floors of living. Community swimming pool and tennis courts. Off street parking. First floor:Dining room, powder room, great room with kitchen/living room , Private back and side yards with outdoor furniture and grill. Master...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Light, airy, summery, large 3 bedroom home decorated with rose colored florals and blue accents. Well equipped kitchen with comfortable dining room. Private outdoor deck with Adirondack chairs, dining table and 4 chairs, gas grill and beautiful potted flowers. Comfortable den with TV, VCR and DVD....
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Washer
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A pool and hot tub help make the perfect Nantucket vacation home for spring, summer or fall! Here you will be able to enjoy your vacation without spending the whole day at the beach (which is only a 10 minute walk). Your family and friends will equally enjoy the grounds of this home - 3 private...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 3 Bedroom, 2.5 Bath house has 2 king size Beds and one room with 2 Bunk Beds. There is a Master Bedroom with king size Bed and en suite bathroom with Huge Shower and washer and Dryer. All Bedrooms are located on second floor and the hallway bathroom, has a shower and tub. The first floor has a...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home with a charming Nantucket antique style exterior and an attractive modern functional interior. Located conveniently in Naushop with access to community pool and tennis. First floor: Entrance hall, powder room, den (w / sleep sofa), lovely living room with fireplace and vaulted...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paved driveway w/ lots of parking; large, well landscaped front yard. Enter into the spacious open living/dining/kitchen room w/ beautiful view of the pool and backyard. The home has hardwood floor throughout except for carpeted, large family room in the lower level. The gourmet kitchen is on the...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Featured in the April 2010 design issue of Nantucket Today, this adorable Nantucket country cottage is an ideal spot to enjoy an island vacation; a short distance from downtown and conveniently located to shopping, markets and beaches. 1st fl: Living room, dining area, galley kitchen includes...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Cable/satellite TV
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    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely, bright, airy summer house with many spacious rooms. High ceilings, billiard room, two master suites, large eat-in kitchen with brick floor and an adobe fireplace. French doors lead to a slate patio/swimming pool area and a big yard protected by a hedge. Spectacular property close to town...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely Nantucket summer home is ideally located near 'Sconset center. The property boasts a 5 bedroom main house, a guest apartment and a heated pool. New furnishings were added in 2008. There is a lovely garden with a patio by tall privet and a sprawling private lawn. Many other bonus...
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    Siasconset, Nantucket 2564
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious home has a largeback yard and enjoys the use of a Community pool. House has WIFI First floor: living room, dining room, kitchen, laundry and half bath. Second Floor two masters, each with it own baath, two twin rooms that share a bath. Additional amenities include: beach towels,...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please be advised that 1 Week Minimum Stay applies to this property during the peak season: Mid- June through Mid-September.
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 2000, this house is tastefully furnished, spacious and cheerful.There is a nice furnished patio for outdoor gathering with friends and family. Perfectly located in Naushop Village and has a convenient distance to Downtown Nantucket and beach. There are a swimming pool, tennis court and...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Custom built Graham Goldsmith home designed to accommodate multi-generational families and features over 7,500 sq ft of living space. 1st fl: Large living room with fireplace, open dining room with hallway to gourmet kitchen, 2 dishwashers, Subzero refrigerator, Wolfe gas range. All living areas...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Recently built this 3 bedroom Main House with a 1 bedroom guest suite in the Carriage House will delight you. Tucked away in Madequecham, it's just a short drive down a sandy road to one the islands best beaches & everything is brand new! The first floor of the main house welcomes you into the...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated high on the Quidnet moors on nearly 4 acres, High Point is an exceptional family compound with sweeping views of the Atlantic Ocean, Sankaty Lighthouse, and Nantucket’s Eastern Shore. The Main House features 6BR/6.5BA, a 15′ x 36′ heated salt water pool, an outdoor spa, a fire pit,...
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    Siasconset, Nantucket 2554
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated for the 2015 summer season, this 5 bedroom 5 ½ bathroom house with pool and cabana is located across the street from Fisherman’s beach in Surfside, and can sleep 12 comfortably. The house is tastefully decorated and features a large rear deck, pool, outdoor shower, high end...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    Homeport is a brand new air conditioned home with expansive waterviews including Great Point Lighthouse, Coatue and sunsets. First floor: Flagstone path through front yard leads into entrance hall, den w/ fireplace, wet bar w/ frigerator and slider to water side deck. Bedroom w/ full bath and...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are home is an immaculate, spacious 3 bedroom 3 bathrooms house witch sleeps 6 people. Situated in upmarket Naushop development, With access to tennis courts ,clubhouse , swimming pool and playground . Make family memories and Enjoy all that Nantucket has to offer whilst staying in a cool calm...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1st Floor: Large living area featuring custom built ins, window seating and fireplace . Chef's kitchen with granite island. dining area, and a mahogany paneled office. State of the art Nuvo surround sound system in every room. 1/2 bath off kitchen. French doors to outside yard and in ground pool....
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated home with living room, eat in kitchen and all new appliances. Master suite with bath and a Guest room with bath on first floor. 1/2 bath off mudroom . French doors to private yard. Second floor has two bright bedrooms . One bedroom has three beds/trundles, one bedroom has two...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great house with plenty of entertainment opportunities. Enjoy spectacular ocean views from main house. Short distance to Pebble Beach in Tom Nevers. FIRST FLOOR: Den with fireplace; three bedrooms and two full baths; front entry way looks through the den with fireplace and TV to a fully screened in...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely new house on Thistle Way. Flexible floor plan features a wonderful gathering area on the first floor and a second floor family room plus central A/C First Floor has a spacious L shaped living.dining/kitchen. Kitchen features marble counters, Wolf Range and Sub /zero refrigeration....
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully appointed property just one mile from Surfside Beach set on 2 private acres. This custom designed home is filled with natural light and offers expansive living areas inside and out. Gourmet kitchen, hardwood floors, central air conditioning, and heated pool with cabana complete this...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Long white stone driveway leads to this recently renovated 5+ acre oceanfront compound. Enjoy the outdoor pool and spa or take a short stroll down the steps to the ocean! First Floor: Open entry hall leads to Master bedroom with en-suite bath and spectacular ocean side views. Guest bedroom with...
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    Siasconset, Nantucket 2254
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfect vacation home has a professionally landscaped yard, an outdoor patio with grill, mountain bikes, beach chairs, towels...anything and everything you need to make your vacation complete. The Ultimate Sport Room is on the first level and features 3 built-in TV's, pool table, ping pong and...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Four bedroom, 2 bath West of Town/Cliff area home with pool, pool house, and fire pit on a private setting with easy access to beaches, Town and the Madaket bike path. Relax poolside or on one of the decks. New for the 2016 season is a BBQ grill island with seating. First Floor: A small covered...
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    Nantucket, Massachusetts 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxury property conveniently located in Old Historic District close to fine-dine restaurants, museums, and artisans shops. Enjoy the best of all worlds: pool, jacuzzi and outdoor shower for your indulgence of this elegant Nantucket property. With a peaceful, private in-town location, bright...
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    Nantucket, Massachusetts 02554
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely newer home on quiet 8-acre estate in Polpis. Wonderful totally private setting with swimming pool and harbor access for boating and windsurfing. A spacious and very attractively decorated and air conditioned estate with main house & cottage. Additional amenities include: beach towels, wood...
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    Siasconset, Nantucket 2554
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***Surfside Knockout*** This stunning 4 bedroom 3.5 bath home has all the bells whistles you could want for a dream vacation!! It's spacious, beautifully decorated and well appointed. Summer living at it's best with a private swimming pool , spa, sun deck w/ built in BBQ, screened in porch, and...
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    Location Information
    Nantucket, Massachusetts 2554
    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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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely home in Polpis has 2nd floor water views and deeded beach access. There is a 4-bedroom Main House and a seperate one bedroom studio, as well as a brand new pool. There are spacious decks for outdoor entertaining! Main Floor: Kitchen with breakfast nook, dining room, family room with...
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    Location Information
    Nantucket, Massachusetts 2554
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, NEW, 2016 waterfront home for rent with beach access and an outdoor pool! This new home has 5 bedrooms and 6.5 baths including an outdoor shower and a spa. First Floor: Kitchen, dining room, living room with TV, hallway bathroom, laundry room, master bedroom with full bath. There are 6...
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    Location Information
    Siasconset, Nantucket 02554
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular property in Madequecham with salt water swimming pool and tennis court. This home on the south shore sits on 3 landscaped acres with stone walls, a long shell driveway and circular brick parking area, was completely redone in 2008 and abuts acres of conservation land. Downstairs: 4...
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    Location Information
    Siasconset, Nantucket 2554
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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