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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.
    19 Matching Rentals in NantucketView all 1 218 rentals
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    Luxury 8br 7ba Home, Pool,guest House1 / 44
    (6)Excellent
    8 Bedrooms, 8 Bathrooms, Sleeps 22 Quick View
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    6 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    8 Bedrooms, 8 Bathrooms, Sleeps 23 Quick View
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    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Hot Tub
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    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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    02554, Nantucket, Massachusetts
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Patio
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    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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    02554, Siasconset, Nantucket
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    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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    02554, Siasconset, Nantucket
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Patio
    Suitability
    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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    2554, Nantucket, Massachusetts
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Washer
    • 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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    2564, Siasconset, Nantucket
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CISCO BEACH HOUSE – Fabulous Cisco house with excellent views of Hummock Pond and the Atlantic Ocean plus a swimming pool, spa, pool house, lovely gardens & a koi pond. Spacious, attractive oak post and beam, upscale 4 bedroom, 3.5 bathroom upside down house in great location. Convenient to...
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    02554, Nantucket, Massachusetts
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    Suitability
    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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    2554, Nantucket, Massachusetts
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    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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    02554, Nantucket, Massachusetts
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Patio
    • Air Conditioning
    • Hot Tub
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one-of-a-kind family compound sits on almost six private acres overlooking Weeweeder Marsh. Surrounded by conservation the property boasts a six bedroom main house with central air conditioning, an infinity edge pool, cabana, par-three golf course (three holes, nine tee boxes) and an outdoor...
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    2554, Nantucket, Massachusetts
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    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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    02554, Nantucket, Massachusetts
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Secure Parking
    Suitability
    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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    02554, Nantucket, Massachusetts
    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
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    Suitability
    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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    Location Information
    2554, Nantucket, Massachusetts
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    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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    Location Information
    02554, Nantucket, Massachusetts
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CISCO BEACH HOUSE - Fabulous Cisco house with excellent views of Hummock Pond and the Atlantic Ocean plus a swimming pool, spa, pool house, lovely gardens & a koi pond. Spacious, attractive oak post and beam, upscale 4 bedroom, 3.5 bathroom upside down house in great location. Convenient to...
    View all property information
    Location Information
    2554, Nantucket, Massachusetts
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy beautiful Nantucket island from this newly constructed gem in the private community of Naushop Village. Boasting 2 master suites, 3 additional bedrooms, and 4.5 baths, this 2,630-square-foot home is the perfect launch pad for exploring Nantucket! When you’re not exploring the nearby beaches,...
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    Location Information
    02554, Siasconset, Nantucket
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A blissful retreat awaits at this charming 4-bedroom, 2.5-bathroom vacation cottage on Nantucket island. Up to 6 guests will experience outdoor living at its finest, relaxing by the private pool or lounging on 2 of the islands most popular beaches less than 3 miles away. Venture into town or take...
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    02554, Siasconset, Nantucket
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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