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Provincetown Luxury Holiday Rentals

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    Travellers to Provincetown are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    20 Matching Rentals in ProvincetownView all 137 rentals
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    Unique and Spacious East End Artist Home1 / 15
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored antique home brings the allure of Venice to Provincetown. Beautiful artist home offered as a seasonal monthly rental! This recently renovated home is located on a quiet street just east of the center of town. Offering wonderful privacy, the home is situated on gorgeous landscaped grounds...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    PROVINCETOWN MASS.CAPE COD MANSION.UNIQUE POOL1 / 28
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Private, Unique Upscale Provincetown Home
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    Amenities & Details
    • Mountain Views
    • Central Heating
    • Ocean Views
    • Wi-Fi
    • Sauna
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2018
    This house was wonderful for a multi-generational family getaway.There was plenty of space for all of us to spread out. We were able to put babies on one side and grandparents...
    Reviewed 11 October 2016
    We have found our favorite place for a quiet getaway. Private but close to town. The bedrooms were the perfect size for all of us. We ate out most of the time but the fully...
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    About this property
    This property is our family home and is located in the West End of Provincetown. It's private and borders the National Seashore and is in excellent location with great architectural details. walls of windows, including a rooftop overlooking the Atlantic Ocean, and a pool,,and large entertaining...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan a beachfront getaway for twelve guests at this 5BR/3BA home, where generous picture windows afford water views from almost every room. Spend leisurely vacation days on the two-story patio overlooking Cape Cod Bay. With lounge seating, a gas grill, and three al fresco dining areas, the space...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Grill
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The iconic Wharf House is a unique and unparalleled waterfront luxury property with spectacular views of Long Point and the harbor. A 1,000 square foot private deck extends into the Bay and is surrounded by water at high tide. Enjoy the changing nautical scenery and moonlit Cape Cod Bay through...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 3 Bathrooms, Sleeps 1 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Atwood Cottage -Large Cap Home in the Heart of the West End! Enjoy spacious accommodations in a traditional Ptown Antique! Invite your family and friends to share this marvelous home located in the heart of the West End. Steps from Captain jacks Wharf, close to the Red Inn and Victor's Restaurant....
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 1
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk into a bright elegantly designed contemporary open living space, with refined comfortable furniture and a gourmet kitchen; fully stocked with Bosch appliances. The expansive kitchen island can seat up to six and the dining table can expand to accommodate ten people for dinner. This home has...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Ocean Views
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the fully renovated and updated Jimmy Majestic Cottage located in the fabulous East End across from the Provincetown Tennis Club. This property is located 200 yards from the beach with its own parking and beach access. The owner has added meticulous upgrades that are great for...
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    Location Information
    Provincetown, Cape Cod 02657
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in an exclusive and desirable West End neighborhood where you can maintain privacy and peace but with a 5 minute bike ride or 10 minute walk you can enjoy P'town’s best restaurants, attractions and beaches. Our home has open floor plan with lots of natural light, a large deck with sun all...
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    Location Information
    Provincetown, Cape Cod 02657
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Shared Garden
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This classic Cape is in the quiet East End of Town, on Bradford Street and Allerton. Once the home of noted Provincetown sculptor Lila Katzen, the house has a large, front to back living room with fireplace and widepine floors; a two sided galley kitchen and a guest bedroom. The former sculpting...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    West End, Spacious, Great Amenities, Private Gardens, Bring Your Dog !!!1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2017
    Definitely a great rental for a great price . 3 full bedrooms and 2 full baths! Steps from Commercial Street the heart of Provincetown . Minutes to the beaches. Open concept...
    Reviewed 26 July 2016
    I just placed this review on the Dyer's Beach House site but I guess this is where I belong. My friends and I have rented the 2nd floor of this home for the last 3 years and...
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    About this property
    Large, spacious 3 bedroom home on the edge of the West End. Large private gardens. Walk all over town as this home is close to everything. Relax and enjoy all the Provincetown has to offer. Coming for an event, summer vacation, spring fling or fall foliage trip, this home will create the mood you...
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    Provincetown, Cape Cod 02657
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bath condo is very unique and comfortable. Located on two floors with the kitchen, living room with on the wall flat screen tv and main bedroom with private bath on the first floor. On the second floor are two bedrooms and another full bath. The second floor even has a private...
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    Provincetown, Cape Cod 02657
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Hot Tub
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is a Saturday to Saturday rental mid- June to Mid-September. Memorial Day weekend has a 4 night minimum. This Shaker Style home offers every amenity and convenience along with smart contemporary style and luxury finishes; central air, multi-zoned Sonos music system, premium washer/ dryer,...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern n private w/ a central westside, the ability to walk everywhere make this the best n least expensive option for a group of 8 or less . 4 br's, 3 baths, 4-5 beds, 2 kitchens, 4 parking spaces, 2 laundry rooms, 4 TV's, 2 Blu-Rays,wifi, 2 grills Plus Prem. cable in high season n 6 Bikes for...
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    Location Information
    Provincetown, Cape Cod 02657
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Balcony
    • Patio
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A rare historic gem located in Provincetown's Gallery District at the top of Pearl St. This exclusive unit is one of two redeveloped from a 19th-century barn that later served as the Cape School of Art and the studio and residence of the painter Edwin Dickinson.  
 Now a modern and luxurious 2 bed,...
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    Provincetown, Cape Cod 02657
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Balcony
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A rare historic gem located in Provincetown's Gallery District at the top of Pearl St. This exclusive unit is one of two redeveloped from a 19th-century barn that later served as the Cape School of Art and the studio and residence of the American painter Edwin Dickinson. Now a modern and luxurious...
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    Location Information
    Provincetown, Cape Cod 02657
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Charming 3-4 Bedroom West End Provincetown House1 / 39
    (13)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Charming and Quiet Home Perfect for Groups
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    • Sauna
    • Grill
    • Balcony
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    It really doesn't get much better in terms of location. The house is barely a block from the gym, around the corner from a bike rental shop, 3 min to the main grocery store...
    Reviewed 18 September 2017
    The house is in a excellent location, just 2 blocks away from commercial street, and a 5 min bike ride to the beach. Super convenient to shopping, yet a very quite location...
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    About this property
    Our private home is located off the beaten track in a quiet West End of Provincetown neighborhood 2 blocks to Commercial Street. It is two blocks away from Commercial street close to the Boat Slip. Our 1600 sq ft renovated 1860's home has 3-4 bedrooms and 3 full bathrooms with beautiful wide pine...
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    Provincetown, Cape Cod 02657
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Direct Waterfront, Spacious West End Apartment, Beach Access1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    Having rented this unit multiple times, I can say this is the most beautiful spot in Provincetown. The home is large enough for my group of friends, and is ideal for...
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    About this property
    This wonderful waterfront 3+ bedroom condo has all that your vacation needs to make it a very special visit to Provincetown. Panoramic harbor views from large panoramic wall of windows from the living room and great waterfront decks. It is a large space. There are two small private waterfront decks...
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    Location Information
    Provincetown, Cape Cod 02657
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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