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North Side Holiday Rentals

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    Travellers to North Side are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 19 Rentals in North Side
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    Captain's Quarters  BRAND NEW and Waiting for YOU1 / 8
    (5)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    VILLA AMOUR ,Romantic , Art Lovers Paradise ,1 / 80
    (50)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Silk Cotton1 / 14
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2015
    We stayed here Feb 28 to March 7, 2015 as a group of four adult couples. We had an absolutely amazing vacation. The house is amazing and the view is stunning. Richard and...
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    About this property
    This luxurious 7800 square foot 5 bedroom multi-level rental villa is located on a hillside plateau overlooking the historic port of Charlotte Amalie, St. Thomas, U.S. Virgin Islands. Its southern exposure is perfectly situated to capture the cool tropical breezes, Caribbean sun and breathtaking...
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    North Side, St. Thomas 00802
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Stone Cottage1 / 8
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Reviewed 3 November 2015
    Expectations were met and then some. We were greeted in town and led to the cottage, we were given lots of info of the area which was nice. The cottage was clean, inspiring...
    Reviewed 1 November 2014
    Though we have not had a chance to return to Stone Cottage in over two years, I wanted to resonate all the high praise you have read about this villa, as we have rented this...
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    About this property
    This very charming one bedroom, fully air-conditioned small home is the perfect romantic hideaway!<br /><br />Set within a gated estate on St. Thomas's cool north side, Stone Cottage offers a secure retreat, away from the beaten tourist track.<br /><br />Well equipped and nicely furnished, it...
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    North Side, St. Thomas 00802
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Caribia Cottage1 / 17
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2016
    This was one of the best vacations my wife and I have experienced. I have nothing but good things to say about our villa and we both look forward to staying there again. The...
    Reviewed 24 September 2012
    Who knew what we were getting into when we drove up, up, up the mountain? We arrived at Caribia Cottage, saw the view, the amazing pool, the iguanas chillin on the branches a...
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    About this property
    This perfect couple's hideaway, set on a breezy and cool hillside overlooking picturesque Charlotte Amalie and the harbor, affords both privacy in a relaxed and peaceful setting and easy access to town, beaches, and nightlife.<br /><br />This sleek and pristine cottage is fully screened, and has a...
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    North Side, St. Thomas 00802
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Ocean Views
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our spectacular Cannon Cliffs Villa is available for your next escape to paradise. The Villa is located on the tranquil North Side of St. Thomas on Peterborg Peninsula. Although the area is a simple twenty minute drive from Cyril King Airport, it seems worlds away from the hustle and bustle of...
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    North Side, St. Thomas 00802
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    The Beach House, St. Thomas, U. S. Virgin Islands1 / 24
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Washer
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2014
    The Beach House was just like the photos we saw and more. House and location is beautiful. Our private pocket beach was bigger than expected and plenty of room for our family of...
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    About this property
    The beach house is a unique property on st. Thomas. If privacy is what you're looking for the beach house is the place for you. This magnificent property is located 40 feet above sea level, on three acres with 700 feet of shoreline where a wooden stairway leads you to a small, completely secluded...
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    Location Information
    North Side, St. Thomas 00802
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    TreeTops Perched High on St Peter. Mnt.1 / 21
    (10)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • Grill
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2015
    The well-maintained property is located high on the St Peter Mountain. The view from the wrap around deck and the swimming pool area is absolutely breathtaking. The house has...
    Reviewed 5 December 2014
    My husband and I took our niece for her 16th birthday and the villa exceeded our expectations. The separate downstairs room with its own bathroom and balcony afforded our niece...
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    About this property
    Romantic, Very Private Villa Perched High on St Peter Mountain on the Lush Northside of St. Thomas. TreeTops offers beautiful ocean vistas that are among the very best that the island has to offer. TreeTops overlooks Magen's Bay, The Atlantic Ocean, The British Virgin Islands and many other...
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    North Side, St. Thomas
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Fairwinds: Privacy,Stunning Views Lg Pool,Spacious1 / 8
    (3)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Satellite TV
    • Internet Access
    • Ocean Views
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    We have visited a few of the islands over the past couple of years, St Lucia being our go to until now. Fairwinds in St Thomas provided a perfect spot to enjoy amazing views...
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    About this property
    Exclusive spacious hilltop villa offers breathtaking views of the aquamarine Caribbean from Puerto Rico to St John and the BVI's. Enjoy warm sun or cool shade any time of day from Fairwinds expansive decks, a perfect wedding site. All 3 bedroom suites feature large baths and private balconies with...
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    Location Information
    North Side, St. Thomas
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Kyalami1 / 9
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2014
    This is a huge villa set on a large parcel of land overlooking part of the Charlotte Amalie harbour. The view would be even better if the trees were to be trimmed.The interior...
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    About this property
    Kyalami is is a Caribbean mansion that was once the site of grand parties in years past with famous celebrities. The property has been renovated and equipped with the latest amenities and guests may now enjoy the grandeur of this aristocratic and renowned property that is nestled hillside above...
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    Location Information
    North Side, St. Thomas 00802
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Lupa1 / 25
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2016
    The moment we walked through the Massive doors inviting us to Casa Lupa we knew we had made the right decision. My husband and I were there with our 3 children and son-in-law...
    Reviewed 29 March 2015
    Casa Lupa was much more than we expected. The pictures do not capture the beauty of the location and the great scenery. We especially liked the large outdoor seating and...
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    About this property
    When you arrive at Casa Lupa, the big, magic panorama of blue Magens Bay unfolds before you - a riveting and dramatic ocean view. This new four-bedroom villa overlooks the expanse of the Bay from its location just above the shoreline. A staircase flanked by palm trees takes you down to the main...
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    North Side, St. Thomas 00802
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Patio
    • Private Outdoor Pool (Unheated)
    • Parking
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    VILLA MARTI HIGHLIGHTS: • Spacious terrace with views of the ocean and Charlotte Amalie. • Private Pool and pool deck built into hillside • Beautiful gardens and landscaping • Two master suites • Completely separate apartment with full kitchen and 3rd bedroom suite •Ten minutes to Magens Bay beach,...
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    North Side, St. Thomas 00802
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a breezy knoll just a couple minutes' drive from famous Magens Bay Beach, Villa Gardenia is one of our most beautifully finished and decorated villas. Serpentine garden planters flank Villa Gardenia's entry gate. The garden courtyard, graced with a trickling fountain filled with tropical...
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    North Side, St. Thomas 00802
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jaw-dropping views! Luxurious Lenon Haus is an amazingly elegant 2-bedroom, 2-bath masonry villa with a brand new lagoon-style pool and a million dollar ocean view, overlooking world-renowned Magen's Bay. You're just minutes away from Magen's Bay Beach, listed by TripAdvisor as one of the top 10...
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    Location Information
    North Side, St. Thomas 00802
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Edge of Paradise villa offers the ultimate seclusion within nature's hideaway. Lush island flora embrace this gated, 4-bedroom private waterfront estate, set just above a perfect little beach on Magens Bay, on the northern shore of St. Thomas. Add to this the live reefs just beyond the beach, where...
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    North Side, St. Thomas 00802
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    North Side, St. Thomas 00802
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    30% Off NOW Only $3843 for the Weeek1 / 28
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Ocean Views
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    From the second we got there and walked through the gates to the property the view took our breath away. The house was perfect for our group and we used the pool daily. We used...
    Reviewed 1 June 2017
    We stayed here for 5 days for our honeymoon and brought our wedding party with us. There were plenty of space for everyone and the house was just perfect! The view alone was to...
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    About this property
    COMMON QUESTIONS: 1. How many beds are there? Answer: 3 queens, 3 twins, 1 full size crib, 2 pack and plays. If you have more than 9 you can bring blow up mattresses if you would like and there are large cushions on the outside lounge chairs that can be brought in for little ones to sleep on...
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    Location Information
    North Side, St. Thomas 00802
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • DVD Player
    • Parking
    • Washer
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    North Side, St. Thomas 00802
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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