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Sailing in the Virgin Islands

Charlotte Amalie yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$947

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$1,803

“Absolute Paradise!!!!” Thanks to Tom we had the perfect getaway!!! Fast booking, we were provided with tons of information before we even left and the deposit returned asap. This condo was in the best place - you were in your own world yet so close to everything. We had privacy, everyone was pleasant and perfect weather. All that was needed was right there. The view was beautiful, the pool 2 minutes away - walking and Sapphire Beach 5 minutes away - walking. And lets not leave out the Off the Grid food truck at the top of the hill. We are early risers so we snorkeled in the morning, walked the beach in the afternoon and made good use of the pool 7am to 10pm with cocktails and appetizers at the Sapphire and Grill. The ferry to St. Thomas is a 5 minute drive too!!! This is the place you want to be and we will definitely be booking this amazing place again. Thanks to you Tom and your condo - you rock!!!!

Responds fast! avg. 3 hours 18 minutes

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$160

Sapphire 1 Bedroom-Free H/S WIFI & No Excessive Owner Fees #257

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$206

OCEANFRONT CONDO, SERENE, UNCROWDED GENTLE WINDS

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$316

Responds fast! avg. 1 hour 21 minutes

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Price per night from

$343

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

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Price per night from

$987

Cariso Suite

Frederiksted apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“An authentic taste of the "American Paradise" with best imaginab” We found the Cariso Suite so perfect for us that we have been there several times over the years. The home is very comfortable, the decor is exceptional with personal artistic touch, and we loved having such a well-equipped kitchen when we wanted to eat-in. Sugar hill is a very short walk to our favorite beaches for swimming, snorkeling and lounging either under bright blue sunny skies or beneath the palms and other natural shade. The private pool on the Sugar Hill estate is also a treat, nestled on the hillside with spectacular sunsets surrounded by diverse tropical landscaping, as well as cozy garden spots that surround the Cariso itself ... especially the hammock under our favorite mahogany tree. The owners offer such attentive warm hospitality, with lots of "insider tips" directed to our own personal interests. They have made discovering the cultural gems of St. Croix, diverse recreational activities, traditional island events, the best restaurants, tourist sights, favorite shopping spots, local specialties, peaceful hide-aways (our first visit was our honeymoon), etc. so much easier and more enjoyable. We have sometimes recommended Sugar Hill's other rental suites to close friends so we could all be on island at the same time and vacation together. You can really get the flavor of island life in the neighborhood and the closeby historic town of Frederiksted is so authentic compared to glitzy, noisy tourist towns we have seen elsewhere. You really feel well taken care of at Sugar Hill by the Sea with such accommodating host and hostess.

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Price per night from

$286

Studio Condo on the Waterfront at Bolongo Bay

Bolongo Bay condo

  • 1 bathroom
  • sleeps 2

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Price per night from

$190

St Croix, U.S. Virgin Island Condo Near the Beach

Frederiksted townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$86

Westin St. John Luxury -- Three-Bedroom Pool Villa

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$2,295

Beautiful Sapphire Beach St. Thomas, USVI

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

“Perfect Stay at Sapphire Bay” We just returned from the most fabulous week in St Thomas at the Sapphire Beach condo. The condo location could not be more perfect. Just steps to the beach with the most serine views of the island. It is a quick 2 min drive to Red Hook harbor for great restaurants, bars, grocery store and ferry to BVI or St John. The owners were so accommodating bringing in a full size crib, high chair and pack and play for my 1 YO. The house keeper Norma gave us a complete run down of the area, where to eat and what to do during our stay. Being a family with 2 kids, this was the perfect stay for us. Full kitchen in the unit, washer and dryer, satellite TV, games and movies for the kids--and the convenience of going back and forth between the beach and home when needed. The island was nothing but beautiful and after visiting many beaches on the island, this was by far the best. If you don’t snorkel, you will start on this trip. The water is so calm and clear with amazing fish, turtles and coral. Plus gear is provided at the condo! A trip to the Mountain Top for a banana daiquiri is a must. For dinner, Fish Tails had the freshest seafood and best sushi around. For Caribbean fare, don’t skip Cuzzin's and Glady's in Charlotte Amalie-- absolutely delicious! We cannot wait to return to paradise-- maybe next time without the kiddos!

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$362

Striking Ocean Views, Privacy,

Water Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$488

Luxury All-Inclusive Sailing Catamaran

East End yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$2,451

Beautiful 2015 Saba 50 Catamaran Sail Boat

East End yacht

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$4,015

Luxury Villa with Large Pool Above Honeymoon Beach

Water Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$493

Sailboat Ragamuffin Floating Bed and Breakfast INCL meals drinks water toys

Water Island b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$230

Live the ‘Suite Life’ - All Inclusive Private Yacht

Charlotte Amalie yacht

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$5,736

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Price per night from

$1,066

Soulshine Charters

Virgin Islands National Park yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$1,951

Westin St. Johns, 2 Bedroom Bay Vista Villa Loft, April 21-28

Cruz Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,017

Responds fast! avg. 16 minutes

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Price per night from

$1,278

St. Thomas USVI 3 bedroom plus Cottage Villa

Peterborg villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Truly Exceptional Property!” Villa Sunrose was a truly exceptional property. The villa was exceedingly well appointed, very tasteful and spacious. All the bedrooms were extremely well decorated and comfortable, and the cottage was a once in a lifetime experience. The main living areas and kitchen were spacious and beautiful, and accommodated our group wonderfully. The owners have thought of everything, and make your stay warm and inviting, from having beach chairs and coolers to kitchen supplies ready for your use. Like the inside, the outdoor decks/living areas went far beyond our expectations, and we thoroughly enjoyed our time in the hammocks, glider and chairs, and meals and games at the outdoor tables. The views from all the decks of St. John and the BVIs were breathtaking day and night. The binoculars were a fabulous treat. The decks, like the inside, were so very well appointed and decorated, and we truly enjoyed all the small touches throughout the many decks.The kids loved the pool, and we adults appreciated the ample covered decking to enjoy the outside while taking a break from the sun. The outdoor shower was a hit, the boys and dads especially loved this. Thank you for a truly exceptional stay at your villa. Your graciousness and sharing of your exceptional property have left us all with a trip of a lifetime.

1 of 3 match: Rental types, Car not required, Climbing frame

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Price per night from

$499

Tranquil Two-Bedroom Retreat with Ocean Views!

Charlotte Amalie villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Rental types, Car not required, Climbing frame

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Price per night from

$241

Luxury 3 Day Catamaran Sailing Trip in USVI St. Thomas & St. John

Charlotte Amalie houseboat

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$6,023

Yacht Serena | Luxury Crewed All-Inclusive Charters | USVI, BVI, ST BARTHS

Water Island yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$2,771

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Price per night from

$1,176

Your Perfect Beachfront Condo in Paradise - Sapphire Beach

Smith Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$275

Serenity - Private Caribbean Style Pool Villa

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$259

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Price per night from

$746

Waterfront Escape: Paradise at a Great Price!

East End studio

  • Studio
  • 1 bathroom
  • sleeps 4

“Amazing Experience” I loved my stay at this condo! Great location! Owner was super friendly and helpful. The condo was very clean and newly renovated, exactly like the photos shows. I could have not asked for a better vacation. Will definitely come back again.

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$316

“Great time at Bliss” Bliss is not large but perfect for 3 to 4 people. We enjoyed the view of Cruz Bay and the proximity to town. Cynthia has all the necessities in Bliss and it was nice to use the cooler and beach chairs. We rented a jeep from amalie at the airport in St Thomas, I would recommend renting a vehicle, as the walk to town and back is possible, but requires a lot of effort. The beaches around the island are beautiful and it is great to be able to explore. I would recommend going to Chateau Bordeaux for lunch, it has a great view of Coral Bay and wonderful food. Thanks Cynthia, you have a great villa and would love to stay again.

1 of 3 match: Rental types, Climbing frame, Car not required

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Price per night from

$263

View of Paradise (Fully Renovated Condo)

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$458

Sapphire Beach Front (Fully Renovated)

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$458

Calicaribe--hill top villa with views of Caribbean

Cruz Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Fantastic Villa” Your Review is Pending Please read and confirm your review for Property #284227 below. Review #4627412 Fantastic Villa Our family spent two unforgettable weeks in late July and early august at Calicaribe, celebrating our 50th wedding anniversary, We can't say enough about Calicaribe. We loved the villa -- its layout and tasteful decor. The views of St Thomas, other islands, and Cruz Bay from the property, especially the guest house and the pool area, are breathtaking. Although the heat and humidity were high during the peak hours of each day, temperatures and humidity lowered late in the afternoon so that we could enjoy wine and cheese and the view, including spectacular sunsets, on the patio and dinner on the verandah. Pictures of the property on various websites don't do it justice. Calicaribe is much better than we expected. It is clean and very well maintained. Calicaribe is blessed with an excellent local property manager, Steve Black, who has lived in Cruz Bay for 25 years and is a constructive civic activist. Whenever we needed anything, Steve was prompt in his response. St John is truly paradise. We were fortunate to have a rental jeep to get around the island and to have our daughter and her partner do all the driving. The roads are challenging because the island is very hilly and the roads have very sharp turns, which means that one does not need to worry about exceeding the 20 mph speed limit. Opportunities for snorkeling and scuba diving abound. The beaches (St John has 39 of them) are beautiful. We swam at four of them: Trunk Bay, Little Lameshur Bay, Hawksnest Bay, and Maho Bay. We ate out only three times because my daughter's partner loves to cook, and having dinner on the verandah was a pleasant experience. The Fish Trap and Zozo's are excellent restaurants in Cruz Bay, although the latter may be too expensive for some folks. We highly recommend a sojourn at Calicaribe. You'll get plenty of bang for your bucks.

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Price per night from

$1,148

Starfish Studio on Crystal Cove Sapphire Beach

Smith Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$224

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Price per night from

$686

Driftwood on Crystal Clear Waters of Sapphire Beach!!

Smith Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$269

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