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Sailing in the Virgin Islands

Charlotte Amalie yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$947

Satinwood: private, breezy eco-villa with an amazing View

Coral Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$419

Sweet Wind Villa overlooking Hurricane Hole

Coral Bay house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Sweet Wind is outstanding” We just returned from 9 wonderful days at Nina"s Sweet Wind Villa. The view is spectacular, the trade winds always kept the villa very comfortable and the location to great snorkeling and beautiful beaches is a big plus. Nina is a great hostess and close by if you need any hints on where to go or places to eat but she is never in the way. She even was so kind to fillet a Mahi Mahi I bought in Cruz Bay!! The "Pod" set up of the Villa makes it really nice. The living, dinning and kitchen area is separate but right next to two pods that are the sleeping and bathroom areas. Great for 3 couples or a family. The East end of the Island is also very peaceful and quiet. We certainly plan to return.

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$688

Responds fast! avg. 3 hours 57 minutes

1 of 3 match: Rental types, Pets allowed, Car not required

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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, Pets allowed, 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

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$206

Responds fast! avg. 1 hour 21 minutes

1 of 3 match: Rental types, Pets allowed, Car not required

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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

1 of 3 match: Rental types, Pets allowed, Car not required

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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.

1 of 3 match: Rental types, Pets allowed, Car not required

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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

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

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$362

Fantastic Ocean Views and Breezes

Cruz Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Can't wait to go back!” We loved Villa Mar de amores from the moment we got there. Amazing views, great vibes, lovely decorations, high ceilings, comfy beds, great kitchen, just perfect. It's even nicer than the pictures. We all started smiling when we climbed to the top of the hill in our Jeep. Perfect amount of space for the five of us. Could sit on that deck any time of day and be totally entranced. The owner is great, and the on island managers were also great. We booked the house again for next year before we left!

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$574

Marina Vista - Ocean Views 2Bed/2Bath Condo overlooking Redhook

East End apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$431

Striking Ocean Views, Privacy,

Water Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$488

Luxury All-Inclusive Sailing Catamaran

East End yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Pets allowed, Car not required

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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, Pets allowed, 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

2 of 3 match: Rental types, Pets allowed, 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, Pets allowed, 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

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$5,736

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$1,066

💙VILLA BLISS💙 Don’t Settle For An Ordinary Rental For Your Island Time.

Christiansted villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$689

Soulshine Charters

Virgin Islands National Park yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Pets allowed, Car not required

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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

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$1,017

Green house farms and rentals

Christiansted house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$207

Perfect 2BR Villa in the Heart of Cruz Bay

Cruz Bay villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$459

Responds fast! avg. 16 minutes

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$1,278

Scenic Hilltop Paradise Villas

Charlotte Amalie apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$286

FORTUNA CARAMBOLAS, FIG TREE

Charlotte Amalie apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$207

Banana Grove Villa, Ocean Views and Pool!

Cruz Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$257

Breadfruit

Charlotte Amalie apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Car not required, Pets allowed

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Price per night from

$89

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, Pets allowed

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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

1 of 3 match: Car not required, Pets allowed, Rental types

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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

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$2,771

1 of 3 match: Rental types, Pets allowed, Car not required

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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

1 of 3 match: Rental types, Pets allowed, Car not required

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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, Pets allowed, Car not required

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Price per night from

$259

1 of 3 match: Rental types, Pets allowed, Car not required

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Price per night from

$746

Viewing 38 of 64
rentals in US Virgin Isles

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