Vacation Rentals & Villas in St. Thomas

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Calypso Condo, Luxury on the Water at Gentle Winds

Christiansted apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Calypso condo stay was paradise!!!” We recently returned from a weeks vacation to St. Croix where we stayed at Calypso Condo C-2 in the gated community of Gentle Winds and had a fabulous time!!! The condo was immaculate upon arrival and Angela, the unit manager, stocked us with some groceries I requested so we didn't have to go out at night when we first arrived. There were six of us and with the three bedrooms, three bathrooms, three balconies and the loft area we did not feel crowded. Barbara, the owner, thought of everything to make our stay enjoyable and a home away from home. The book Life in the Left Lane, the bottle of champagne in the fridge, the starfish necklaces and the gift certificate to the Snack shack were complimentary gifts to us for staying there. It was a vey nice finishing touch by Barbara and very much appreciated. The kitchen was very well-equipped. There were so many books, Wii games, VHS movies, DVDs, and board games for all ages to choose from. It was nice having a grill to cookout on since we don't always like to eat out and as we found out food in St. Croix is expensive. I would definitely come back to St. Croix and stay at Calypso Condo again in a heartbeat !!!! The view was breathtaking, the beach gorgeous and the pool refreshing. The grounds at Gentle Winds were beautifully kept and the people there including the guard, the groundskeepers, and the woman who ran the Snack Shack were very polite. Staying there in early June had its benefits. I truly felt we had the whole place to ourselves. Besides us there were maybe 6 units out of 65 that were occupied at the time. No fighting for chaise lounges at the beach or pool.. A nice perk of the off season. Before leaving for St. Croix Barbara made sure we had directions from the airport to the condo and how to access the lockbox should the unit be locked. She also stressed checking out her website which had extremely helpful tips and suggestions one should know before arriving. I was also impressed that early on in our stay Barbara called and sent me an email checking in with us to see that everything was going well. We did so many fun activities while in St. Croix- stand up paddle boarding , snorkeling, kayaking, relaxing on the beach, shopping in Christiansted, touring the Cruzan Rum Factory, watching the sunset at Off the Wall restaurant while playing bingo and watching the sunrise at Point Udall. Needless to say we were all very sad to leave but have so many fond memories and beautiful pictures.

Match: Climbing frame Shared outdoor pool (unheated) Table tennis

All filters match

Price per night from

$441

OCEANFRONT CONDO, SERENE, UNCROWDED GENTLE WINDS

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Climbing frame Shared outdoor pool (unheated) Table tennis

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Price per night from

$316

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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.

2 of 3 match: Table tennis, Climbing frame, Shared outdoor pool (unheated)

2 of 3 filters match

Price per night from

$499

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

2 of 3 match: Shared outdoor pool (unheated), Climbing frame, Table tennis

2 of 3 filters match

Price per night from

$987

Find the Perfect Caribbean Getaway at Gentle Winds!

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Climbing frame, Shared outdoor pool (unheated), Table tennis

2 of 3 filters match

Price per night from

$240

GORGEOUS CONDO East End Beachfront Condo, Elysian Beach Resort

East End condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$345

EXQUISITE Condo East End Elysian Beach Resort

East End condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$345

The Hideaway Hull Bay Cottage 7

Charlotte Amalie villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$573

Caribbean Sugar Apple Retreat

Charlotte Amalie condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$206

Gentle Winds 2Bedroom 2 Bath

Christiansted villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 36 minutes

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$345

Suite St. John at Gallows Point

Cruz Bay villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

“Beautiful views, quiet and convenient” From the initial reservation to check-out, service was terrific. The property has everything you might need from beach chairs and towels to groceries. The proximity to town is also a big plus. Our condo was spotless and very comfortable. Excellent all around. We will definitely rent again!

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$798

Margaritaville St Thomas - Studio, Smith Bay next to Coki Beach,Coral World

Charlotte Amalie condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 43 minutes

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$320

Suite 3A - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

Suite 9C - Gallows Point Resort Oceanfront Upper

Cruz Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$683

Suite 15D - Gallows Point Resort Oceanfront Upper

Cruz Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$683

Suite 15A - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

Sunset Ridge Villas, Unit D

Cruz Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 53 minutes

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$689

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$631

Sunny Days in St. Croix

Christiansted condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$241

Suite 15B - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

Windows By The Sea at SeaClusion Oceanfront Condo St Croix USVI Cane Bay

Christiansted condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$287

SeaClusion 2 Oceanfront Condo on Cane Bay in St Croix USVI

Christiansted condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$287

Suite 8D - Gallows Point Resort Oceanfront Upper Level

Cruz Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$683

Suite 12D - Gallows Point Resort Harbor View Upper

Cruz Bay house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

Amazing Beachfront Penthouse on the #1 Beach

Smith Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$487

Suite 10A - Gallows Point Resort Harbor View Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$487

Suite 8B - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$567

Rare Brand New Luxury Beachfront Villa

East End condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$654

Suite 9A - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$567

The Hideaway Hull Bay Beachfront Villa 1

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$2,764

The Hideaway Hull Bay 18 Bedroom Beachfront Estate - Sleeps 36

Charlotte Amalie house

  • 18 bedrooms
  • 16 bathrooms
  • sleeps 36

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$14,347

The Hideaway Hull Bay Beachfront Villa 2

Charlotte Amalie villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$687

"Suite Papaya"

Coral Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$412

Sapphire Sanctuary By the Sea

Smith Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$189

InterOcean Views

Christiansted apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Table tennis, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$92

Responds fast! avg. 16 minutes

1 of 3 match: Table tennis, Shared outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$1,278

Responds fast! avg. 2 hours 14 minutes

1 of 3 match: Climbing frame, Shared outdoor pool (unheated), Table tennis

1 of 3 filters match

Price per night from

$7,681

Westin St. John Resort Villas, Beautiful One bedroom villas, well equipped

Virgin Islands National Park villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Shared outdoor pool (unheated), Table tennis

1 of 3 filters match

Price per night from

$737

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