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: Shared outdoor pool (unheated) Games room Table tennis

All filters match

Price per night from

$442

OCEANFRONT CONDO, SERENE, UNCROWDED GENTLE WINDS

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Games room Table tennis

All filters match

Price per night from

$316

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Responds fast! avg. 2 hours 14 minutes

2 of 3 match: Shared outdoor pool (unheated), Games room, Table tennis

2 of 3 filters match

Price per night from

$7,684

The Hideaway Hull Bay Cottage 1

Charlotte Amalie cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Table tennis, Shared outdoor pool (unheated), Games room

2 of 3 filters match

Price per night from

$401

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

2 of 3 match: Shared outdoor pool (unheated), Games room, 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: Games room, Shared outdoor pool (unheated), Table tennis

2 of 3 filters match

Price per night from

$240

Escape Winter at Westin St. John Resort, USVI

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Table tennis, Shared outdoor pool (unheated), Games room

2 of 3 filters match

Price per night from

$2,009

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.

2 of 3 match: Table tennis, Shared outdoor pool (unheated), Games room

2 of 3 filters match

Price per night from

$688

The Westin St. John Resort Premier Villa 2BRM Sleeps 6 with 2 Balconies

Cruz Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Table tennis, Shared outdoor pool (unheated), Games room

2 of 3 filters match

Price per night from

$804

Responds fast! avg. 1 hour 43 minutes

1 of 3 match: Shared outdoor pool (unheated), Table tennis, Games room

1 of 3 filters match

Price per night from

$264

GORGEOUS CONDO East End Beachfront Condo, Elysian Beach Resort

East End condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Table tennis, Games room, 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: Table tennis, Games room, 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: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$574

Caribbean Sugar Apple Retreat

Charlotte Amalie condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$207

Gentle Winds 2Bedroom 2 Bath

Christiansted villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 36 minutes

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$345

Rare Brand New Luxury Beachfront Villa

East End condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$656

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: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$798

Amazing Beachfront Penthouse on the #1 Beach

Smith Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$488

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: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$321

Suite 8B - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

Suite 3A - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

Suite 9A - Gallows Point Resort Oceanfront Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

Suite 10A - Gallows Point Resort Harbor View Garden

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$488

Suite 9C - Gallows Point Resort Oceanfront Upper

Cruz Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Table tennis, Games room, 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: Table tennis, Games room, 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: Table tennis, Games room, 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: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$689

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$632

Sunny Days in St. Croix

Christiansted condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Table tennis, Games room, 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: Table tennis, Games room, 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: Table tennis, Games room, 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: Table tennis, Games room, 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: Table tennis, Games room, 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: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$568

The Hideaway Hull Bay Beachfront Villa 2

Charlotte Amalie villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$689

The Hideaway Hull Bay Beachfront Villa 1

North Side villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$2,772

The Hideaway Hull Bay 18 Bedroom Beachfront Estate - Sleeps 36

Charlotte Amalie house

  • 18 bedrooms
  • 16 bathrooms
  • sleeps 36

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$14,386

"Suite Papaya"

Coral Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Table tennis, Games room, Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$414

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