Vacation Rentals & Villas in St. Thomas

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Find the Perfect Caribbean Getaway at Gentle Winds!

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Table tennis Safe

All filters match

Price per night from

$240

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Responds fast! avg. 2 hours 14 minutes

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

2 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

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

2 of 3 filters match

Price per night from

$737

AMAZING Beachfront Condo, On the East End at the Elysian Beach Resort,

East End condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$345

Club St Croix Studio

Christiansted condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

2 of 3 filters match

Price per night from

$230

Sapphire Fully Renovated

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$458

The Hideaway Hull Bay Cottage 5

Charlotte Amalie cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

2 of 3 filters match

Price per night from

$400

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.

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

2 of 3 filters match

Price per night from

$442

OCEANFRONT CONDO, SERENE, UNCROWDED GENTLE WINDS

Christiansted apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$316

Westin St. John 3 Bdrm/ 3 Bath Thanksgiving Week

Cruz Bay villa

  • 4 bathrooms
  • sleeps 10

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

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Price per night from

$987

Eco Serendib Villa & Spa - Luxury in Harmony with Nature

Cruz Bay villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 16

“Want for nothing -- and I mean nothing!” From the incredibly spacious and luxurious suites to the world class swimming pool to the on-site massage therapy sanctuaries to the full on-site gym with sauna, steam and soaking tub to the Epicurean theater to the on-site fruit, vegetable and herb garden to the meeting facilities and beyond -- all served up astride one of the most amazing views on St. John -- it's not only possible to spend several weeks here without the need to leave the grounds, it's actually desirable. Still, see the parks and head downtown for some amazing cuisine just to round out the stay. And enjoy one of the best support staffs on the island. Well done, all!

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

2 of 3 filters match

Price per night from

$3,436

Coconuts: Panoramic ocean views and sunsets

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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

2 of 3 filters match

Price per night from

$458

Studio Condo on Bolongo Bay

Bolongo Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

2 of 3 filters match

Price per night from

$190

Beach Bungalow

Christiansted apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$138

Studio Condo on the Waterfront at Bolongo Bay

Bolongo Bay condo

  • 1 bathroom
  • sleeps 2

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

2 of 3 filters match

Price per night from

$190

Second Floor Condo Directly on Sugar Beach

Christiansted condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

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

2 of 3 filters match

Price per night from

$229

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

2 of 3 filters match

Price per night from

$1,176

Driftwood on Crystal Clear Waters of Sapphire Beach!!

Smith Bay condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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

2 of 3 filters match

Price per night from

$269

Sapphire Beach side condo

Virgin Islands National Park condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$401

The Hideaway Hull Bay Cottage 2

Charlotte Amalie cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$572

The Hideaway Hull Bay Cottage 8

Charlotte Amalie cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$744

The Hideaway Hull Bay Cottage 6

Charlotte Amalie cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

2 of 3 filters match

Price per night from

$400

Rare Brand New Luxury 2BR Beachfront 2FL condo

East End apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$738

An Enchanting Caribbean Interlude affordable 4 you

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$167

Two Bedroom Villa at Sapphire Beach Resort

St Thomas East villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$458

“Week in paradise!” Our stay in the Little Palm Suite was wonderful! The suite was exactly as described in the posting and was accurately displayed in the photos. The view of Fish Bay off the deck was amazing! It was a beautiful sight to look forward to every morning. The suite was very clean and well-stocked with necessities. Both the inside and outside (grounds) at the suite were extremely well-maintained. We appreciated having beach towels and beach chairs provided for us to use for our daily trip(s) to the beaches. Michael was a wonderful host! The information he provided to prior to our trip was extremely helpful as we made our plans. He was so helpful to us during our stay as well with directions and with restaurant and beach recommendations. We enjoyed all of the restaurants that he recommended. Our personal favorites were the Sun Dog Cafe for breakfast/lunch and the Lime Inn and Fish Trap for dinner. We loved being able to eat every meal outside for an entire week! The ice cream shop at the end of Mongoose Junction was also a favorite. Our favorite north side beaches were Hawksnest (smaller and not very busy) and Trunk Bay (busier, but so beautiful and picturesque). We really enjoyed the laid-back pace on St. John and had a truly relaxing week. I really enjoyed staying a little bit outside of Cruz Bay and the location in Fish Bay was perfect. We would highly recommend Little Palm Suite! Thank you, Michael for sharing your home with us and for helping us enjoy our week in paradise!

Responds fast! avg. 1 hour 21 minutes

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

2 of 3 filters match

Price per night from

$327

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

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$2,295

“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.

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

2 of 3 filters match

Price per night from

$263

Marriott Frenchman's Cove 2/2 Gorgeous, Spacious, Villa - 2 Units available -4BR

Charlotte Amalie hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$558

Comfortable Cruz Bay Condo with Awesome Views and Convenient Walk

Cruz Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

2 of 3 filters match

Price per night from

$402

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

2 of 3 filters match

Price per night from

$275

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

2 of 3 filters match

Price per night from

$1,066

Your Perfect Beachfront Condo in Paradise - Sapphire Beach

Smith Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$275

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

2 of 3 filters match

Price per night from

$190

Two bedroom beachfront condo at Sapphire Beach

East End apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Excellent location!” We enjoyed our stay at Linda's place. The two level apartment is located right at the beach with a million dollar view. The apartment is quite spacious and accommodated our family of 4 very comfortably. The apartment had everything we needed for a comfortable stay and even had some snorkeling pieces and beach chairs. The kitches is equipped and fully functioning and we cooked a couple of times. My family loves st Thomas and we would love to come back! We highly recommend the apartment!

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

2 of 3 filters match

Price per night from

$454

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

2 of 3 filters match

Price per night from

$190

Beachfront Villa with a Down Island View-Priceless

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

“Well maintained, quality furnished condo with very helpful owner.” We have stayed in several different condos @ Sapphire Beach in several different price ranges. John's is by far the best maintained despite it not being the highest end priced. It also has a great bar/eating area on the lower deck. Renting from John is like renting from a friend or family member. There were no surprises from John other than I had over paid without realizing & he contacted me to let me know he was sending me a check.

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

2 of 3 filters match

Price per night from

$402

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.

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

2 of 3 filters match

Price per night from

$316

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