Flag Hill, Saint Thomas Rentals

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Great rentals within 20 miles that match your search

Swogjan's Dragon 7A Carolina

Coral Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$401

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.

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Price per night from

$688

“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

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Price per night from

$160

Studio Condo on the Waterfront at Bolongo Bay

Bolongo Bay condo

  • 1 bathroom
  • sleeps 2

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Price per night from

$190

White Seagull -Just For Two- POOL SALE NOW

Cruz Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Spectacular View and Wonderful Hospitality!” We just returned from a wonderful 8-day stay in the White Seagull, at "Just For Two" on St. John. This was a return trip for us, having stayed there, last May, as well. We rarely return to the same location, preferring to seek new adventures. This was a rare exception and a testimony to the wonder of this place - both St. John and Jacqueline's hospitality. The room is wonderfully decorated and comfortable, with 270 degree views of the Caribbean. We overlook Great Cruz Bay and Chocolate Hole from our windows, with views of St. Thomas from the Sky Lounge. It's amazing to wake to the early sunrise and see the ocean view, by simply sitting up in the bed. We took wonderful photos of the sunsets from the rooftop Sky Lounge and our location near the top of a mountain, overlooking the island. Jacqueline readily gave us access to her private patio, as well, providing wonderful views of Great Cruz Bay and relaxing surroundings to talk or simply play cards, in paradise! The room is well decorated with antiques and personal items. There was good Wi-Fi access and a TV with limited channels, but we rarely used them. A fireplace was available, but we can't imagine using it, except in the dead of "winter"! The room offers a small kitchenette, suitable for simple breakfasts or lunch preparation. There is access to a grill in the courtyard, as well. However, we mostly enjoyed the wonderful food at all the restaurants on the island. You definitely need to rent a car and we have had great experience with Courtesy Rental. The roads are steep, somewhat narrow and you get the challenge of driving on the left side. It's a challenge, but quickly becomes comfortable. The roads Just For Two are steep, but enjoyable. There is a back way that allows a "less steep" option, if it is rainy. Next year is our 25th anniversary and we are planning to return, yet again. It's hard to argue with perfection - especially for a milestone date.

Responds fast! avg. 3 hours 17 minutes

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Price per night from

$603

Our place in St Thomas 1BR Suite

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 44 minutes

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Price per night from

$194

Luxury 5 Bedroom Villa Overlooking Magens Bay

Peterborg villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$2,175

Sapphire Beach~20 steps off patio to ocean~Amazing

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$287

Casa Azul at Crystal Cove, St. Thomas

Red Hook condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$442

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

$5,739

Coral Rays - Stunning Island Style Headquarters

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

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Price per night from

$861

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Price per night from

$458

Coral Cove | Oceanfront Retreat

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,722

Luxury 4/4 Villa with Pool, Privacy, 180° Ocean Views! All on one level

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$967

Dancing Dolphins

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

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Price per night from

$804

Responds fast! avg. 16 minutes

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Price per night from

$1,279

Villa Circe

Coral Bay villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,108

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

Villa at the Edge of the World

Charlotte Amalie condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$402

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

$270

Stunning Ocean View Spacious Villa Private Pool - Cruz Bay St John USVI

Cruz Bay villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,492

Serenity - Private Caribbean Style Pool Villa

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$259

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.

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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.

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Price per night from

$263

Rare Brand New Luxury 2BR Beachfront 2FL condo

East End apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$738

Easy Breezes - Family Luxury & Romantic Getaways

Coral Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$568

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Price per night from

$275

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

Ada by the Sea

Coral Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$695

The Dancing Orchid Villa

Charlotte Amalie villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Freezer Horse riding

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Price per night from

$861

The Dancing Orchid B&B Villa, Ocean Room

Charlotte Amalie b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Freezer Horse riding

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Price per night from

$287

The Dancing Orchid B&B Villa, Jungle Room

Charlotte Amalie b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$287

Just For 2- Tropical Orchid Hot/Tub/SPA ~ SALE NOW

Cruz Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“spectacular views with affordable villa” My husband and I had wonderful time in the Tropical Garden villa we rented from Jacqueline. This is not the typical rental where you pick up your key and you're on your own. Jacqueline met us after we arrived on the ferry and rented our jeep to follow her up to the villa. Her home is part of the property to which her four rental villas are connected, and everything is well kept. She was so friendly and helpful providing advice and making sure we had everything we needed. By the end of the week, we had become friends. The Tropical Garden villa has a spectacular view overlooking Great Cruz Bay, Chocolate Hole, and Heart Bay, which you can enjoy from the deck, living room and bedroom. It is on the lower level and has a secluded feeling. It has a full kitchen and a gas grill in the garden. There is a hot tub with a view that you can find at the end of the path through the tropical garden. The beach chairs and cooler that were provided were very much appreciated during our many outings to different gorgeous beaches every day. We have fond memories of waking up and seeing that incredible view and enjoying our breakfast on the deck. We also enjoyed staying in the White Seagull villa for the latter part of the trip when it was available. We would stay in either one again. Jacqueline went above and beyond to make our stay extra special. We were sad to leave but very happy to have a new friend in St. John!

Responds fast! avg. 3 hours 17 minutes

Match: Freezer Horse riding

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Price per night from

$458

Beauty, Comfort, Value! Your Home in the Caribbean

Charlotte Amalie house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Magical Vacation” Thank You Gail & Curlson for allowing us to rent from you. The instant we got to your place, we felt like we were "home". The location of your property is perfect, a short drive to Red Hook and close to some gorgeous beaches. The villa included many "little" amenities such as beach towels, paper goods, hairdryers, that really made my packing job much easier! The kids had the best time swimming in the pool & hot tub and ask daily when we can go back! I think even breakfast tasted better because we were able to eat it every morning on the patio overlooking St. John and Sapphire Beach. Whenever we had a concern or question, you were a quick phone call or email away. And the place looked exactly as it does in your pictures. This was one of the best vacations our family has ever taken. Thank you from the bottom of my heart - Take Care!

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Price per night from

$543

Memory Daze

Coral Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$620

Villa Nesta

Coral Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$373

Bungalow Blue | Private Island Home

Coral Bay bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$287

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