Flag Hill, Saint Thomas Rentals

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Great rentals within 20 miles that match your search

Playcation in Paradise work away from the office with blue ocean & cool breezes.

Virgin Islands National Park villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$573

Responds fast! avg. 16 minutes

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$1,278

Villa L'Agave

Cruz Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$660

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

Cruz Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$803

Romantic Beachfront Villa

Virgin Islands National Park house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$331

2017 Fountaine Pajot Helia 44 Catamaran

Water Island yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$918

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

Virgin Islands National Park villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$737

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$2,495

Two Tickets To Paradise Cottage, Pool & Tiki Bar

Charlotte Amalie cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$316

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

Coral Cove | Oceanfront Retreat

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,717

Villa Circe

Coral Bay villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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$1,105

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$207

Retreat Along the Coral Bay Shore of St. John

Coral Bay villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$630

Bungalow Blue | Private Island Home

Coral Bay bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$287

Villa Madeline | Cozy Hillside Villa

Coral Bay villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

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$453

Escape Winter at Westin St. John Resort, USVI

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$2,004

Brand New - Sleek, Ultra Modern, Cottage for Two

Cruz Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$361

Newly refurbished Longview Villa with Heated 40ft pool and stunning views

West End villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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$572

Lidskjalf at Annaberg - Walk to Francis Bay Beach!

Virgin Islands National Park villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$500

VILLA AMOUR ,Romantic , Art Lovers Paradise ,

North Side villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Perfect!” Title says it all. PERFECT island vacation home. Better than advertised. We had 7 adults and 2 infants and had plenty of room to relax. Pool, views are incredible. Convenient enough to travel the rest of the island (although you may ask yourself "why leave!". Rick and Steve are great hosts, responsive to any questions you might have. Recommend renting SUV and also that you give yourself plenty of time at the airport when departing. Highly recommend Villa Amour and would definitely return!

Responds fast! avg. 1 hour 0 minutes

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$802

Drake's View: Voted Best View in the Caribbean

Coral Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Awesome family vacation” This was our second visit to Drakes View and we again enjoyed everything the property has to offer...views, a well equpped kitchen, hot tub and ample space for our 3 generations to be together for Thanksgiving week. In spite of an abnormally rainy week, we made the best of our beach time and enjoyed the views from the villa when we were forced inside. We lovedbeing able to stay overlooking Coral Bay,our favorite side of St. Johns. We explored several new beaches and snorkeling apots. Thanks to the Roberts family and their wonderful concierge team of Dorothy and Fernando.

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$911

Spectacular Sunsets & Ocean Views Remodeled Villa

Cruz Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

“Awesome View” We recently stayed here and it was perfect. The villa was very clean and well maintained. They have everything you need there (beach towels, cooler, chairs, pots, pans, appliances, wifi). There is a/c in both bedrooms and it cools the place off very nice at night. It has a large glass door that opens up to the deck where you have one of the best views of the island. The view is simply breath-taking. Relaxing in the evening on the deck with the view was one of my highlights of the vacation. The property is about 5 minutes from town. Their property management company met us at ferry dock and gave us tour of the town and villa. This is an awesome property and wouldn't hesitate to stay there again. I don't have one complaint about this villa. Highly recommended!

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Price per night from

$1,031

Sale! $180/night Dec 18-23, 2023 Last minute cancellation.

Coral Bay cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$315

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!

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$453

'Spirit On The Water' Playful, Private, Peaceful Cliffside Villa

East End villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 20

“The Spirit On The Water was simply magical!” A group of us were visiting the Usvi on vacation for the first time and we were there for 4 days or so. The Spirit On The Water was a fantastic choice not only for a location to call "home" for the time we were there but also for the warmth and incredible hospitality of the owners!!! Both Ed and June were extremely welcoming from the moment that we arrived, they were always eager to lend a helping hand, to suggest a place to visit and to provide directions whenever we needed it. The house was impeccably clean and organized!! The location and the view are absolutely breathtaking... in fact, I think I could've spent the entire vacation just basking in the sun on the incredible infinity pool and deck that they have there!!! I would absolutely highly recommend staying there and making friends with Ed and June... they're great people, and they provide a great place with great services above and beyond anything that you might expect in a five start hotel :)

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$4,294

Villa in Paradise w/Private Pool! Walk to beach!

East End villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect vacation in St Thomas” Spent end of January, beginning of February at Laverne's place in Pavilions and Pools. Everything was perfect. The condo was clean and very comfortable. It was great having your own pool just outside the door. The property was quiet and peaceful and We really enjoyed our stay here. The girls at the front desk, the maintenance people, everyone at the facility were extremely friendly and very responsive to any of our requests. Vicars, the on site restaurant was excellent. If you go there, order the steamed mussels appetizer. It was fabulous. Every morning there are bagels, muffins, cereal, juice and coffee if you don't feel like making your own breakfast. We also used the grill to cook a few steaks during our stay. The only slight drawback was the walk to the beach, it was approximately 5 minutes long, but seemed worse if you are carrying beach chairs, towels, etc. However, once you get to the beach the walk was worth it. Sapphire Beach is a really nice beach, with changing and rest room facilities and a vendor (Banana Bar) that serves sandwiches, drinks etc. From the beach it's a short walk to the Marina where you can see the Tarpon & Barracudas swimming in the clear waters. Red hook was a great area for restaurants or a trip to St Johns and it's only a few minutes away. We did not have a car and didn't need one. The Safari taxis stop right in front of the hotel, and regular taxis are not that expensive and easy to find. Don't miss the fiddle player at Latitude 18 on the other side of the Red Hook Harbor.

Responds fast! avg. 3 hours 24 minutes

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$229

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.

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Price per night from

$498

Villa Mirino, Ocean front, Intimate East End Home

East End villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

“Beyond Expectations” I would not stay anywhere else on the island. The house itself is in immaculate condition with huge sliding glass doors in every room allowing for amazing views of the Caribbean from every room. I loved waking up to the breathtaking sunrise every morning and the house's beautiful décor encourages complete relaxation. Whether watching TV, playing Xbox/Playstation or listening to music via the surround sound system, it felt like our every whim was met. The kitchen is stocked with gourmet appliances and cookware which made my ability to create fantastic meals for us easy and fun. When we tired of laying by the pool, the beach was less than a mile away and the Red Hook night life was right down the street. This villa is truly one of the premier locations on the island. I cannot wait for the next trip back

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$859

Limin'House Luxury 4 Bedroom Caribbean Villa Fully updated and renovated!

West End villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Loved this house!” The layout of Limin house was perfect, lots of private areas to chill and a lovely open air veranda to come together. The attention to detail was noted from the great margarita and ice machines to flashlights in all rooms. Loved to be able to make coffee in the bedroom and the sit on the balcony early in the morning and watch the scene unfold below. We loved the huge outside BBQ and took advantage of having half our dinners in. Pool was fantastic with great views and gardens all around the property were lovely. Outdoor showers were great anytime of day! We had issues with our main fridge, but Deb (Manager) was very attentive and helpful and brought us ice if we needed. The freezer worked and there was a bar fridge by the pool so we all got lots of exercise. We understand things go wrong and it is hard to get parts etc on the island. The house more than made up for this and we didn't really care too much. we hope to be back in 2 years and would definitely stay at Limin House.

Responds fast! avg. 38 minutes

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$819

“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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$263

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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$1,145

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

Charlotte Amalie hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$557

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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$602

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

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$457

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!

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$573

Stunning Ocean Views Villa Catalina

Cruz Bay villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

“Fabulous St. John Get away!” My husband, 16 year old daughter, her friend, and myself vacationed at Villa Catalina from June 5-June 12, 2012. From being met at the ferry dock, Myrtle took care of every need we had. The home was incredible and very comfortable for our stay. The kitchen is well stocked, the bedrooms very comfortable, and the beach towels, chairs, and ice chest are a definite plus! Villa Catalina is just minutes from Cruz Bay and very convenient to beaches, restaurants, shops, etc. The deck and pool area are great in the mornings and evenings, and the grill was a must have as we cooked plenty meals out in the evenings. There was a grocery on our way back in to the villa which had a great meat selection as well as wines. The thing I think I would say i liked least is the third bedroom being accessed from outside and down stairs. Though this was not a problem for the 4 of us it was just a little inconvenient. What we loved most was the peace and quiet of the area, the great breezes blowing across the decks in the evenings. This was a wonderful place to stay and we cant wait to return. A definite slice of heaven!

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$516

⛵ Sail charter Catamaran NEW! Caribbean BVI's

Brewers Bay yacht

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

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Price per night from

$2,299

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