Flag Hill, Saint Thomas Rentals

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Great rentals within 20 miles that match your search

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.

Match: Kettle Horse riding

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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

Match: Kettle Horse riding

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Price per night from

$160

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.

Match: Kettle Horse riding

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Price per night from

$913

Studio Condo on the Waterfront at Bolongo Bay

Bolongo Bay condo

  • 1 bathroom
  • sleeps 2

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Price per night from

$190

Studio Condo on Bolongo Bay

Bolongo Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$190

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

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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

Responds fast! avg. 16 minutes

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Price per night from

$1,279

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

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

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

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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: Kettle 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

Match: Kettle Horse riding

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Price per night from

$287

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

Bananakeet

Coral Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$488

The Dancing Orchid B&B Villa, Garden Room

Charlotte Amalie b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Kettle Horse riding

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Price per night from

$287

Jewel's View

Coral Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$293

Ocean Garden- Just For Two -SALE NOW

Cruz Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 17 minutes

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Price per night from

$431

Villa Madeline | Cozy Hillside Villa

Coral Bay villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

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Price per night from

$454

Island Horizons | Million Dollar View

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Kettle Horse riding

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Price per night from

$700

Mayan Sky

Coral Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$620

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

Coral Bay cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Kettle Horse riding

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Price per night from

$316

Beauty, Comfort, Value! Your Home in the Caribbean

St Thomas East townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Kettle Horse riding

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Price per night from

$543

Villa Ventosa

Coral Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Kettle Horse riding

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Price per night from

$568

Spring Specials! Million Dollar Views! 1BR/1BA - Free WiFi Point Pleasant

Smith Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$183

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