Road Town Rentals

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61 Houses

AnaCapri Estate

Road Town villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 12

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$655

Great rentals within 20 miles that match your search

Prettyview Villa

Sage Mountain National Park villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$315

Escape Winter at Westin St. John Resort, USVI

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$2,004

An Enchanting Caribbean Interlude affordable 4 you

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$166

Brand New - Sleek, Ultra Modern, Cottage for Two

Cruz Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$361

Bellamare at Mahoe Bay, Virgin Gorda

Spanish Town villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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$802

Serenity - Private Caribbean Style Pool Villa

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$258

Tamarind - Virgin Gorda Overlooking North Sound

Virgin Gorda villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,718

Beauty, Comfort, Value! Your Home in the Caribbean

St Thomas East townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$542

Suite 8C - Gallows Point Resort Oceanfront Upper Level

Cruz Bay villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$682

Villa Nautilus, East End, St. Thomas

East End condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 20 minutes

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Price per night from

$430

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

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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$315

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

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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$542

'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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Price per night from

$4,294

Great Expectations St. John vacation rental villa

Cruz Bay villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 20

“Re-impressed” I spent time at Great Expectations for one month, each, in 2010 and 2011 with family and friends. We had an amazing time. Its really a beautiful property, and its true, everything you need, they supply. in 2013 we tried a new place on a different island. What a mistake. the place did not live up to its on line review or pics. This year we went back to G E and were even more pleased (which none of us thought was possible)! The new pool is amazing. Infinity in style, large, with amazing views. Can't wait for next year!

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Price per night from

$1,465

Villa ValMarc, Mahoe Bay,Virgin Gorda, BVI villa 4 bdrm 4 bath with pool

Virgin Gorda villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$638

LOBLOLLY VILLA VIRGIN GORDA BVI

Virgin Gorda villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$959

Villa Towanda, Belmont Estates Tortola

West End villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$561

“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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Price per night from

$1,145

CARIBBEAN Beachfront Condo,Georgeous Views, Elysian Beach Resort

East End apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“I really cannot imagine any place more enjoyable for us” We recently stayed at Nancy's condos for the first three days of our 10 day stay. All I can say is that I wished we had stayed there the entire time! We headed to a resort and even my 12 and 7 year old boys (who had plenty to keep them busy at the resort) kept saying that they wished we were back at "Nancy's condos." The beach and the water were simply amazing. No having to fight for pool or beach chairs. I was pleasantly surprised at how well appointed the kitchen was with excellent cookware and general supplies with many guests "paying it forward," with items they left. We did the same. There is really nothing negative I can say at all, as evidenced by the fact that we already booked for next year immediately upon arriving home!

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Price per night from

$344

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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Price per night from

$457

BEAUTIFUL Beachfront Condo, Elysian Beach Resort, East End

East End apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

“Perfect location in St. Thomas” I had the pleasure of staying at Nancy's condo along with my wife, our 2 children, and another couple, 6 of us in total. The condo was the perfect size for all of us, and having a kitchen made preparing for excursions (having a nice breakfast, and preparing picnic lunches) a breeze. There is also laundry facilities in the condo, and with the breeze coming off the water we almost never needed to use the AC. The Location on Cowpet bay was very close to the ferry to St. Johns, restaurants, nightlife and shopping. Although Redhook is only about a mile away, it was not easily walkable due to the narrow streets, so you will want to get a taxi to go into town. My daughter loved playing in the pool, there were many other families around so she always had somebody to play with. My wife and I enjoyed walking on the beach, and the restaurant (Caribbean Fish Market) has amazing sea food, and a wonderful ambiance. At night I loved the ability to sit on the patio, listen to the waves and relax before preparing for another exciting day.

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$344

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

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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$441

Comfortable Cruz Bay Condo with Awesome Views and Convenient Walk

Cruz Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$401

Breathtaking Views from Sapphire Village II

Red Hook condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 13 minutes

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$184

“Perfect getaway with a spectacular view” We absolutely loved our stay at Blue Palm Villa. The facilities are excellent and the location is beyond description! Waking up every morning to see the incredible blue of Coral Bay encircled by lush mountains was unbelievable. The Villa not only has an unbelievable view, but the facilities themselves are beautiful. The pictures do not do it justice. The pool is gorgeous. The amenities are modern and aesthetically wonderful. The gardens around the villa are exquisite. Honestly, it was hard to pull ourselves away from the Villa to go visit other places. It was so nice to relax in that little paradise. But the Villa is also close to many delicious restaurants and awesome beaches. Overall, we do not think there is a better way to see the Virgin Islands than by staying at Blue Palm Villa! We recommend it wholeheartedly!

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$457

CASA DEL PALMAS - Perfectly Private Caribbean Comfort

Virgin Islands National Park villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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$790

A Place in the Sun

Coral Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$401

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$686

NEWLY RENOVATED: Beach Dreams a Luxury Beach Front Villa in Mahoe Bay

Nail Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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$1,598

Westin St. Johns, 2 Bedroom Bay Vista Villa Loft, April 21-28

Cruz Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,015

Coral Cove | Oceanfront Retreat

Coral Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,718

The Garden of Eden Cottage Collection - Caribbean

Virgin Islands National Park cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$400

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