Road Town Rentals

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323 Houses

Blackbeard's Hideaway Tortola BritishVirginIslands

Road Town house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$1,038

The Best Caribbean sailing vacations for the best price; No Bad Days Sailing

Road Town yacht

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,248

Ocean Beach Suites and Villas Bedroom 2

Road Town villa

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 5

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

105 ft Luxury Trimaran

Road Town yacht

10 bedrooms / 10 bathrooms / sleeps 20

Price per night from

$486

Ocean Beach Suites and Villas Bedroom 9

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

AnaCapri Estate

Road Town villa

4 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$650

Ocean Beach Suites and Villas Bedroom 10

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 12

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 3

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 7

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 11

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 6

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 8

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 4

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Ocean Beach Suites and Villas Bedroom 1

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Oca Maloca Tortola Sunny 1-bedroom air-conditioned Apartment

Road Town apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$215

Catamaran Lagoon 42

Road Town yacht

5 bedrooms / 4 bathrooms / sleeps 9

Price per night from

$1,637

Fort Hill's Hidden Secret

Road Town apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$154

Modern 3-bedroom villa with pool

Road Town villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,019

Great rentals within 20 miles that match your search

Charming luxury villa/ Super views/ Sleeps 2-8

St. John house

4 bedrooms / 5 bathrooms / sleeps 8

“My happy place” A beautiful and well maintained villa with a breathtaking view of Coral Bay and the Francis Drake channel. Not the hustle and bustle of Cruz Bay but still close to great restaurants in Coral Bay. Separate living and sleeping buildings isa great idea.

Responds fast! avg. 3 hours 29 minutes

Price per night from

$537

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.

Price per night from

$398

Spectacular Sunsets & Ocean Views Remodeled Villa

Cruz Bay villa

3 bedrooms / 4 bathrooms / sleeps 10

“Great location, beautiful view, all the amenities you need!” We just returned from our honeymoon in St. John and Heavenly Villas was perfect for our time on the island, and the views from the deck are incredible. The villa is the perfect size for a couple, or a very small group, and had everything we needed. We had breakfast and coffee on the deck each morning, and spent most evenings there watching the sunset before going out for dinner. We also took advantage of the beach chairs, snorkel gear, and cooler and didn't have to worry about buying anything aside from food and drinks while we were down there. Josh, the property manager, was very helpful, and everything went smoothly when we arrived to check in, meeting us at the ferry dock, and he also helped us get in touch with our jeep rental company. He also had the villa provisioned for us with food and drinks we had requested. The villa is located a short 2 minute drive from downtown Cruz Bay, and a short drive to all the beautiful beaches, so it made it easy for us to get anywhere on the island. Scott, the owner, was very helpful and super responsive throughout the booking process, and made everything super easy and stress-free, which was much appreciated. We will definitely be returning and recommending Heavenly Villas to friends!

Price per night from

$909

Captain's View - Best Views In Town, Day or Night

Cruz Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

“The best view of paradise!!” Captain's View is certainly a delight of St. John's. I visited there in the summer of 2011 and the accommodations were perfect! Plenty of room for listening to island tunes and enjoying lunch or dinner at the villa. Capt's View is close enough to town to walk down and enjoy all the fine dining and night life that St. John's has to offer without having to rent a car. The aC kept me cool at night on the evenings it was needed and the bed was very comfortable. All is all a great place to stay while in St. John and would absolutely stay there again!

Price per night from

$273

Coconuts: Panoramic ocean views and sunsets

Cruz Bay villa

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$454

Satinwood: private, breezy eco-villa with an amazing View

Coral Bay villa

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$375

Harbor View - Big Views & Sunsets In Cruz Bay

Cruz Bay apartment

1 bedroom / 1 bathroom / sleeps 2

“Best view in the islands!” For several years now, my favorite form of relaxation at Harbor View is kicking back in the evening and watching the setting sun slide down behind St. Thomas ...while sipping away at something with a lime in it. Great location. Just a couple minute walk downhill to the ferry dock, restaurants, the Dolphin grocery and easy-going night life in Cruz Bay. Super staff at St. John Properties.

Price per night from

$199

Sweet Wind Villa overlooking Hurricane Hole

Coral Bay house

3 bedrooms / 3 bathrooms / sleeps 8

“Incredible views, wonderful stay” My husband and I booked this rental last minute after finding an incredibly low airfare to St John, and weren't quite sure what to expect. What a amazing find! Sweet Winds is just outside of Coral Bay, overlooking Hurricane Hole, and words can't do justice to the view you'll have from this property. Even the pictures fall short of showing the incredible view we enjoyed from every room in the villa. Sweet Winds is nicely appointed, impeccably clean, and friendly to groups and families as each of the three bedrooms has a bathroom ensuite. Nina Hahler, the owner, lives next door where she paints and tends to her garden (which is also lovely with bougainvillea and gardenia in full bloom). Nina was very accommodating without being intrusive in any way, and gave us a ton of great tips on the best snorkeling spots and restaurants on the East side of the island. She also has kayaks, beach towels and chairs, and all sorts of beach items for kids available to her renters. If you want to break from the packs of tourists, and you don't require the amenities of a big resort, Sweet Winds and the Coral Bay area can't be beat, in our opinion. We highly highly recommend this rental and look forward to coming back with family next year.

Price per night from

$567

Ocean Front Mediterranean Villa with Private Dock

West End villa

4 bedrooms / 4 bathrooms / sleeps 8

“As usual, Steele Point Estates (Gestalt) was an incredible vacat” First of all, Irina was most helpful and kind in helping us make our plans. Previously, we have made our reservations through "agencies". Dealing directly with property owner was a tremendous improvement for me. Irina was cheerful, prompt and fun to work with. We have stayed in Gestalt one time previously. The charm is still there! The property has been maintained well and we found absolutely no issues with our accommodations. The views are phenomenal. It is also nice to be isolated yet so close to West End and the scrumptious Jolly Roger for meals and entertainment. We have been spoiled by enjoying Steele Point on previous visits. Irina arranged a tour of Blackbeards this trip and all I can say is, "Oh my gosh!" Now I know what heaven will be like! I should note, we are renting all three villas on the property in May 2011 for our daughters wedding. A special day in a special place for our family. Thanks Irina.

Price per night from

$1,363

Westin St John 3BR Pool Villa: 2022 Summer, Christmas & New Years

Cruz Bay villa

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,784

Poi Pu St John Villa - great views & total privacy

Cruz Bay house

3 bedrooms / 2 bathrooms / sleeps 6

“Lifetime Memories” My family and friends rented Poi Pu for a week this past June. We had an amazing time. We loved the rock double shower. Several nights we cooked dinner and everyone ate out on the deck what a beautiful experience. It was also located close to some of the most beautiful beaches ever. The house was very clean, great amenities, cozy, and we were comfortable. If we needed anything we could call the property management and they were prompt to offer advice or their services if needed. It was also the little things that made our stay like the beach accessories that we were able to use instead of having to rent them daily. Those costs could have added up quickly. A beautiful home with a beautiful view. We can't wait to return. Also we were traveling with our 10 month old daughter. She took her very first steps at Poi Pu. We made lasting memories for our family.

Price per night from

$392

Mooncottage: Most Romantic St. John Petite Luxury Villa in peaceful Coral Bay

Coral Bay villa

2 bedrooms / 4 bathrooms / sleeps 4

“The PERFECT Honeymoon” There truly are not enough positive ways to sum up our 10 nights at Mooncottage. From the very beginning, Brian was a tremendous help as we were researching locations to spend our honeymoon. He made sure to provide us any local "tips" we would need so that there were no surprises along the way. It's hard to trust all of the incredible review online (can Mooncottage really be THAT amazing?!) - but they are all true! The home is beautiful - pictures don't even begin to do justice to the stunning views - and the amount of space was perfect for the 2 of us. We wanted a honeymoon location where we could just relax and never feel like we were on a schedule, and Mooncottage provided the perfect accommodations for that. We spent mornings and nights just taking in all of the scenery below us, and spent our days visiting different beaches, restaurants, and bars each day. We came to embrace the (very bumpy) drive up/down the road to the house, and it's really kind of fun once you get used to it! The privacy is well worth the short extra drive -- and we loved being in Coral Bay on the less populated end of the island. We've already passed the name of the home along to a few of our friends who are looking for a special getaway -- and we can't wait to go back ourselves!

Price per night from

$811

Quart-A-Nancy Point, Cooper Island, BVI

Cooper Island house

3 bedrooms / 2 bathrooms / sleeps 8

“We want to return!” We had 12 glorious days at Quart-A-Nancy Point. What a fabulous spot. This was truly the most relaxing vacation we have ever taken. We have sailed to Cooper Island for the last 10 years, and decided to rent a house this time. The best decision ever! The views are spectacular, the hermit crabs very entertaining, snorkeling and kayaking for exercise, and enjoying reading on the beautiful outdoor living room porch (love the hammock!). Everything about this home is ideal. We'll be back. Thank you to Fred and Candia for allowing us to rent your paradise.

Price per night from

$454

Bigger Splash, Private Villa-The Baths w/Concierge

The Baths villa

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$454

Drake's View: Voted Best View in the Caribbean

Coral Bay villa

4 bedrooms / 5 bathrooms / sleeps 8

“Incredible, Gorgeous View!” Our family stayed at Drake's View June 13th - July 1st, 2013. We needed a villa with 4 bedrooms. It was the "view" from Drake's View that won it over! Wow, what an incredible, gorgeous view of Coral Bay & the Bvi's! The Kit, LR & DR areas are all on the upper level & flow into each other so you always feel a part of what's going on & with several seating areas, you can have your space too! There are 3 bdrms on the lower level in the main house & a private 1 bdrm cottage. All are equal with a/C & kg beds with 1 in the main house having the option to be made into twins. Entry to 1 of the bedrooms in the main house is off the porch so you have to walk outside to get to it. The kit was well equipped & used & so was the BBQ grill. We ate about ½ our meals at the villa while enjoying the view! We used the pool & hot tub just about every day after coming back from the beach. The pool gets good sun until mid-day & is larger than most. It has a gradual slope to deep end & has a built-in bench all along the length of the pool. You can sit there or in the hot tub & enjoy a nice view. The villa has plenty of outdoor seating space, sun & shade, to gather as a group or find a quiet space to yourself! Even though you could see a couple villas on other hillsides, they were far enough away & situated to where we felt complete privacy! In the evenings we enjoyed listening to music on the stereo...speakers worked great...while playing Scrabble & card games. The villa only has 1 TV...no big deal because we don't typically watch TV. The large capacity W/D are on the lower level & conveniently located near the pool's ½ bath for wet suits & towels & near the bdrms. They were used often during our 18 night stay & worked great! We loved Drake's View & the Bordeaux Mtn location...the view, close to Maho Bay & close to our family's favorite Coral Bay restaurant...Shipwreck Landing!

Price per night from

$903

'Billion$ View' New Deluxe 2FL Beachfront Villa

East End apartment

1 bedroom / 2 bathrooms / sleeps 7

Price per night from

$649

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!

Price per night from

$449

Your Perfect Beachfront Condo in Paradise #2

Smith Bay condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$244

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