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Trunk Bay Rentals

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125 Houses

KAYAKS! - POOL! - AND THE BEST BEACH ON TORTOLA! 3 BEDROOM PRIVATE VILLA WITH AC

Sage Mountain National Park villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$382

Coral Bay Eco Retreat:Tropical Living Off the Grid, Hike to Beach!

Coral Bay cottage

2 bedrooms / 2 bathrooms / sleeps 2

“Self-contained, off-the-grid mountaintop luxury with a view” Anyone who thinks living off the grid requires sacrifice of comfort clearly hasn't stayed here. Your water is provided by the rain. Your electricity is provided by the sun. A huge deck, cushy living spaces with beds in open air... windows? There aren't any. Shower? Outside. Yes, the toilets flush. And the view is a never-ending masterpiece of sea and sky. Complete privacy here on the mountain top. No neighbors.. except for an occasional island donkey. If you like quiet, romantic places, this is it. The stairs up are steep so if you can't climb, don't come here. But if you can climb stairs, you need to try this place, one of the cheapest luxuries on St. John. and one of the most powerful boosts for the soul one can imagine.

Price per night from

$204

Blackbeard's Hideaway Tortola BritishVirginIslands

Road Town house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$1,042

Chateau Margot

St. John villa

6 bedrooms / 6 bathrooms / sleeps 14

“Wonderful” Chateau Margot was perfect for a family celebration and holiday. The three seperate buildings gave privacy and comfort for the three different families on this trip. The terrace was perfect to enjoy the spectacular views and get together for breakfast and afternoon cocktails. The house is very well appointed, tastefully furnished and very quiet.

Price per night from

$852

Surfside Gardens - Spectacular Ocean Views, Steps Away from the Surf

Road Town villa

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 12 minutes

Price per night from

$343

Luxury 5 Bedroom Waterfront Villa

Virgin Gorda house

5 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$9,106

Harbour Heights - Beautiful 4 Bed Home - Sleeps 8 - Stunning Views - Pool

Road Town villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$398

Extasea Yacht Charters

Road Town yacht

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$2,938

This is The One!

Coral Bay cottage

1 bedroom / 1 bathroom / sleeps 3

“A great place to stay!” Engaging with Judy Kane right from the start was fantastic. Her sage advice on how best to prepare for our trip with hints as to where to shop, car rentals, ferries and what to expect once we arrived let us know we had landed with a winner. She is a delight; fun loving, outgoing and concerned without being overbearing. The cottage is charming, better in person than the photos on line. It's breathtaking to sit on the deck with mountains that surround you. Birds are everywhere. We spent quite a bit of time reading, enjoying the scenery. The house itself is well stocked with every kind of device you might wish for - TV, DVD player, internet connection, books, games and even iPod speakers. The amount of information Judy has accumulated - a mammoth loose leaf filled with news clippings and articles along with books published about the area - provided us with recommendations for activities to keep us delighted. Each day, we struck out to a different beach to discover new sea life and coral formations we never would have found on our own. Having a car is a must. Judy made that clear to me. We were concerned about driving on the left and the narrow roads. It isn't for the faint of heart, but if you drive slowly and ignore the locals who might honk at you, you will soon adapt. I felt like I was on a freeway by the time I drove in St. Thomas to get back to the airport. I can't wait to return next year. St. John never disappoints me and Lower Carolina makes it even more alluring.

Responds fast! avg. 2 hours 27 minutes

Price per night from

$229

Villa Towanda, Belmont Estates Tortola

West End villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 15 minutes

Price per night from

$809

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

$1,444

5 bedroom 5 Baths Villa Del Mar post hurricane renovation has been completed

Belmont villa

5 bedrooms / 5 bathrooms / sleeps 14

Responds fast! avg. 1 hour 54 minutes

Price per night from

$1,254

Total Relaxation in Cane Garden Bay - Cottage #1

Road Town cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 53 minutes

Price per night from

$241

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. 3 hours 9 minutes

Price per night from

$836

Mango Manor Guest House

Road Town guest house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 25 minutes

Price per night from

$572

"Happy Our" - Island vibe & terrific location,views, rates

Coral Bay house

3 bedrooms / 3 bathrooms / sleeps 6

“Outstanding location for a family vacation!” "Happy Our" is a happy and comfortable home with a colorful island décor and two spectacular views - Coral Bay Harbor and Hurricane Hole. Amazing sunrises are a perfect way to start the day, the changing colors of the Caribbean throughout the day, and moonrises and a sky full of stars in the evening are equally beautiful. The location is great - close to all the great restaurants in Coral Bay and only a few minutes scenic drive in either direction to the most amazing beaches. Loved the snorkeling - turtles, fish, rays, you name it! The house had everything we needed and it is was perfect for our memorable family vacation. Plenty of space for everyone in the "great room" and on the deck, but lots of bedroom privacy too. This house is clean and well maintained and the property manager, Tom, is wonderful. Hated to leave, but we'll be back!

Responds fast! avg. 2 hours 42 minutes

Price per night from

$252

Ocean Beach Suites and Villas Bedroom 2

Road Town villa

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$464

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

Coral Bay villa

2 bedrooms / 4 bathrooms / sleeps 4

“We didn't want to leave!” My husband and I stayed at Mooncottage for too short a time in april 2014. We loved it and will hope to go back one day. The layout of the cottage is perfect for a couple. Separate sleeping cottage allows for one to sleep-in undisturbed while the other makes coffee. The island/asian decor is very attractive and the house was fully equipped with everything we needed. But the very best feature is the view which is absolutely to die for. Once there, you will be happy to skip a day at the beach and just bask in the breezy air, taking an occasional dip in the tiny pool, positioned perfectly between the bedroom and the deck. The drive in is pretty hair-raising, but once you get the hang of the very steep and very rough roads (typical in Carol Bay and much of St. John) and the perilously steep driveway, you'll be so glad you made the journey!

Price per night from

$718

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

$1,368

Ocean Beach Suites and Villas Bedroom 5

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$464

Catamaran All Inclusive Crewed Charter BVI/USVI 4 cabins up to 8 guests

Road Town yacht

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 52 minutes

Price per night from

$1,487

Easy Breezes - Family Luxury & Romantic Getaways

Coral Bay villa

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$474

“Incredible return to Steele Point” Having stayed at Steele Point in the early 2000's, I was really looking forward to my return, as the house and property are like no other I have ever experienced. But my return was much greater than I expected - the house, on a peninsula at the end of the island of Tortola - always had the most majestic views and the feeling that you were part of nature. But since I was there, it had been remodeled and had become exquisitely plush and more comfortable than ever before (including a brand new master bedroom suite with a view that dreams are made of). Great attention to detail and comfort was evident everywhere, and the staff was extremely gracious in every regard. It is impossible to name everything I enjoyed about my stay - but it was the most fantastic vacation experience I have had in a long time. The house is its own resort and every thing we wanted to do - from snorkeling in crystal blue waters, to fine dining with a view of 12 islands at sunset, to reading in a number of stone outcroppings or hammocks overlooking the sea, to relaxing by the pool, to even sleeping in the most comfortable beds and linens - it was all available without leaving the property. I can't say enough about how much I enjoyed my stay. My only regret was having to leave and I am already working feverishly to plan to return again next year !! I highly recommend Steele Point - I truly believe it is a magical place and the experience of a lifetime !

Price per night from

$2,507

Breezy Home with Views of Coral Bay and the Caribbean Sea!

Cruz Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$255

Price per night from

$833

The Pink House

Jost Van Dyke house

8 bedrooms / 8 bathrooms / sleeps 22

“Pink Paridise” We absolutely loved our vacation here. The house is beautiful & well equipped. The sunsets are phenominal from the porch! We had 6 adult family members & there was plenty of space for privacy, as well as plenty of room for gatherings for dinners, etc. Frankie is an excellent contact for whatever you might need & is very resposive to your needs. A short walk down the beach delivers you to great beach bars & resturants. The beach is secluded with rarely anyone there. We even had a beach wedding right in front of the house! We highly recommend the "pink house"!!

Price per night from

$755

The Retreat - Stunning Secluded Oceanfront Villa

St. John villa

2 bedrooms / 2 bathrooms / sleeps 10

“Even better than expected” This villa was what I expected, except even more amazing. To begin with it is in excellent shape, and was remarkably clean on our arrival, and I am someone who is critical about those things in particular. The garage doors make it so that no matter where you are in the house you feel like you're outside. I don't think there was one thing that we looked for an couldn't find. The view is just remarkable. There are a couple of villas that are being constructed, but the construction noise is an occasional saw, or hammer, or some distant music, nothing that was at all disturbing. We ate mostly in Coral Bay because of proximity, although the drive to Cruz Bay was only about 30 minutes, so really not that bad on a lazy vacation. I am the ultimate mosquito magnet, and yes there were mosquitos, but nothing more than I expected. I was extremely pleased to find that all of the screens are in perfect shape, which I was a little nervous about. We left the screen to the courtyard closed all the time which I think helped, and also closed all the screens around dusk and dawn. It was really an incredible house. I can't imagine staying anywhere else on a return trip to St. John.

Price per night from

$496

105 ft Luxury Trimaran

Road Town yacht

10 bedrooms / 10 bathrooms / sleeps 20

Price per night from

$567

"Suite Papaya"

Coral Bay villa

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$241

'Tortola Adventure' Private Villa w/OceanView Pool

Belmont villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$448

Coconut Hill Cottage - Breathtaking views of Coral Bay on St John

Coral Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 28 minutes

Price per night from

$371

St. John Villa Rental with pool, Coral Bay

Coral Bay villa

3 bedrooms / 4 bathrooms / sleeps 6

“Beautiful Villa!” My family (myself, my husband, my two young sons and my sister and her family with two young daughters - all kids under 6) traveled to St. John and stayed at this beautiful villa for about eight days. The home is spacious, with a beautiful living room, kitchen and dining area. It easily accomodated all of us without feeling cramped. There is also a nice breakfast bar. The kitchen was well stocked with dishes, ect and there were plenty of pots,pans, and new appliances. The owner also graciously offered anything to us that was in the pantry. The wrap around deck gives views of the mountains as well as coral bay and the grill is right off the kitchen, which is really convenient. The bedrooms, which all have bathrooms, were really nice, with newer furniture and nice screen doors that allowed a great breeze (although there was a/C but we never needed it). There was also a nice outdoor covered sitting area, which was really nice. The gardens are so well maintained and the pool bar/pool area was great and the kids loved it. The home does have wifi with a nice desk area as well and a nice, new washer and dryer. I have been down to St. John a number of times and the drive to this villa is relatively easy as driving in St. John goes and Coral Bay is also beautiful and there are many restaurants/shopping areas are very close to this location. Laslty, the owner was excellent, meeting my sister's family and showing them the way to the home and offering to get anything we needed before our arrival. There were chairs, plenty of beach towels, two buckets for the beach and some noodles for the pool available to us as well. Overall, I would highly recommend this villa to anyone, including those with small children.

Responds fast! avg. 2 hours 48 minutes

Price per night from

$798

Ocean Beach Suites and Villas Bedroom 9

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$463

Tea Treehouse: Most Romantic St. John Couples Cottage

Coral Bay villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$566

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 34 minutes

Price per night from

$539

4-3 bedroom Villa Del Mar Boat trips to out islands available

West End villa

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 54 minutes

Price per night from

$1,117

AnaCapri Estate

Road Town villa

4 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$654

Allamanda Estate A Dream Villa With Amazing Views

Tortola villa

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,703

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