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Trunk Bay Rentals

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99 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

$377

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

$201

Blackbeard's Hideaway Tortola BritishVirginIslands

Road Town house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 45 minutes

Price per night from

$1,047

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

$857

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

Road Town villa

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 36 minutes

Price per night from

$344

Luxury 5 Bedroom Waterfront Villa

Virgin Gorda house

5 bedrooms / 6 bathrooms / sleeps 10

Price per night from

$9,161

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

Road Town villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 36 minutes

Price per night from

$344

Extasea Yacht Charters

Road Town yacht

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$2,634

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. 3 hours 37 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 34 minutes

Price per night from

$813

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

$1,249

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

Belmont villa

5 bedrooms / 5 bathrooms / sleeps 14

Responds fast! avg. 2 hours 41 minutes

Price per night from

$1,260

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. 2 hours 42 minutes

Price per night from

$819

Ocean Beach Suites and Villas Bedroom 2

Road Town villa

2 bedrooms / 1 bathroom / sleeps 2

Price per night from

$401

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

$720

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.

Responds fast! avg. 3 hours 45 minutes

Price per night from

$1,375

Ocean Beach Suites and Villas Bedroom 5

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

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

Road Town yacht

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,604

Easy Breezes - Family Luxury & Romantic Getaways

Coral Bay villa

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$693

“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 !

Responds fast! avg. 3 hours 45 minutes

Price per night from

$2,520

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

Cruz Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$270

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

$707

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

$491

"Suite Papaya"

Coral Bay villa

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$373

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

Coral Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$373

Ocean Beach Suites and Villas Bedroom 9

Road Town villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$401

Tea Treehouse: Most Romantic St. John Couples Cottage

Coral Bay villa

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$567

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 50 minutes

Price per night from

$542

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

West End villa

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 41 minutes

Price per night from

$1,123

AnaCapri Estate

Road Town villa

4 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$655

Allamanda Estate A Dream Villa With Amazing Views

Tortola villa

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,472

Great Escape

St. John villa

4 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$857

Honeymoon Hikers Cottage- Coral Bay,USVI- St. John

Coral Bay villa

1 bedroom / 2 bathrooms / sleeps 2

“Amazing Vacation Rental” I have stayed at this property owner's other rental and did not think I could top that..I was wrong! This property was just as, if not more gorgeous than her other place, Mimosa. The views were amazing and we always felt like we exploring the island, even if we never left the villa. One thing that made this great was how easy it was to talk to and work with the owner, easiest vacation I have ever planned. The place was clean and bug/dirt free. I have stayed in quite a few places around St. John and this is by far the nicest. I already booked my vacation for next winter at this property and can't wait. It is private but still has easy access to hiking, swimming, getting to town, it is just an all around great place and I cannot wait to go back. I highly recommend this rental, and I'm picky!

Price per night from

$401

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

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