Trunk Bay Rentals

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314 Houses

Mini Cooper - The Cooper Bay Villas - Tortola BVI

Trunk Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$1,260

MM Cooper Bay - The Cooper Bay Villas - Tortola BVI

Trunk Bay villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

Price per night from

$1,719

Maxi Cooper - The Cooper Bay Villas - Tortola BVI

Trunk Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$1,432

Cooper Bay Villas

Trunk Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 59 minutes

Price per night from

$1,684

New on tripadvisor ! An absolutely breathtaking spot...

Trunk Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Price per night from

$2,291

Great rentals within 20 miles that match your search

Bellamare at Mahoe Bay, Virgin Gorda

Spanish Town villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$802

Serenity - Private Caribbean Style Pool Villa: $295./nt or less!

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$258

@Sapphire Beach Playa Brisa y Mar

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$573

Villa Madeira

St. John villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$601

Tamarind - Virgin Gorda Overlooking North Sound

Virgin Gorda villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$745

⛵ Sail charter Catamaran NEW! Caribbean BVI's

Brewers Bay yacht

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

Price per night from

$2,262

Beachfront Condo - 37 Steps from thr water

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$343

Brigadoon: A 2Bd/2Ba Brand New Villa In Red Hook

St Thomas East villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$258

Luxury All-Inclusive Sailing Catamaran

East End yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$2,447

Reef Side Delight

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 53 minutes

Price per night from

$430

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

Swogjan's Dragon 7A Carolina

Coral Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$326

Starfish Studio on Crystal Cove Sapphire Beach

Smith Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$224

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.

Price per night from

$542

Lion's Gate Getaway - Lush tropical setting

East End house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Incredible Getaway” This is a great place to stay when vacationing in St. Thomas. Max is an incredible host and generously shares her home and her knowledge of the islands. Rent a car if you don't like trekking up the hill, but we made it okay without one.

Responds fast! avg. 3 hours 7 minutes

Price per night from

$161

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

$200

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

Coral Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$418

Price per night from

$1,800

Lidskjalf at Annaberg - Walk to Francis Bay Beach!

Virgin Islands National Park villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$501

Poi Pu St John Villa - great views & total privacy

Cruz Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“St John is just the best little island around.” The villa is wide open, very spacious. Open the big doors and you let the cool breezes in. There are always breezes at Poi Pu. It's great to have your own pool right there, even if you have spent the day at the beach. It's close to town for shopping and dinning, but there is nothing like dinning right there on the deck with the breezes and all those stars. I will be going back it's just the best place to be with friends. Carol

Responds fast! avg. 2 hours 26 minutes

Price per night from

$396

Quart-A-Nancy Point, Cooper Island, BVI

Cooper Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$459

“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

$818

“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. 2 hours 29 minutes

Price per night from

$160

Bigger Splash, Private Villa-The Baths w/Concierge

The Baths villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$459

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.

Responds fast! avg. 2 hours 3 minutes

Price per night from

$315

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

$911

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!

Price per night from

$1,031

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

$276

Pura Vida: Large Deck w/ Pergola and Pool Overlooking Ocean

Cruz Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$630

'Billion$ View' New Deluxe 2FL Beachfront Villa

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 7

Price per night from

$654

Luxury Honeymoon Suite/ Wifi/ Gated/ Privacy/ Private Pool/ Hot Tub

East End apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Best Place On Earth!!” Where do I begin... My husband and I were on our honeymoon. Dana and Jason were the best hosts-they gave you privacy, but if you need assistance they were always there to help. They made us feel at home in the HarmonySuite with happy smiles and open arms. We were given breakfast every morning-tastes of the Island foods- DELICIOUS ; ) It was amazing to see the iguanas that would come up to the deck to visit. The rooms were well-kept and well-stocked Dana and Jason have everything at your hands. The pictures don't lie the VIEWS were phenomenal-(I think I have a billion pictures of just the view) It was awesome to wake up and come home every day to the spectacular views. The pool/cabana and hot tub were extra touches to this fantastic getaway and are exclusively for your enjoyment . The people on the island are the best so sweet, helpful, and genuine-always great to be around, the beaches are jaw dropping we never wanted to get out- recommending COKI BEACH/ MAGENS BAY and night life was amazing recommending DUFFY'S LOVE SHACK/ SENOR FROGS (RED HOOK) all of this plus much more all located about 6-8 minutes away (car recommended). Can't wait to go back to the best place on earth!! Dana & Jason we love you, Thank You for making our honeymoon a time to remember forever..God Bless

Responds fast! avg. 1 hour 4 minutes

Price per night from

$338

Ocean View Villa!!! 2 bedrooms, 2 Bathrooms ( sleeps 4 to 6 ).

Jost Van Dyke villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 31 minutes

Price per night from

$504

Luxury 5 Bedroom Waterfront Villa

Virgin Gorda house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$12

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