Chocolate Hole, Saint John Rentals

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392 rentals

Great rentals within 20 miles that match your search

Beautiful 2015 Saba 50 Catamaran Sail Boat

East End yacht

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$4,016

The Peter Bay 1BR Honeymoon Suite at St. John

St. John villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$683

Suite 8C - Gallows Point Resort Oceanfront Upper Level

Cruz Bay villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

Price per night from

$683

Yacht Catatonic-Crewed All-Inclusive BVI Charters

Charlotte Amalie yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$3,032

Catamaran Lagoon 42

Road Town yacht

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$1,640

Luxury 5 Bedroom Villa Overlooking Magens Bay

Peterborg villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$2,174

Luxury Villa with Large Pool Above Honeymoon Beach

Water Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$493

Escape Winter at Westin St. John Resort, USVI

Cruz Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$2,008

An Enchanting Caribbean Interlude affordable 4 you

Cruz Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$167

Sailing in the Virgin Islands

Charlotte Amalie yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$947

Spectacular Views Day & Eve in Treetop Apartment

Cruz Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$311

Two Bedroom Villa at Sapphire Beach Resort

St Thomas East villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$458

Serenity - Private Caribbean Style Pool Villa

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$259

@Sapphire Beach Playa Brisa y Mar

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$574

Studio Condo on Bolongo Bay

Bolongo Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$190

Villa Madeira

St. John villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$602

Our place in St Thomas 1BR Suite

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 44 minutes

Price per night from

$194

Christian Villa

St Thomas Central villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

Price per night from

$1,205

Antillean Yacht Charters

Water Island yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$1,652

⛵ Sail charter Catamaran NEW! Caribbean BVI's

Brewers Bay yacht

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

Price per night from

$2,295

Striking Ocean Views, Privacy,

Water Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$488

Beachfront Condo - 37 Steps from thr water

St Thomas East condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$343

Luxury All-Inclusive Sailing Catamaran

East End yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$2,451

Reef Side Delight

East End condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$431

Private Day Sail, Snorkeling & Week Long Charters

Charlotte Amalie yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$2,983

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

$378

Starfish Studio on Crystal Cove Sapphire Beach

Smith Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$224

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.

Price per night from

$161

Relax 4 Us at Bolongo Bay ~ USVI

Charlotte Amalie apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent property and great destination!” Our stay here was wonderful! We just came back a few weeks ago (Jan 7-14) from our trip and we are ready to book for the next year! We had such a great time: Accommodations - The apartment is very clean and modern. It has nice comfortable beds and lovely décor in every room. The kitchen is stocked with all necessary utensils and appliances. Bathrooms are clean and modern. I loved the cherry wood doors and marble countertops all around. There is a large balcony that you can eat or relax out on. Beach chairs, towels etc. is also provided for you. Beach - you can go downstairs and you are at the Bolongo Bay beach, its lovely, you have all the water sports options that you would find at a typical resort right there. If you walk past the restaurants and the hotel (5 minute walk along the beach), there is a great snorkeling spot past the rocks, very cool! We had a rental car so we also drove (about 15 min) to Smith Bay. This beach is pure heaven! It seems to be mainly visited by locals and is not crowded with perfect white sand and beautiful calm blue waters. Pool - There are a couple of pools that you can use. We used the one by the beach; it had a tap to wash off the sand as well. The pool was nice and clean and the water was pretty warm. Food - Like I mentioned you have everything you need to prepare your food 'at home' if you are on a budget or have specific dietary needs. There are many supermarkets that deliver or you can shop in a warehouse type place (CostUless) or a supermarket (Pueblo) or some local stands that are all around. There are three popular restaurants directly in the Bolongo Bay area so you don't ever have to leave the area if you choose not to: • Iggys - casual burger type place• Mims - fancier place that serves sea food• Lobster Grill - very fancy There is a lot to do on the island and its neighbors, but we have small kids so we took it easy this time and just enjoy the water. Next time we rent this apartment, we will explore the island.

Responds fast! avg. 2 hours 12 minutes

Price per night from

$221

Responds fast! avg. 3 hours 57 minutes

Price per night from

$1,804

Lidskjalf at Annaberg - Walk to Francis Bay Beach!

Virgin Islands National Park villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$501

Quart-A-Nancy Point, Cooper Island, BVI

Cooper Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$460

“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

$820

VILLA AMOUR ,Romantic , Art Lovers Paradise ,

North Side villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Perfect!” Title says it all. PERFECT island vacation home. Better than advertised. We had 7 adults and 2 infants and had plenty of room to relax. Pool, views are incredible. Convenient enough to travel the rest of the island (although you may ask yourself "why leave!". Rick and Steve are great hosts, responsive to any questions you might have. Recommend renting SUV and also that you give yourself plenty of time at the airport when departing. Highly recommend Villa Amour and would definitely return!

Responds fast! avg. 1 hour 0 minutes

Price per night from

$804

Sapphire 1 Bedroom-Free H/S WIFI & No Excessive Owner Fees #257

East End apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$206

Drake's View: Voted Best View in the Caribbean

Coral Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Awesome family vacation” This was our second visit to Drakes View and we again enjoyed everything the property has to offer...views, a well equpped kitchen, hot tub and ample space for our 3 generations to be together for Thanksgiving week. In spite of an abnormally rainy week, we made the best of our beach time and enjoyed the views from the villa when we were forced inside. We lovedbeing able to stay overlooking Coral Bay,our favorite side of St. Johns. We explored several new beaches and snorkeling apots. Thanks to the Roberts family and their wonderful concierge team of Dorothy and Fernando.

Price per night from

$912

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

Price per night from

$339

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!

Price per night from

$1,468

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rentals in Chocolate Hole, Saint John

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