This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Chocolate Hole Vacation Rentals Show this location only Back to top
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Rated #1 Villa on St. John -- Great Expectations
8BR/8BA
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Sleeps 16
– Chocolate Hole #7515
$5250 - $17500 per week 7 night min stay
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Spectacular Panoramic Views, Rates Discounted for Summer
4BR+/4BA
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Sleeps 8
– Chocolate Hole #193441
$3500 - $5495 per week 7 night min stay
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Spectacular Luxury Waterfront Villa Summer Discounts!
6BR+/6BA
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Sleeps 12-16
– Chocolate Hole #111780
$1285 per night low season
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Special $2,900 Per/wk Open June 25-July 2
4BR/4BA
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Sleeps 8
– Chocolate Hole #35285
$500 - $786 per night
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Andante by the Sea, St. John, USVI 3BR/3BA Oceanfront Villa
3BR/3BA
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Sleeps 6
– Chocolate Hole #5388
$2900- $5800/wk
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Hike to the Beach! Swimming, Snorkeling, Kayaking All Right Outside Your Door!
2BR+/2BA
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Sleeps 10
– Chocolate Hole #283380
$1850 - $4500 per week
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Blue Agave- Dazzling Sunsets, Sunny Pool, Panoramic Ocean View
4BR/4BA
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Sleeps 8
– Chocolate Hole #240912
$2700
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Affordable Luxurious Ocean View Villa Catalina, St John USVI
3BR+/3BA
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Sleeps 8
– Chocolate Hole #175479
From $ 1,900.00 and $ 3,200.00 wkly
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Unbelievable Ocean View.Villa Mar De Amores in St John USVI
3BR/2BA
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Sleeps 2-6
– Chocolate Hole #120366
From $1,900.00 to $3,200.00 wkly
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Luxury Villa -Ocean Views -Private & Close to Town
3BR/2BA
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Sleeps 6
– Chocolate Hole #161585
$2000- $4100/wk
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It's Always Summer at Seascape!
2BR+/2.25BA
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Sleeps 4-6
– Chocolate Hole #124092
$1750- $3850/wk
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Honeymooners Free Upgrade to Our Pool/Spa Villa June 9-19, 25-July2, Call Owner
1BR/1BA
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Sleeps 2
– Chocolate Hole #35289
$1400- $2500/wk
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USVI St John Rental Classic Beachfront W/ Wonderful Views and Breezes
3BR+/3BA
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Sleeps 6-9
– Chocolate Hole #219123
$3000- $6000/wk
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Beachfront,Sail,Snorkel, Bali Hut @ Lime in De Coconut Resort Villa
4BR/4BA
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Sleeps 8
– Chocolate Hole #372210
$6900 - $10900 per week
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Kayaking, Snorkeling, Swimming Steps from Your Door at Aussie Suite
2BR/0BA
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Sleeps 4
– Chocolate Hole #404687
$1450 - $3850 per week
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Dream Come True - Oceanfront Villa on Devers Bay, St. John.
3BR/3.5BA
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Sleeps 6
– Chocolate Hole #385403
In $4515- $5215 Off $2695-$3535
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Ciellodonna - Harborside Location, 4+ Bedrooms, a/C, Pool, Lovely Views
5BR/4BA
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Sleeps 12
– Chocolate Hole #477315
$2905 - $6860 perweek
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Summer/Winter Specials! Jazz Villa - 4 Bedrooms, a/C, 40' Pool, 180 Degree Views
4BR/4BA
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Sleeps 8-9
– Chocolate Hole #477272
Rates from $2590/wk - $5915/wk
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Calypso Del Sol - 3BR/3BA Deluxe - Perfect for Your August Vacation!
3BR/3BA
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Sleeps 6
– Chocolate Hole #262712
From $414/nt - $2900/wk
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Beachfront House 20 Yards from the Ocean
2BR+/2BA
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Sleeps 4-6
– Chocolate Hole #233104
$249- $549/nt
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Spectacular Private Beachfront Villa for 2-10
5BR/5BA
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Sleeps 10
– Chocolate Hole #234140
$5500- $9500/wk
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Cool Oceanfront Suite Free Kayaks & Snorkels! Tropical Reef
1BR+/1BA
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Sleeps 2
– Chocolate Hole #311026
From $1595/wk
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Hummingbirds in the Yard & Privacy at the Pool
2BR/2BA
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Sleeps 4
– Chocolate Hole #201458
$1680- 2800/wk
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Kismet - an Oasis in Paradise with 360° Views of the Caribbean
5BR+/6BA
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Sleeps 12
– Chocolate Hole #305562
$2,143-$5,143/nt - $15,000-$36,000/wk
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Affordable St. John
2BR/2BA
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Sleeps 3-4
– Chocolate Hole #198517
$1575 - $2275/wk
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Bongo Bongo - St. John's Coolest Two Bedroom Villa
2BR/2BA
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Sleeps 4
– Chocolate Hole #247756
$3400- $4450/wk
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Molly's Cottage
2BR+/1.75BA
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Sleeps 4-6
– Chocolate Hole #289193
$1120- $2730/wk
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2 Bedroom Villa at Westin St. John's Resort
3BR+/2BA
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Sleeps 2-8
– Chocolate Hole #425546
$4,000 for the week US
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Spectacular Sunsets and the Night Lights of St. Thomas
4BR/4BA
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Sleeps 8
– Chocolate Hole #413787
$1,890 - $5,145/WK
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Reefside Villa: Snorkeling Paradise; Private Beach.
5BR/5.5BA
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Sleeps 10
– Chocolate Hole #368637
From $4620 wk
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Haiku is Private Retreat on Acre of Land Overlooking Two Bays
3BR/2BA
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Sleeps 6
– Chocolate Hole #369011
$1890 to $3675 per week
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Kia Ora Villa - Comfortable and Casual with Sea Views
3BR/3BA
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Sleeps 6
– Chocolate Hole #315772
$250 - $440 per night 5-7 night min stay
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Ambiance - Lovely 5 Bedroom Villa with Stunning Views!
5BR/4.5BA
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Sleeps 11
– Chocolate Hole #422317
From $3,995/week
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Best of Both Worlds: Scenic Views and Beach Access
4BR/3BA
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Sleeps 8
– Chocolate Hole #460333
$3030 - $5467 per week 7 night min stay
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La Papaya - 5 Bdrm Beauty Overlooking Beautiful Chocolate Hole.
5BR/4BA
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Sleeps 10
– Chocolate Hole #423807
From $3,495
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Time Out - Charming Two Bedroom Overlooking Beautiful Chocolate Hole!
2BR/2BA
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Sleeps 4
– Chocolate Hole #424338
From $2,400
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Coyaba - Fabulous 2 Bdrm Villa, Luxury with a Stunning View!
2BR/2BA
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Sleeps 4
– Chocolate Hole #422627
From $3,495
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Treasure Ridge - Perfect Place to Relax and Enjoy the Sunset!
3BR/3BA
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Sleeps 6
– Chocolate Hole #424379
From $1,995- $3995/week
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Orchid Hill Villa
2BR/2BA
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Sleeps 2-4
– Chocolate Hole #447617
From $3150 - $4850 per week
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Sopra Mare Ocean Front -$2,649 30% Off Til 10/15!!
2BR+/2BA
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Sleeps 4-5
– Chocolate Hole #251854
$2,850/wk Dollars
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Estate Rose: St John Luxury 3 Bed 4.5 Bath, Pool, Spa Vacation Villa
3BR/4.5BA
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Sleeps 6
– Chocolate Hole #319893
$4900- $6500/wk
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Last Minute Specials! Outstanding Water Views from Popular 4 Bdrm Hilltop Villa
4BR+/5BA
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Sleeps 8-10
– Chocolate Hole #116635
$300- $830/nt
- St John Dome House 1BR/1BA – Sleeps 4 – Chocolate Hole #272853
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Villa Eden's Whim
5BR/5BA
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Sleeps 10
– Chocolate Hole #144630ha
$5400 - $8800 per week
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Longview Villa, St. John USVI, 2BR/2.5BA Sweeping Views
2BR+/2BA
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Sleeps 4-5
– Chocolate Hole #412645
$2310 - $3255 per week 7 night min stay
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Iguana Inn Private Spectacular Ocean View Home
2BR/2.5BA
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Sleeps 4
– Chocolate Hole #323405
From $2400/wk
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La Barracuda Villa, St John, Extraordinary Views and Sunsets
4BR+/4BA
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Sleeps 8-10
– Chocolate Hole #302087
$2500- $5000/wk
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Summer Specials! Charming 3 Bed/3 Bath Villa with Pool, Hot Tub & Views
3BR/3BA
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Sleeps 6-8
– Chocolate Hole #452907
$3,850 - $4,550/wk
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Weekly Summer Specials! Charming Caribbean 2 Bed/2 Bath Villa with Views & Spa
2BR+/2BA
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Sleeps 4-6
– Chocolate Hole #424200
$1,049 to $2,940 U.S.
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Ocean Garden - Two Deluxe King Master Bedroom Suites
2BR/2BA
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Sleeps 4
– Chocolate Hole #286940
$1715- $3185/wk
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Arcadia Chocolate Hole
1BR+/1BA
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Sleeps 2-4
– Chocolate Hole #271477
$1700- $2700/wk
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Popular 4BR/4BA St. John Villa 'Southern Cross'
4BR/4BA
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Sleeps 8
– Chocolate Hole #211760
$2700- $6400
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Last Minute Specials! Deluxe Waterfront 3 Bedroom - Dramatic South Shore Views!
3BR/3BA
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Sleeps 6-8
– Chocolate Hole #137801
$1610 to $3350 per week
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Poi Pu St John Villa - Great Views & Total Privacy
2BR+/1BA
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Sleeps 6-8
– Chocolate Hole #314592
$335 - $530 per night 6-7 night min stay
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Cute Cozy Cottage on St. John
1BR/1BA
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Sleeps 2
– Chocolate Hole #150547
$950- $1350/wk US Dollars
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Harborview with Thirty Foot Pool
2BR/2BA
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Sleeps 2-4
– Chocolate Hole #176987
$350-$600/nt - $2400-$4200/wk
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Villa Angelica-an Affordable, Well Located,Private Retreat.
2BR+/2BA
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Sleeps 6
– Chocolate Hole #413208
$250 per night 2 night min stay
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"Allesandra"
3BR+/3BA
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Sleeps 6-7
– Chocolate Hole #206049
$3100- $5900/wk
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Chococruz - a Revitalizing Blend of Chocolate Hole & Cruz Bay
3BR/3BA
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Sleeps 6
– Chocolate Hole #281976
$2,950- $6,950/wk
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"Oceanport"
4BR/4BA
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Sleeps 8
– Chocolate Hole #349154
From $1900- $4200/wk
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Sea Forever
4BR/4BA
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Sleeps 8
– Chocolate Hole #376573
From $3,600 per week
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Conveniently Located Charming Cottage Has Ocean Views and Pool
1BR/1BA
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Sleeps 2
– Chocolate Hole #391011
$190.00/night plus tax
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Family-Friendly
1BR/1BA
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Sleeps 6
– Chocolate Hole #453191
$300 - $400 per night 5 night min stay
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Paddleboard Couples Love Our Romantic Apartment! $150/nt Introductory Special!!!
1BR/1BA
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Sleeps 1-2
– Chocolate Hole #480242
$190 - $300 per night 3 night min stay
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Ebb Tide
4BR+/4BA
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Sleeps 9
– Chocolate Hole #376518
$2,600- $5,700/wk
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'Mystery Villa' Win a Week Under Construction
2BR+/2BA
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Sleeps 4-5
– Chocolate Hole #465589
$3,475 Dollars
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Avalon
5BR/5.5BA
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Sleeps 10
– Chocolate Hole #376484
$5,400- $10,000
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Chocolate Hole Gem!
3BR/3BA
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Sleeps 2-6
– Chocolate Hole #438078
$2,600- $5,100 weekly Dollars
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Crystal Seaview
5BR/5BA
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Sleeps 10
– Chocolate Hole #376478
$4,000- $8,200
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Solaris
4BR/4.5BA
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Sleeps 8
– Chocolate Hole #376525
$2,160- $7,000/wk
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Sunset Beach
4BR/4BA
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Sleeps 8
– Chocolate Hole #376543
From $3,120 a wk
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Best Deal Around on This Charming 5 Bedroom Caribbean Cottage!
5BR+/4BA
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Sleeps 10-12
– Chocolate Hole #418090
starts at $81.25 a night pp cash prices
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Kismet Atop Maria's Bluff, St. John
5BR/6BA
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Sleeps 12
– Chocolate Hole #3248746ha
$1429 - $4786 per night
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Kismet
5BR/6BA
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Sleeps 10
– Chocolate Hole #3219066ha
$2143 - $4786 per night
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Classic St John Beachfront Rental W/ Pool & Wonderful Views
3BR/3BA
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Sleeps 9
– Chocolate Hole #100224ha
$429 per night
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Chococruz - a Revitalizing Blend of Chocolate Hole & Great Cruz Bay
3BR/2BA
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Sleeps 6
– Chocolate Hole #299545ha
$3850 - $6950 per week
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Crystal Seaview
5BR/5BA
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Sleeps 10
– Chocolate Hole #3213164ha
$671 - $1171 per night
- Seagate Villa, Waterfront - 20% Discount 5BR/5BA – Sleeps 11 – Chocolate Hole #223009ha
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Sunset Beach
4BR/4BA
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Sleeps 8
– Chocolate Hole #3213184ha
$643 - $1086 per night
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Arcadia St. John Cottage, the Perfect Gateway in St. John's Chocolate Hole
1BR+/1BA
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Sleeps 4
– Chocolate Hole #183120ha
$200 - $414 per night
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Avalon
5BR/5BA
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Sleeps 12
– Chocolate Hole #3213158ha
$857 - $1429 per night
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Ebb Tide
4BR/4BA
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Sleeps 8-9
– Chocolate Hole #3213165ha
$429 - $814 per night
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Vida De Mar
5BR/5BA
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Sleeps 10
– Chocolate Hole #3213189ha
$964 - $1700 per night
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Popular Tropical Retreat - Close to Town
3BR/2BA
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Sleeps 6-8
– Chocolate Hole #3020888ha
$270 - $530 per night
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Casa Mare
4BR/5BA
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Sleeps 8
– Chocolate Hole #3237801ha
$929 - $1500 per night
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Introductory Specials - Private Deluxe Tropical Getaway W/ Pool and Ocean Views!
3BR/3BA
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Sleeps 6
– Chocolate Hole #3534950ha
$1960 - $4200 per week
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Rated #1 Villa on St. John -- Great Expectations
8BR/8BA
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Sleeps 16
– Chocolate Hole #7515
Overview of Chocolate Hole Vacation Rentals
Seasons to Visit Chocolate Hole Vacation Rentals
Chocolate Hole is a small community on the island of St. John in the U.S. Virgin Islands. Its Caribbean location results in a year-round warm tropical climate. Temperatures average 70 to 80 degrees Fahrenheit through most of the year, climbing to the mid-90s in the warmer summer months. Technically, the summer season is from June to October and the winter goes from December to April but there really isn’t much seasonal difference. Some people prefer to visit during the milder winter months as it allows them an opportunity to escape from the freezing northern hemisphere weather. Rain showers occur throughout the year and generally are a welcome relief from the heat. The showers tend to be short lived and occur during the late afternoon or evening. Occasionally, you may wake in the morning to the sound of rain and by the time you are up for breakfast, the skies will have clear. The only downside of St. John’s climate is that it is subject to seasonal hurricanes which occur occasionally in the late summer and fall months. Most often, they occur during August and September but they have been known to develop as early as June or sweep through in October.
Attractions near Chocolate Hole Resort Rentals
St. John is unique in that two-thirds of the island is protected National Park. This has allowed the island to retain its natural charm and assets, and avoid commercialization that is so common in the Caribbean. The Reef Bay Trail is a winding hiking trail on St. John where you can explore the island and is a must for nature lovers. Take along your binoculars and camera so that you can capture your sightings of the birds and wildlife along the trail. You can also join up a guided tour of the National Park which is both informative and a wonderful nature experience.
The Virgin Islands are known for their magnificent coral reefs, wrecks and scuba diving attractions. A number of dive schools on St. John have daily diving charters to the various dive sites. If you’d like to upgrade your dive qualification while on holiday, you can join a specialty wreck, deep or night dive course. If you don’t want to spend all your time under the water, join a cruise that takes you snorkeling instead. Many of the reefs are quite shallow so you can still have a wonderful interactive experience with the marine life without having to rig up all your scuba gear. You can also join a unique snuba diving excursion where you don’t need any certification.
Sailing is another popular pastime on St. John. Cruises and yacht charters can be arranged at one of the harbors and this is a wonderful way to explore the Virgin Islands. If you’d prefer to stick closer to the coast, join up with a sea kayak excursion and follow the coastline to secluded cloves and beaches. Deep sea and sport fishing charters can take you out to the deep waters to catch game fish.
Secluded Luxury at Chocolate Hole Villas
The Virgin Islands are a slice of paradise, particularly the island of St John. Chocolate Hole is a small community where the landscape and luxurious villa lifestyle are almost as decedent as its name. Choose from spacious eco lodges set on the hillside overlooking the bay or quaint beachfront cottages set just off the beach. The furnishings are stylish and no expense has been spared in equipping the vacation homes with every modern convenience.
Visitors to USVI St. John Vacation Rentals
Chocolate Hole attracts visitors who enjoy the pristine beauty of St. John but still want some luxurious accommodations during their stay. People who love the island life and enjoy a wide variety of water sports will feel right at home on St. John.