Holiday rentals near Chocolate Hole
We found 3,237 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals within easy reach of Chocolate Hole that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a pool. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chocolate Hole
Showing deals for:19 June - 26 June
Image gallery for “Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”
9.89.8 out of 10, Exceptional, (105 reviews)
Exceptional
(105 reviews)
“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”
St. John
9% off
Price is AU$3,609
AU$3,609
for 7 nights, 1 villa
AU$516 per night
includes taxes & fees
Image gallery for Secluded Island Escape w/ King Bed, Lush Gardens & Shared Pool Access
9.89.8 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Secluded Island Escape w/ King Bed, Lush Gardens & Shared Pool Access
St. John
8% off
Price is AU$3,781
AU$3,781
for 7 nights, 1 cottage
AU$540 per night
includes taxes & fees
Image gallery for 2-bedroom condo with WiFi, AC View of water from deck Pool
9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
2-bedroom condo with WiFi, AC View of water from deck Pool
St. Thomas
9% off
Price is AU$2,499
AU$2,499
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
Image gallery for Affordable, oceanfront and walk to private beach gem
1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Affordable, oceanfront and walk to private beach gem
St. Thomas
8% off
Price is AU$3,755
AU$3,755
for 7 nights, 1 apartment
AU$536 per night
includes taxes & fees
Image gallery for SPECIAL PRICING! !!
1010 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
SPECIAL PRICING! !!
St. Thomas
8% off
Price is AU$6,340
AU$6,340
for 7 nights, 1 villa
AU$906 per night
includes taxes & fees
Image gallery for Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Spectacular beachfront villa. Great SNORKELING, kayaking, sunrise & sunset views
St. John
8% off
Price is AU$7,482
AU$7,482
for 7 nights, 1 villa
AU$1,069 per night
includes taxes & fees
Image gallery for Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
1010 out of 10, Exceptional, (87 reviews)
Exceptional
(87 reviews)
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
St. Thomas
7% off
Price is AU$4,561
AU$4,561
for 7 nights, 1 apartment
AU$652 per night
includes taxes & fees
Image gallery for CHECK OUT THE VIEW! Fantastic Affordable Oceanfront Studio - Listen to the Waves
9.89.8 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
CHECK OUT THE VIEW! Fantastic Affordable Oceanfront Studio - Listen to the Waves
St. Thomas
7% off
Price is AU$1,835
AU$1,835
for 7 nights, 1 apartment
AU$262 per night
includes taxes & fees
Image gallery for Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views
9.89.8 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views
St. John
8% off
Price is AU$3,781
AU$3,781
for 7 nights, 1 cottage
AU$540 per night
includes taxes & fees
Image gallery for Orchid at Casa Tre Fiori - Peaceful Paradise!
1010 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Orchid at Casa Tre Fiori - Peaceful Paradise!
St. John
7% off
Price is AU$2,767
AU$2,767
for 7 nights, 1 apartment
AU$395 per night
includes taxes & fees
Image gallery for Private Paradise! One level, panoramic views from every room!
1010 out of 10, Exceptional, (142 reviews)
Exceptional
(142 reviews)
Private Paradise! One level, panoramic views from every room!
St. Thomas
8% off
Price is AU$9,484
AU$9,484
for 7 nights, 1 villa
AU$1,355 per night
includes taxes & fees
Image gallery for 1BD/2BA Tropical Seaside Escape, 40 yards from Sapphire Beach!
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
1BD/2BA Tropical Seaside Escape, 40 yards from Sapphire Beach!
St. Thomas
8% off
Price is AU$4,213
AU$4,213
for 7 nights, 1 apartment
AU$602 per night
includes taxes & fees
Image gallery for 5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
1010 out of 10, Exceptional, (127 reviews)
Exceptional
(127 reviews)
5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
St. Thomas
8% off
Price is AU$4,129
AU$4,129
for 7 nights, 1 apartment
AU$590 per night
includes taxes & fees
Image gallery for Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
St. Thomas
7% off
Price is AU$2,883
AU$2,883
for 7 nights, 1 apartment
AU$412 per night
includes taxes & fees
Image gallery for Sapphire Beach Resort Rental
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Sapphire Beach Resort Rental
St. Thomas
21% off
Price is AU$5,692
AU$5,692
for 7 nights, 1 apartment
AU$813 per night
includes taxes & fees
Image gallery for New central located 2BR/3BD/2BA condo gated community with 2 pools & pickleball
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
New central located 2BR/3BD/2BA condo gated community with 2 pools & pickleball
St. Thomas
8% off
Price is AU$4,764
AU$4,764
for 7 nights, 1 apartment
AU$681 per night
includes taxes & fees
Image gallery for Welcome To YOUR CARIBBEAN DREAM
9.69.6 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Welcome To YOUR CARIBBEAN DREAM
St. Thomas
8% off
Price is AU$2,015
AU$2,015
for 7 nights, 1 apartment
AU$288 per night
includes taxes & fees
Image gallery for Beach, Bed and Beyond! WiFi included , New Tiled Shower!
9.69.6 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
St. Thomas
9% off
Price is AU$3,426
AU$3,426
for 7 nights, 1 apartment
AU$489 per night
includes taxes & fees
Image gallery for Corner Suite "Glass House on the Sea" Modern Luxury on Sapphire Beach
1010 out of 10, Exceptional, (147 reviews)
Exceptional
(147 reviews)
Corner Suite "Glass House on the Sea" Modern Luxury on Sapphire Beach
St. Thomas
8% off
Price is AU$3,699
AU$3,699
for 7 nights, 1 apartment
AU$528 per night
includes taxes & fees
Image gallery for Tropical Palm Villa- Ocean Views From All Rooms, Solar Power, Private Pool
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Tropical Palm Villa- Ocean Views From All Rooms, Solar Power, Private Pool
St. Thomas
8% off
Price is AU$9,209
AU$9,209
for 7 nights, 1 villa
AU$1,316 per night
includes taxes & fees
Image gallery for 2 Bedroom/2 Bath condo on the Beach! This is a double unit 1,300sq. ft.
1010 out of 10, Exceptional, (147 reviews)
Exceptional
(147 reviews)
2 Bedroom/2 Bath condo on the Beach! This is a double unit 1,300sq. ft.
St. Thomas
8% off
Price is AU$9,301
AU$9,301
for 7 nights, 1 apartment
AU$1,329 per night
includes taxes & fees
Image gallery for 2bed 2 bath with Shared Pool and a View. 7 mins to Cruz Bay! 15 mins to Beaches.
9.89.8 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
2bed 2 bath with Shared Pool and a View. 7 mins to Cruz Bay! 15 mins to Beaches.
St. John
8% off
Price is AU$4,622
AU$4,622
for 7 nights, 1 apartment
AU$660 per night
includes taxes & fees
Image gallery for 2bed 2bath with a shared Pool and a View. 7 mins to Cruz Bay! 15 mins to Beaches
9.89.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
2bed 2bath with a shared Pool and a View. 7 mins to Cruz Bay! 15 mins to Beaches
St. John
8% off
Price is AU$4,622
AU$4,622
for 7 nights, 1 apartment
AU$660 per night
includes taxes & fees
Image gallery for Walking distance to the Gorgeous Sapphire Beach!
1010 out of 10, Exceptional, (91 reviews)
Exceptional
(91 reviews)
Walking distance to the Gorgeous Sapphire Beach!
St. Thomas
8% off
Price is AU$2,696
AU$2,696
for 7 nights, 1 apartment
AU$385 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chocolate Hole
Luxury & Location! 6 Primary Bedrooms all Waterfront
6 bedrooms · 5.5 bathrooms
1010 out of 10
Exceptional
exceptional
24 reviews
(24 reviews)
Ocean Garden - Two suites with large king bedroom
2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptional
exceptional
15 reviews
(15 reviews)
Amazing Ocean Views and close to town
3 bedrooms · 2 bathrooms
1010 out of 10
Exceptional
exceptional
149 reviews
(149 reviews)
Villa L'Agave - Your Tropical Rendezvous Paradise
3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptional
exceptional
74 reviews
(74 reviews)
Best Views of Chocolate Hole - 5 mins from Cruz Bay - Solar with battery backup
5 bedrooms · 3.5 bathrooms
1010 out of 10
Exceptional
exceptional
20 reviews
(20 reviews)
Villa Island Paradise
Sleeps 3 · 2 bedrooms
9.49.4 out of 10
Exceptional
exceptional
18 reviews
(18 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value