Holiday rentals near Whistling Cay
We found 2,672 holiday rentals — enter your dates for availability
Choose the right holiday home within close proximity to Whistling Cay. Holiday homes provide the best amenities for your family, friends or furry companion, such as parking and a hot tub. At the end of the day, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Whistling Cay
Showing deals for:31 Oct - 7 Nov
Image gallery for Johnny Horn Trail House St. John Overlooking Coral Bay
9.49.4 out of 10 rating
Exceptional
(85 reviews)
Johnny Horn Trail House St. John Overlooking Coral Bay
St. John, St John
8% off
Price is AU$2,966
AU$2,966
AU$424 per night
includes taxes & fees
Image gallery for Privacy. Romantic Private Pool Villa @ Sapphire. Generator
9.49.4 out of 10 rating
Exceptional
(18 reviews)
Privacy. Romantic Private Pool Villa @ Sapphire. Generator
Red Hook, St Thomas
7% off
Price is AU$2,707
AU$2,707
AU$387 per night
includes taxes & fees
Image gallery for Good Vibes Only OceanFront Villa🌴Private Pool-Modern-Sun Decks-Spectacular Views
1010 out of 10 rating
Exceptional
(82 reviews)
Good Vibes Only OceanFront Villa🌴Private Pool-Modern-Sun Decks-Spectacular Views
St. Thomas, St Thomas
5% off
Price is AU$8,975
AU$8,975
AU$1,282 per night
includes taxes & fees
Image gallery for Isla Paradiso, your own private oasis
8.28.2 out of 10 rating
Very good
(12 reviews)
Isla Paradiso, your own private oasis
St. Thomas, St Thomas
12% off
Price is AU$11,991
AU$11,991
AU$1,713 per night
includes taxes & fees
Image gallery for Sugarview Villa MainHouse: Coral Bay w/Pool, Ocean Views
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Sugarview Villa MainHouse: Coral Bay w/Pool, Ocean Views
St. John, St John
8% off
Price is AU$6,547
AU$6,547
AU$935 per night
includes taxes & fees
Image gallery for Unforgettable views, amazing sunsets minutes from Cruz Bay and the beach.
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Unforgettable views, amazing sunsets minutes from Cruz Bay and the beach.
St. John, St John
7% off
Price is AU$8,381
AU$8,381
AU$1,197 per night
includes taxes & fees
Image gallery for 5 bedroom Atlantic Waterfront
9.89.8 out of 10 rating
Exceptional
(36 reviews)
5 bedroom Atlantic Waterfront
St. Thomas, VI
7% off
Price is AU$8,678
AU$8,678
AU$1,240 per night
includes taxes & fees
Image gallery for Caribe Breeze, all solar, private peaceful villa and pool, new owners
9.89.8 out of 10 rating
Exceptional
(65 reviews)
Caribe Breeze, all solar, private peaceful villa and pool, new owners
St. John, VI
8% off
Price is AU$5,696
AU$5,696
AU$814 per night
includes taxes & fees
Image gallery for Sapphire Beach, Crystal Cove Condo. Prime Location. Steps to Turquoise Water!
9.89.8 out of 10 rating
Exceptional
(50 reviews)
Sapphire Beach, Crystal Cove Condo. Prime Location. Steps to Turquoise Water!
Red Hook
8% off
Price is AU$3,743
AU$3,743
AU$535 per night
includes taxes & fees
Image gallery for Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool
1010 out of 10 rating
Exceptional
(25 reviews)
Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool
St. Thomas, St Thomas
8% off
Price is AU$20,182
AU$20,182
AU$2,883 per night
includes taxes & fees
Image gallery for "Caribbean" One Bedroom in the Garden of Eden Cottage Collection
1010 out of 10 rating
Exceptional
(31 reviews)
"Caribbean" One Bedroom in the Garden of Eden Cottage Collection
St. John
7% off
Price is AU$3,262
AU$3,262
AU$466 per night
includes taxes & fees
Image gallery for 5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
1010 out of 10 rating
Exceptional
(114 reviews)
5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
Red Hook, St Thomas
8% off
Price is AU$3,982
AU$3,982
AU$569 per night
includes taxes & fees
Image gallery for Immerse Yourself in Luxury at our breathtaking beachfront Condo!
1010 out of 10 rating
Exceptional
(15 reviews)
Immerse Yourself in Luxury at our breathtaking beachfront Condo!
Red Hook, St Thomas
8% off
Price is AU$7,499
AU$7,499
AU$1,071 per night
includes taxes & fees
Image gallery for Red Hook - 2 bedroom private villa and pool on the east end of St. Thomas, USVI
9.89.8 out of 10 rating
Exceptional
(58 reviews)
Red Hook - 2 bedroom private villa and pool on the east end of St. Thomas, USVI
St. Thomas, St Thomas
7% off
Price is AU$7,368
AU$7,368
AU$1,053 per night
includes taxes & fees
Image gallery for Spectacular waterfront villa/private beach GREAT SNORKELING, sunrise/sunset view
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Spectacular waterfront villa/private beach GREAT SNORKELING, sunrise/sunset view
St. John, VI
8% off
Price is AU$8,246
AU$8,246
AU$1,178 per night
includes taxes & fees
Image gallery for NEW 1BR Condo w/ Private Courtyard, Perfect Location Steps from Beach & Pool
9.89.8 out of 10 rating
Exceptional
(50 reviews)
NEW 1BR Condo w/ Private Courtyard, Perfect Location Steps from Beach & Pool
St. Thomas
5% off
Price is AU$2,373
AU$2,373
AU$339 per night
includes taxes & fees
Image gallery for Beach Front Villa with Down Island View - Priceless!
9.49.4 out of 10 rating
Exceptional
(162 reviews)
Beach Front Villa with Down Island View - Priceless!
Red Hook, VI
8% off
Price is AU$5,049
AU$5,049
AU$721 per night
includes taxes & fees
Image gallery for Breathtaking Views from Sapphire Village
9.69.6 out of 10 rating
Exceptional
(89 reviews)
Breathtaking Views from Sapphire Village
Red Hook, St Thomas
9% off
Price is AU$2,669
AU$2,669
AU$381 per night
includes taxes & fees
Image gallery for Blue Wrasse - Cute Little Cottage with Gorgeous Deck Views
9.89.8 out of 10 rating
Exceptional
(178 reviews)
Blue Wrasse - Cute Little Cottage with Gorgeous Deck Views
St. John, St John
6% off
Price is AU$3,187
AU$3,187
AU$455 per night
includes taxes & fees
Image gallery for Turquoise blue ocean views. Spacious 4 bedroom/4bath Condo.
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Turquoise blue ocean views. Spacious 4 bedroom/4bath Condo.
St. Thomas, St Thomas
8% off
Price is AU$8,253
AU$8,253
AU$1,179 per night
includes taxes & fees
Image gallery for Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!
9.49.4 out of 10 rating
Exceptional
(96 reviews)
Gorgeous Condo At Sapphire on St Thomas. Walk-in Level. Killer Island Views!
Red Hook
8% off
Price is AU$2,032
AU$2,032
AU$290 per night
includes taxes & fees
Image gallery for 1 bedroom Crystal Cove condo on Sapphire Beach. Gated community, private beach.
1010 out of 10 rating
Exceptional
(29 reviews)
1 bedroom Crystal Cove condo on Sapphire Beach. Gated community, private beach.
Red Hook, St Thomas
8% off
Price is AU$3,617
AU$3,617
AU$517 per night
includes taxes & fees
Image gallery for Ocean Front Condo at Sapphire Beach
1010 out of 10 rating
Exceptional
(18 reviews)
Ocean Front Condo at Sapphire Beach
Red Hook, St Thomas
8% off
Price is AU$2,518
AU$2,518
AU$360 per night
includes taxes & fees
Image gallery for Luxury Condo - Stunning Ocean View at Sapphire Beach.
9.69.6 out of 10 rating
Exceptional
(90 reviews)
Luxury Condo - Stunning Ocean View at Sapphire Beach.
Red Hook
15% off
Price is AU$2,377
AU$2,377
AU$340 per night
includes taxes & fees
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Find the best place to stay - Whistling Cay
2024 Winner Vrbo's Vacation Rental of the Year: Villa Cin Cin!
Sleeps 20 · 5 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Blue Wrasse - Cute Little Cottage with Gorgeous Deck Views
Sleeps 6 · 1 bedroom · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
178 reviews(178 reviews)
Arc Du Soleil- Ultimate Island Living, Refreshing Salt Water Pool, Stunning View
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Stunning Views, Peaceful Location, Large Pool & Minutes from Cruz Bay
Sleeps 10 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
67 reviews(67 reviews)
Grande Bay Resort - Mojo Blue Luxury Studio Beachfront!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
187 reviews(187 reviews)
Oceanport Villa : Great location, stunning views with pool and spa
Sleeps 8 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
57 reviews(57 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