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 NZ$3,258
NZ$3,258
NZ$465 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 NZ$2,972
NZ$2,972
NZ$425 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 NZ$9,842
NZ$9,842
NZ$1,406 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 NZ$13,394
NZ$13,394
NZ$1,913 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 NZ$7,191
NZ$7,191
NZ$1,027 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 NZ$9,205
NZ$9,205
NZ$1,315 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 NZ$9,539
NZ$9,539
NZ$1,363 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 NZ$6,256
NZ$6,256
NZ$894 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 NZ$22,758
NZ$22,758
NZ$3,251 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 NZ$4,109
NZ$4,109
NZ$587 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 NZ$3,585
NZ$3,585
NZ$512 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 NZ$4,370
NZ$4,370
NZ$624 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 NZ$8,168
NZ$8,168
NZ$1,167 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 NZ$8,033
NZ$8,033
NZ$1,148 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 NZ$9,057
NZ$9,057
NZ$1,294 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 NZ$2,607
NZ$2,607
NZ$372 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 NZ$5,543
NZ$5,543
NZ$792 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 NZ$2,932
NZ$2,932
NZ$419 per night
includes taxes & fees
Image gallery for Sapphire Beachside walkout condo E 106
9.89.8 out of 10 rating
Exceptional
(79 reviews)
Sapphire Beachside walkout condo E 106
Red Hook
8% off
Price is NZ$4,921
NZ$4,921
NZ$703 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
(179 reviews)
Blue Wrasse - Cute Little Cottage with Gorgeous Deck Views
St. John, St John
6% off
Price is NZ$3,501
NZ$3,501
NZ$500 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 NZ$9,087
NZ$9,087
NZ$1,298 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
7% off
Price is NZ$2,233
NZ$2,233
NZ$319 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 NZ$3,970
NZ$3,970
NZ$567 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 NZ$2,767
NZ$2,767
NZ$395 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Whistling Cay
Showing deals for: 31 Oct - 3 Nov
Searenity Villa in Cruz Bay with private pool and sunset view
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
The current price is NZ$3,062
NZ$3,062
for 3 nights, 1 villa
NZ$1,021 per night
includes taxes & fees
NEWEST House on St John! Gorgeous!! Secluded Pool, 6 min from ferry, Sleeps 12
Sleeps 12 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is NZ$12,184
NZ$12,184
for 3 nights, 1 home
NZ$4,061 per night
includes taxes & fees
Unforgettable views, amazing sunsets minutes from Cruz Bay and the beach.
Sleeps 10 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
The current price is NZ$5,157
NZ$5,157
for 3 nights, 1 home
NZ$1,719 per night
includes taxes & fees
Amazing Water Front Villa West End Tortola
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
96 reviews(96 reviews)
The current price is NZ$3,357
NZ$3,357
for 3 nights, 1 villa
NZ$1,119 per night
includes taxes & fees
Caribe Breeze, all solar, private peaceful villa and pool, new owners
Sleeps 8 · 2 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
The current price is NZ$3,101
NZ$3,101
for 3 nights, 1 villa
NZ$1,034 per night
includes taxes & fees
Ocean and Island Views with Spectacular Sunsets and Alfresco Atmosphere
Sleeps 8 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
123 reviews(123 reviews)
The current price is NZ$4,011
NZ$4,011
for 3 nights, 1 villa
NZ$1,337 per night
includes taxes & fees
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