Cheap Vacations in Water Island

Choose two or more items and save on your trip:

Water Island vacations

Price found within the past 48 hours. Click for updated prices.
Hotel 1829

Hotel 1829

3.5 out of 5
Price was $1,101, price is now $877 per person
$877
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Save 100% on your flight
Price was $2,927, price is now $2,042 per person
$2,042
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was $1,957, price is now $1,385 per person
$1,385
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was $2,123, price is now $1,546 per person
$1,546
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Save 100% on your flight
Price was $3,609, price is now $2,747 per person
$2,747
per person
Apr 26 - May 2
found 1 day ago
Roundtrip flight included
New York (JFK) to St. Thomas (STT)
Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was $1,664, price is now $1,374 per person
$1,374
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Price was $1,042, price is now $878 per person
$878
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The Saint Resort

The Saint Resort

3 out of 5
Price was $2,149, price is now $1,839 per person
$1,839
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was $1,597, price is now $1,379 per person
$1,379
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $2,971, price is now $2,588 per person
$2,588
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)

3-night Water Island vacations

Price found within the past 48 hours. Click for updated prices.
Hotel 1829

Hotel 1829

3.5 out of 5
Price was $910, price is now $790 per person
$790
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was $1,957, price is now $1,385 per person
$1,385
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was $2,123, price is now $1,546 per person
$1,546
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was $1,664, price is now $1,374 per person
$1,374
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Price was $1,042, price is now $878 per person
$878
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The Saint Resort

The Saint Resort

3 out of 5
Price was $1,915, price is now $1,627 per person
$1,627
per person
Apr 3 - Apr 6
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to St. Thomas (STT)
Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was $1,597, price is now $1,379 per person
$1,379
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Point Pleasant Resort

Point Pleasant Resort

4 out of 5
Price was $1,719, price is now $1,498 per person
$1,498
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
St John Inn

St John Inn

3 out of 5
Price was $1,304, price is now $1,139 per person
$1,139
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Lindbergh Bay Hotel and Villas

Lindbergh Bay Hotel and Villas

3.5 out of 5
Price was $979, price is now $856 per person
$856
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The Cottage at Villa Indigo

The Cottage at Villa Indigo

3 out of 5
Price was $1,164, price is now $1,028 per person
$1,028
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)

4-night Water Island vacations

Price found within the past 48 hours. Click for updated prices.
Lindbergh Bay Hotel and Villas

Lindbergh Bay Hotel and Villas

3.5 out of 5
Price was $815, price is now $656 per person
$656
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Save 100% on your flight
Price was $1,700, price is now $1,139 per person
$1,139
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Save 100% on your flight
Price was $2,097, price is now $1,544 per person
$1,544
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,799, price is now $1,338 per person
$1,338
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Two Sandals – A Boutique Hotel

Two Sandals – A Boutique Hotel

3.5 out of 5
Price was $1,135, price is now $851 per person
$851
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Save 100% on your flight
Price was $1,553, price is now $1,167 per person
$1,167
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Price was $899, price is now $686 per person
$686
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
At Home in the Tropics

At Home in the Tropics

3 out of 5
Price was $1,424, price is now $1,134 per person
$1,134
per person
Apr 26 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Hotel 1829

Hotel 1829

3.5 out of 5
Price was $1,101, price is now $877 per person
$877
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was $1,506, price is now $1,219 per person
$1,219
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
St John Inn

St John Inn

3 out of 5
Price was $1,248, price is now $1,037 per person
$1,037
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)

5-night Water Island vacations

Price found within the past 48 hours. Click for updated prices.
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Price was $1,094, price is now $897 per person
$897
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Save 100% on your flight
Price was $2,522, price is now $1,795 per person
$1,795
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
At Home in the Tropics

At Home in the Tropics

3 out of 5
Price was $1,345, price is now $967 per person
$967
per person
Apr 8 - Apr 13
found 16 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Secret Harbour Beach Resort

Secret Harbour Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,676, price is now $2,057 per person
$2,057
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to St. Thomas (STT)
Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Save 100% on your flight
Price was $3,014, price is now $2,322 per person
$2,322
per person
Apr 25 - Apr 30
found 16 hours ago
Roundtrip flight included
New York (JFK) to St. Thomas (STT)
Villa Island Paradise

Villa Island Paradise

4 out of 5
Save 100% on your flight
Price was $2,112, price is now $1,629 per person
$1,629
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Save 100% on your flight
Price was $2,847, price is now $2,234 per person
$2,234
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Save 100% on your flight
Price was $2,440, price is now $1,917 per person
$1,917
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,144, price is now $1,696 per person
$1,696
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
St John Inn

St John Inn

3 out of 5
Price was $1,530, price is now $1,217 per person
$1,217
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The Cottage at Villa Indigo

The Cottage at Villa Indigo

3 out of 5
Price was $1,254, price is now $1,043 per person
$1,043
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The Landmark Apartment

The Landmark Apartment

2.5 out of 5
Price was $1,376, price is now $1,162 per person
$1,162
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)

6-7 night Water Island vacations

Price found within the past 48 hours. Click for updated prices.
Sunset Gardens Guesthouse

Sunset Gardens Guesthouse

2.5 out of 5
Price was $853, price is now $671 per person
$671
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Save 100% on your flight
Price was $3,245, price is now $2,057 per person
$2,057
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Save 100% on your flight
Price was $2,652, price is now $1,686 per person
$1,686
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Save 100% on your flight
Price was $2,927, price is now $2,042 per person
$2,042
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,245, price is now $886 per person
$886
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Save 100% on your flight
Price was $3,609, price is now $2,747 per person
$2,747
per person
Apr 26 - May 2
found 1 day ago
Roundtrip flight included
New York (JFK) to St. Thomas (STT)
Hotel 1829

Hotel 1829

3.5 out of 5
Save 100% on your flight
Price was $1,473, price is now $1,129 per person
$1,129
per person
Apr 12 - Apr 18
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Thomas (STT)
Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,548, price is now $1,956 per person
$1,956
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
At Home in the Tropics

At Home in the Tropics

3 out of 5
Price was $1,524, price is now $1,177 per person
$1,177
per person
Apr 7 - Apr 13
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to St. Thomas (STT)
Villa Island Paradise

Villa Island Paradise

4 out of 5
Save 100% on your flight
Price was $2,314, price is now $1,788 per person
$1,788
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Lindbergh Bay Hotel and Villas

Lindbergh Bay Hotel and Villas

3.5 out of 5
Price was $1,086, price is now $841 per person
$841
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
St John Inn

St John Inn

3 out of 5
Save 100% on your flight
Price was $1,736, price is now $1,356 per person
$1,356
per person
Apr 10 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)

Flight deals to Water Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, Apr 12 - Thu, Apr 16
MIA
Miami
STT
St. Thomas
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Apr 12 from Miami to St. Thomas, returning Thu, Apr 16, priced at $171 found 6 days ago
Tue, Mar 17 - Sat, Mar 28
FLL
Fort Lauderdale
STT
St. Thomas
$189 Roundtrip, found 2 hours ago
$189
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Mar 17 from Fort Lauderdale to St. Thomas, returning Sat, Mar 28, priced at $189 found 2 hours ago
Mon, Apr 20 - Wed, Apr 29
ATL
Atlanta
STT
St. Thomas
$189 Roundtrip, found 9 hours ago
$189
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Mon, Apr 20 from Atlanta to St. Thomas, returning Wed, Apr 29, priced at $189 found 9 hours ago

Top rated hotels for your Water Island vacation

Virgin Islands Campground

Virgin Islands Campground

2 out of 5
64 Water Island St. Thomas
0.25 mi from city center
Get rates
With a stay at Virgin Islands Campground in St. Thomas, you'll be by the ocean and within the region of Honeymoon Beach and Virgin Islands National Park.
Kitchen
Parking included
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
2.24 mi from city center
$257 nightly
The price is $286 total per night
$286 total
Apr 1 - Apr 2
Total with taxes and fees
With a stay at Bluebeard's Castle Resort in St. Thomas, you'll be within a 15-minute drive of Bolongo Bay and Magens Bay Beach.
Pool
Hot Tub
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
5.71 mi from city center
$575 nightly
The price is $647 total per night
$647 total
Mar 10 - Mar 11
Total with taxes and fees
Located in St. Thomas, Margaritaville Vacation Club - St. Thomas is in a rural location, a 3-minute drive from Coki Point Beach and 6 minutes from Sapphire Beach.
Pool
Parking included
Don't see what you're looking for?
See all available properties in Water Island
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.