Cheap Vacations in Caribbean Islands

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Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,394, price is now $768 per person
$768
per person
Nov 27 - Nov 30
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,588, price is now $972 per person
$972
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Save 100% on your flight
Price was $2,034, price is now $1,470 per person
$1,470
per person
Dec 7 - Dec 12
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,303, price is now $996 per person
$996
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Paradiso by Island Properties Online

Paradiso by Island Properties Online

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $3,676, price is now $2,938 per person
$2,938
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Bougainvillea by Island Properties Online

Bougainvillea by Island Properties Online

3.5 out of 5
Oyster Pond
Price was $2,698, price is now $2,218 per person
$2,218
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Alizee by Island Properties Online

Alizee by Island Properties Online

3.5 out of 5
Save 100% on your flight
Price was $3,352, price is now $2,796 per person
$2,796
per person
Nov 27 - Dec 3
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $1,211, price is now $1,040 per person
$1,040
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
La Vista Hotel

La Vista Hotel

3 out of 5
Pelican Key
Price was $1,289, price is now $1,126 per person
$1,126
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Azure Hotel and Art Studio

Azure Hotel and Art Studio

3 out of 5
Price was $1,009, price is now $885 per person
$885
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

3-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Philips Scott House Calinago

Philips Scott House Calinago

3 out of 5
Price was $727, price is now $642 per person
$642
per person
Nov 27 - Nov 30
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,394, price is now $768 per person
$768
per person
Nov 27 - Nov 30
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,281, price is now $755 per person
$755
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,592, price is now $1,030 per person
$1,030
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,594, price is now $1,209 per person
$1,209
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,008, price is now $768 per person
$768
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,095, price is now $892 per person
$892
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Price was $1,396, price is now $1,196 per person
$1,196
per person
Nov 26 - Nov 29
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Philipsburg (SXM)
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Price was $1,473, price is now $1,299 per person
$1,299
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Azure Hotel and Art Studio

Azure Hotel and Art Studio

3 out of 5
Price was $885, price is now $793 per person
$793
per person
Dec 17 - Dec 20
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
La Vista Hotel

La Vista Hotel

3 out of 5
Price was $1,118, price is now $1,004 per person
$1,004
per person
Nov 22 - Nov 25
found 22 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Philipsburg (SXM)
The Forest Suites at Anse Marcel | Boutique Hotel & Restaurant

The Forest Suites at Anse Marcel | Boutique Hotel & Restaurant

4 out of 5
Price was $843, price is now $757 per person
$757
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

4-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
Price was $980, price is now $787 per person
$787
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,588, price is now $972 per person
$972
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,624, price is now $1,098 per person
$1,098
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,432, price is now $1,080 per person
$1,080
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Save 100% on your flight
Price was $1,904, price is now $1,444 per person
$1,444
per person
Dec 16 - Dec 20
found 15 hours ago
Roundtrip flight included
Miami (MIA) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,303, price is now $996 per person
$996
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,816, price is now $1,405 per person
$1,405
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $1,027, price is now $813 per person
$813
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,526, price is now $1,209 per person
$1,209
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Price was $1,183, price is now $958 per person
$958
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Price was $3,346, price is now $2,729 per person
$2,729
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $980, price is now $803 per person
$803
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

5-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $1,046, price is now $784 per person
$784
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,939, price is now $1,079 per person
$1,079
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $2,023, price is now $1,309 per person
$1,309
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,300, price is now $881 per person
$881
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Price was $3,581, price is now $2,514 per person
$2,514
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
Save 100% on your flight
Price was $2,034, price is now $1,470 per person
$1,470
per person
Dec 7 - Dec 12
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,698, price is now $1,230 per person
$1,230
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,358, price is now $1,025 per person
$1,025
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $2,196, price is now $1,664 per person
$1,664
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,585, price is now $1,210 per person
$1,210
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Price was $1,244, price is now $960 per person
$960
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
La Vista Hotel

La Vista Hotel

3 out of 5
Price was $1,967, price is now $1,533 per person
$1,533
per person
Nov 30 - Dec 5
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)

6-7 night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,199, price is now $1,054 per person
$1,054
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $2,581, price is now $1,524 per person
$1,524
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $2,080, price is now $1,528 per person
$1,528
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $2,439, price is now $1,881 per person
$1,881
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $2,799, price is now $2,171 per person
$2,171
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $3,432, price is now $2,681 per person
$2,681
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $2,196, price is now $1,718 per person
$1,718
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Save 100% on your flight
Price was $1,468, price is now $1,152 per person
$1,152
per person
Nov 27 - Dec 3
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $2,345, price is now $1,851 per person
$1,851
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $2,002, price is now $1,596 per person
$1,596
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Paradiso by Island Properties Online

Paradiso by Island Properties Online

4 out of 5
Save 100% on your flight
Price was $3,676, price is now $2,938 per person
$2,938
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Bougainvillea by Island Properties Online

Bougainvillea by Island Properties Online

3.5 out of 5
Save 100% on your flight
Price was $2,882, price is now $2,318 per person
$2,318
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

Top rated hotels for your Caribbean Islands vacation

Grand Hyatt Baha Mar

Grand Hyatt Baha Mar

4.5 out of 5
One Baha Mar Boulevard Nassau New Providence
Free Cancellation
Reserve now, pay when you stay
637 mi from city center
The price is $443 total per night
$443 total
per night
Oct 25 - Oct 26
When you stay at Grand Hyatt Baha Mar in Nassau, you'll be on the beach, within a 5-minute drive of Royal Blue Golf Club and Cable Beach.
Wyndham Alltra Punta Cana All-Inclusive Resort

Wyndham Alltra Punta Cana All-Inclusive Resort

4 out of 5
Playas Uvero Alto Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
120.96 mi from city center
The price is $271 total per night
$271 total
per night
Oct 25 - Oct 26
Located in Punta Cana (Uvero Alto), Wyndham Alltra Punta Cana All-Inclusive Resort is within a 15-minute drive of Sirenis Aquagames Water Park and Macao Beach.
Hotel Riu Montego Bay - Adults Only - All Inclusive

Hotel Riu Montego Bay - Adults Only - All Inclusive

4 out of 5
Mahoe Bay, Ironshore Montego Bay Saint James
489.91 mi from city center
Get rates
When you stay at Hotel Riu Montego Bay - Adults Only - All Inclusive in Montego Bay, you'll be on the beach, within a 15-minute drive of Rose Hall Great House and Doctor's Cave Beach.
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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.