Cheap Vacations in Caribbean Islands

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Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,100, price is now $772 per person
$772
per person
Dec 9 - 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
Oyster Pond
Price was $2,119, price is now $1,115 per person
$1,115
per person
Dec 9 - 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
Pelican Key
Price was $1,898, price is now $1,048 per person
$1,048
per person
Dec 9 - Dec 14
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
Pelican Key
Save 100% on your flight
Price was $1,430, price is now $876 per person
$876
per person
Dec 13 - Dec 17
found 9 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
Point Blanche
Price was $1,793, price is now $1,143 per person
$1,143
per person
Dec 9 - 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 $3,758, price is now $2,447 per person
$2,447
per person
Dec 9 - 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 $1,623, price is now $1,123 per person
$1,123
per person
Dec 9 - 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 $2,097, price is now $1,509 per person
$1,509
per person
Dec 9 - Dec 14
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 $1,453, price is now $1,048 per person
$1,048
per person
Dec 9 - 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
Downtown Philipsburg
Price was $1,140, price is now $833 per person
$833
per person
Dec 9 - Dec 14
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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,008, price is now $620 per person
$620
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,501, price is now $948 per person
$948
per person
Dec 10 - Dec 13
found 10 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 $1,349, price is now $878 per person
$878
per person
Dec 10 - Dec 13
found 10 hours 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 $1,499, price is now $1,093 per person
$1,093
per person
Dec 10 - Dec 13
found 10 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 $1,305, price is now $958 per person
$958
per person
Dec 10 - Dec 13
found 10 hours 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 $1,204, price is now $935 per person
$935
per person
Dec 10 - Dec 13
found 10 hours 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 $911, price is now $721 per person
$721
per person
Dec 10 - Dec 13
found 10 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 $1,101, price is now $872 per person
$872
per person
Dec 10 - Dec 13
found 10 hours 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 $889, price is now $709 per person
$709
per person
Dec 10 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Price was $1,058, price is now $861 per person
$861
per person
Dec 10 - Dec 13
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
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 $890, price is now $729 per person
$729
per person
Dec 10 - Dec 13
found 10 hours 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 $2,051, price is now $1,704 per person
$1,704
per person
Dec 10 - Dec 13
found 10 hours 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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,047, price is now $752 per person
$752
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 $1,832, price is now $1,021 per person
$1,021
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 $1,661, price is now $975 per person
$975
per person
Dec 10 - Dec 14
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 $1,430, price is now $876 per person
$876
per person
Dec 13 - Dec 17
found 9 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 $1,571, price is now $1,039 per person
$1,039
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 $1,428, price is now $1,033 per person
$1,033
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 $1,826, price is now $1,354 per person
$1,354
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 $3,210, price is now $2,396 per person
$2,396
per person
Dec 10 - Dec 14
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 $1,564, price is now $1,171 per person
$1,171
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $1,049, price is now $805 per person
$805
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
Price was $2,098, price is now $1,616 per person
$1,616
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
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 $985, price is now $761 per person
$761
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.
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 $1,037, price is now $771 per person
$771
per person
Dec 9 - 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 $2,119, price is now $1,115 per person
$1,115
per person
Dec 9 - 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 $1,898, price is now $1,048 per person
$1,048
per person
Dec 9 - Dec 14
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 $1,894, price is now $1,100 per person
$1,100
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,793, price is now $1,143 per person
$1,143
per person
Dec 9 - 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 $3,758, price is now $2,447 per person
$2,447
per person
Dec 9 - 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 $1,623, price is now $1,123 per person
$1,123
per person
Dec 9 - 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 $1,100, price is now $772 per person
$772
per person
Dec 9 - 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 $2,097, price is now $1,509 per person
$1,509
per person
Dec 9 - Dec 14
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 $1,453, price is now $1,048 per person
$1,048
per person
Dec 9 - 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 $1,140, price is now $833 per person
$833
per person
Dec 9 - 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
Price was $2,359, price is now $1,766 per person
$1,766
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)

6-7 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 $1,135, price is now $824 per person
$824
per person
Dec 9 - Dec 15
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 $2,453, price is now $1,247 per person
$1,247
per person
Dec 9 - Dec 15
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 $2,198, price is now $1,171 per person
$1,171
per person
Dec 9 - Dec 15
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 $2,062, price is now $1,267 per person
$1,267
per person
Dec 9 - Dec 15
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 $1,276, price is now $836 per person
$836
per person
Dec 9 - Dec 15
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 $1,917, price is now $1,292 per person
$1,292
per person
Dec 9 - Dec 15
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 $2,411, price is now $1,676 per person
$1,676
per person
Dec 9 - Dec 15
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 $1,654, price is now $1,167 per person
$1,167
per person
Dec 9 - Dec 15
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 $1,279, price is now $910 per person
$910
per person
Dec 9 - Dec 15
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 $2,509, price is now $1,899 per person
$1,899
per person
Nov 28 - Dec 5
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,342, price is now $1,017 per person
$1,017
per person
Dec 10 - Dec 16
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 $1,564, price is now $1,187 per person
$1,187
per person
Dec 9 - Dec 15
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
$358 nightly
The price is $392 total per night
$392 total
Nov 4 - Nov 5
Total with taxes and fees
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.
Pool
Spa
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
$271 nightly
The price is $271 total per night
$271 total
Oct 25 - Oct 26
Total with taxes and fees
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.
Pool
Breakfast included
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.
Pool
Hot Tub
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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.