Cheap Vacations in Caribbean Islands

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Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $1,620, price is now $1,297 per person
$1,297
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,921, price is now $1,387 per person
$1,387
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,822, price is now $1,334 per person
$1,334
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,925, price is now $1,445 per person
$1,445
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,962, price is now $1,618 per person
$1,618
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,660, price is now $1,390 per person
$1,390
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4 out of 5
Oyster Pond
Price was $2,237, price is now $1,883 per person
$1,883
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $1,716, price is now $1,454 per person
$1,454
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $2,974, price is now $2,524 per person
$2,524
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,602, price is now $1,372 per person
$1,372
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)

3-night Caribbean Islands vacations

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

La Vista Hotel

3 out of 5
Price was $881, price is now $747 per person
$747
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,921, price is now $1,387 per person
$1,387
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,822, price is now $1,334 per person
$1,334
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip 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 $1,620, price is now $1,297 per person
$1,297
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,962, price is now $1,618 per person
$1,618
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,660, price is now $1,390 per person
$1,390
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,716, price is now $1,454 per person
$1,454
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4 out of 5
Price was $1,755, price is now $1,490 per person
$1,490
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $2,974, price is now $2,524 per person
$2,524
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,443, price is now $1,231 per person
$1,231
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,602, price is now $1,372 per person
$1,372
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,514, price is now $1,303 per person
$1,303
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $926, price is now $645 per person
$645
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,546, price is now $857 per person
$857
per person
Dec 11 - Dec 15
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
Save 100% on your flight
Price was $1,710, price is now $956 per person
$956
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,242, price is now $703 per person
$703
per person
Dec 9 - Dec 13
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,684, price is now $1,110 per person
$1,110
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $1,450, price is now $1,015 per person
$1,015
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,353, price is now $966 per person
$966
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Save 100% on your flight
Price was $3,037, price is now $2,215 per person
$2,215
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,178, price is now $859 per person
$859
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $928, price is now $679 per person
$679
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $1,925, price is now $1,445 per person
$1,445
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Price was $1,120, price is now $844 per person
$844
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)

5-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Azure Hotel and Art Studio

Azure Hotel and Art Studio

3 out of 5
Price was $1,061, price is now $865 per person
$865
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,054, price is now $1,088 per person
$1,088
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,819, price is now $990 per person
$990
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $1,731, price is now $952 per person
$952
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $1,363, price is now $967 per person
$967
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $2,819, price is now $2,035 per person
$2,035
per person
Dec 3 - Dec 8
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,246, price is now $931 per person
$931
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
La Vista Hotel

La Vista Hotel

3 out of 5
Save 100% on your flight
Price was $1,704, price is now $1,288 per person
$1,288
per person
Nov 29 - Dec 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,400, price is now $1,120 per person
$1,120
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Cupecoy Beach Club

Cupecoy Beach Club

3 out of 5
Price was $1,599, price is now $1,307 per person
$1,307
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Bougainvillea by Island Properties Online

Bougainvillea by Island Properties Online

3.5 out of 5
Price was $2,955, price is now $2,534 per person
$2,534
per person
Dec 3 - Dec 8
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Price was $1,174, price is now $1,025 per person
$1,025
per person
Dec 8 - Dec 13
found 20 hours 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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,358, price is now $888 per person
$888
per person
Dec 5 - Dec 12
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $2,552, price is now $1,336 per person
$1,336
per person
Dec 10 - Dec 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $2,431, price is now $1,351 per person
$1,351
per person
Nov 30 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,872, price is now $1,665 per person
$1,665
per person
Dec 5 - Dec 12
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Save 100% on your flight
Price was $2,936, price is now $1,983 per person
$1,983
per person
Dec 5 - Dec 12
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $2,044, price is now $1,414 per person
$1,414
per person
Dec 5 - Dec 12
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Belair Beach Hotel

Belair Beach Hotel

3 out of 5
Save 100% on your flight
Price was $1,678, price is now $1,191 per person
$1,191
per person
Dec 5 - Dec 12
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,853, price is now $2,040 per person
$2,040
per person
Dec 5 - Dec 12
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $2,094, price is now $1,517 per person
$1,517
per person
Dec 5 - Dec 12
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Save 100% on your flight
Price was $1,378, price is now $1,002 per person
$1,002
per person
Dec 5 - Dec 12
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Horizon View Beach Hotel

Horizon View Beach Hotel

3 out of 5
Price was $1,514, price is now $1,119 per person
$1,119
per person
Dec 5 - Dec 12
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,151, price is now $1,599 per person
$1,599
per person
Dec 5 - Dec 12
found 16 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
$368 nightly
The price is $403 total per night
$403 total
Nov 1 - Nov 2
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.
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
$253 nightly
The price is $253 total per night
$253 total
Oct 20 - Oct 21
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.
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 10-minute drive of Montego Bay Convention Centre and Rose Hall Great House.
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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.