Cheap Vacations in Caribbean Islands

Choose two or more items and save on your trip:

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 $1,114, price is now $718 per person
$718
per person
Apr 24 - Apr 27
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 $2,210, price is now $1,098 per person
$1,098
per person
Apr 12 - Apr 18
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 $2,399, price is now $1,431 per person
$1,431
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,334, price is now $885 per person
$885
per person
Apr 12 - Apr 18
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
Save 100% on your flight
Price was $1,713, price is now $1,197 per person
$1,197
per person
Apr 12 - Apr 18
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
Downtown Philipsburg
Save 100% on your flight
Price was $2,131, price is now $1,581 per person
$1,581
per person
Apr 12 - Apr 18
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
Save 100% on your flight
Price was $2,150, price is now $1,635 per person
$1,635
per person
Apr 12 - Apr 18
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
Point Blanche
Save 100% on your flight
Price was $1,763, price is now $1,343 per person
$1,343
per person
Apr 12 - Apr 18
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
Save 100% on your flight
Price was $1,598, price is now $1,248 per person
$1,248
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,732, price is now $1,357 per person
$1,357
per person
Apr 12 - Apr 18
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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $769, price is now $639 per person
$639
per person
Apr 24 - Apr 27
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 $1,441, price is now $725 per person
$725
per person
Apr 14 - Apr 17
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 $1,442, price is now $892 per person
$892
per person
Apr 24 - Apr 27
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 $1,114, price is now $718 per person
$718
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,109, price is now $798 per person
$798
per person
May 7 - May 10
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 $1,026, price is now $740 per person
$740
per person
Apr 24 - Apr 27
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 $1,286, price is now $957 per person
$957
per person
Apr 24 - Apr 27
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 $1,205, price is now $922 per person
$922
per person
Apr 14 - Apr 17
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 $1,097, price is now $841 per person
$841
per person
Apr 24 - Apr 27
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 $1,112, price is now $878 per person
$878
per person
Apr 24 - Apr 27
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 $923, price is now $748 per person
$748
per person
Apr 14 - Apr 17
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 $910, price is now $738 per person
$738
per person
Apr 24 - Apr 27
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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $890, price is now $671 per person
$671
per person
Apr 24 - Apr 28
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 $1,700, price is now $919 per person
$919
per person
Apr 24 - Apr 28
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 $2,399, price is now $1,431 per person
$1,431
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip 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 $1,349, price is now $840 per person
$840
per person
Apr 24 - Apr 28
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 $1,562, price is now $1,093 per person
$1,093
per person
Apr 24 - Apr 28
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 $1,168, price is now $835 per person
$835
per person
Apr 24 - Apr 28
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 $1,063, price is now $781 per person
$781
per person
Apr 24 - Apr 28
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 $1,327, price is now $1,007 per person
$1,007
per person
Apr 24 - Apr 28
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 $1,326, price is now $1,041 per person
$1,041
per person
Apr 24 - Apr 28
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 $2,046, price is now $1,634 per person
$1,634
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip 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 $2,182, price is now $1,761 per person
$1,761
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,724, price is now $1,424 per person
$1,424
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)

5-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,370, price is now $1,120 per person
$1,120
per person
Apr 28 - May 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 $2,245, price is now $1,154 per person
$1,154
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,537, price is now $1,541 per person
$1,541
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip 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 $2,102, price is now $1,424 per person
$1,424
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $2,369, price is now $1,669 per person
$1,669
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,732, price is now $1,240 per person
$1,240
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $2,042, price is now $1,484 per person
$1,484
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip 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 $2,639, price is now $2,109 per person
$2,109
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $2,282, price is now $1,833 per person
$1,833
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $1,454, price is now $1,169 per person
$1,169
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,941, price is now $1,586 per person
$1,586
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $2,089, price is now $1,716 per person
$1,716
per person
Apr 16 - Apr 21
found 1 day 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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,334, price is now $885 per person
$885
per person
Apr 12 - Apr 18
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 $2,210, price is now $1,098 per person
$1,098
per person
Apr 12 - Apr 18
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 $3,501, price is now $1,924 per person
$1,924
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,063, price is now $1,262 per person
$1,262
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,619, price is now $1,001 per person
$1,001
per person
May 5 - May 11
found 12 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
Save 100% on your flight
Price was $1,713, price is now $1,197 per person
$1,197
per person
Apr 12 - Apr 18
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 $2,131, price is now $1,581 per person
$1,581
per person
Apr 12 - Apr 18
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
Save 100% on your flight
Price was $2,150, price is now $1,635 per person
$1,635
per person
Apr 12 - Apr 18
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
Save 100% on your flight
Price was $1,763, price is now $1,343 per person
$1,343
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $1,265, price is now $977 per person
$977
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip 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 $1,631, price is now $1,266 per person
$1,266
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Save 100% on your flight
Price was $1,598, price is now $1,248 per person
$1,248
per person
Apr 12 - Apr 18
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
$479 nightly
The price is $525 total per night
$525 total
Apr 12 - Apr 13
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
Serenade Punta Cana Beach & Spa Resort - All Inclusive

Serenade Punta Cana Beach & Spa Resort - All Inclusive

4.5 out of 5
Carretera Cabeza de Toro Punta Cana La Altagracia
Free Cancellation
Reserve now, pay when you stay
134.26 mi from city center
Get rates
With a stay at Serenade Punta Cana Beach & Spa Resort - All Inclusive in Punta Cana, you'll be within a 15-minute drive of Cabeza de Toro Beach and Downtown Punta Cana.
On private beach
Pool
Hotel Riu Republica - Adults only - All Inclusive

Hotel Riu Republica - Adults only - All Inclusive

4 out of 5
Playa Arena Gorda Punta Cana
126.6 mi from city center
Get rates
With a stay at Hotel Riu Republica - Adults only - All Inclusive in Punta Cana (Bávaro), you'll be within a 15-minute drive of Arena Gorda Beach and Cana Bay Golf Club.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Caribbean Islands
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.