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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Maho
Price was $890, price is now $640 per person
$640
per person
Apr 25 - Apr 30
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
Price was $2,286, price is now $959 per person
$959
per person
Apr 25 - Apr 30
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 $1,988, price is now $984 per person
$984
per person
Apr 25 - Apr 30
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
Oyster Pond
Price was $1,185, price is now $724 per person
$724
per person
Apr 25 - Apr 30
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 $1,683, price is now $1,034 per person
$1,034
per person
Apr 25 - Apr 30
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 $2,036, price is now $1,261 per person
$1,261
per person
Apr 25 - Apr 30
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
Price was $1,973, price is now $1,312 per person
$1,312
per person
Apr 25 - Apr 30
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 $1,145, price is now $789 per person
$789
per person
Apr 25 - Apr 30
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 $1,638, price is now $1,141 per person
$1,141
per person
Apr 25 - Apr 30
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 $1,405, price is now $1,011 per person
$1,011
per person
Apr 27 - May 2
found 1 day ago
Roundtrip 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 $982, price is now $878 per person
$878
per person
Apr 17 - Apr 20
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
Price was $1,772, price is now $1,100 per person
$1,100
per person
Apr 17 - Apr 20
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 $1,671, price is now $1,177 per person
$1,177
per person
Apr 17 - Apr 20
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 $1,385, price is now $1,000 per person
$1,000
per person
Apr 17 - Apr 20
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 $1,715, price is now $1,365 per person
$1,365
per person
Apr 17 - Apr 20
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 $1,524, price is now $1,241 per person
$1,241
per person
Apr 17 - Apr 20
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 $1,154, price is now $947 per person
$947
per person
Apr 17 - Apr 20
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 $1,083, price is now $903 per person
$903
per person
Apr 17 - Apr 20
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 $1,449, price is now $1,209 per person
$1,209
per person
Apr 23 - Apr 26
found 23 hours 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 $1,377, price is now $1,157 per person
$1,157
per person
Apr 17 - Apr 20
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
Price was $1,544, price is now $1,367 per person
$1,367
per person
May 5 - May 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,303, price is now $1,172 per person
$1,172
per person
May 5 - May 8
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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $783, price is now $627 per person
$627
per person
Apr 29 - 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
Price was $1,816, price is now $945 per person
$945
per person
Apr 29 - May 3
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 $2,137, price is now $1,190 per person
$1,190
per person
Apr 19 - Apr 23
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 $1,221, price is now $752 per person
$752
per person
Apr 29 - May 3
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 $1,062, price is now $730 per person
$730
per person
Apr 29 - May 3
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 $943, price is now $682 per person
$682
per person
Apr 29 - May 3
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 $1,617, price is now $1,183 per person
$1,183
per person
Apr 29 - May 3
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 $1,552, price is now $1,166 per person
$1,166
per person
Apr 29 - May 3
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 $1,243, price is now $944 per person
$944
per person
Apr 29 - May 3
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 $2,116, price is now $1,670 per person
$1,670
per person
Apr 26 - Apr 30
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 $1,496, price is now $1,206 per person
$1,206
per person
Apr 19 - Apr 23
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 $1,200, price is now $968 per person
$968
per person
Apr 29 - May 3
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.
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $890, price is now $640 per person
$640
per person
Apr 25 - Apr 30
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
Price was $2,286, price is now $959 per person
$959
per person
Apr 25 - Apr 30
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 $1,988, price is now $984 per person
$984
per person
Apr 25 - Apr 30
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 $1,185, price is now $724 per person
$724
per person
Apr 25 - Apr 30
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 $1,683, price is now $1,034 per person
$1,034
per person
Apr 25 - Apr 30
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 $2,036, price is now $1,261 per person
$1,261
per person
Apr 25 - Apr 30
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 $1,973, price is now $1,312 per person
$1,312
per person
Apr 25 - Apr 30
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 $1,145, price is now $789 per person
$789
per person
Apr 25 - Apr 30
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 $1,638, price is now $1,141 per person
$1,141
per person
Apr 25 - Apr 30
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 $1,405, price is now $1,011 per person
$1,011
per person
Apr 27 - May 2
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 $1,604, price is now $1,179 per person
$1,179
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Cupecoy Beach Club

Cupecoy Beach Club

3 out of 5
Price was $1,689, price is now $1,331 per person
$1,331
per person
May 2 - May 7
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)

6-7 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
Save 100% on your flight
Price was $1,167, price is now $734 per person
$734
per person
Apr 26 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $3,008, price is now $1,167 per person
$1,167
per person
Apr 26 - May 3
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 $2,569, price is now $1,256 per person
$1,256
per person
Apr 20 - Apr 26
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
Save 100% on your flight
Price was $1,883, price is now $1,019 per person
$1,019
per person
Apr 26 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,370, price is now $785 per person
$785
per person
Apr 26 - May 3
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 $2,609, price is now $1,559 per person
$1,559
per person
Apr 26 - May 3
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 $2,385, price is now $1,453 per person
$1,453
per person
Apr 26 - May 3
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
Save 100% on your flight
Price was $1,883, price is now $1,214 per person
$1,214
per person
Apr 26 - May 3
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
Save 100% on your flight
Price was $1,446, price is now $937 per person
$937
per person
Apr 26 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $2,258, price is now $1,562 per person
$1,562
per person
Apr 20 - Apr 26
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 $1,697, price is now $1,191 per person
$1,191
per person
Apr 20 - Apr 26
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 $1,909, price is now $1,357 per person
$1,357
per person
May 1 - May 8
found 24 hours 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
637 mi from city center
The price is $465 total per night
$465 total
per night
Apr 13 - Apr 14
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
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
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
The price is $373 total per night
$373 total
per night
Apr 12 - Apr 13
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
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.