Cheap Vacations in Caribbean Islands

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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 $2,050, price is now $1,647 per person
$1,647
per person
Apr 17 - Apr 23
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
Pelican Key
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)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Save 100% on your flight
Price was $3,354, price is now $2,028 per person
$2,028
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
Oyster Pond
Price was $2,703, price is now $1,869 per person
$1,869
per person
Apr 17 - Apr 23
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
Price was $2,241, price is now $1,658 per person
$1,658
per person
Apr 17 - Apr 23
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
Point Blanche
Price was $2,686, price is now $1,991 per person
$1,991
per person
Apr 17 - Apr 23
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 $2,607, price is now $1,950 per person
$1,950
per person
Apr 17 - Apr 23
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 $3,030, price is now $2,289 per person
$2,289
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $2,724, price is now $2,085 per person
$2,085
per person
Apr 17 - Apr 23
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 $2,510, price is now $1,993 per person
$1,993
per person
Apr 17 - Apr 23
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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $791, price is now $567 per person
$567
per person
Apr 14 - Apr 17
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)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,014, price is now $619 per person
$619
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
Save 100% on your flight
Price was $1,209, price is now $769 per person
$769
per person
Apr 14 - Apr 17
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 23 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 $783, price is now $571 per person
$571
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 $951, price is now $703 per person
$703
per person
Apr 14 - Apr 17
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)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,006, price is now $794 per person
$794
per person
Apr 14 - Apr 17
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 $1,114, price is now $882 per person
$882
per person
Apr 14 - Apr 17
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)
Commodore Suites, SureStay Collection by Best Western

Commodore Suites, SureStay Collection by Best Western

3.5 out of 5
Price was $910, price is now $740 per person
$740
per person
Apr 14 - Apr 17
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 $1,141, price is now $952 per person
$952
per person
Apr 16 - 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
Save 100% on your flight
Price was $2,145, price is now $1,198 per person
$1,198
per person
Apr 16 - 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
Save 100% on your flight
Price was $1,984, price is now $1,148 per person
$1,148
per person
Apr 16 - 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 $1,607, price is now $1,060 per person
$1,060
per person
Apr 16 - 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 $1,831, price is now $1,371 per person
$1,371
per person
Apr 16 - 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 $1,299, price is now $992 per person
$992
per person
Apr 16 - Apr 20
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 $1,543, price is now $1,197 per person
$1,197
per person
Apr 16 - 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 $1,792, price is now $1,402 per person
$1,402
per person
Apr 16 - Apr 20
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 $1,595, price is now $1,278 per person
$1,278
per person
Apr 16 - Apr 20
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 $1,470, price is now $1,192 per person
$1,192
per person
Apr 16 - 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 $1,177, price is now $984 per person
$984
per person
Apr 16 - 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 $1,268, price is now $1,070 per person
$1,070
per person
Apr 30 - May 4
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 $1,043, price is now $781 per person
$781
per person
Apr 20 - Apr 25
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
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 $2,277, price is now $1,188 per person
$1,188
per person
Apr 20 - Apr 25
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 $1,692, price is now $1,035 per person
$1,035
per person
Apr 20 - Apr 25
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
Save 100% on your flight
Price was $1,931, price is now $1,267 per person
$1,267
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 $1,787, price is now $1,208 per person
$1,208
per person
Apr 15 - 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 $1,141, price is now $785 per person
$785
per person
Apr 26 - May 1
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 $1,385, price is now $957 per person
$957
per person
Apr 15 - Apr 20
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 $1,395, price is now $981 per person
$981
per person
Apr 20 - Apr 25
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 $1,677, price is now $1,328 per person
$1,328
per person
Apr 20 - Apr 25
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 $1,298, price is now $1,028 per person
$1,028
per person
Apr 20 - Apr 25
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 $2,413, price is now $1,941 per person
$1,941
per person
Apr 20 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

6-7 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
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 24 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
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)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Save 100% on your flight
Price was $3,354, price is now $2,028 per person
$2,028
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
Price was $2,703, price is now $1,869 per person
$1,869
per person
Apr 17 - Apr 23
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 $2,241, price is now $1,658 per person
$1,658
per person
Apr 17 - Apr 23
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 $2,686, price is now $1,991 per person
$1,991
per person
Apr 17 - Apr 23
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 $2,607, price is now $1,950 per person
$1,950
per person
Apr 17 - Apr 23
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 $3,030, price is now $2,289 per person
$2,289
per person
Apr 17 - Apr 23
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 $2,724, price is now $2,085 per person
$2,085
per person
Apr 17 - Apr 23
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 $2,510, price is now $1,993 per person
$1,993
per person
Apr 17 - Apr 23
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 $2,050, price is now $1,647 per person
$1,647
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip 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 $3,069, price is now $2,519 per person
$2,519
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip 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.
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.
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.
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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.