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 $906, price is now $695 per person
$695
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,744, price is now $867 per person
$867
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,164, price is now $771 per person
$771
per person
Jun 18 - Jun 20
found 23 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $1,011, price is now $701 per person
$701
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,175, price is now $843 per person
$843
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,222, price is now $931 per person
$931
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,086, price is now $833 per person
$833
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Oyster Pond
Price was $1,904, price is now $1,465 per person
$1,465
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $1,091, price is now $847 per person
$847
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,120, price is now $877 per person
$877
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

3-night Caribbean Islands vacations

Price found within the past 48 hours. Click for updated prices.
Sea Palace

Sea Palace

3 out of 5
Price was $705, price is now $629 per person
$629
per person
Jun 9 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,437, price is now $680 per person
$680
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,292, price is now $707 per person
$707
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $906, price is now $644 per person
$644
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,062, price is now $763 per person
$763
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $971, price is now $744 per person
$744
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,018, price is now $782 per person
$782
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $827, price is now $640 per person
$640
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,003, price is now $782 per person
$782
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,084, price is now $860 per person
$860
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Hilton Vacation Club Royal Palm St. Maarten

Hilton Vacation Club Royal Palm St. Maarten

4 out of 5
Price was $1,221, price is now $1,081 per person
$1,081
per person
Jun 9 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten

4 out of 5
Price was $1,571, price is now $1,465 per person
$1,465
per person
Jun 9 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $906, price is now $695 per person
$695
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,744, price is now $867 per person
$867
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,754, price is now $995 per person
$995
per person
Jun 24 - Jun 28
found 1 hour ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,011, price is now $701 per person
$701
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,175, price is now $843 per person
$843
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,222, price is now $931 per person
$931
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,086, price is now $833 per person
$833
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,091, price is now $847 per person
$847
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,120, price is now $877 per person
$877
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,496, price is now $1,186 per person
$1,186
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,217, price is now $979 per person
$979
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Royal Islander Resort La Plage

Royal Islander Resort La Plage

4 out of 5
Price was $1,076, price is now $871 per person
$871
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

5-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
Price was $2,017, price is now $933 per person
$933
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $2,302, price is now $1,241 per person
$1,241
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,879, price is now $1,214 per person
$1,214
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,638, price is now $1,182 per person
$1,182
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,788, price is now $1,337 per person
$1,337
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $2,391, price is now $1,796 per person
$1,796
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,553, price is now $1,172 per person
$1,172
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,709, price is now $1,292 per person
$1,292
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,323, price is now $1,017 per person
$1,017
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,848, price is now $1,450 per person
$1,450
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,740, price is now $1,386 per person
$1,386
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $1,376, price is now $1,098 per person
$1,098
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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
Price was $1,641, price is now $1,204 per person
$1,204
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $2,797, price is now $1,351 per person
$1,351
per person
Jun 1 - Jun 8
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
Save 100% on your flight
Price was $3,096, price is now $1,535 per person
$1,535
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 $2,583, price is now $1,549 per person
$1,549
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,316, price is now $1,548 per person
$1,548
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Save 100% on your flight
Price was $3,144, price is now $2,179 per person
$2,179
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $2,292, price is now $1,649 per person
$1,649
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,963, price is now $1,417 per person
$1,417
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $2,150, price is now $1,562 per person
$1,562
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $2,441, price is now $1,841 per person
$1,841
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $1,715, price is now $1,317 per person
$1,317
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Price was $1,904, price is now $1,465 per person
$1,465
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)

Top rated hotels for your Caribbean Islands vacation

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
120.96 mi from city center
$259 nightly
The price is $259 total per night
$259 total
Jun 1 - Jun 2
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
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
$393 nightly
The price is $430 total per night
$430 total
May 31 - Jun 1
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
Princess Grand Jamaica Resort - All Inclusive

Princess Grand Jamaica Resort - All Inclusive

4.5 out of 5
Industry Cove Green Island Hanover
515.39 mi from city center
$455 nightly
The price is $455 total per night
$455 total
May 4 - May 5
Total with taxes and fees
When you stay at Princess Grand Jamaica Resort - All Inclusive in Green Island, you'll be on the beach and 6 minutes by car from Half Moon Beach.
Pool
Breakfast included
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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.