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 $1,311, price is now $919 per person
$919
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $2,193, price is now $1,152 per person
$1,152
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $2,318, price is now $1,346 per person
$1,346
per person
Jun 24 - Jun 29
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 $1,544, price is now $1,110 per person
$1,110
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,921, price is now $1,461 per person
$1,461
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,419, price is now $1,092 per person
$1,092
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,179, price is now $919 per person
$919
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,576, price is now $1,229 per person
$1,229
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,468, price is now $1,146 per person
$1,146
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was $1,446, price is now $1,132 per person
$1,132
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)

3-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 $620, price is now $540 per person
$540
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,751, price is now $890 per person
$890
per person
May 30 - Jun 2
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Sea Palace

Sea Palace

3 out of 5
Price was $672, price is now $577 per person
$577
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
OASIS Apartments Simpson Bay

OASIS Apartments Simpson Bay

4 out of 5
Price was $989, price is now $898 per person
$898
per person
Jun 24 - Jun 27
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Port de Plaisance Resort, Trademark Collection by Wyndham

Port de Plaisance Resort, Trademark Collection by Wyndham

3.5 out of 5
Price was $844, price is now $778 per person
$778
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Baker's Suites

Baker's Suites

3.5 out of 5
Price was $598, price is now $552 per person
$552
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
La Vista Hotel

La Vista Hotel

3 out of 5
Price was $671, price is now $623 per person
$623
per person
Jun 16 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,250, price is now $786 per person
$786
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $835, price is now $686 per person
$686
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $942, price is now $809 per person
$809
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,079, price is now $929 per person
$929
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $874, price is now $754 per person
$754
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $1,032, price is now $823 per person
$823
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $1,888, price is now $1,027 per person
$1,027
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,248, price is now $879 per person
$879
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,472, price is now $1,062 per person
$1,062
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,223, price is now $961 per person
$961
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,365, price is now $1,082 per person
$1,082
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,264, price is now $1,006 per person
$1,006
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,200, price is now $964 per person
$964
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,470, price is now $1,203 per person
$1,203
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $1,371, price is now $1,122 per person
$1,122
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Royal Islander Resort La Plage

Royal Islander Resort La Plage

4 out of 5
Price was $1,294, price is now $1,071 per person
$1,071
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Sapphire Beach Club Resort

Sapphire Beach Club Resort

3 out of 5
Price was $998, price is now $831 per person
$831
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)

5-night 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
Price was $1,311, price is now $919 per person
$919
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $2,193, price is now $1,152 per person
$1,152
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $2,318, price is now $1,346 per person
$1,346
per person
Jun 24 - Jun 29
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 $1,544, price is now $1,110 per person
$1,110
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,921, price is now $1,461 per person
$1,461
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,419, price is now $1,092 per person
$1,092
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,179, price is now $919 per person
$919
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,576, price is now $1,229 per person
$1,229
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,468, price is now $1,146 per person
$1,146
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,446, price is now $1,132 per person
$1,132
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Forest

The Forest

4 out of 5
Price was $1,425, price is now $1,137 per person
$1,137
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $1,977, price is now $1,582 per person
$1,582
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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
Price was $1,489, price is now $1,142 per person
$1,142
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $3,909, price is now $1,803 per person
$1,803
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,817, price is now $1,177 per person
$1,177
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,655, price is now $1,213 per person
$1,213
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Philipsburg (SXM)
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,547, price is now $1,146 per person
$1,146
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,950, price is now $1,452 per person
$1,452
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,856, price is now $1,389 per person
$1,389
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $2,565, price is now $1,930 per person
$1,930
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $1,654, price is now $1,266 per person
$1,266
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Oceans at Divi Little Bay

Oceans at Divi Little Bay

4 out of 5
Price was $2,132, price is now $1,639 per person
$1,639
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Philipsburg (SXM)
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Price was $1,805, price is now $1,404 per person
$1,404
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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
$263 nightly
The price is $263 total per night
$263 total
May 19 - May 20
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.