Search Deals onCaribbean Islands Vacation Packages
Caribbean Islands Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa
Save 100% on your flight
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
The Villas at Simpson Bay Resort
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Princess Heights Luxury Boutique Condo Hotel
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 3.5-star family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orient Bay Beach and Dawn Beach are located nearby.
Holland House Beach Hotel
Save 100% on your flight
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Orient Bay Beach and Maho Beach are located nearby.
Sea Palace by Capital Vacations
Save 100% on your flight
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 3-star beach aparthotel in Philipsburg. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Divi Little Bay Beach Resort
Save 100% on your flight
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Oceans at Divi Little Bay
Save 100% on your flight
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star hotel in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Orient Bay Beach are located nearby.
Hotel La Plantation
Save 100% on your flight
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Orient Bay Beach and Orient Bay are located nearby.
Caribbean Islands Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Caribbean Islands Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Discover Other Travel Deals
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations