The growth and yield of tomatoes in greenhouses covered by heat insulation film were investigated in Ishigaki, a subtropical area of Japan with high temperature and high solar radiation. High-density planting of tomatoes was carried out in June, July, August, October, and November, with a low node-order pinching system. The plants were grown in two greenhouses, one covered by a thermal barrier film (TBF) for heat insulation and the other covered by a polyolefin film (PO). Under TBF, the maximum temperature was up to 3.6°C lower than that under PO, and the mean temperature was 0.4°C lower. The leaf area index (LAI) of the June planting was 3.0 under TBF and 3.4 under PO, significantly lower than the LAIs of the other plantings, which ranged from 3.9 to 5.4. The specific leaf area (SLA) varied with the cultivation season, with that under TBF and PO being highest in November plantings grown in winter. SLA under TBF was higher than that under PO in the same cultivation seasons. The amount of total aboveground dry matter was significantly lower in the June planting under TBF and showed no difference in other plantings. Distribution to fruit was higher under TBF than under PO, especially in summer cultivation. The yields under TBF were significantly higher than those under PO in the July planting, and the yields under PO were significantly higher in the November planting. Under TBF, the rate of fruit cracking was reduced in the June, July, and August plantings. Under TBF and PO, plantings in October and November produced puffy fruits. The light use efficiency under TBF was higher than that under PO in the same cultivation seasons, apart from the June planting. Tomato cultivation under TBF reduced the damage from intense solar radiation during summer. TBF enabled penetration of sufficient solar radiation to distribute photosynthates to each part of the plant because of a limited sink and abundant solar radiation in a subtropical summer. These results indicate that TBF and sink-limited cultivation are effective systems for use in the high temperature and high solar radiation environments of tropical and subtropical regions.