The best time of year would be February-March. the weather is warmest, least amount of rain and least amount of wind. Mostly sunny pleasant days. It is still in season for most places however tourist attractions are quieter than over Dec-Jan peak season. Glencairn is a lovely safe, residential area. As long as you rent a car you will be able to visit most of Cape Towns sights within an hours drive. Cape Town CBD is about 35 minutes drive. Stellenbosch wine-lands about 50 minutes. Cape point nature reserve about 20 minutes.