The most convenient place to find gay-friendly hotels in Medellín is in El Poblado, the district in the south where most of the scene is located. If you live here, the bars and clubs around Provenza and Parque Lleras are practically on your doorstep and you can get by with short distances in the evening. El Poblado is considered prosperous, safe and developed for tourism, with many hotels of different categories, restaurants and cafés. The fact that two men book a double room is usually not an issue.
You are not fixed on El Poblado. A quieter, very local alternative is Laureles-Estadio, with wide, tree-lined streets and shorter distances to the stadium and Avenida Nutibara, but a little further away from the nighttime scene. If you want to live centrally and culturally, look around the area around the center, which is lively during the day but is considered less pleasant in the evening. The districts are well connected via the metro, which makes the choice of location more flexible. Which area is worthwhile depends on what is in the foreground: night owls are best off in El Poblado, guests seeking peace and quiet in Laureles. If your visit falls during the Pride days at the end of June, plan early, then central houses in El Poblado are quickly booked up. Because of the mild climate, Medellín is often called the city of eternal spring, but you rarely need air conditioning.