As jitterbug said, Tim Bamboo is within walking distance to town. No pool. AC rooms and I think are $60/night. Restaurant & bar. Breakfast may be included.

Winnifred Breeze in Fairy Hill is a great guesthouse, but not easily assessable to the main road. A car/driver is recommended. I’ve walked down to the road (less than 5 minutes), but not up as the road is steep. The spacious AC rooms are around $60/night. No bar.

Another Guesthouse I’m considering is Fairy Hill Palms in Fairy Hill Gardens. You are the only occupant in this two bedroom house. Walking distance to Winnifred Beach, Boston and Blue Lagoon. No AC.

You might also look into The Polish Princess Guesthouse. Another place I’m considering. I don’t have a lot of details to share about this place other than I met the owner and adore her and admire the way she runs the business. The reviews are good.

Being first time overnighters, my recommendation is Match Resort off Folly Road. It’s a 7 minute drive from down town Port Antonio, about less than 15 minutes from the San San and Boston areas. They have a restaurant & bar plus a pool. WIFI AC Rooms are also around $70/night. Friendly staff and excellent food. Easy, two minute walk from the hotel to the main road to catch a taxi.

Although not as plentiful as Negril, there is no lack of red plate drivers in Port Antonio. But a lot don’t drive at night and are usually concentrated down town. Once you leave the Knutsford bus, hail for one and secure him for your stay so you can call that specific driver when needed. The wait for one on the road may not be long, but the cars fill up with folks coming from down town.

Frenchman’s Cove beach is gorgeous, but expensive. $10 to get in, more for the lounger and lots more for the food and drinks. If you are planning to spend the entire day there it’s going to co$t you. But Winnifred is a challenge to get to due to the harsh road, but a favorite of visitors. Water shoes are a highly recommended due to the rocky sparse, rocky spots. See a rasta name I-Cliff for lounge chairs and cold red stripes.