New amenities meet old island ways in the village of Boscobel, Jamaica. Situated in the hills of the parish of St. Mary, the Summerwind villa overlooks a former banana port, now the beautifully redeveloped James Bond Beach featuring white sand, water sports centre, restaurant, bar and expansive lawns that frequently host concerts by local and international artists. Nearby city Ochos Rios is a port of call for cruise ships and caters to tourists with scuba diving, restaurants, charter fishing, dolphin encounters, craft markets and fine duty-free shopping.   

Four miles to the east is the historically vibrant Oracabessa. Once a former fishing and banana town, Oracabessa was the site of a freedom fighting movement in the mid-19th century that revitalized the area's economy and artist community. Oracabessa now boasts a well-maintained downtown displaying architecture in the Jamaican vernacular tradition, a popular covered farmer's market, bars, shops and luxury villas including Goldeneye, Golden Clouds and Firefly Estate. Goldeneye has been a home to James Bond novelist Ian Fleming, reggae artist Bob Marley and Island Records founder Chris Blackwell. The Oracabessa Bay Fish Sanctuary protects the area's delicate marine ecosystem and is home to hard and soft corals, moray eels, king crab and lobster. Deeper waters are renowned for sport fishing including marlin and tuna.

Once a modest agricultural community, this beautiful area of the Caribbean has transformed into a vacation paradise. 

If you have ever wanted to see Jamaica...the REAL Jamaica, we invite you to experience Jamaica with us!


Summerwind offers the luxury and convenience of villa living alongside the serenity of nature as only the tropics can provide. Large windows open upon sweeping sea views and landscapes full of life and alive with color. Local Jamaican culture abounds. Shopping and ocean-side activities are plentiful and authentic Jamaican food is only a wish away!

Experience all the wonders that our rental villa has to offer. Relax on the sun-drenched beach, swim, golf, read on the veranda or unwind indoors where blue hand-applied stucco ceilings mimic the ocean waves and the bright tropical sky. Experience a private Jamaican getaway second to none. Experience Summerwind.

Jamaica is only a three and a half hour flight from Milwaukee or Chicago to Montego Bay. Land travel to Summerwind from Montego Bay is approximately two hours. 






The 3500 sq ft house is perched on the hillside overlooking the bright blue Caribbean. The view from the veranda is both soothing and refreshing. Nighttime stargazing is a must! The newly developed James Bond Beach is only one and a half miles from the villa. 

Our three guest suites are on the top floor of the villa and are furnished with large beds (up to two in each room) along with a private bath with shower. Beds include 1 King, 3 Queen and 2 Full. The villa is also equipped with an additional Full bed that can be brought up, couches, love seats and 2 air mattresses. Each room is 16' x 16', large enough to accommodate additional beds if needed. There is an additional suite on the second floor, also with its own bathroom, that can accommodate additional guests. No matter the size of your party, rental of the villa will be private. The staff will be on hand in the lower unit for your assistance and security.

Enjoy delicious, authentic Jamaican food during your stay at Summerwind. Fresh seafood, exotic fruits, locally grown Blue Mountain coffee and rare tropical teas. Visit our Cuisine page for more information. 

Nightlife can be whatever you choose - quiet time on the veranda or dancing to Reggae music in the local nightclubs. The sunsets and sunrises are not to be missed!




 Advantages of staying at Summerwind

"Villa renting has privacy and everything in the villa is yours to use while staying at Summerwind - music, snorkeling gear and food in the kitchen; all with a 'help yourself atmosphere'. Summerwind proudly offers our guests a personal chef as well as on-site staff and security. But you will only see the people you wish to see. The staff will become "invisible" if that is what you desire, appearing only at those times when you ask them to serve you or while homemade Jamaican meals are being prepared. You are welcome to help with food preparation if you wish or just enjoy watching and learning about Jamaican cuisine. We can help you with choices that are endless during your vacation. Land travel can be arranged for you: rental cars, local taxi, and buses. Remember...the best part is that there are no lines, no worrying about missing a meal, and NO CROWDS.  The buttons to push for an elevator are gone....."

Come feel the freedom of living in a Jamaican home!