This Negril, Jamaica resort is clothing-optional and offers both all-inclusive and B&B packages. Families are welcome along with couples. There's no real beach, but you can swim off the rocks at the base of the resort, and a free shuttle runs to nearby Negril. The 30-room hotel has a spa and rooms with oceanfront verandas, and suites.
The Rex Resorts' Hawksbill Beach Resort in Antigua has a secluded clothing-optional beach -- the only one on the island. The resort has 26 rooms on 37 acres of lush property, including detached cottages. All-inclusive rates include room, drinks and dining, water sports, tennis, entertainment, and tips.
LaSource is not a nudist resort but does have a nude (mostly topless) beach. The Grenada resort has 100 rooms on Pink Gin Beach, four restaurants, and a dedication to holistic relaxation and exercise through yoga, tai chi, and other activities. LaSource has multiple restaurants and bars as well as a full array of land and water sports, and welcomes solo travelers as well as couples.
A handful of charter yachts in the Caribbean, such as the Billy Jean and the Endless Summer II out of the British Virgin Islands, specialize in nude cruises. Such charters are especially popular for small groups looking for a degree of privacy on their vacation. Nudist and naturist groups also occasionally charter large cruise ships for nude Caribbean cruises.