DOMINICAN REPUBLIC
Jason Matthews, (North Coast Management, (Cabrera, Dominican Republic
20 properties (low season, $1,750-$22,750; high season, $3,150-$32,550).
Overall portfolio: $$
Matthews's portfolio comprises mostly large (five bedrooms and up) partially to fully staffed beach- or waterfront homes on the Dominican Republic's Costa Verde. He's lived in the country for eight years and is well versed in its pluses and pitfalls—and knows what to look for (and to look out for) when selecting homes for his carefully chosen list. All properties come with daily housekeeping, and many have full staff. His concierge team can handle any special requests that your villa's staff cannot (809-589-7065; jason@northcoastmanagement.com; northcoastmanagement.com).

GRENADA
Nick Hughes, (Spice Isle Villas, Grenada
28 properties (low season, $950-$18,700; high season, $1,250-$27,500).
Overall portfolio: $$
A Grenada resident for 13 years, Hughes knows the owners and staff at every one of his listings and is never more than 20 minutes away should a problem arise. Ranging from affordable cottages to a fully staffed waterfront "castle," all properties come with an ocean view, housekeeping at least three days a week—and Hughes's encouragement to get out and explore the lush island and meet its friendly residents. Whether it's a car rental or a hiking tour, he's happy to make the proper arrangements (473-439-2486; spiceislevillas@(spiceisle.com; spiceislevillas.com).

Carriacou
Carolyn Alexander, Down Island Ltd., Carriacou, Grenada
20 properties (low season, $400-$2,100; high season, $525-$2,500).
Overall portfolio: $
Willing to sacrifice creature comforts to escape the tourist hordes? Alexander will acquaint you with this tiny island, where chickens and donkeys and goats walk down the main street past little old ladies cooking bread in outdoor ovens. There are no organized excursions, but the properties often come with DSL and cable TV, and Alexander can book interisland flights and four-wheel-drive rentals for you. Her villas generally don't come with air-conditioning or staff, but you can arrange for meals to be delivered (473-443-8182; islander@(islandvillas.com; islandvillas.com).

JAMAICA
Linda Smith, Jamaica Villas by Linda Smith, Cabin John, Maryland
67 properties (low season, $1,900-$61,555; high season, $3,750-$72,800).
Overall portfolio: $$
Smith has been renting homes on Jamaica for 24 years and spends several months on the island each year. When inspecting and evaluating properties, she moves into them for several days so she can sleep in every bedroom and bathe in every bathroom, (enabling her to know their individual characteristics. All of her listings include full staff personally trained by Smith herself (301-229-4300; linda@jamaicavillas.com; (jamaicavillas.com).