Editors' Personal Picks: Top Caribbean Villas

Villa Booking Tips | 20 Amazing (And Affordable!) Villas

The villa's listed square footage doesn't seem right: 1,455 square feet. Really? It doesn't seem comparable to my house. Must be because my home doesn't have a private plunge pool. Or a terrace so close to Petit Piton I could play racquetball off its wall. Or a master bedroom with a brilliant white interior and shutters that slide open to a ridiculous view of it all. I lie there thinking there are four additions this place needs though: my wife and three daughters. From $250 per person per night. viceroyhotelsandresorts.com — Robert Stephens

"Another drink?" Marcel asks, pressing a glass into my hand. Who am I to refuse my favorite and practically personal bartender? And he's right: It's hot and I'm parched. It's been a strenuous day of lounging by the pool and watching local kids play baseball on the villa's private diamond. But it's time for my massage. After that, I'll slip into the glass-walled shower in my room, then dress for dinner. This evening's plans are equally strenuous: dinner on the terrace (the chef has spent the afternoon roasting a whole pig for us), watching the sunset over the distant horizon and yet another round of drinks. From $95 per person per night; sleeps 22. goldendolphinvilla.com— Lori Barbely

Rum punch and eucalyptus-scented towels await outside our villa's front door. This soaring clifftop estate peering over Anguilla's Little Bay is our home for the next week. Chef Shamash and butler Hasan greet my sister and me with welcoming smiles as we take in the ancient woodcarvings and abstract paitings that pepper the interior, the occasional pop of red or aqua the perfect Caribbean touch. Hasan doesn't show us to our own rooms, but to our own floors, where each of the five bedrooms open to a glass-railed balcony. I look out and watch as the travertine blanketing the lanai seems to fall off to the turquoise sea. I could get used to this. Full estate from $365 per person per night in low season; sleeps 20. Single estate from $428 per person per night in low season; sleeps 10. anivillas.com —Audrey St. Clair

Here at La Petite Sereine on St. Barts, desires are anticipated. Take the morning: The breakfast chef readies croissants while I drink in espresso and views of Lorient Bay. And it's quiet — this villa, completed December 2012, belongs to a new wave of villas with a new kind of privacy. Five bedrooms have separate outside entries, and the living space spills onto two levels, each with a pool. Close the pocket doors and the open-air living room becoms a home cinema. And if weather or mood prompts, dinner moves to the enclosed garden. It's all created so that at day's end, you realize you don't need a thing. From $700 per person per night; sleeps 10. sibarth.com/lps — Brooke Morton

I don't know what it is about an outdoor shower that I love so much. Maybe it's the feeling of bathing in a downpour, the effect of fluttering palms, or more simply, a view unobstructed by tile. This is why I want to move into Bungalow 180, a modern enclave finished in concrete and hardwood. Every bedroom has its own outdoor shower. There will be paddle boarding, beach lounging and afternoons spent with cold Medallas on the Malecon, the waterfront strip in town. And then I'll return for a dip in my black-bottom pool. Best part, though: a hot shower amid a coqui-frog concert before I sleep, and another in the morning as Vieques awakes. From $78 per person per night; sleeps 6. https://flipkey.com— Zach Stovall

I have a healthy sense of entitlement. So when it comes to travel, no luxury is too indulgent. And during many stays in swanky villas all over the Caribbean, I've certainly felt privileged. But guilty? Never. Not until Villa Kishti, with my own infinity pool, hot tub, gym — even the ocean seemed like it was put here just for me. In a four-bedroom suite that's bigger than my apartment, floor-to-ceiling windows and a cunning arrangement of mirrors make me feel like I'm surrounded by the Caribbean on all sides (even from the commode); I feel undeserving. At sunset, when the houseman sparks the fire pit, serving dinner for one in its glow on the terrace, I feel embarrassed to be here. But so grateful that I am. From $400 per person per night; sleeps 8. villakishtianguilla.com — Sarah Greaves-Gabbadon