Best Staffed Villas in the Caribbean

Fresh cocktails prepared by your own bartender!
Fresh cocktails prepared by your own bartender!


The only thing better than staying in a Caribbean villa is staying in a staffed Caribbean villa. After all, who really wants to cook on vacation? Some travelers like the idea of grilling their own fresh-caught fish, but being wined and dined while watching a tropical sunset is hard to beat. We are frequently asked if our property rates include cook or chef services, so we thought we would make a list of our favorite staffed villas.

Renting a villa with a private chef or villa cook is an easy way to take your vacation to the next level, but there’s three ways to go about it.

1. Rent a staffed villa with a 5 Star chef


An accomplished chef is ideal if you want gourmet, restaurant-style meals. Chefs often have their own servers and five-star menus, and will let customize to your taste. The food is often superior to restaurant quality, and many guests who hire chefs never leave their villa. Here’s a few of our favorite villas that come with five-star chefs:

Anguilla
Ani Villa North
Ani Villa South
Kishti Villa on Meads East
Nevaeh Villa (Heavenly Rate)
The Beach House

Bahamas
Three Bees at Harbour Island

Barbados
Footprints
Greensleeves Villa
Moon Reach
The Dream Villa

Belize
Cayo Espanto

British Virgin Islands
St. Bernards Hill House
Valley Trunk Estate

Dominican Republic
Ani Villa Amber
Blue Oasis
Ocean Eleven

Jamaica
Silent Waters Villa

St. Barts
Wake Up
Silver Rainbow Villa

St. Lucia
Arc En Ciel Villa
Villa Susanna

St. Martin
Amalia
Casa de la Playa
Sandyline Villa

Turks and Caicos
Awa Villa
Hawksbill Villa
Triton Villa
Delicious feast prepared by a villa chef
Delicious feast prepared by a villa chef

2. Rent a staffed villa with a cook


A cook is ideal if you want simple, home-cooked meals. Most cooks serve food family-style, with wholesome dishes and local ingredients. This is a great option for an affordable, family-friendly vacation.

Barbados
Fosters House Villa
Sandy Cove #201
Solandra Villa

Dominican Republic
Casa de Campo #146
Casa de Campo #602
Casa de Campo #3613
Las Colinas 17

Jamaica
Cielo Villa
Fairwinds at Tryall
Serenity Villa at Tryall

St. Lucia
Cadasse Villa
La Mer
Villa Hall
Freshly grilled fare from your personal cook
Freshly grilled fare from your personal cook

3. Hire a cook or chef to your villa


A chef or cook can be arranged at any villa for an additional cost. No matter what island you travel to, you can have a restaurant experience at your villa. In most cases, the chef or cook will be paid on a per-meal basis, and it’s a fun way to celebrate an anniversary, birthday, or engagement.

If you want to stay in a luxury Caribbean villa without ever lifting a finger, you’ll love renting a staffed villa. A full staff ensures that you can kick back and relax, and there’s no better place to find the perfect villa rental than through WhereToStay. Follow the link to any of the properties on this list, and one of our villa experts will match you with the Caribbean destination of your dreams.

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