Nothing says ‘luxury vacation’ more than checking-in to fully-staffed accommodation. Our beautiful Caribbean villas with private chefs and butlers guarantee to take your vacation to another level, with first-class service and private access to your own villa pool and facilities.
From Barbados and St. Martin to Jamaica and the Dominican Republic, our beautiful staffed villas bring the experience of a top end hotel to your private getaway. As soon as you arrive you’ll be treated like royalty, thanks to the diligence of your in-house butler. Accompanied by the promise of restaurant-quality cuisine prepared by your own private chef.
Accompanying many of our villas, you’ll also find additional staff including housekeepers, maids and gardeners. The result? Hassle-free vacation bliss. You can also expect our staffed Caribbean villas to offer a host of luxury amenities to accompany the 5-star hospitality. With service this good it may prove too difficult to check-out! Luckily, we offer great deals on long-term stays too.
Barbados villas with staff
When you think of where to go for a luxury Caribbean stay, Barbados has to be top of your list. An independent British Commonwealth nation in the eastern Caribbean, this coral island may be relatively small in size, but it is home to more tourist attractions than most Caribbean islands combined. Not to mention some truly lavish staffed villa rentals!
Soak up 80 pristine white-sand beaches, immerse yourself in the vibrant port capital of Bridgetown or explore the botanical gardens, caves and 17th century plantation houses such as St. Nicholas Abbey.
You can’t come to Barbados and not enjoy one of its annual festivals or its local quintessential traditions, which include taking afternoon tea and watching a cricket match. Off dry land, enjoy a catamaran cruise, scuba diving, snorkelling and a plethora of adrenaline-fuelled water sports.
- 4 bedrooms | Sleeps 8 | St. Peter, Barbados
With its prime beachfront location along the Platinum Coast, Leamington Pavilion promises classic Caribbean escapism. Unwind within the timeless open plan interior, which features WiFi, A/C and a home gym. Outside soak up the private pool, sunbeds, daybeds and tennis courts. Be wooed by the beautiful, multiple dining areas, one of which features in a magnificent stone grotto.
As one of our most beautiful Caribbean villas with private chefs and butlers, you can also be assured of 5-star hotel-quality service throughout your villa stay. For water sports fans and beachgoers, Leamington Pavilion provides direct access to the pristine white sand of Platinum beach.
You’ll find Leamington Pavilion fully-staffed with a chef, butler, housekeeper, laundress, maids and security guard.
Sugar Hill – Illusion
- 4 bedrooms | Sleeps 8 | St. James, Barbados
Perfect for those looking to enjoy a resort-style vacation, Sugar Hill – Illusion is one of our most striking staffed Caribbean villas. Soak up this custom-built private villa which can be found in the exclusive Sugar Hill Resort gated community, along the west coast of Barbados.
Stepping inside the air-conditioned villa, you’ll find it equipped with everything you need for a 5-star stay. Amenities include WiFi, a home gym and elevator. Outside you can make the most of the private pool and multiple relaxation areas, which are accompanied by a putting green and an outdoor kitchen with alfresco dining. When staying at Sugar Hill – Illusion you’ll also enjoy access to the Sugar Hill Resort clubhouse, with its acclaimed restaurant, 2 communal pools and 4 championship tennis courts.
You’ll find Sugar Hill – Illusion staffed with a chef, butler and a housekeeper/laundress.
- 5 bedrooms | Sleeps 10 | St. James, Barbados
For modernist fans, The Dream really is a dream come true! This contemporary beachfront villa is located in the exclusive enclave of The Garden, just south of Mullins Bay on the west coast of Barbados. Inside, The Dream features a chic interior with A/C, WiFi, a media room and pool table, alongside impressive full-height doors. These lead out to the private pool and a generous sunny terrace with outdoor kitchen and alfresco dining terrace.
Guests looking to unwind won’t have to travel far, as the chic daybeds and sun loungers will surely tempt you. Take in the sea views from the terrace or enjoy a sunset beach stroll. As beautiful Caribbean villas with private chefs and butlers go, The Dream is also a staffed 5-star villa ready to impress.
You’ll find The Dream staffed by a chef, butler, 2 housekeepers and a laundress.
- 6 bedrooms | Sleeps 12 | St. James, Barbados
Searching for some 5-star zen? Offering access to a private beach, Seaclusion promises an extraordinary Caribbean adventure. The impressive air-conditioned villa is fully-staffed and equipped with WiFi, a host of reception rooms, plus a media room, cocktail bar and home gym. Outside, the large sea-facing terrace features an additional cocktail bar and an oceanfront gazebo, perfect for intimate dining.
When you feel like switching off, dive into the infinity-edge lap pool. When you’re all swimmed out, drift over to the built-in bar with sunken seats, or take a stroll around the delightful gardens. With zen gardens and a koi fish pond to take in, our VIP villa Seaclusion sets the scene for a replenishing and mindful vacation.
You’ll find Seaclusion fully-staffed with a chef, butler, housekeeper, laundress, 24/7 security, property manager and concierge.
Jamaica villa rentals with staff
For many, Jamaica is the place to go for authentic Caribbean vibes. With its lush rainforests, dramatic mountains and reef-framed coastline, Jamaica is every bit what a Caribbean paradise ought to be. You’ll find most of the luxury staffed villas tucked away in the all-inclusive resorts along Montego Bay.
The island offers a colorful backdrop of contrasts, with British-colonial architecture dancing with the island’s reggae music heritage. Take time to visit Kingston, which is home to the Bob Marley Museum. Or zone out for the day and visit the majestic waterfalls and scenic beach at Dunn’s River Falls and Park.
Out on the water, explore the diving and snorkelling locations around Negril or amaze yourself by meeting a dolphin up close, at Dolphin Cove in Ocho Rios. Tempt your tastebuds with traditional Jamaican cuisine, either cooked by your private chef or enjoyed out at one of the many restaurants and lively cafes.
Montego Bay 39
- 5 bedrooms | Sleeps 10 | Jamaica
Located in the island’s exclusive Tryall Club, the secluded sea-view villa Montego Bay 39 sets the scene for an effortless island escape. As beautiful Caribbean villas with private chefs and butlers go, you’ll enjoy 2 butlers at Montego Bay 39. Plus you’ll spot more staff on hand, for unbeatable luxury during your stay. Take in the views from the airy WiFi-enabled interior, which features A/C, en-suite bedrooms and open plan living.
For those looking to take in the scenery, the spacious veranda offers access to a wet bar and an extensive alfresco dining space. If you’re looking to dive into full vacation mode, you’ll find the heated infinity pool and jacuzzi calling. For guests looking to read a book or enjoy a cocktail, take a stroll and discover one of the serene seating areas nestled within the lush, tropical garden.
You’ll find Montego Bay 39 staffed with a chef, 2 butlers, 2 housekeepers, laundress and 2 gardeners.
Ocho Rios 12
12 bedrooms | Sleeps 24 | Jamaica
Located on the north coast of Jamaica, in the charming port town of Ocho Rios, this prime 14-acre estate promises to take your Caribbean vacation to another level! The area boasts a strong literary history, being the resort in which Ian Fleming lived and wrote many of his James Bond novels.
This impressive 12-bedroom villa is fully staffed and ready to offer 5-star service. Within the air-conditioned rooms you’ll find scenic bedrooms, lavish entertainment areas and a modern home gym. Explore the enchanting grounds, which are home to a treasure trove of surprises, including its very own gushing waterfall! Within the landscaped gardens you’ll also find tennis courts, an ocean view pool, 2 private beaches and breath taking vistas to write home about.
This villa is fully-staffed with a private butler, chef, housekeeper, a houseman, barman, gardeners and 24-hour security (including a manned gatehouse).
Staffed villas in Saint Martin
For fusion food and fun times, head to Saint Martin. Part of the Leeward Islands in the Caribbean Sea, Saint Martin is an island of two halves. To the north you have the French territory of Saint-Martin and to the south, the autonomous Dutch state of Sint Maarten. As well as savoring the incredible fusion food, soak up a wide selection of popular resort beaches, tranquil coves and surfing spots. That’s of course if you have the inclination to leave your fully staffed villa for the day!
For knock-out views, trek up to the panoramic Island summit of Pic Paradis. Those with a head for heights will enjoy the treetop adventure park at Loterie Farm. Self-confessed yachties should head to Simpson Bay Lagoon, for its yacht clubs, waterfront bars and restaurants. Head out on the water with a boat tour or with rental equipment from one of the many water sports companies. Enjoy buying a souvenir at one of the many duty-free shops and as the sun goes down, enjoy a sunset beach stroll or experience the vibrant nightlife.
Baie Rouge Hillside 11
- 6 bedrooms | Sleeps 12 | St. Martin
For those hunting for a beachfront haven in St. Martin with private chef and butler, the search is over. With its exclusive location on Baie Rouge beach, this impressive 3-storey villa promises an exclusive Caribbean escape. Inside Baie Rouge Hillside 11, you’ll enjoy stylish sea view rooms with A/C and WiFi.
A home spa and gym provide added luxury, whilst outdoors the 2 private pools and sun terrace set the scene for full vacation mode. Dip into the infinity-edge pool or unwind on the built-in pool daybed. What’s more, the direct beach access makes Baie Rouge Hillside 11 perfect for VIP groups looking to enjoy a scenic Caribbean stay, with a difference.
You’ll find Baie Rouge Hillside 11 staffed by a chef, butler, housekeeper and concierge.
Plum Bay 4
10 bedrooms | Sleeps 20 | St. Martin
Enjoying a prime location along Plum Bay beach, is the sprawling estate of Plum Bay 4. Within this lavish WiFi-enabled villa you’ll find an opulent interior to kick back in and entertain. Guests will enjoy the synthetic private tennis courts and have access to kayaks, surfboards and stand-up-paddleboards (available for an extra charge). Included in this oceanfront villa rental is also a retinue of in-house staff, ready to elevate your vacation.
Plus Plum Bay 4 is nestled within 4.8 acres of beautiful landscaped gardens, complete with a 100 yards golf hole and direct access to Plum Bay beach. Dive into the stunning private pool or enjoy island cuisine, with a professionally-cooked meal under the scenic gazebo.
You’ll find Plum Bay 4 staffed with a daily chef, maid, estate manager, gardener and 24-hour maintenance hotline.
Dominican Republic villas with staff
Home to the Caribbean’s tallest mountain of Pico Duarte, the Dominican Republic shares the island of Hispaniola in the west, with Haiti. Offering a captivating Caribbean setting, immerse yourself within its varied typrogaphy, from lush rainforests and savannahs to highlands, waterfalls and pristine beaches. Not sure where to start? Begin with a day trip to the spectacular Los Haitises national park.
When you’re all hiked out, explore the Spanish colonial landmarks still standing in the island capital of Santo Domingo, or enjoy a carefree moment on the fairways of the 26 resident golf courses. When you want nothing more than to switch off by the ocean, take on the sweeping sands of the island’s 200 beaches or soak up the luxury of your staffed, 5-star villa.
Casa de Campo 2
- 6 bedrooms | Sleeps 12 | Dominican Republic
Dreaming of an ocean view? Casa de Campo 2 delivers! This luxury Caribbean vacation rental features in the island’s most exclusive 5-star resort community. With its beachfront setting, groups of 12 will enjoy the ultimate villa stay. The contemporary style of Casa de Campo 2 is complemented outside by a fabulous infinity pool, a jacuzzi and an ocean view gazebo with seating.
Within the exclusive Casa de Campo resort, you’ll be able to enjoy a private resort beach, golf course, fitness center, tennis courts and equestrian center. The on-site marina will also be a big plus for boating fans and those who enjoy water sports. Guests are conveniently placed for reaching Minitas Beach and the visitor attractions of La Romana.
You’ll find Casa de Campo 2 staffed with a private chef, a waiter and housekeepers.
Casa de Campo 9
- 9 bedrooms | Sleeps 12 | Dominican Republic
Set within a lush ocean-front setting complete with private boat dock, Casa de Campo 9 offers an unrivalled Caribbean experience. With vibrant and uplifting receptions complemented by A/C, WiFi and media room, this fully-staffed villa promises a carefree vacation.
Outside Casa de Campo 9, soak up the scenic private pool and covered alfresco dining terrace with BBQ. Guests staying at the exclusive Campo resort also have access to a marina, an artisan village, a private beach and a host of a la carte restaurants, for when you fancy dining out. Active guests will also relish the world-renowned golf courses here, alongside the tennis center, watersports service, fitness center and polo fields with equestrian center. For those looking to explore island life, the lively city of La Romana is also nearby.
Casa de Campo 9 is fully-staffed with a butler, cook service, housekeeper, gardener and communal security guard.
Book with Top Villas
When booking one of our beautiful Caribbean villas with chefs and butlers, you are guaranteed a first-class service. Our Guest Experience team is on hand to help enhance your vacation with our amazing travel extras.
What’s more, many of our Caribbean villas also offer complimentary perks* when booked directly through Top Villas. These are subject to each villa, but can include a meet-and-greet service at the airport, free return airport transfers, a welcome drinks package, early check-in, late-check out and even an evening of live reggae music.
*Complimentary perks are dependent on the villa booked. T’s & C’s apply.
Choosing our flex properties
Many of our Caribbean villas also benefit from our new flex cancellation policy. These favorable cancellation terms put you in the driving seat. Simply cancel within the specified time for a full refund, or amend your dates for free!
To benefit from this extra peace-of-mind, reserve a vacation home with one of the following badges:
Flex 14 – Cancel for a full refund or amend your dates free of charge, up to 14 days before check in.*
Flex 30 – Cancel for a full refund or amend dates free of charge, up to 30 days before check in.*
*T’s & C’s apply.