For many of us, a deluxe Caribbean villa is the dream winter vacation.
A gorgeous villa on a sweet cove of sandy beach. A chef to whip up seafood dinners. Staff to serve us lemon drop martinis by the pool and keep the place tidy.
And, most important, precious time to spend laughing with family or friends, creating memories that are really priceless.
Well, after a few villa vacations of our own (often with fabulous private pool suites), we’ve sussed out the best Caribbean villas – so you can turn that dream into reality!
The best Caribbean villas for a dreamy vacay
Top islands to rent Caribbean villas
You can rent a Caribbean villa on most islands.
But some islands have more choice of villas, suiting pretty well every budget. Others offer a more exclusive vacation experience for those wanting to splurge on pure luxury.
Here are 7 islands you should look at for a fabulous Caribbean villa vacation (all prices are in USD).
1) Best St. Barts villas
Oooh, let’s go French!
An overseas territory of France, Saint Barthelemy (commonly known as St. Barth, St. Barths or St. Barts) is très chic – tropical with a French twist!
Super-models and celebs especially like St. Barts for their Caribbean villa holidays.
We have a whole St. Barts travel guide, so check it out for more information about the island.
From St. Barts, you can also do day trips to the dual nation island of St. Martin and St. Maarten. (Or you could split your stay between St. Barts and St. Martin.)
Sibarth Bespoke Villa Rentals:
This luxury villa rental company calls St. Barts home, so they know their stuff. Sibarth’s in-home concierge team can be reached 24/7 – maybe you’ve run out of champagne and need more at 2:00 am?
Some of the properties rented through Sibarth Bespoke Villa Rentals come with sticker shock though – so be prepared!
We particularly love the looks of the “barefoot and bohemian” Villa Palm House.
Surrounded by very old lataniers (fan palms) and inspired by nature, this 2-bedroom and 2-bath villa is located at Anse de Lezards, one of the island’s prime surfing spots. (You can use the surfboards provided.)
It’s built as separate pavilions, all connected – the wood-walled living room is in one pavilion and the ensuite bedrooms occupy their own separate pavilions. There’s also a petite swimming pool and lounge chairs.
The Villa Palm House rents for $4,900 a week in the winter months (December to March).
Eden Rock villa rentals:
For years, the original luxury hotel on the island – Eden Rock St. Barths – has been catnip for Hollywood A-listers, past and present, like Greta Garbo and Leonardo DiCaprio.
Now you can upgrade your stay and rent a villa at this iconic hotel.
And don’t worry. You still get access to the hotel’s beach facilities on beautiful St Jean Bay when you rent one of the 130+ luxury villas through Eden Rock Villa Rental.
Newspapers and a continental breakfast from the hotel are delivered to your villa each morning too.
St. Barth Properties:
Another one of the island’s best villa rental companies is St. Barth Properties.
It was founded by Peg Walsh in 1989. She spends six months a year on the island with her husband, making villa and hotel inspections, as she searches out the finest properties for her collection.
Her villas in St. Barts include 1-bedroom getaways.
Or maybe you want to splash out in Villa Dunes? The Real Housewives of New York City stayed at this swish 6-bedroom villa.
It has not one but two heated pools – an 80-foot lap pool plus a 40-foot pool for family fun. Stay fit in the air-conditioned gym.
To swim at Grand Saline Beach, just walk up and then down a hill, and voilà, you’re there.
Oh, and Villa Dunes is only a mere $95,000 week in the winter high season.
2) Luxury villas in Jamaica
“Everything’s all right” in Jamaica!
The third largest Caribbean island and birthplace of Bob Marley, Jamaica is known for its laid-back island vibe.
There’s also lots to do in Jamaica.
In Ocho Rios, you can climb the 600-foot Dunn’s River Falls and go ziplining. Montego Bay on the north coast has great golf courses.
You can eat jerk chicken, dive at coral reefs in the Montego Bay Marine Park or simply soak up the warmth on any number of tropical white sand beaches, rum punch in hand.
Considered one of the best honeymoon destinations in the Caribbean, Jamaica has an extensive selection of villa rentals – making it a popular destination for Caribbean villa holidays too.
Round Hill Hotel and Villas:
Some of the best Caribbean villas are found at the elegant Round Hill Hotel and Villas.
For half a century now, Round Hill has been the villa resort of choice for the rich and famous like John and Jackie Kennedy, Ralph Lauren, Paul McCartney, Heidi Klum, and recently, Prince Harry and Meghan Markle.
Round Hill has 27 Jamaica villas tucked among meandering paths and lush gardens.
They feature open-air living rooms, polished wood floors, custom artwork, mahogany four-poster beds and colorful Ralph Lauren designer touches.
Each villa has its own staff too, who take care of you throughout your stay, including making your breakfast.
There are three categories of Jamaica villa rentals at Round Hill:
1) Premium Luxury Villas
These spacious villas (up to 8,850 square feet in size) have 2 to 6 bedrooms, two pools and a game room with pool table.
2) Luxury Villas
Ranging from 3 to 6 bedrooms, these villas each have their own pool.
3) Deluxe Villas
Some of these 2- to 4-bedroom Round Hill villas have their own pools. Several are built on the hill offering expansive views of the bay.
Bonus: 5-star resort amenities
The beauty of staying in a villa at Round Hill is that you get access to all of the resort’s services plus all the benefits offered by a villa stay.
Resort activities include tennis (on five tennis courts), hobie cat sailing, water-skiing and tubing, snorkeling and yoga classes.
There’s also a new state-of-the-art fitness center and a full-service spa.
Tryall Club, Jamaica:
The Tryall Club is a collection of luxury fully-staffed villas set within an historic 2,200-acre estate in Sandy Bay.
The villas, which are privately owned, range from 1-bedroom condos to expansive oceanfront and hillside houses accommodating large families.
Exuding a traditional Jamaican plantation feel (think breezy verandas and hand-carved mahogany furniture), Sugar Hill gets our vote as the perfect villa for a multi-generational family holiday.
Surrounded by manicured lawns and lush gardens, the 3-acre estate consists of a 4-bedroom main villa and 4-bedroom guest house.
Time for a dip? Dive into the aqua glass-tiled pool. Kids can play pool, ping-pong and fusbol in the large recreation room. A fully equipped gym makes working out inviting.
There’s even a wood burning pizza oven for your chef to make pizza.
What to do at the Tryall Club? The resort’s tennis courts, championship golf course and hobie cats for sailing should keep you busy – if you feel so inclined.
Bluefields Bay villas:
A member of Small Luxury Hotels of the World, Bluefields Bay Villas has six exclusive villas on Jamaica’s south coast.
Ranging from 2 to 6 bedrooms, they feature private pools. Some are set on an idyllic velvety sand beach; others are tucked away among tropical gardens.
The villas come fully staffed, with a private chef, butler and housekeeper. And they’re perfect for families, as 9 hours of child care a day are part of the all-inclusive rates.
You also have free use of sea kayaks, hydrobikes, SUP boards, snorkeling gear and a sailboat. And the hotel’s beach area is staffed, of course. Feel like an early morning game of tennis? There’s a tennis court too.
For a change of scene, sip cocktails at the Treehouse, a combined bar, living and dining room space, open to all guests, offering gorgeous seafront views.
Private Jamaica villa rentals:
To rent a villa in Jamaica that’s not associated with a hotel or resort, check out Jamaica Villas by Linda Smith.
Consistently named one of the top villa specialists for Jamaica by Conde Nast Traveler, Smith has built a trusted reputation renting luxury homes on the island.
Smith has a portfolio of almost 100 luxury villas in Jamaica, most in Montego Bay and Discovery Bay.
She inspects all villas herself, and the owners make the changes to their homes that she suggests.
Want a 5-bedroom waterfront villa in Ocho Rios, with a private pool, two sea kayaks, paddleboards and a wonderful private cove for swimming in clear turquoise water?
Then ask about Scotch on the Rocks.
Not big enough? Then maybe you need Sundown on the Beach.
This 5-bedroom villa comes with an additional 4-bedroom guest house.
The property features its own private 125-foot sand beach, huge swimming pool, fishing dock and a staff of seven (butler, chef, housekeepers, gardener, laundress and night watchman).
3) Long Bay Villas, Anguilla
You wake up to exercise in the gym.
Later, a butler hands you an icy mojito or margarita as you melt into a shaded lounge chair on a picture-perfect white sand beach.
Then it’s time for an in-villa massage arranged by your personal concierge.
And for dinner? Hmmm. Dine in? Or out at one of the island’s top-notch restaurants like Pimms at Cap Juluca?
Say hello to the villa experience at Long Bay Villas on the chi-chi island of Anguilla!
Long Bay Villas is one of the smallest but swankiest Caribbean villa resorts. It has only three newly renovated villas: Sand Villa, Sea Villa and Sky Villa.
Each villa sleeps 12 people in 5 ensuite bedrooms.
The bathrooms boast outdoor showers. (If you haven’t yet lathered up in an outdoor shower, you’re in for a sensual treat. Many of the world’s top hotel bathrooms feature outdoor showers.)
The villas also have a private pool and hot tub each. Naturally, they’re staffed by housekeepers and butlers.
Unlike some villas, which are all-inclusive, rates at Long Bay Villas include continental breakfast, as well as beach club services.
But for other meals, you can choose to whip these up yourself in the full kitchen, or a chef can be arranged to cook for you. (You also have the option of eating out.)
4) Mayreau villas
The postcard-perfect island of Mayreau is found in the Grenadines – a beautiful chain of Caribbean islands favored by yachties and those seeking an “old Caribbean” vibe.
Mayreau is the island for that true barefoot Caribbean getaway.
Water so turquoise it rivals Bora Bora’s lagoon.
Population 250 – there are more cute goats than people!
One quaint church, one main road, one legendary Caribbean bar – “Robert Righteous,” run by a colorful Rastafarian.
Mayreau is also home to TRIBU Villas.
These villas are set on 12 acres of private beachfront.
Each villa has its own main house with a common open-plan living and dining area (with kitchen) and a large swimming pool.
Outside each villa, stone stairs climb up the hill to its four separate sleeping pavilions.
Each pavilion houses a bedroom, bathroom and private terrace.
The pavilions feature polished wood floors, soaring ceilings, furnishings from Bali and Central America, a fridge with water and snacks, sprays of fresh bougainvillea in vases for pops of color, and air-conditioning (of course!).
Each bedroom pavilion is different. Some have outdoor showers. Ours had a private plunge pool.
A chef cooks your meals, accompanied by delicious French wines. A bartender creates artisanal drinks – chocolate martinis, anyone?
And staff cater to pretty well every whim.
Shared villa experience:
What’s unique about TRIBU villas is that they offer a shared villa experience.
Say you’re a couple, and you don’t really want to vacation with all your extended family. You want a couples holiday.
Still, you’d love an exclusive Caribbean vacation in a villa. Yet your wallet cries “Ouch!” at the prospect of renting a whole Caribbean villa just for the two of you.
You only have to “rent” one of the ensuite bedroom pavilions at TRIBU. And you share the rest of the villa with the occupants of the other three pavilions.
It’s a little like booking one room in a hotel – except that your rate for the one-bedroom pavilion plus use of the shared villa includes the cost of drinks, chef services for meals, cleaning staff, etc.
Spend your time swimming or lazing about under a palm tree on the sand, just the two of you.
Then later in the afternoon, join other villa guests for cocktails before dining communally with everyone by candlelight.
Chances are your fellow guests will be like-minded. (After all, they’re also intrigued by the concept of a shared villa vacation on a secluded island.) You might even make new friends who you want to rent a villa with again!
Of course, if you want to travel with three other couples to book out the whole villa for your group, that option is also available.
Villa and sailing vacation:
How to make that villa vacation even more special?
Combine your Mayreau villa holiday with sailing in the Caribbean too.
Tradewinds, TRIBU Villas’ parent company, has some 50 luxury catamarans in prime sailing spots around the world, including the Grenadines.
Originally, Tradewinds was a members-only program.
But they’ve now branched out to offer non-members the opportunity to also book a cabin in one of their 4- or 5-berth, fully crewed yachts.
The idea? Combine a 3- or 4-night villa stay with three or four nights sailing on a yacht.
You fly into the island of Canouan (SVG Air offers flights from Barbados) for the sailing part of your adventure, then transfer to Mayreau for the TRIBU Villas experience (or vice versa).
The cabins on these chartered yachts are modern and comfortable. Not as big, of course, as on a cruise ship. But not as squishy as you might think!
Well-designed, they each come with a queen-size bed, private bathroom with a glass shower, window and ceiling hatches for light, and a closet and shelves for storage.
The yachts are air-conditioned too.
We’d wake up, dive off the boat for a quick swim, stuff ourselves on cheesy egg-and-bacon “pies” for breakfast, then snorkel with turtles or take out the yacht’s SUP board for a paddle.
One day, we swam to the private island of Petit St. Vincent (favored by Oprah Winfrey) for drinks with our toes in the sand.
Another day, we went scuba diving to hunt lionfish (our boat captain was also our dive guide) – and learned all about how lionfish are ravaging the Caribbean’s reefs.
Come sunset, we’d meet for sundowners on the flybridge up top, then dine under the stars on ahi tuna or freshly-caught lobster – and count ourselves blessed to be in paradise.
5) Mustique villas
What’s special about Mustique Island?
Like Mayreau, Mustique is part of St Vincent and the Grenadines.
A small private island, it was bought by British aristocrat Colin Tennant (Lord Glenconner) in 1958. It became the place where celebrities and royalty could party and play away from the prying eyes of the public.
Princess Margaret, for example, received a 10-acre plot from Glenconner in 1960, which she developed into the renowned Les Jolies Eaux estate.
And, pssst… Margaret had an affair with a landscape gardener here who was 17 years younger than her.
Fast forward to today. Mustique Island is still the exclusive haunt of the rich and famous.
You’re guaranteed extreme privacy – a former Scotland Yard chief heads up the island’s security. (Because security is so strict, no photos were taken of Kate and Prince William when they vacationed there with their family in 2018.)
The Mustique Company, which governs the island and is run by the island’s 100 or so homeowners, has forbidden the building of more than 120 luxury homes (which helps preserve the natural beauty of the island).
Many of these villas are rented out, and they are some of the choicest and most deluxe Caribbean homes for rent.
Les Jolies Eaux:
So you’re feeling very royal, are you? Then you must stay in Princess Margaret’s former home, Les Jolies Eaux (meaning “Beautiful Waters”).
Featured in Netflix’s The Crown, the 5-bedroom villa sits on a private peninsula at the southern tip of the island. The décor is a mix of 18th century European and Caribbean influences.
Surrounded by decades-old cedar trees (to thwart the prying eyes of paparazzi), it features two swimming pools (one an infinity pool), an outdoor gazebo, stunning panoramic views and beautiful tropical gardens filled with calla lilies.
The villa is staffed by a butler, chef, gardener and two housekeepers – and it can be yours for a week for some $25,000 to $40,000 (depending on when you go).
Other Mustique villa rentals:
Other villa choices range from estates suited to entertaining and grand dinner parties to quiet places hidden in the hills.
To find the right Mustique villa for you, check out Wimco Villas. They’re one of the biggest Caribbean villa rental companies.
There are only two hotels on Mustique: the Cotton House and Firefly Mustique. You may end up popping into their restaurants for dinner.
Or perhaps you’ll hit Basil’s Bar – if you’re lucky, you may run into Mick Jagger there.
6) Luxury vacation villas in Barbados
We got engaged in Barbados – at the charming Colony Club – so this island holds a special place in our hearts.
And with a well-deserved reputation for posh accommodations, Barbados is another one of the best islands for luxury Caribbean villa rentals.
Villas & Apartments Abroad:
Founded by travel specialist Sylvia Delvaille Jones, Villas & Apartments Abroad rents out a collection of hand-picked vacation villas around the world, specializing mainly in large properties.
On Barbados, the agency has some 40+ villas in its portfolio.
Bon Vivant, for example, is an 8-bedroom villa with 8 bathrooms in the chi-chi Sandy Lane enclave.
The main house has 5 bedrooms and an indoor raquetball court. It’s complemented by a guest villa with 2 bedrooms and another cottage overlooking the pool (the romantic “Nest”) with a hanging bed and sunken bathtub.
Villas of Distinction:
Based in New York, Villas of Distinction handles more than 2,500 properties in 50 countries around the world, including over 180 villas in Barbados.
Listings include 1-bedroom cottages to gorgeous sprawling 10-bedroom mansions.
Watch out for early booking discounts and shoulder-season promotions, for example, a transportation credit that can be applied toward a rental car.
Blue Sky Luxury:
Locally based in Barbados, Blue Sky Luxury is a member of the Barbados Hotel and Tourism Association.
The advantage to being a local company is that their team on the ground knows the properties well and can quickly trouble shoot any issues that may arise.
The level of staff service varies – from weekly maid service for some apartments and smaller homes to a completely staffed household of butler, chef, housekeeper and maid at “flagship” villas.
The company has been renting villas and holiday homes in Barbados for over 40 years, and offers a selection of some 130 Barbados villas.
Ask about a discount for stays over 7 nights.
Hammerton Barbados is a boutique UK-based agency which works with all the major Barbados villa rental companies (like Blue Sky Luxury above).
They have 250+ vacation homes in Barbados in their portfolio – and they have property managers on location in Barbados.
For example, you might like Belair for a family vacation. Recently refurbished, this popular villa hugs the white sands of Mullins Beach. It has 4 bedrooms in the main house plus 2 more bedrooms in an adjacent cottage.
Hammerton rents out mainly to guests who live in the U.S., UK and Canada. And they get good feedback from their happy clients.
Windermere and Cragmere Villas, available through Crane Villas, are two vacation villas a short walk away from Crane Beach.
Crane Beach is one of the best beaches in Barbados. Its waves are great for boogie boarding, and you can rent chairs and umbrellas on the beach.
Suites at the Crane Resort:
The Crane Villas are also close to the Crane Resort, which has 1- and 2-bedroom suites.
These luxury suites feature fully-equipped granite kitchens, bedrooms with artisan-crafted mahogany furniture, private pools and outdoor dining gazebos.
Okay, so you don’t have butlers or private staff – but you do have access to the resort’s four restaurants, cascading pools and Serenity Spa.
And you get to hang out on Crane Beach, which is stunningly beautiful with powder-soft sand. It’s reached via a long staircase leading down from the hotel’s dramatic cliffside perch or glass-front beach elevator.
No review of Barbados villa rentals would be complete without at least mention of the Villa at Sandy Lane.
We’ve already mentioned that the Sandy Lane area is very upscale.
Then there’s the Sandy Lane resort. Perhaps you’ve heard of it? The ultra-luxurious pink resort on the west coast of Barbados is one of the most prestigious in the Caribbean.
But you can up the wow factor of your stay even further by tossing your bags in its 5-bedroom villa.
Think 7,300 square feet of space, private pool, complimentary airport transfers, free green fees at two golf courses, use of a luxury vehicle, nine tennis courts at your disposal, unlimited motorized and non-motorized water sports and dedicated staff (a butler, chef and housekeeper) to look after you.
7) Casa de Campo Resort & Villas, Dominican Republic
George W. Bush has stayed here. So have Bill Clinton, Beyonce and Kim Kardashian West.
We’re talking about Casa de Campo.
With gorgeous Minitas Beach at its doorstep, this renowned luxury Caribbean resort sprawls over 7,000 acres on the peaceful southern coast of the Dominican Republic.
In addition to its 247 rooms, it has some 50 private villas, ranging in size from 3 to 11+ bedrooms. The largest oceanfront villas sleep 27 guests. All Casa de Campo villas have private pools.
You get breakfast prepared for you daily in your villa, butler service from 7:30 am to 6:30 pm (for bartending, etc.) and complimentary golf carts to zip around the resort.
You won’t get bored at Casa de Campo either – it offers every possible activity you can think of.
There are 3 Pete Dye-designed golf courses, including Teeth of the Dog, possibly the Caribbean’s premier golf course.
You can take horse jumping lessons and go on trail rides at the equestrian center. Tennis? Yep, there are 13 courts. Water sports are available. The resort even has a marina (deep sea fishing, anyone?) and shooting center too.
Throw in more than a dozen restaurants, spa, beach club, fitness center and 3-mile jogging track, and you have the perfect Caribbean villa vacation to satisfy even the pickiest in your party.
Other luxury vacation rentals, Caribbean
Launched in 1979, LaCure Villas is a Canadian company with a global portfolio of 6,000 properties, including 630+ villas in the Caribbean.
For example, Villa Kathleen in Antigua is a 6-bedroom stone villa in Galley Bay, starting at $2,600 night.
By day, swim in your private pool and play tennis on your own flood-lit championship-sized tennis court. At night, dine alfresco on a shady furnished patio. And you’re just a 5-minute walk from Galley Bay Beach.
LaCure Villas’ team of experts work with you to arrange your custom-designed program, including restaurant bookings, chauffeur-driven car, special activities, private chef, etc.
Based in St Thomas, McLaughlin Anderson Luxury Villas is also in the biz of Caribbean vacation rentals.
They specialize in villa rentals in the British Virgin Islands, U.S. Virgin Islands and Grenada.
They’re the onsite island manager for St Thomas (naturally). They also have island managers on each of St Croix, St John, Tortola, Little Thatch, Virgin Gorda and Grenada for on-call service.
How about the fully serviced 2-bedroom Ritz-Carlton Club residences on St. Thomas?
Or maybe you’d like St. Bernard’s Hill House, an 8-acre hilltop estate on Tortola with amazing 300-degree views?
Your stay at this 5-bedroom gingerbread-trimmed property includes daily use of the 30-foot luxury powerboat “BVI Beverley.” It’s captained by a PADI dive master, who can take you snorkeling, wakeboarding and scuba diving.
Alternatives to Caribbean luxury villas
Featured in Architectural Digest, Casa Tres Vidas comprises three lovely villas, each with a private pool and direct beach access.
They can be rented separately. Or you can rent all three villas together, for more than 12,000 square feet of space with a whopping 10-bedrooms and 12-bathrooms.
Add private staff and you have the perfect private Mexican getaway.
Best of all, Casa Tres Vidas is reasonably affordable (certainly when compared to the Caribbean villa rentals covered above).
Luxury Costa Rica villa rentals:
Interested in an exclusive villa rental in Costa Rica instead?
We’ve also stayed at a luxury 3-bedroom condo in Costa Rica through Papagayo Luxury.
This rental company handles gorgeous villas located on the exclusive Papagayo Peninsula.
With our own golf-cart for tootling around the beachfront community, we got a mini-taste of a villa vacation – except without the chef. (We didn’t need a chef for the two of us, or a whole 3-bedroom place – like, how many bedrooms could the two of us use? But, hey, it was fun!)
Now you know some of the best villas in the Caribbean (and elsewhere)!
For a carefree Caribbean vacation, you can’t do much better than renting a luxury villa.
Staff will pamper you silly and can take care of the cooking, cleaning and other chores, so you can focus on spending quality time with friends or family.
And with most luxury Caribbean villas offering complimentary concierge services too, they’ll book your fishing trip, golf tee time and other excursions too.
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Photo credits: 17 to 19, 22 to 26 © Janice and George Mucalov, SandInMySuitcase | Caribbean villa images courtesy of the respective villa agencies and hotels