For many of us, luxury Caribbean villa rentals are 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.
How did we get interested in villa rentals?
One time when George and I were visiting Puerto Vallarta, we sussed out the beachfront Casa Tres Vidas (the “House of Three Lives”).
Featured in Architectural Digest, Casa Tres Vidas comprises three lovely villas, each with a private pool.
They can be rented separately (via the sister Quinta Maria Cortez hotel), or all 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 Pacific beachfront getaway.
Best of all, Casa Tres Vidas is reasonably affordable (certainly when compared to the Caribbean villa rentals covered below, some of which are truly spectacular!).
Checking out Casa Tres Vidas sparked our interest in villa vacations.
Read more about Casa Tres Vidas: See our post on boutique Puerto Vallarta hotels
My luxury Caribbean villa experience
But I’d never really experienced a true villa holiday – until recently.
The postcard-perfect island of Mayreau in the Grenadines – a beautiful chain of Caribbean islands favored by yachties and those seeking an “old Caribbean” vibe.
I even flew by private jet from Barbados to get there, which of course jazzed up that vacation-like-a-multi-millionaire feeling even more.
5 islands with the best Caribbean villa rentals
You can rent a Caribbean villa on pretty well 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 five islands you should look at to rent Caribbean villas.
1) Mayreau villas
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 the island for that true barefoot Caribbean getaway.
The villa I stayed at on Mayreau is part of TRIBU Villas. These two luxury 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 – one has an outdoor shower, mine had a private plunge pool.
We had a chef who cooked our meals, accompanied by delicious French wines. A bartender created artisanal drinks – chocolate martinis, anyone?
Staff catered to our 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 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.
The cabins 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 baked egg, cheese 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, I went scuba diving with another guest and our captain (also a dive guide) – and learned all about how lionfish are ravaging the Caribbean’s reefs.
Recommended reading: You’ll be interested in my fascinating dive in the Caribbean to hunt lionfish (I promise it’s a good read!)
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 for being in paradise.
How to charter a yacht: Chartered yacht holidays aren’t for the rich and famous – really!
2) Jamaica villa rentals
Jamaica is the third largest Caribbean island.
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.
Why vacation in Jamaica?
“Everything’s all right” in Jamaica. The birthplace of Bob Marley, Jamaica is known for its laid-back island vibe.
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 wamth on a tropical beach, rum punch in hand.
Hotel villas in Jamaica:
One of the reasons to consider renting a villa in Jamaica (apart from the island’s natural beauty) is that Jamaica is home to several top luxury resorts that boast private villas.
You get access to all the hotel services (like restaurants and a spa) plus the benefits offered by a villa stay.
Two top-notch options for resort villas in Jamaica are Round Hill Hotel and Villas and the Tryall Club.
Round Hill Hotel and Villas:
For half a century now, the elegant Round Hill Hotel and Villas 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.
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 villas have their own pools. Several are built on the hill offering expansive views of the bay.
Each villa has its own staff too, who take care of you throughout your stay, including making your breakfast.
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.
Two of the newest villas are more like vacation chateaux, each serviced by a staff of six. They also come with personal golf carts for getting around the property.
What to do? The club’s tennis courts, championship golf course and hobie cats for sailing should keep you busy, if you feel so inclined.
Private Jamaica villa rentals:
To rent a villa in Jamaica (a private villa not associated with a hotel or resort), check out Jamaica Villas by Linda Smith.
Consistently named a top rental specialist for Jamaica by Conde Nast Traveler, Linda Smith has built a trusted reputation renting luxury villas in Jamaica.
Smith has a portfolio of almost 100 homes, 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?
Ask about “Scotch on the Rocks.”
Not big enough? Then maybe you need “Sundown on the Beach.”
It’s a 5-bedroom villa with an additional 4-bedroom guest house that comes with 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) Mustique villa rentals
What’s special about Mustique Island?
Like Mayreau, Mustique is part of St Vincent and the Grenadines.
A small private island, it was founded by British aristocrat Colin Tenant (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.
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.
Many of these are rented out, and they are some of the chicest 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”).
The 5-bedroom villa on a private peninsula on the southern tip of the island features two swimming pools (one an infinity pool), stunning views and beautiful tropical gardens.
Pssst… Margaret had an affair with a landscape gardener here who was 17 years younger than her.
Other Mustique villa rentals:
Other villa choices range from estates suited to entertaining and grand dinner parties to quiet places hidden in the hills.
Several of the villas on Mustique have been written up in Architectural Digest.
Wimco Villas can help find suitable accommodation.
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.
The elegant Cotton House has 18 colonial-style rooms, suites and cottages with four-poster beds.
Perched on a hill with views of the Caribbean sea, the boutique Firefly Mustique has just seven rooms with super comfy beds and stone terraces.
Its great little bar has amazing sunset views, the restaurant serves up delicious food (yummy pizza!) and the sweet pool is unique with sea pebble tiles.
Are you a sucker for sinfully luxurious hotels? Then check out these 27+ fabulous resorts with private pool suites
4) St Barts villa rentals
Oooh, let’s go French!
We spent the day recently in St Barts while on a Star Clippers cruise – checking out the designer shops in the pretty capital of Gustavia and swimming at Shell Beach.
While damaged by Hurricane Irma in 2017, the island has bounced back completely.
Celebs have returned for their Caribbean villa holidays and come-hither Instagram shots, including Mariah Carey, Kate Middleton’s brother and super-model Emily Ratajkowski (who said goodbye to 2018 on St Barts).
Two companies rule for St Barts rentals: Sibarth Bespoke Villa Rentals and St Barth Properties.
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?
Properties rented through Sibarth Bespoke Villa Rentals come with sticker shock though – unless you’re a real multi-millionaire, in which case $4,500 USD a week for a little one-bedroom (that’s not even on the beach) is maybe normal.
We think the sweet cottage on Flamands Beach at $6,000 USD week is better value (plus it has two bedrooms).
St Barth Properties:
Named best villa rental company in the Caribbean Journal Traveler’s Choice Awards for 2019, St Barth Properties was founded by Peg Walsh in 1989.
She spends six months a year on the island with her husband (making villa and hotel inspections).
Her St Barth villa rentals range from 1-bedroom getaways to a swish 5-bedroom villa near Gustavia that goes for $30,000 to $50,000 week in the winter high season.
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 the hotel.
Don’t worry, you still get access to the hotels’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.
Why not add a pre- or post-villa stay at a great hotel in Grand Case on St Martin? You’ll love these two boutique St. Martin hotels
5) Barbados villa rentals
We got engaged in Barbados – at the charming Colony Club – so this island holds a special place in our hearts.
With a well-deserved reputation for posh accommodations, Barbados is also one of the best islands for luxurious Caribbean vacation 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, it 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, 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 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 villas in Barbados.
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 rent out 250+ vacation homes in Barbados – and they have property managers on location in Barbados.
Hammerton rents out mainly to guests who live in the U.S., UK and Canada and gets 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, 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.
No butlers or private staff – but you have access to the resort’s four restaurants, cascading pools and Serenity Spa.
Crane Beach – which is stunningly beautiful with powder-soft sand – is reached via a long staircase leading down from the hotel’s dramatic cliffside perch or glass-front beach elevator.
Because it’s only a seven-minute cab ride from the the airport, the Crane Resort is a great place to stay before flying on to Mayreau (discussed above), for example.
After my villa stay in Mayreau, I stopped for a lovely lunch here before I caught my ongoing flight back to Canada.
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.
Other luxury vacation rentals, Caribbean
In addition to Wimco Villas and other big name Caribbean villa rental agencies covered above, check out La Cure Villas and McLaughlin Anderson.
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, “Arawak House” in Antigua is a sweet 3-bedroom villa in Emerald Cove, starting at only $560 USD night. By day, swim in your private lap pool; at night, dine alfresco on a shady furnished patio. A path leads through the garden to the soft sands of your private beach.
Or you can snag the contemporary, two-storey “Kai Zen” villa on a secluded, white sand beach in Grand Cayman. Cost? From $750 USD night.
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 specializes in villa rentals in the British and U.S. Virgin Islands as well as Grenada.
It’s the onsite island manager for St Thomas (naturally) and has island managers on each of St Croix, St John, Tortola, Little Thatch, Virgin Gorda and Grenada for on-call service.
Rental options range from beach houses to the fully serviced 2- and 3-bedroom Ritz-Carlton Club residences on St Thomas to “St Bernard’s Hill House,” an 8-acre hilltop estate on Tortola with amazing 300-degree views.
More Caribbean travel information
See the Caribbean travel guides on Amazon. (As an Amazon associate, we earn from qualifying purchases.)
Alternative: Luxury Costa Rica villa rental
Interested in an exclusive villa rental in Costa Rica instead?
George and I have also stayed at a condo in Costa Rica through Papagayo Luxury Villa Rentals.
With our own golf-cart for toodling around the exclusive Pacific beachfront community, sprinkled with gorgeous huge villas, 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!)
Recommended reading: A luxury condo, beach club and moonlight golf buggy rides on Costa Rica’s secret Papagayo Peninsula – check it out!
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Photo credits: 5, 8 to 10, 13 to 18 © Janice and George Mucalov, SandInMySuitcase | Remaining images courtesy of the respective villa companies and hotels, except 1 and where noted