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Vacation Like a Multi-millionaire at These Posh Caribbean Villas!

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!

Some of the best Carribean villa rentals are found on Anguilla, Barbados, Jamaica, Mayreau, Mustique, St. Barts and the Dominican Republic.
Some of the best Carribean villa rentals are found on Anguilla, Barbados, Dominican Republic, Jamaica, Mayreau, Mustique and St. Barts

The best Caribbean villas for a dreamy vacay

Luxury villa rentals, Caribbean: Contents

Top islands for Caribbean villa rentals

1) Luxury St. Barts villa rentals – Sibarth Bespoke Villas Rentals, Eden Rock villas + St. Barth Properties

2) Best Jamaica villas – Round Hill, Tryall Club, Bluefields Bay Villas + private villas in Jamaica

3) Anguilla villas (Long Bay Villas)

4) Mayreau villas – “Share” a villa + split villa/yacht experience

5) Villas in Mustique – Princess Margaret’s former home, other Mustique villas, Cotton House + Firefly

6) Luxury Barbados villas – Villas & Apartments Abroad, Villas of Distinction, Blue Sky Luxury, Hammerton Barbados, Crane villas, Crane Resort suites + Sandy Lane

7) Dominican Republic villas (Casa de Campo)

Other luxury Caribbean villa specialists – LaCure Villas + McLaughlin Anderson

Alternatives to Caribbean villa vacations – Casa Tres Vidas (Puerto Vallarta) + Papagayo Luxury Villas (Costa Rica)

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

The French-influenced island of St. Barts has some of the fanciest vacation villas in the Caribbean.
Gustavia Harbor in St. Barts

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.

Villa Palm House is a sweet 2-bedroom villa on St. Barts.
Villa Palm House is a sweet 2-bedroom villa on St. Barts

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.

Eden Rock’s 6-bedroom Blackstone villa is sophisticated and mod.
Eden Rock’s 6-bedroom Blackstone villa is sophisticated and mod

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

The Dunes is a celebrity-worthy St. Barts villa boasting 2 swimming pools.
The Dunes is a celebrity-worthy St. Barts villa boasting 2 swimming pools

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

Life’s a beach in Jamaica!
Life’s a beach 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.

Jamaica has a wide variety of Caribbean villas for rent.
As one of the largest Caribbean islands, Jamaica has a wide variety of Caribbean rental homes

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.

In Montego Bay, Round Hill Hotel and Villas consists of 27 villas and a 36-room beachfront hotel.
In Montego Bay, Round Hill Hotel and Villas consists of 27 villas and a 36-room beachfront hotel

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.

Round Hill has won “World’s Leading Villa Resort” from the World Travel Awards for 12+ consecutive years.
Round Hill has won “World’s Leading Villa Resort” from the World Travel Awards for 12+ consecutive years

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.

Sugar Hill is a favorite Tryall Club villa in Jamaica.
Set atop a hill overlooking the Caribbean Sea, Sugar Hill is a favorite Tryall Club villa

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 bedroom in the Cottonwood Cottage at Bluefields Bay, Jamaica
A bedroom in the Cottonwood Cottage at Bluefields Bay, Jamaica

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

Jamaica Villas by Linda Smith has a great selection of 90+ villas in Jamaica to rent.
Jamaica Villas by Linda Smith has a great selection of 90+ villas in Jamaica to rent

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.

Look! The Scotch on the Rocks villa  has its own private pier for swimming in the sea!
Look! The Scotch on the Rocks villa has its own private pier for swimming in the sea!

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.

“Sundown on the Beach” is one Jamaica villa rental we’d happily book for a family reunion.
Sundown on the Beach is one Jamaica villa rental we’d happily book for a family reunion

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

Chillaxing by the pool at Long Bay Villas
Chillaxing by the pool at Long Bay Villas

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!

The Long Bay Villas in Anguilla are 3 of the finest luxury villas in the Caribbean.
The Long Bay Villas in Anguilla are 3 of the finest luxury villas in the Caribbean

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

Boats anchored off a beautiful bay in Mayreau
Boats and a beautiful beach – island living doesn’t get much better (especially if you’re enjoying a villa stay!)

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.

The Catholic stone church on Mayreau was built in 1917
This little Catholic stone church on Mayreau was built in 1917

TRIBU Villas

The Grenadine Islands have the loveliest blue waters
Can you say blue? Mayreau and the Grenadine Islands have the loveliest blue waters

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.

TRIBU Villas currently has two 4-bedroom luxury villas on Mayreau
TRIBU Villas currently has two 4-bedroom luxury villas on Mayreau

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.

Each TRIBU bedroom pavilion is individually decorated, but they all have sea views
Each TRIBU bedroom pavilion is individually decorated, but they all have sea views

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.

No worries.

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.

The beach in front of TRIBU villas on Mayreau
The beach in front of TRIBU villas on Mayreau

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

It’s pretty relaxing on our catamaran…

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.

Two Tradewinds' catamarans anchored off Mayreau
Two Tradewinds’ catamarans anchored off Mayreau

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.

A cheesy egg-and-bacon "pie" is a good start to a busy day of snorkeling and swimming.
Cheesy egg-and-bacon pies are a good start to a busy day of snorkeling and swimming

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.

What's for lunch today on our yacht? Mmmm... Seared Ahi tuna...
What’s for lunch today on our yacht? Mmmm… Seared Ahi tuna…

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.

Princess Margaret in 1965 at age 35 (Credit: Wikipedia)

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

Princess Margaret hosted Mick Jagger at her Mustique villa, Les Jolies Eaux
Princess Margaret hosted Mick Jagger at her Mustique villa, 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.

Mustique hotels

Basil’s Bar is the place for good times – and celebrity spotting (Credit: Basil’s Bar)

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.

Check out Basil's for live music, guest DJ nights and themed parties
Check out Basil’s for live music, guest DJ nights and themed parties (Credit: Basil’s Bar)

Hotels in Mustique

You don’t have to rent a villa on Mustique. You can still soak up the Mustique vibe (and rub shoulder with the rich and famous) by staying in one of the two hotels in Mustique.

The elegant Cotton House has 18 colonial-style rooms, suites and cottages with four-poster beds.

And 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.

Deck of the Billy Mitchell suite at Firefly, one of two hotels on Mustique
Deck of the Billy Mitchell suite at the Firefly Mustique hotel

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.

Colony Club beach, Barbados
We couldn’t resist adding a pic of the Colony Club beach – the sand is so powdery soft!

Villas & Apartments Abroad

A Barbados villa rental from Villas & Apartments Abroad
Would this 8-bedroom Barbados villa rental (Bon Vivant) suit your needs?

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

Built of coral stone, the Porters Great House Cottage sleeps up to 6 and is a short distance from Folkstone Beach

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

This luxurious two-storey villa on Gibbes Beach (from Blue Sky Luxury) comes with a swimming pool and two staff

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

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.

Crane Villas

Cragmere Villa in Barbados has 5 ensuite bedrooms
Cragmere Villa in Barbados has 5 ensuite bedrooms – and this view!

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 Resort in Barbados is popular with honeymooners

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.

Crane Beach has been rated one of the 10 best beaches in the world
Crane Beach has been rated one of the 10 best beaches in the world

Sandy Lane

The Sandy Lane Resort is perhaps the most deluxe hotel in Barbados
So pretty in pink! The Sandy Lane Resort is perhaps the most deluxe hotel in Barbados

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.

The Villa at Sandy Lane, Barbados
The Villa at Sandy Lane gives you access to the resort’s golf, tennis, watersports and dreamy spa

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

Casa de Campo is a legendary Caribbean villa resort
Casa de Campo is a legendary Caribbean villa resort

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.

The white sands of Minitas Beach are pristine!
The white sands of Minitas Beach are pristine!

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

Tennis court, pool, 6 bedrooms and a beach nearby - meet Villa Kathleen on Antigua.
Tennis court, pool, 6 bedrooms and a beach nearby – meet Villa Kathleen!

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.

Alternatives to Caribbean luxury villas

Puerto Vallarta

Casa Tres Vidas is a wonderfully eclectic collection of 3 villas in Puerto Vallarta that can be combined for an extra-large gathering.
Casa Tres Vidas is a wonderfully eclectic collection of three villas in Puerto Vallarta that can be combined for an extra-large gathering

One time when visiting Puerto Vallarta, we stayed at Quinta Maria Cortez, where we checked out its sister property, Casa Tres Vidas (“House of Three Lives”).

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.

Vida Sol, one of the 3 villas in Casa Tres Vidas in Puerto Vallarta
Vida Sol, one of the 3 villas in Casa Tres Vidas in Puerto Vallarta

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

We stayed in this deluxe 3-bedroom hillside condo on the Papagayo Peninsula

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!)

Seacliff Point, one of the villas in Costa Rica for rent through Papagayo Luxury Villa Rentals
Seacliff Point, one of the villas in Costa Rica for rent through Papagayo Luxury Villa Rentals

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.


Discover more fabulous hotels for a tropical vacation!

Puerto Vallarta: Check out these gorgeous boutique hotels in Puerto Vallarta, from affordable inns to secluded celeb-worthy villa hotels.

St. Martin and St. Maarten: Here’s a complete guide to the top hotels in St. Martin and St. Maarten.

Cabo San Lucas: The best resorts in Cabo San Lucas are some of the most deluxe in the world! Many have suites with private plunge pools.

Our top travel tips and resources

Hotels: is great for scoring a “wow” hotel – or at least a decent one. (We especially like their flexible cancellation policy!)

Vacation homes, condos and rentals: We prefer and use Vrbo (Vacation Rentals by Owner).

Tours: For the best local food, walking and other guided tours, plus skip-the-line tickets to attractions, check out Viator (a TripAdvisor company) and GetYourGuide.

Car rental: Renting a car is often one of the best ways to explore off the beaten path. Discover Cars searches car rental companies so you get the best rates.

Travel insurance: SafetyWing is designed for frequent travelers, long-term adventurers and digital nomads. It covers medical expenses, lost checked luggage, trip interruption and more. We also have and recommend Medjet for global air medical transportation and travel security.

Travel gear: See our travel shop to find the best luggage, accessories and other travel gear. (We suggest these comfy travel sandals for city walking, the beach and kicking about.)

Need more help planning your trip? Check out our travel tips and resources guide for airline booking tips, ways to save money, how to find great hotels and other crazy useful trip planning info.

Pssst! If you make a booking or purchase through our site, we may earn a small commission (at no cost to you). Thanks!

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Best Caribbean villas
Best luxury Caribbean villas

Photo credits: 17 to 19, 22 to 26 © Janice and George Mucalov, SandInMySuitcase | Caribbean villa images courtesy of the respective villa agencies and hotels

About the authors

Luxury travel journalists and SATW, NATJA and TMAC “Best Travel Blog” award winners, Janice and George Mucalov are the publishers of Sand In My Suitcase. Between them, they’ve traveled to all 7 continents. See About.

Find destination guides, global food-and-wine stories, luxury hotel reviews, articles on cultural explorations and soft adventure trips, cruise reviews, insanely useful travel tips and more!