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Vacation like a multi-millionaire at these posh Caribbean villas!

Please only travel when it’s safe to do so.

For many of us, luxury Caribbean villas 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.

Luxury villas, Caribbean: Contents

Top 5 Caribbean islands for villa rentals:

Mayreau villas
“Rent” just one bedroom in a villa (TRIBU) | Villa-and-sailing combo

Jamaica villas
Best Jamaica resort villas | Private villas in Jamaica

Mustique villas
Princess Margaret’s home | Hotels on Mustique | Agencies for Mustique rentals (Wimco Villas and Mustique Company)

St. Barts villas
St Barts villa rentals through Sibarth, St Barth Properties and Eden Rock

Barbados villas
Private Barbados rentals (Blue Sky Luxury, etc.) | Crane Villas and Crane Resort | The Villa at Sandy Lane

Other Caribbean house rental agencies

Alternative: Costa Rica villa rentals

Caribbean villas

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”).

Casa Tres Vidas villa rental in 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

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.

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

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.

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

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 beautiful Caribbean villas

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

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.

St Barth is one of the hippest islands for a Caribbean villa vacation
St Barth is one of the hippest islands for a Caribbean villa vacation (Credit: Shellona Beach Club)

1) 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!)

Ahhh… Mayreau.

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.

Robert Righteous serves killer rum punches in his colorful Caribbean bar on Mayreau
Robert Righteous serves killer rum punches in his colorful Caribbean bar on Mayreau

Mayreau is the island for that true barefoot Caribbean getaway.

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

TRIBU Villas:

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.

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 – one has an outdoor shower, mine 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

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.

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 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:

How to make that villa vacation even more special?

Combine your Mayreau villa holiday with sailing in the Caribbean too.

It’s pretty relaxing on our catamaran…

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.

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.

A cheesy egg-and-bacon “pie” is 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, 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!)

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 for being in paradise.

Our days were spent swimming, snorkeling, scuba diving – and eating!

TRIBU Villas and Tradewinds

There are plans to build several additional swanky, four-bedroom villas on the Mayreau property.

For more information and to book, see the Tradewinds website and the TRIBU Villas Mayreau webpage.

How to charter a yacht: Chartered yacht holidays aren’t for the rich and famous – really!

2) Jamaica villas

Caribbean villas
Jamaica is famous for its Caribbean villa vacations

Jamaica is the third largest Caribbean island.

With an extensive selection of villa rentals, Jamaica is a popular destination for Caribbean villa holidays.

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.

Life's a beach in Jamaica at the Tryall Club!
Life’s a beach in Jamaica! (Credit: Tryall Club)

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.

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.

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.

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

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.

Round Hill Hotel and Villas

Check prices and availability here

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.

Your Caribbean home-away-from-home in Jamaica? This is the "Sunset" villa at the Tryall Club
Your Caribbean home-away-from-home in Jamaica? This is the “Sunset” villa at the Tryall Club

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 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 out luxury villas in Jamaica.

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

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.

"Scotch on the Rocks" is one of the finest luxury villas in Jamaica for rent
“Scotch on the Rocks” is one of the finest luxury villas in Jamaica for rent

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.”

This Jamaica villa has its own private pier for swimming in the sea
Look! The villa also has its own private pier for swimming in the sea!

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).

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

Jamaica Villas by Linda Smith

To rent a luxury villa on Jamaica, check out this collection of luxury Linda Smith villas.

3) Mustique villas

What’s special about Mustique?

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.

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

Fast forward to today. Mustique 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.

Beautiful Brittania Bay in Mustique
Beautiful Brittania Bay in Mustique (Credit: Mustique Island)

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”).

Princess Margaret hosted Mick Jagger at her Mustique villa, Les Jolies Eaux
Princess Margaret hosted Mick Jagger at her Mustique villa, Les Jolies Eaux (Credit: Mustique Company)

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.

Mustique villas

To rent a luxury villa on Mustique, see Wimco Villas’s website. Also check the Mustique Company’s website.

Mustique hotels:

There are only two hotels on Mustique: the Cotton House and Firefly Mustique.

You may end up popping into their restaurants for dinner.

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

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)

Cotton House:

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

Afternoon tea at the Cotton House, one of the two Mustique hotels
There are only two Mustique Island hotels (Credit: Cotton House)


Perched on a hill with views of the Caribbean sea, the boutique Firefly 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 (Credit: Firefly Mustique)

Firefly Mustique Hotel

Check prices and availability here

Are you a sucker for sinfully luxurious hotels? Then check out these 27+ fabulous resorts with private pool suites

4) St Barts villas

Oooh, let’s go French! Saint Barthelemy (commonly known as St Barth or St Barts) is très chic. Think St. Tropez meets the tropics.

Shell Beach on St Barts is made up of pretty pink shells
We hung out recently on Shell beach in St Barts – the beach is made up of pretty pink shells (Credit: Shellona Beach Club)

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.

The beach club attracts villa vacationers and visitors who come in from their private yachts (Credit: Shellona Beach Club)

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).

St Barts villa rentals:

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 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).

Sibarth Villa rentals

Check the website here

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.

"Legends B" by St Barth Properties has an infinity pool with views over Gustavia
“Legends B” by St Barth Properties has an infinity pool with views over Gustavia

St Barth Properties

Check the website here

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.

You get access to its beach facilities on beautiful St Jean Bay when you rent one of Eden Rock Villa Rental’s 130+ luxury villas.

Newspapers and a continental breakfast from the hotel are delivered to your villa each morning too.

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

Eden Rock Villa Rental

Check the website here

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 villas

We got engaged in Barbados – at the charming Colony Club – so this island holds a special place in our hearts.

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

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.

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

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 & Apartments Abroad

Check the website here

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 throughout Barbados.

Listings include 1-bedroom cottages to gorgeous sprawling 10-bedroom mansions.

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

Watch out for early booking discounts and shoulder-season promotions, for example, a transportation credit that can be applied toward a rental car.

Villas of Distinction

Check the website here

Blue Sky Luxury:

Locally based in Barbados, Blue Sky Luxury is a member of the Barbados Hotel and Tourism Association.

And 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.

This luxurious two-storey villa on Gibbes Beach comes with a swimming pool and two staff

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.

Blue Sky Luxury

Check the website here

Crane Villas:

Windermere and Cragmere 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.

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

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.

The Crane Resort in Barbados is popular with honeymooners

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.

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

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, for example.

After my villa stay in Mayreau, I stopped for a lovely lunch here before I caught my ongoing flight back to Canada.

Crane Resort, Barbados

Check prices and availability here

Sandy Lane:

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.

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

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.

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

Other Caribbean villa rental agencies

In addition to Wimco Villas and other big name villa rental companies covered above, check out La Cure Villas and McLaughlin Anderson.

LaCure Villas:

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.

“Arawak House” can be rented on Antigua through LaCure Villas

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.

This Grand Cayman villa offers 4,000+ square feet of living on a sugar white beach
This Grand Cayman villa (“Kai Zen”) offers 4,000+ square feet of living on a sugar white 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.

La Cure Villas

Check the website here

McLaughlin Anderson:

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.

If Virgin Gorda interests you, ask about this Caribbean villa from McLaughlin Anderson
If Virgin Gorda interests you, ask about this Caribbean villa from McLaughlin Anderson

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.

McLaughlin Anderson

Check the website here

Alternative: Luxury Costa Rica villa rental

Interested in an exclusive villa rental in Costa Rica instead?

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

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 (which we didn’t need for the two of us) and the actual villa (which again we didn’t need; like, how many bedrooms could the two of us use?).

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

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: 2 to 4, 7 to 9, 12 to 18 © Janice and George Mucalov, SandInMySuitcase | Lead image courtesy Jamaica Villas by Linda Smith | Remaining images courtesy of the respective villa companies and hotels, except where noted

About the authors:

Janice and George Mucalov

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

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

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