Luxury Caribbean villas & vacation home rentals for the festive season
Find a stay
Caribbean villas you will love for the festive season

Our Caribbean villas for rent
View All (1073)
Discover our 1073 rental villas in Caribbean Festive

The perfect festive stay

in the Caribbean

Golden beaches, balmy blue seas, and seemingly endless swaying palm trees paint the picture of the glorious Caribbean. The idyllic region isn’t just a sublime option for an unforgettable festive holiday, though. Each island has its own vibrancy and culture, with plenty of fascinating heritage sites, culinary traditions and natural wonders to enhance your luxury Caribbean villa escape this winter.

With over 700 serene islands scattered across the Caribbean Sea, you’ll find absolutely no shortage of locations for a blissful festive getaway. We have over 1,000 villas in the Caribbean in some of the world's most incredible holiday destinations. Luxury is the standard for most, with many nations and territories — including Grand Cayman and the British Virgin Islands — famed for their exclusive beaches, world-class golf courses and fine-dining restaurants. Opt for a beachfront Caribbean villa or vacation rental this winter and enjoy direct access to white sand beaches where you can swim, snorkel or sunbathe to your heart’s content.


Jamaica is certainly an excellent choice for a Christmas holiday in the Caribbean. Lush, tropical forests and pristine sandy beaches make this island paradise the perfect escape from the stress of everyday life. Other fabulous options include the laid-back atmosphere and charm of Turks and Caicos and the vibrancy of Barbados - the birthplace of rum cocktails and spicy Bajan dishes.


St Barts tempts this festive season with an array of fine-dining restaurants, private marinas and beguiling white-sand beaches, while the Dominican Republic offers national parks, secret waterfalls and colonial architecture. Discover the two halves of St Martin, go Dutch or French in this exotic fusion of Caribbean and European culture. Or hide away in the untouched beauty of Anguilla, for a truly authentic slice of Caribbean life.


Nature lovers will feel right at home thanks to the Caribbean’s extraordinary array of lush mountain ranges, scenic national parks, and magical marine reserves. A visit to the gorgeous US Virgin Islands will introduce you to some of the region’s finest natural wonders; especially the island of St John, where 60% of the island is a protected National Park.

Things you can't miss in the Caribbean
  • Be sure to sample local culinary delicacies, every island has its own specialities, which represent the cultural diversity and unique history of each.
  • If you are an animal lover, Grand Cayman is the ideal choice for a Caribbean island trip. Here you can swim with dolphins, turtles, and even stingrays at Stingray City - be sure to check the cruise ship schedules before setting off to avoid any crowds.
  • If you are a golf lover, the Dominican Republic is the ideal destination. The island is home to an array of excellent course, as well as many UNESCO world heritage sites for history buffs to explore.

Our insider tips for the Caribbean

“When in search of sun and sand, there is no better place than the Caribbean. Each island has its own special charms and, of course, spellbinding beaches to explore. I love starting each day with a dip in the clear blue water before enjoying breakfast under the gentle morning sun.”
Mason Kramer Travel Advisor
Mason Kramer

Why stay with us?

RULES 2
Curated and inspected homes, villas & chalets
LUXURY LINENS TOILETRIES
Luxury linen and toiletries
OUT
Round the clock support
CLEAN
Complimentary weekly clean
CHECKLIST
Dedicated concierge
LOYALTY PROGRAMME
Earn & redeem Accor ALL loyalty Reward points
MEET GREET
Personal Meet & Greet

Enhance your festive Caribbean stay

Your luxury onefinestay rental villa in The Caribbean comes with a host of additional services, including wellness activities, sports and equipment hire, dinner reservations, a personal chef, childcare, car hire, entertainment, and celebratory decorations. Just ask your dedicated concierge for more details.
While weekly housekeeping for all our homes and most of our villas & chalets is complimentary, we can always arrange more if needed.

Additional housekeeping

Explore your dream destination with VIP car rental. Your dedicated concierge can arrange delivery of your rental car to your door on arrival.

Car rental

Let’s mix things up with a margarita or three, as your cocktail waiter keeps the drinks flowing while you relax by the pool.

Cocktail

Leave the little ones in safe hands while you enjoy some together time with our childcare services, led by experienced professionals.

Childcare

Don’t worry if you’ve forgotten the pushchair, we have everything our younger guests need to rent including a selection of age-appropriate toys.

Child toy & equipment rental

Your dedicated concierge can arrange fantastic experiences including helicopter trips or a horseback ride along a tropical beach.

Experiences

Find out more about the culture of your destination through its food. For all you gastronomes, we’ll book you a table at the best restaurants in town.

Gastronomy

Looking forward to some treats and a bottle or two of wine? Your personal concierge can arrange grocery deliveries on arrival and during your stay.

Grocery delivery

Find peace on the ocean with boat rental complete with your own skipper. Chase that elusive marlin, snorkel or discover a secret cove.

Private boat charter

You’re here to enjoy yourself and make the most of every second. So sit back, relax, and let your personal butler take care of all the details.

Private butler

Using the best fresh ingredients, your private chef can create a meal to remember. Why not learn a few culinary tricks with in-home cooking lessons?

Private chef

Birthdays or anniversaries deserve something special. Let your dedicated concierge arrange a cake or flower arrangement to celebrate.

Special occasion

Ready to try skiing or diving for the first time? We’ll make sure you have all the sports equipment you need to tick off that bucket-list activity.

Sports equipment rental

Let your dedicated concierge take all the hassle out of transfers so you can start your dream vacation from the moment you step off the plane.

Transfer

Find your inner peace with a massage or wellness treatment at your villa, or visit the destination’s best spas for some indulgent ‘you’ time.

Wellness/In-home spa

Essential Caribbean information

When to visit the Caribbean

JAN
26°C
78F
FEB
26°C
78F
MAR
26°C
78F
APR
27°C
80F
MAY
28°C
82F
JUN
29°C
84F
JUL
29°C
84F
AUG
29°C
84F
SEP
29°C
84F
OCT
28°C
82F
NOV
27°C
80F
DEC
27°C
80F

Please note: these are the average temperatures reported but can vary greatly due to weather conditions, such as heat waves etc. We kindly invite you to contact us for more information, including confirmation that your chosen villa has air conditioning, to ensure a comfortable stay.

A festive season in the Caribbean

  • December to March is the high season in the Caribbean thanks to less rainfall, low humidity and pleasant daily temperatures of 25℃ to 35℃ (77℉ to 95℉). It’s a brilliant time for a Caribbean villa getaway, especially if you want to spend most of your trip lounging around on the beach.

How to get there

Make the journey as memorable as the arrival. Your dedicated concierge can arrange transportation from the closest airport to your Caribbean villa.

By plane

The majority of the Caribbean islands are reachable by air, with most featuring international airports offering both charter routes and private jet facilities. There are direct flights from a handful of US and Canadian cities, as well as several routes departing from the UK and Europe. You’ll be able to arrange a VIP airport transfer to your private villa with your concierge, too.

By boat

Some more remote places, such as scenic St John in the US Virgin Islands and Turks & Caicos’ smaller islands, are only reachable by boat. You can organise transfers in advance with your concierge. The Caribbean is a hotspot for leisurely cruises, too, giving you the option of visiting several islands before settling on one for your villa getaway. The region is additionally a prime yachting destination, especially places like Anguilla, BVI and St Martin.

By car

Hiring a car gives you the freedom to explore beyond your Caribbean villa. Most islands have well-kept roads, although you might want to select a 4x4 if you’re planning on visiting more remote spots. You may need a local licence to drive, but this can usually be issued by the car rental company when you pick up your vehicle.

Local Tips

  • If you plan on taking advantage of the beautiful blue waters, be sure to pack reef-safe sunscreen to ensure you protect the coral reefs and stay safe from the sun at the same time.
  • Make sure to have local currency on hand at all times as ATMs on many Caribbean islands are few and far between.
  • Buy a cooler at the beginning of your trip: they are allowed on beaches in the Caribbean and it is a great way to stay fresh and hydrated with cool drinks throughout the day.

Join the onefinestay community

Be the first to hear about our latest destinations, discover our newest homes and win in our exclusive competitions.

Our awards