11 Top Luxury Vacation Rentals in the Caribbean

What do you think of when we say tropical getaways? We’re not surprised if many of you think of the Caribbean. From the warm weather to the glorious beaches with soft sand and the pampering spas, there are so many things to enjoy in the Caribbean. Luckily, you can have them all by staying at one of the best luxury vacation rentals in the Caribbean! These villas are the perfect base for your trip! They offer you world-class amenities and services and an unforgettable experience. With plenty of space and countless opulent rooms, you can bring your entire family and your BFFs! From the ones in Turks & Caicos to the ones in St Barths, here are our favorite luxury Caribbean vacation rentals!

Greensleeves

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The first option on this list is none other than Greensleeves, one of the most prestigious luxury vacation rentals in the Caribbean. This fully renovated villa is chic and elegant. You can kick off your day at the villa by enjoying your morning coffee in the lounge area. Or, you can also slip into the round swimming pool, surrounded by loungers and umbrellas, in case you want to rest quickly. Additionally, this villa has three dining areas on-site! The main one and the outdoor pavilion can seat up to 20 people. But for a more intimate experience, feel free to dine alfresco in the garden!

No matter how long your stay is, you’ll never spend a day feeling bored. On-site is an impressive cinema that’ll entertain everyone. Apart from that, you can also keep yourself busy at the state-of-the-art home gym! Feel free to challenge your friend on the tennis court for something more competitive. The show-stealer, though, is the beach! Apply sunscreen, wear sunglasses, relax on the lounger, and ask the butler to hand you a cocktail! No wonder it’s named one of the best luxury Caribbean vacation rentals!

Villa Ela

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Up next is Villa Ela, a beachfront villa that’s ideal for beachgoers. This villa is set right on Flamands Beach, offering you views of the endless ocean. But the location isn’t the only thing it’s proud of. The main house features a spacious living room with spotless white sofas and a small table where everyone can gather and have quality time. Additionally, there’s a fully loaded kitchen as well as a dining area, too. Best of all, you can enjoy the breezes and ocean views from literally anywhere!

Moreover, there’s a two-story bungalow across the main villa. It’s where you can find the ocean-view bedrooms, which are our favorites. You can find two bedrooms on the upper level, one of which is the Master Bedroom. It comes with an oversized bathroom along with a bathtub. There are two more bedrooms on the lower floor, which offer easier access to the beach. For recreation, guests can have some friendly competition on the tennis court or take a refreshing dip in the pool.

Villa Neo

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Best for Small Groups. While the list of opulent villas in the Caribbean can go on and on, Villa Neo is easily a standout. We think this is one of, if not the best, options for small families or groups of friends. This hillside villa comes with six bedrooms, each with a king-sized bed! This means everyone in the group can have their own room unless you want to stay with your couple. The rooms are spacious, comfy, and flooded with light thanks to the floor-to-ceiling windows. Not to mention, all of them allow you to wake up to the views of the green hills and blue ocean. Talk about perfection!

After a good night’s sleep, feel free to spend your morning on the wooden terrace and take in the mountain views. Then, slip into the refreshing infinity pool with your loved one! Fun fact: this is the biggest pool in St. Barths! After that, enjoy your breakfast poolside and visit the sandy St. Jean Beach. Don’t worry; it’s only around 10 minutes away from the villa! After a day on the beach, retreat back to the villa and relax in the sauna. But if you still have plenty of energy left, you can work out in the home gym instead!

Bajacu

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Designed by a famous Mexican architect, Bajacu is another great addition to our list of the best luxury Caribbean vacation rentals. This villa features a private beach and allows you to be a stone’s throw away from the turquoise waters. Also, did you know that Bajacu has the only fully private beach on the islands of Turks and Caicos? Pretty impressive, isn’t it? Even when the weather isn’t friendly, you can still have plenty of fun inside the villa. Inside, you’ll find a gourmet kitchen with marble countertops where you can show off your cooking skills! But if you can’t cook, maybe watching the private chef will help!

That’s not all, though! After enjoying the memorable food in the dining area, why don’t you play everyone’s favorite movie in the family room? Featuring air-conditioning and comfy furniture, you’ll be pampered with hours of entertainment. Additionally, there’s also a modern home gym and spa on the property. If you want, you can also book a personal trainer and therapist. This villa offers six lavish bedrooms with private en-suites and can accommodate up to 12. For the best experience, stay in the Master Bedroom! It comes with standard amenities, a freestanding bathtub, a walk-in closet, and a huge private terrace.

We were met on arrival by all the staff. They were friendly, attentive and anticipated our every need. The staff, which was our main question prior to arrival, turned out to be the best thing on the vacation. January 11th was the 50th wedding anniversary for my wife and I and we had our four children and 5 grandchildren for what turned out to be a memorable week.

– Para Chandrasoma (Stayed in January 2023)

Ani

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Best All-Inclusive Villa. The jaw-dropping Ani is one of the best luxury vacation rentals in the Caribbean for those who want to experience an all-inclusive experience. This estate consists of two five-bedroom villas, and it features everything you need and more! Both of the villas are equally gorgeous. They come with their own living area and dining areas. We appreciate that the dining areas are available indoors and outdoors! Personally, we find dining by the pool to be the better experience. Chilling in the pool with your family members is fun, too! However, if the weather doesn’t permit, you can have some quality time in the beautifully furnished living room instead. Turn on the Apple TV and grab your favorite snacks from the gourmet kitchen!

To keep everyone, including your little one, busy, Ani also features a fun games room, where you can find a billiard table as well as a shuffleboard. But if you prefer something more active, you can train your body at the private gym, which is right next to the tennis court. Yes, this Caribbean villa also boasts a private tennis court! It’s a nice way to kill time and have a friendly competition with your loved ones. Also, it’s worth mentioning that this estate also offers free snorkeling equipment, just in case you’re into water sports. Lastly, there are 10 bedrooms on the property. Psst! Two of the master bedrooms are in the North Villa, and there’s one in the South Villa!

Villa Wake Up

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Best Design. Want to wake up in the idyllic St. Barth? Then you should consider booking Villa Wake Up, one of the most stunning luxury vacation rentals in the Caribbean. This chic and private villa is extremely attractive, and we’re huge fans of its design. Constructed over three levels, this modern villa is fitted with the most modern amenities. This villa also boasts two elevators to allow you to transport yourself from one floor to another effortlessly! Super convenient, right? Whether you want to spend your time in the living room, cook in the fully-equipped kitchen, or spend some time in the home theater, everything is only one press away!

When you take a look at the outdoor area, you’ll find a refreshing infinity pool. It’s the outdoor living space star and is accompanied by a jacuzzi. That’s not the only facility for rejuvenation, though. The villa’s lower level is where you’ll spot a huge, modern gym. In addition to that, there’s also a sauna and private massage room. The property has 6 bright and airy bedrooms, perfect for a group of 12. Our favorite, though, is the Master Suite. Set on the upper level, it overlooks the pool and boasts a living area, a spacious terrace, and a couple’s bathroom.

Elsewhere

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With everything Elsewhere offers, it’s easily considered one of the top luxury vacation rentals in the Caribbean. One of the biggest reasons behind this villa’s popularity is its top-notch service. With a professional chef, butler, gardener, housekeeper, and other staff, this full-service villa will never let you lift a finger. The attentive services from the staff will make your experience here memorable. In addition to that, we also love how there are so many spots for you to relax. There’s a wide array of verandahs as well as terraces. On top of that, the upper-level lounges allow you to admire the sea’s beautiful views without interruption.

As one of the top luxury Caribbean vacation rentals, you can rest assured that the overall design of this villa is stunning. The lines between indoor and outdoor spaces are blurred, making the villa feel super spacious. Also, the calming neutral color palette makes you feel at home. Those who need to finish their work can take advantage of the office, while those who want to keep their bodies in shape can work out at the fitness center instead. Able to accommodate 20 people, there are 10 spacious bedrooms on the property, each with a spotless en-suite bathroom.

We spent almost a week with 7 couples at Elsewhere and had a fantastic time. The accommodations were perfect.  We had two meals provided per day; excellent food – catering to the group’s needs / tastes. The butler service and housekeeping were way above any expectations we had. The beach is a 15 minute walk, but worth it.

– Mark (Stayed in May 2022)

Seaclusion Oasis

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Conveniently located on the shores of Green Bay Beach is the Seaclusion Oasis, the epitome of a luxurious lifestyle. With plenty of glass to expand your view, this villa is nothing short of sleek and modern. The indoor-outdoor living area is one of the villa’s highlights. It boasts a terrace, which is an extension of the great room, where you’ll find a cozy lounge area and kitchen and dining areas. This means you’ll have plenty of space to relax! Once you’re on the terrace, you’ll be able to admire the breathtaking views of the beach and the pool, which is another highlight. The infinity pool is the best spot to enjoy sunsets.

Another way to enjoy this villa is by having a romantic dinner al fresco. Enjoy your favorite wine under the umbrella while the others are firing up the gas BBQ! Also, have we mentioned that this villa consists of two beautifully appointed homes? The main villa is where you can find most of the fun. It features a pool table, a media room, as well as a home gym. The second villa houses five luxurious bedrooms, which is ideal for large groups that want to have uninterrupted rest.

Cove Spring House

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Best Amenities. While there are a lot of luxury vacation rentals in the Caribbean, only a few can match Cove Spring House. So, what makes this villa so impressive? First of all, it comes with its own private beach! Talk about exclusivity! In addition, this vacation house also boasts a beautiful 75 ft swimming pool, a waterfall, and a jacuzzi, perfect for those longing for rejuvenation. On top of that, the landscaped gardens and colorful flowers make this villa even more relaxing. Best of all, it’s set on the West Coast of Barbados, so uninterrupted views of the turquoise sea are guaranteed.

Named one of the top luxury Caribbean vacation rentals, this mansion can accommodate up to 20 people at once. In the main house, you’ll find seven massive suites. The other bedrooms can be found in a separate house. Lucky for you, all of them are generous in size and fitted with huge verandahs and sparkling Italian marble bathrooms. It’s not a luxury villa if it doesn’t have a state-of-the-art gym, right? The gym on this property is modern and big and open 24/7! Fret not; a personal trainer is also ready to help you achieve your goals! After a nice workout session, soothe your tired muscles at the wonderful spa center!

Hawksbill Estate

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Another great addition to our list of the top luxury vacation rentals in the Caribbean is the exquisite Hawksbill Estate. This upscale estate is set over multiple buildings and is located on more than four acres of land. One of the things we love the most about this place is its personalized experience. Guests can choose whether to rent the estate as a five, six, or even eight-bedroom villa. In addition to that, there’s also an additional Beach House that features 3 more bedrooms, offering you 11 bedrooms in total. This makes it the perfect option for multi-generational family gatherings as well as special celebrations like weddings.

The heart of the estate is none other than the great room. With super high ceilings and luxurious decor, it’s arguably the most beautiful part of the estate. The great room’s living area is super cozy, and it’s the best spot on-site for everyone to gather and have a nice chat. The main building also proudly boasts a games room with a wide variety of games. If movie nights are your thing, you should ask the others to join you in the media room. And when it’s time to relax, we highly suggest taking a dip in the outdoor pool, which has two sections and is accompanied by a hot tub. The beautiful fire pit that offers a lovely atmosphere is just the cherry on top!

Pearls of Long Bay Estate

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Most Luxurious. As the name suggests, the Pearls of Long Bay Estate is set on the sands of Long Bay Beach, one of Providenciales’ world-renowned attractions. This estate is the most luxurious option on our list, comprising three beautiful beachfront villas that offer nothing but top-of-the-world amenities. Manicured gardens surround these picturesque private villas, offering you the utmost privacy. Though three different villas are on the property, all are equal. Every villa has a fully loaded kitchen and everything else you need to satisfy everyone’s hunger. With eight bedrooms, you no longer have to squeeze everyone into the same room! Better yet, each of them comes with a spotless en-suite bathroom. Our favorite has to be the Oceanfront Master Bedroom, though. It occupies the whole top floor and is the comfiest!

Like many other luxury vacation rentals in the Caribbean, this estate also boasts media rooms that can accommodate up to 10, along with things like a popcorn machine, Blu-Ray player, Apple TV, and a 95-inch flat-screen TV. When you’re at this estate, you should also check out the lagoon area, which features two decks for outdoor dining and a pool. And if swimming isn’t really your favorite, feel free to work up a sweat in the air-conditioned gym, which is fitted with the latest equipment!

Our Verdict!

From elevators to direct access to the beach and luxurious gyms, all of the luxury vacation rentals in the Caribbean above will never fail to give you that five-star experience. But if you’re in a hurry, we have compiled some of our favorites based on the following criteria. So, why don’t you give them a look?

• Most Luxurious: Pearls of Long Bay Estate
• Best Amenities: Cove Spring House
• Best Design: Villa Wake Up
• Best All-Inclusive Villa: Ani
• Best for Small Groups: Villa Neo

Things You May Need During Your Stay

• Top Villas Celebration Packages – Most of our villas above are perfect for celebrations. From weddings to anniversaries, you name it! So, why not let Top Villas help you prepare that celebration with its packages? Whether you need sparkling wines, banners, flowers, or others, it’ll have everything ready when you arrive!
• Top Villas Wine & Cheese Gift Basket – Imagine relaxing on the pool deck with a glass of wine in your hand and artisanal cheese crackers, as well as fresh grapes on the table beside you! That sounds like the perfect way to watch the sunset, right? Lucky for you, Top Villas can help make that come true!
• Caribbean Travel Guide – Want to visit the Caribbean but don’t know where to start? This helpful guide will let you know some of the top islands, the top attractions, and many more!