When you think of the Caribbean, the first thing that comes to your mind is sandy and pristine beaches. There’s no wonder about that because this region is all about providing tourists with a dreamy and tropical getaway and exciting coastal adventures. Situated in the Americas, some of the region’s most popular destinations are The Bahamas, Jamaica, Puerto Rico, the Cayman Islands, Haiti, and the U.S. Virgin Islands. But every country here is equally beautiful, and each has something unique to offer for everyone. Scroll down and choose where to stay when you visit the region. It offers a wide array of accommodations that range from cozy huts to honeymoon resorts. For the best stay, check out these top vacation rentals with chef in Caribbean.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 11, 2024.
1. Tropical oceanfront retreat with butler service in Jamaica (from USD 1292)
Seated between quaint towns on the northern coast of Jamaica, this opulent villa rental with a chef has a few unique features that set it apart from other private villas across the country. It sits in a quiet oceanfront area which is expansive enough.
It comes with five distinctively designed bedrooms, one of which is located right in front of the private pool. If you’re not into doing chores, let the professional crew of a housekeeper, chef, and butler handle it in your stead.
2. Stunning abode for 10 in the Dominican Republic (from USD 1360)
If you are eyeing to stay at a luxury villa that offers five-star rated services, then this one is for you. The opulent home is located in the Dominican Republic, and it comes with five bedrooms, nine beds, and a total of six baths. Your accommodation package here comes with a maid, a chef, and a butler.
The stunning abode can host up to 10 guests and also welcomes children if you’re traveling with your family. It is close to many shops, bars, restaurants, and top-notch attractions.
Top guest reviews
Amenities & Room:
we particularly enjoyed the outdoor space the outdoor tv and the pool/hot tubamazing very large outdoor covered patio and fabulous pool and hot tubRead more reviewsHost:
the staff was amazingthe staff was excellent and accommodatingjoseph(who manages the house) was very helpfulwonderful house and staff the house is newly updated and beautifulamazing stay super friendly staffamazing food prepared by the chef defenitly coming back
3. Classy retreat for a large group in the U.S. Virgin Islands (from USD 7943)
You will have a taste of paradise when you choose this classy beachfront retreat with a private chef for your upcoming Caribbean vacation. The place is perfect for you if you’re traveling with a large group of up to 44 members because it has 12 spacious bedrooms. Inside the property, you’ll be welcomed by elegant furnishings and an artistic decor.
Located in the U.S. Virgin Islands, the property is near areas where you can experience a number of outdoor fun, such as diving, snorkeling, hiking, and fishing.
Top guest reviews
Amenities & Room:
this stunning house has a mural of the idyllic surroundings in the dining/living room areain the pool you can easily lose yourself in the beautiful surroundingswe had passion fruit chefs stock the kitchen and cater several mealsHost:
werner was an excellent host always availablegreat property werner and his staff were excellent hoststhanks again to werner and his entire staff for making our trip so memorablethank you to brian werner and the staff for making this trip a true slice of heavenwe received a real treat when we met the owner werner who happened to be in townRead more reviewsLocation:
the villa is in a perfect and beautiful locationthe villa at coral gardens beach estate is a beautiful place to stay for a large groupmy fiancé and i were looking for the perfect place to get marriedif you are looking a wonderful place to stay in st
4. Lovely villa with astounding views in the Dominican Republic (from USD 429)
This cozy six-bedroom, eight-bath villa rental is spacious and designed with classy furnishings. It is a lovely vacation rental in the Caribbean with a chef and a maid and offers a wide variety of amenities for a more enjoyable stay. For instance, it comes with a well-stocked kitchen, a balcony, a patio, and an outdoor swimming pool.
Located in the Dominican Republic, the property is surrounded by tropical trees and breathtaking views. If you want to feel comfortable while appreciating the views, you can lounge about on the sunbed outside the home.
Top guest reviews
Amenities & Room:
air conditioners in every room work in excellent conditionsthe pool area is amazing exactly as seen in the picturesCleanliness:
we loved the clean beautiful tropical home with the large pool and outside areathe house is simply gorgeous and spotlessperfect place to stay in confresi home is beautiful clean and convenientHost:
the owner cindy could not have been any more helpful from the startthe staff went above and beyond all the time the owners were super great to deal withthe staff is top notch julio the handiman is a pleasure especiallyhighly recommended and cindy/john were very responsiveeverything was great from the booking process speaking with the owner the housekeeper and property managerRead more reviewsLocation:
ocean world is walking distance free to visitthis villa was the perfect place for a girl’s trip to celebrate my 70th birthdaythe house is wonderful the location excellent and the staff
5. Elegant house with four spacious bedroom in The Bahamas (from USD 1129)
You will get to eat sumptuous meals prepared by a professional chef when you stay at this luxurious beachfront vacation rental in The Bahamas. You can also expect modern amenities once you check in here. The lavish home has four spacious bedrooms, four full baths, and a gourmet kitchen. An outdoor grilling facility is also included in your rent here. The place is conveniently near the airport and is also close to wondrous attractions in Exuma.
Top guest reviews
Amenities & Room:
the kitchen was laid out just right as we always congregated around the huge counterthe kitchen is well equipped & designed to enjoy cooking with friends ( or family)Cleanliness:
the house was spotless and outfitted very wellHost:
the property manager was very friendly and easy to get ahold of for any questions we hadcindy & esther were helpful in finding the right people for usthe owners and manager have done a great job providing a beautiful comfortable and efficient space and homeso considerate and attentive to guests needsesther is very responsive and prompt if there are any issues as are the ownersRead more reviewsLocation:
great location to everythingbest location for everything the pictures don’t do it justicethis is our fourth trip to exuma and by far the best place we've stayed
6. Charming cottage with an infinity pool in St. Vincent and the Grenadines (from USD 458)
Set in St. Vincent and the Grenadines, this luxurious cottage is close to a number of stunning beaches. It is tucked away on a hillside, so you’ll definitely witness stunning views. With a queen-sized bed and an infinity pool, it is a vacation rental for two that is ideal for a romantic getaway.
You and your loved one or companion can enjoy a high-quality dinner prepared by a chef. You can also bond together in the modern, well-stocked kitchen while preparing home-cooked meals.
Top guest reviews
Amenities & Room:
we did not need to use the air conditioning and kept sufficiently cool with the large fanCleanliness:
beautiful clean beach crystal clear water and very safeproperty was extremely well maintained and cleanHost:
the service provided by julie and martin(the owners) was superb without being obtrusiveour hosts julie and martin were incredibly hospitable and helpful hostsour hosts julie and martin were incredibly hospitable and helpful hostsmartin and julie’s attention to their guests extended to their support staff as wellthe owners are still as awesome and accommodatingRead more reviewsLocation:
we would definitely recommend this location to anyonewe love walking and managed to walk an average of around four miles each daywe were looking for relaxation in a beautiful location and boy did we find ita must come back place for sureit is a short walk down the hill to the beautiful beaches restaurants and shops
7. Gorgeous oceanfront dwelling with a private beach in St. Lucia (from USD 700)
Situated in St. Lucia, this paradise-like villa has everything you need for an unforgettable vacation. You can enjoy the services of the full staff that includes a chef. You can also access the pristine private beach at any time of the day. Sun loungers are also provided in case you want to sunbathe.
The gorgeous oceanfront dwelling has three bedrooms, and it can accommodate up to nine guests. The kitchen is loaded with cooking essentials, pantry items, a grill, and an ice maker.
Top guest reviews
Amenities & Room:
comfortable beds good air flow with screens and fans - did not miss air conditioningalthough it was very comfortable sleeping with fansour group of 6 adults and one child was very comfortableHost:
wonderful staff and exceptional cookingthe staff was great-very nice and responsive to any requests we hadthe staff will take care of your every needthe staff is accommodating and unobtrusive but ready and willing to answer all questionsshe is absolutely reliable kind and caring for her guestsRead more reviewsLocation:
this is an absolutely stunning locationif you want a casual but extremely comfortable pleasant beautiful fantastic location to relax and re-energize dont hesitatehe took us to the treetop adventure park at dennery to do the zip linewe had a wonderful time the house and staff were fantastic and the location was perfect for us
8. Luxurious beachfront residence with a media room in Jamaica (from USD 2426)
Don’t just dream of a great vacation. Make it come true by staying at this luxurious residence in Jamaica. The place features an infinity pool, a well-trained chef, and attentive staff. Additionally, it comes with six modern bedrooms, all equipped with safety boxes and air conditioning.
Your safety is also guaranteed when you stay here because this beachfront rental in the Caribbean is equipped with security cameras and is enclosed with high electronic gates. For your entertainment, you can take advantage of the free Wi-Fi or media room here.
Top guest reviews
Read more reviewsHost:
the staff was awesomethe staff of seven that looked after us was simply amazingthe entire staff made our week relaxing and pleasantthe attention from the staff to making sure we were pampered was beyond expectationthe staff works constantly to wait on you hand and foot
9. Opulent haven for 16 in Mexico (from USD 950)
Allow yourself to feel like a VIP even just for a weekend when you stay at this opulent haven in Quintana Roo, Mexico. The place can host up to 16 guests, and it has 6 bedrooms, 9 beds, and a total of 8 bathrooms.
There is also a private pool that you can take advantage of if you want to have fun with your friends or family. For your meals, you can have them planned with the help of the in-house chef. You can also cook your desired meals in the fully equipped and modern kitchen.
10. Modern hideaway with attentive staff in Costa Rica (from USD 957)
Everything you wish for a luxurious getaway is present at this modern hideaway for eight in Costa Rica. With four cozy bedrooms, an astounding pool area, and a professional chef, you’ll feel like you no longer want to go back home and just stay here for good.
The villa also has a gazebo that is perfect for unwinding or dining al fresco. Once you book this accommodation, all you have to do is just relax because the world-class staff will do almost all the things you need for a comfortable vacation.
Top guest reviews
Amenities & Room:
the kitchen had everything one would need and the air conditioning units kept us all comfortable at nightbreathtaking views fabulous infinity pool comfortable and beautifully appointed roomsthe pool isn’t heated and we didn’t get in it nearly as much as we would have likedhaving the private pool and such an incredible view make this a dream vacationfrom the pool (consistently between 85-88 degrees ) to the rooms to ana and her fabulous cooking and personalityCleanliness:
the property is immaculate and the house is sparkly clean and well maintainedfirst off the house was amazing as was the extreme cleanliness of itthe home was clean and well kept with breath taking views as the pictures indicateHost:
friendly and professional staffshe is a delightful hostshe was very helpful in recommending activities and attractionsana is very friendly and efficientall the people in town were very friendly and welcomingRead more reviewsLocation:
this was a great location for a low-key relaxing vacationhowever we've made an exception in this case because this place is so wonderfulinteresting to walk through the rainforest and learn about butterflies trees bats and termites
11. Striking sanctuary with high-end dining and living spaces in St. Lucia (from USD 717)
This stunning villa in St. Lucia is spacious enough to accommodate up to eight guests. It has four bedrooms, seven beds, and four baths. High-end dining and living spaces await you once you book the vacation rental. Even though the villa can’t be classified as all inclusive, the services of a private chef, a housemaid, and a housekeeper are included in the rental fee.
Since the home is just 15 minutes away from the property, you can access an unspoiled beach with sweeping views. Complete your relaxing vacation with massage services–just make sure to inform the staff beforehand so that they can arrange them for you.
Top guest reviews
Amenities & Room:
the pool was well maintained and from the pool deck we could view lovely sunsets each nightCleanliness:
the staff also keep the house clean and provided clean towels in the bathrooms dailythe house is very clean and perfect for a getawaythe villa is very nice and ultra cleanHost:
the staff was amazingplace was great staff was very helpfulthe staff was top notch and pamela is a great cookthe villa owner was polite excellent to communicate and deal withshe and felicia were responsive to every need we hadRead more reviewsLocation:
this home and location is fabulousmango point is amazing property and is the perfect vacation location
A luxurious getaway in the Caribbean
Whether you’re in the Caribbean for just a weekend or for a longer-term stay, never miss out on the spectacular attractions you can explore here. Of course, don’t forget to have fun swimming or strolling on the sandy beaches scattered all over the region. Book one of the top vacation rentals with a chef on our list to experience a luxurious vacation soon.
For more accommodation options, check out some swim-up suites and hotels with a plunge pool also found in the Caribbean.
Frequently asked questions about the top vacation rentals with chef in Caribbean
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