Top 11 Vacation Rentals With Chef In Caribbean - Updated 2024

Plarlene Juliane
Plarlene Juliane 
Contributing Writer
Updated
| 5 min read

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 May 23, 2024.

1. Tropical oceanfront retreat with butler service in Jamaica (from USD 1013)

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.

Stayed at this property?
Ocho Rios, St. Ann Parish, Jamaica
701.02 km (435.6 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
21 reviews   Wifi Available
Entire villa 7 Beds 10 Guests 5 Bedrooms 5 Bathrooms

Accommodates: 10

Top guest reviews
Host:
the staff is outstanding
anna’s villa is amazing the staff is one of a kind
Location:
the location is ideal
Read more reviews

2. Stunning abode for 10 in the Dominican Republic (from USD 1350)

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.

Stayed at this property?
La Romana, La Romana, Dominican Republic
246.57 km (153.3 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
villa 10 Guests 5 Bedrooms 6 Bathrooms

Top guest reviews
Amenities & Room:
we particularly enjoyed the outdoor space the outdoor tv and the pool/hot tub
amazing very large outdoor covered patio and fabulous pool and hot tub
Cleanliness:
the house was extremely clean
loved the villa-roomy clean etc
Host:
the staff was amazing
the staff was excellent and accommodating
joseph(who manages the house) was very helpful
wonderful house and staff the house is newly updated and beautiful
amazing stay super friendly staffamazing food prepared by the chef defenitly coming back
Read more reviews
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3. Classy retreat for a large group in the U.S. Virgin Islands (from USD 7957)

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.

Stayed at this property?
St. Thomas, VI, U.S. Virgin Islands
630.83 km (392.0 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
Wheelchair accessible Visual Aid: Braille
villa 30 Guests 15 Bedrooms 15 Bathrooms

Top guest reviews
Amenities & Room:
this stunning house has a mural of the idyllic surroundings in the dining/living room area
in the pool you can easily lose yourself in the beautiful surroundings
we had passion fruit chefs stock the kitchen and cater several meals
Host:
werner was an excellent host always available
great property werner and his staff were excellent hosts
thanks again to werner and his entire staff for making our trip so memorable
thank you to brian werner and the staff for making this trip a true slice of heaven
we received a real treat when we met the owner werner who happened to be in town
Location:
the villa is in a perfect and beautiful location
the villa at coral gardens beach estate is a beautiful place to stay for a large group
my fiancé and i were looking for the perfect place to get married
if you are looking a wonderful place to stay in st
Read more reviews
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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.

Stayed at this property?
Playa Cofresi, Puerto Plata, Dominican Republic
531 meters (0.4 ft) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
villa 18 Guests 6 Bedrooms 8 Bathrooms

Top guest reviews
Amenities & Room:
air conditioners in every room work in excellent conditions
the pool area is amazing exactly as seen in the pictures
Cleanliness:
we loved the clean beautiful tropical home with the large pool and outside area
the house is simply gorgeous and spotless
perfect place to stay in confresi home is beautiful clean and convenient
Host:
the owner cindy could not have been any more helpful from the start
the staff went above and beyond all the time the owners were super great to deal with
the staff is top notch julio the handiman is a pleasure especially
highly recommended and cindy/john were very responsive
everything was great from the booking process speaking with the owner the housekeeper and property manager
Location:
ocean world is walking distance free to visit
this villa was the perfect place for a girl’s trip to celebrate my 70th birthday
the house is wonderful the location excellent and the staff
Read more reviews
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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.

Stayed at this property?
Tar Bay, Exuma, Bahamas
670.7 km (416.8 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 12 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
the kitchen was laid out just right as we always congregated around the huge counter
the kitchen is well equipped & designed to enjoy cooking with friends ( or family)
Cleanliness:
the house was spotless and outfitted very well
Host:
the property manager was very friendly and easy to get ahold of for any questions we had
cindy & esther were helpful in finding the right people for us
the owners and manager have done a great job providing a beautiful comfortable and efficient space and home
so considerate and attentive to guests needs
esther is very responsive and prompt if there are any issues as are the owners
Location:
great location to everything
best location for everything the pictures don’t do it justice
this is our fourth trip to exuma and by far the best place we've stayed
Read more reviews
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6. Charming cottage with an infinity pool in St. Vincent and the Grenadines (from USD 426)

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.

Stayed at this property?
Bequia, St Vincent & the Grenadines, Saint Vincent and the Grenadines
1264.84 km (786.0 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
cottage 2 Guests 0 Bedrooms 1 Bathroom

Top guest reviews
Amenities & Room:
we did not need to use the air conditioning and kept sufficiently cool with the large fan
Cleanliness:
beautiful clean beach crystal clear water and very safe
property was extremely well maintained and clean
Host:
the service provided by julie and martin(the owners) was superb without being obtrusive
our hosts julie and martin were incredibly hospitable and helpful hosts
our hosts julie and martin were incredibly hospitable and helpful hosts
martin and julie’s attention to their guests extended to their support staff as well
the owners are still as awesome and accommodating
Location:
we would definitely recommend this location to anyone
we love walking and managed to walk an average of around four miles each day
we were looking for relaxation in a beautiful location and boy did we find it
a must come back place for sure
it is a short walk down the hill to the beautiful beaches restaurants and shops
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?
Anse Galet, Saint Lucia, Saint Lucia
1220.19 km (758.2 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
villa 9 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
comfortable beds good air flow with screens and fans - did not miss air conditioning
although it was very comfortable sleeping with fans
our group of 6 adults and one child was very comfortable
Host:
wonderful staff and exceptional cooking
the staff was great-very nice and responsive to any requests we had
the staff will take care of your every need
the staff is accommodating and unobtrusive but ready and willing to answer all questions
she is absolutely reliable kind and caring for her guests
Location:
this is an absolutely stunning location
if you want a casual but extremely comfortable pleasant beautiful fantastic location to relax and re-energize dont hesitate
he took us to the treetop adventure park at dennery to do the zip line
we had a wonderful time the house and staff were fantastic and the location was perfect for us
Read more reviews
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8. Luxurious beachfront residence with a media room in Jamaica (from USD 2205)

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.

Stayed at this property?
Montego Bay, Saint James, Jamaica
764.21 km (474.9 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
Wheelchair accessible Visual Aid: Braille
villa 12 Guests 6 Bedrooms 6 Bathrooms

Top guest reviews
Cleanliness:
it was gorgeous very clean and well appointed
the house was beautiful and always clean
Host:
the staff was awesome
the staff of seven that looked after us was simply amazing
the entire staff made our week relaxing and pleasant
the attention from the staff to making sure we were pampered was beyond expectation
the staff works constantly to wait on you hand and foot
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

9. Opulent haven for 16 in Mexico (from USD 921)

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.

Stayed at this property?
Soliman Bay, Q. Roo, Mexico
1737.56 km (1079.7 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
villa 16 Guests 6 Bedrooms 8 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

10. Modern hideaway with attentive staff in Costa Rica (from USD 949)

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.

Stayed at this property?
Puerto Carrillo, Guanacaste, Costa Rica
1931.55 km (1200.3 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 5 Bathrooms

Top guest reviews
Amenities & Room:
the kitchen had everything one would need and the air conditioning units kept us all comfortable at night
breathtaking views fabulous infinity pool comfortable and beautifully appointed rooms
the pool isn’t heated and we didn’t get in it nearly as much as we would have liked
having the private pool and such an incredible view make this a dream vacation
from the pool (consistently between 85-88 degrees ) to the rooms to ana and her fabulous cooking and personality
Cleanliness:
the property is immaculate and the house is sparkly clean and well maintained
first off the house was amazing as was the extreme cleanliness of it
the home was clean and well kept with breath taking views as the pictures indicate
Host:
friendly and professional staff
she is a delightful host
she was very helpful in recommending activities and attractions
ana is very friendly and efficient
all the people in town were very friendly and welcoming
Location:
this was a great location for a low-key relaxing vacation
however we've made an exception in this case because this place is so wonderful
interesting to walk through the rainforest and learn about butterflies trees bats and termites
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?
Soufriere, Soufriere, Saint Lucia
1223.32 km (760.2 mi) from Ocean World Adventure Park, Puerto Plata, Dominican Republic.
villa 6 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
the pool was well maintained and from the pool deck we could view lovely sunsets each night
Cleanliness:
the staff also keep the house clean and provided clean towels in the bathrooms daily
the house is very clean and perfect for a getaway
the villa is very nice and ultra clean
Host:
the staff was amazing
place was great staff was very helpful
the staff was top notch and pamela is a great cook
the villa owner was polite excellent to communicate and deal with
she and felicia were responsive to every need we had
Location:
this home and location is fabulous
mango point is amazing property and is the perfect vacation location
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Plarlene manages a personal blog at www.plarlenejulianev.tumblr.com. She has also committed to traveling to various Asian countries, specifically Malaysia, Singapore, Thailand, Hong Kong, and...Read more

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