Both islands offer pristine beaches, fine dining and luxurious accommodations. But each has its own atmosphere and distinct characteristics that cater to different styles of tropical island vacation. Which Caribbean island is best for your travel preferences?

Jamaica is known for reggae music, its easy-going atmosphere and spanning landscapes, offering the adventurous visitor plenty to explore. Barbados is known for its boutique hotels, intimate culinary scene and authentic island culture for the reserved and relaxed guest. Keep reading to learn more about which Caribbean destination you should visit next.


The island nation of Jamaica is located in the West Indies about 700 miles off the coast of Florida. Historically a valuable colony due to its sugar production, Jamaica finally became independent from England in 1962. Jamaica’s largest city and capital is Kingston, which is thought to be the birthplace of reggae music and has a relaxing, “no worries” atmosphere. Aside from music, the country is known for its beautiful beaches, golf resorts and the popular natural attraction, Dunn’s River Falls.

Dunn River Falls, Jamaica
Photo Credit: Lakeisha Bennett

Attractions and Activities

Dunn’s River Falls

Dunn’s River Falls is located on the North coast of Jamaica near the town of Ochos Rios. It is one of seven natural waterfalls in The Americas that flows directly into the ocean. Thousands of visitors are attracted to the site every year to climb the step-like falls with a guide. The activity takes about an hour, and you’re able to explore the lagoons and surrounding greenery while venturing up the scenic falls.

Dunn's River Falls

Jamaican Golf

Jamaica is also known for its world-class golf! Montego Bay, Jamaica’s second largest city, is a popular spot among golf enthusiasts. According to Golf Digest, Montego Bay has become the Caribbean’s premier golf destination, boasting multiple, newly-renovated courses for guests to play during their visit. The top three courses to play, also mentioned by Golf Digest, include The Tryall Club, The Ritz-Carlton White Witch G Course and the Wyndham Rose Hall Cinnamon Hill Ocean Course. To book a tee time, rates per player for 18 holes range from $115-$200 for all three courses.

Accommodations and Dining

The easy-going atmosphere, accommodation selection and culinary scene are one-of-a-kind in Jamaica. All-inclusive resorts tend to be more popular here. Many of the all-inclusive resorts are located around Montego Bay for easy access to golf courses and water activities. Because the larger resorts include their own restaurants, independent dining options are fewer. But there are still plenty of casual, family-friendly places to choose from in Jamaica! Fresh seafood is always delicious and available throughout the island. Popular Jamaican dishes often include Ackee, a Jamaican fruit, that is usually paired with cod.

Jamaica vs Barbados

Travel Options

Jamaica is 4,243 square miles and is much larger than many other Caribbean islands. It is fairly easy to get to from the U.S. mainland, thanks to its two international airports. Norman Manley International Airport is located in Kingston, on the Southeast side of the island, and Sangster International Airport is located in Montego Bay, on the Northwest side. If you’re staying at a resort, you’ll most likely fly into Sangster. Flight time from New York City to Jamaica is about 4 hours. Jamaica is a great Caribbean destination for the active and adventurous traveler. To view ThirdHome Exchange and Rental luxury properties, click below.


Offering 60 miles of coastline and located in the eastern Caribbean, is the island nation of Barbados. Like Jamaica, it was also a British colony until its independence in 1966. Due to their relatively recent independence, Barbadian culture remained intertwined with British culture, and many English pastimes were popularized on the island. Traditions such as afternoon tea and cricket matches are still popular among locals. Barbados is known for its luxury boutique hotels, colonial history and unique culture. It is thought to be one of the most prosperous Caribbean islands, touting the 2nd largest GDP per capita among its Caribbean peers.

Jamaica vs. Barbados

Attractions and Activities

Harrison’s Cave

A popular tourist attraction among outdoor explorers offers an experience unlike many others in the Caribbean: Harrison’s Cave. Visitors are able to venture into the caverns below Mount Hillaby. The cave was discovered in 1785, but its plethora of small passageways and nooks underneath the island weren’t fully mapped until the mid-1970s. Both walking tours and a moving tram are available for explorers wanting to take part in the subterranean experience.

Harrison's Cave

Folkestone Marine Park

Family-friendly activities besides lounging beachside are easily accessible in Barbados due to its smaller size. Barbados is known to have one of the lowest crime rates and some of the friendliest locals in the Caribbean. So if you’re wanting to explore the island a bit, activities are always close by and locals are happy to help point you in the right direction. A great option for families is Folkestone Marine Park. It is located on the west coast and is a fabulous spot to snorkel and interact with wildlife. An artificial reef was created by the shipwrecked Stavronikita, a Greek freighter that sank in 1956. Paddle boarding, diving and kayaking are also popular activities in the area.

Accommodations and Dining

Barbados is known for its high-end hotels that offer a unique and authentic island holiday like no other. Large, all-inclusive resorts are not common in Barbados, as affluent, low capacity hotels with intimidate atmospheres populate the island. Sunsets on the west coast of the island are unparalleled. This is especially true when dining at one of many boutique waterfront restaurants in western Barbados. A Caribbean sunset paired with local Barbadian cuisine is a match made in heaven. Barbadian food features a mix of African, Indian, Irish, Creole and British inspiration; a unique combination you won’t want to miss out on.

Travel Options

Barbados is only 166 square miles, about 26 times smaller than Jamaica! Grantley Adams International Airport is the only airport on the island and is located in Christchurch, on the southern coast. It’s important to note that when visiting Barbados, the exchange rate between Barbadian dollars and U.S. dollars is fixed at $2 BBD to every $1 USD. Barbados is a frequently visited destination by smaller groups, families and couples that are looking for a more relaxed yet luxurious stay. Click below to view ThirdHome luxury Exchange and Rental properties in Barbados.

So, which Caribbean island is best for you?

Jamaica and Barbados are both luxurious and fabulous island destinations but are different in their respective ways. Any beachgoer would love to be on either coastline this very minute! But, it truly comes down to your own travel preferences. Jamaica is a great option for non-family travelers or large groups that are looking for an island escape with plenty of amenities. Visitors to Jamaica can expect multiple luxury golf resorts and accommodations. Traveling families and couples looking for a more intimate getaway should visit Barbados. Known for its safe atmosphere and friendly locals, visitors can expect an authentic island escape and child-friendly activities in Barbados. In the end, both Caribbean islands offer opportunities to create unforgettable travel memories.

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ThirdHome is the luxury property and travel club for second home owners that enables its members to explore the world through a variety of travel experiences. If you’re interested in learning more, please click here.

Do you have a luxury Caribbean vacation on the mind but aren’t sure what island to choose for your next trip? Find inspiration below with recommendations on what to do on each Caribbean island and where to stay. All of the gorgeous properties below are part of ThirdHome, the world’s most luxurious home exchange. Read below to find out what island is most your style, and get ready to start packing your swimsuit and sunglasses!

Luxury Caribbean vacations are available for the taking! Plan your trip today.

 Luxury Caribbean Vacations Anguilla


What to do: You’ll want to walk along the brilliant white-sand beach at Shoal Bay East and grab a cocktail at one of the laid-back bars that are scattered along the beach. If scuba diving is of interest to you, Prickly Pear Cays has an underwater cavern where you can dive by sunken shipwrecks.

Where to stay: Click here to view all ThirdHome properties in Anguilla.

Luxury Caribbean Vacations Antigua

Antigua and Barbuda

What to do: Antigua is known for its picture-perfect beaches. Visit Half Moon Bay beach and bodysurf or snorkel. If you are a history enthusiast, Nelson’s Dockyard National Park was made a UNESCO World Heritage Site in 2016 and was once the Caribbean base of the British Royal Navy.

Where to stay: Reserve this spectacular 6-bedroom home with expansive ocean views or click here to view all ThirdHome properties in Antigua and Barbuda.

Luxury Caribbean Vacations Aruba


What to do: Snorkel to view the USS Antilla shipwreck that has turned into an artificial reef, which means it is covered in bright coral and sea life. If you are feeling adventurous, take a hike through Arikok National Wildlife Park to a natural pool that is protected by limestone to break the waves of the ocean.

Where to stay: Stay in a tropical villa nestled on 3 private acres or click here to view all ThirdHome properties in Aruba.

Luxury Caribbean Vacations Bahamas


What to do: If you are taking a family trip, visit Aquaventure Waterpark on Paradise Island and spend all day playing in the 141-acre waterpark. If you are looking for a more adult-oriented activity, go to Arawak Cay (in Nassau) over the weekends when they hold a big fish fry party complete with food, daiquiri bars and reggae music.

Where to stay: Enjoy a luxurious week at The Reef Atlantis or click here to view all ThirdHome properties in the Bahamas.

Luxury Caribbean Vacations Barbados


What to do: For a leisurely stroll with beautiful views, walk along the boardwalk at Rockley Beach. Or, visit Paynes Bay Beach for particularly calm waters that are great for swimming.

Where to stay: Click here to view all ThirdHome properties in Barbados.

Luxury Caribbean Vacations Cayman Islands

Cayman Islands

What to do: Two million tourists visit the Cayman Islands each year, making it an extremely popular spot for luxury Caribbean vacations. While visiting, make sure to take an afternoon to go to Starfish Point, where the calm waters protect thousands of starfish. You can easily spot them, so no snorkel gear is needed.

Where to stay: Click here to view all ThirdHome properties in the Cayman Islands.

Luxury Caribbean Vacations Dominican Republic

Dominican Republic

What to do: Take a day trip to Peninsula de Samana for ample whale watching opportunities. For a slow-paced activity, relax on Playa Rincon, which is a gorgeous beach that has a thick palm forest on one side and the ocean on the other.

Where to stay: Spend a week in a beautiful 4-bedroom oceanfront villa or click here to view all ThirdHome properties in the Dominican Republic.

Luxury Caribbean Vacations Guadeloupe


What to do: Guadeloupe is an archipelago of islands that all boast incredible natural beauty. You can visit dark-sand beaches on Place de Malendure or visit the traditional fishing village of Deshaies.

Where to stay: Vacation on a luxury catamaran yacht through ThirdHome’s Affiliation with TradeWinds.

Luxury Caribbean Vacations Jamaica


What to do: Hike up to Blue Mountain Peak just before sunrise for a view that will stick in your memory forever. Or, visit Kingston for a plate of jerk chicken and a nightlife scene full of unique culture. You can take multiple luxury Caribbean vacations here and still not get bored.

Where to stay: Enjoy complete privacy while staying in an estate home on 55 acres of lush property or click here to view all ThirdHome properties in Jamaica.

Luxury Caribbean Vacations Puerto Rico

Puerto Rico

What to do: Take a walk down the vibrant and colorful streets of San Juan, which is the second-oldest European-founded settlement in the Americas. For a day at the beach, you can’t go wrong visiting Playa Flamenco, which stretches for a mile around a horseshoe-shaped bay.

Where to stay: Reserve a week at a resort property that directly overlooks a spectacular golf course or click here to view all ThirdHome properties in Puerto Rico.

Luxury Caribbean Vacations St. John

St. John

What to do: Two-thirds of St. John is a protected national park, which makes this calm island a beautiful retreat for those who love nature. Snorkel with sea turtles at Caneel Bay, which is within Virgin Islands National Park.

Where to stay: Click here to view all ThirdHome properties in St. John.

Luxury Caribbean Vacations St. Kitts

St. Kitts and Nevis

What to do: This two-island nation is perfect for a low-key vacation. Spend a day wandering through the Botanical Gardens of Nevis to see orchids, palms, water lily ponds, bamboo groves and more.

Where to stay: Resort-style living is waiting for you at this beach club or you can click here to view all ThirdHome properties in St. Kitts and Nevis.

Luxury Caribbean Vacations St. Lucia

St. Lucia

What to do: The twin peaks of the Pitons make for perfect views, but a very challenging hike. If you are up for the challenge, you will be rewarded with expansive views of the island and ocean. For a more relaxing activity, visit the most famous beach on the island, Sugar Beach. It is situated between the two Pitons, which create unique views and an interesting beach experience. Many travelers take luxury Caribbean vacations to St. Lucia for its combination of rugged landscape and beautiful beaches.

Where to stay: Click here to view all ThirdHome properties in St. Lucia.

Luxury Caribbean Vacations St. Maarten

St. Maarten

What to do: There is plenty to do in the Dutch side of this island, and Maho Beach is definitely a must-see experience. Maho Beach is famous for being adjacent to Princess Juliana International Airport, which means planes fly incredibly close to the beach as they are landing.

Where to stay: Stay in a condo that has beachfront access only steps away or click here to view all ThirdHome properties in St. Maarten.

Luxury Caribbean Vacations St. Thomas

St. Thomas

What to do: St. Thomas is one of the most popular destinations for luxury Caribbean vacations, with visitors returning multiple times.  You won’t want to miss climbing up Blackbeard’s Castle, which was built in 1678, for harbor views. For a great beach experience, visit Magens Bay, which is packed with convenient amenities and has kayak rentals.

Where to stay: Bask in the sun at the Ritz-Carlton Destination Club or click here to view all ThirdHome properties in St. Thomas.

Luxury Caribbean Vacations St. Vincent

St. Vincent and the Grenadines

What to do: This chain of islands is in the heart of the Caribbean Sea, and is ideal for those who want to avoid crowds while vacationing. For a relaxed beach experience, visit Saltwhistle Bay where there is a collection of beautiful beaches with a low-key vibe.

Where to stay: Click here to view all ThirdHome properties in St. Vincent and the Grenadines.

Luxury Caribbean Vacations Trinidad and Tobago

Trinidad and Tobago

What to do: Visiting Trinidad and Tobago offers a very unique island experience. Visit the Port of Spain which has authentic restaurants, local markets and a multitude of bars and clubs. For an interesting daytime activity, book a cocoa-cultivation tour in Brasso Seco.

Where to stay: Click here to view all ThirdHome properties in Trinidad and Tobago.

Luxury Caribbean Vacations Turks and Caicos

Turks and Caicos

What to do: Anyone who has taken a lot of luxury Caribbean vacations has most likely visited Turks and Caicos. These tropical isles are a piece of paradise and the crown-jewel beach to visit during your trip is Grace Bay Beach.

Where to stay: Click here to view all ThirdHome properties in Turks and Caicos.

After seeing this list, how many luxury Caribbean vacations are you going to reserve this year with your ThirdHome membership? When reserving your week in the Caribbean, keep in mind that our in-house concierge can help you Enhance Your Stay with arranging the activities we have mentioned in this article and more! 

ThirdHome Exchange members have recently returned from Portland, Oregon and St. Thomas, U.S. Virgin Islands. Keep reading to learn about their ThirdHome experience.

Portland Oregon

Pearl District High-Rise | Portland, Oregon

Visit one of Portland’s most artistic and vibrant districts with this Pearl District High-Rise residence. Featuring room for up to 4 people, this property is a fantastic launching point for a week of gallery crawling, boutique shopping and proximity to world-class outdoor recreation. This property is an hour or less away from Oregon’s wine country, Mt. Hood and the Oregon Coast, giving you a bevy of activities for varied interests. This property is a part of the Pearl District’s fairly recent urban renaissance and revitalization, giving new life to industrial buildings and warehouses. You’ll find modern appointments, industrial architecture and cozy wooden beams woven together into a property as unique as the city in which it resides.

ThirdHome member Steve says, “I can’t say enough about our recent stay at the Pearl District High Rise. My wife and I were looking for a place to visit and came upon the Pearl District posting and decided to give it a try…The condo is beautiful and is in a perfect location. It was just a great stay and we would go back in a heartbeat.” click here to read more of Steve’s review

U.S. Virgin Islands Villa Panorama THIRDHOME Portland Inspiring Experiences

Villa Panorama | Misgunst, U.S. Virgin Islands

Poised over the turquoise waters of Magen’s Bay Beach is the stunning tropical Villa Panorama. True to its name, Villa Panorama features stellar sea views from every angle. The pool deck and lower hot tub deck are perfect for taking in the beauty of the Caribbean. This property includes room for up to 10 guests, making it an ideal family or small group retreat. Nearby you’ll find opportunities for scuba diving, snorkeling, and boating. St. John is a short island hop away for further exploration of the U.S. Virgin Islands. If you’re in need of a refreshing island experience look no further than Villa Panorama.

ThirdHome member Blake says, “ I could go on and on about the VIEWS! The pictures just can’t do the views justice. Every time we would drive up to the Villa, we would be blown away. We stayed post hurricane and had absolutely no issues with travel and the Villa was in pristine condition. The island has really done a nice job with rebuilding efforts. We swam in the hot tub and pool every day. We enjoyed the views from each and every room and balcony. There just wasn’t enough time to do it all!” click here to read more of Blake’s review

Members, click here to view all available weeks and plan your next ThirdHome Exchange trip. Remember, you must be logged in to your account to see availability.

Want more information about our luxury home exchange club? Click here to learn more about ThirdHome.

What are ThirdHome Members saying about their luxury home exchange trips to The Dominican Republic and the United Kingdom this week?

Dominican Republic

La Esperanza | Casa de Campo, Dominican Republic

Sometimes called “the Hamptons of the Dominican Republic” and other times “the Beverly Hills of the D.R.”, Casa de Campo sure does live up to expectation. Comprised of over 1,700 villas ranging in price from $500K to $24 million, visiting Casa de Campo means being in good company. When ThirdHome member, Barbara visited this past month, she only knew as much as the travel guidebooks could tell her. There was no predicting the extent of the pampering she and her party would receive by the property staff. With 3-bedrooms and a pool terrace surrounded by lush greenery, this home is perfect for a winter’s end escape.

ThirdHome member Barbara says, “Casa de Campo is the Beverly Hills of the Caribbean, who knew? Not us…Our home away from home was lovely, beautifully decorated and comfortable without being pretentious…It was truly an exquisite week that we shall never forget! ” click here to read more of Barbara’s review

Dominican Republic Cotswald UK

Fox End | Cotswolds, United Kingdom

Just follow the cookie crumbs from Oxford and you’ll soon arrive at this fairytale cottage in the charming and pastoral Moreton-in-Marsh parish of Cotswold. The building itself dates back to the 1650’s but has been delicately and lovingly updated over the years, a perfect blend of old and new. For reference, tea was introduced to England in 1652, making this property as quintessentially British as teatime. With room for up to 8 people, the word “cottage” more so describes the aesthetic and bucolic qualities of the home rather than the size. Explore the countryside, enjoy tea in the garden, go horseback riding or go fly fishing all from the comfort of this cozy Cotswold home.

ThirdHome members Dean and Lesli say, “We did–fall in love, that is. Hated to leave! This was the perfect storybook cottage in the perfect location. Our family of five were exceedingly comfortable in this well-appointed, gracious and beautifully furnished home…Our visit was exactly what we wanted and needed it to be and it would be our pleasure to have the opportunity to return one day!” click here to read more of Dean and Lesli’s review

Members, click here to view all available weeks and plan your next ThirdHome trip. Remember, you must be logged in to your account to see availability.

Want more information about our luxury home exchange club? Click here to learn more about ThirdHome.

The kids have been fighting in the back of the car for hours, you’ve already stopped three times, and the humidity is oppressive. You finally check in to your resort, the kids get their bathing suits on, and you run triumphantly to the beach. Next thing you know a gust of wind has blown sand in your eyes and your youngest daughter is crying because the water is still a frigid 65 degrees Fahrenheit. Why can’t the beaches be ready when you are? Well, maybe you’ve been booking the wrong beach vacations.

THESE BEACHES ARE CLIMATE CHAMPIONS YEAR-ROUND: Check out THIRDHOME‘s picks for best beach vacations you can take any time of year

Disclaimer: There’s no one perfect climate for everyone. This list attempts to round up temperatures and climates that remain more consistent throughout the year than other popular destinations for beach vacations.

Kailua-Kona beach vacations

Kailua-Kona, Hawaii

Climate: Temperature is typically between 68°F to 87°F (20°C-30°C). Rarely below 65°F (18°C) or above 89°F (31°C)

Hawaiian Christmas should definitely be on your bucket-list if it isn’t already. There’s nothing like a tropical escape in the midst of mainland cold. Kailua-Kona is on the western side of Big Island, which is considered the leeward side of the island. The leeward side of any island is the side that’s protected by the island’s elevation. On Big Island, west is leeward and east is windward. This makes Kaiulua-Kona one of the most protected beach sites (from rain and storms) in Hawaii.

Where to stay: Click here to see all properties in the Kailua-Kona area or book a stay at this ocean view Equity Residences home in September.

Malaga beach vacations

Malaga, Spain

Climate: Temperature is typically between 45°F to 88°F (7°C-31°C). Rarely below 38°F (3°C) or above 97°F (36°C)

Parts of Southern Spain, such as Costa Del Sol, are notorious for their insufferably hot days in the city. Malaga falls in this category during summer months, but receives welcome gusts of cool wind from the Meditteranean, making the dry heat bearable. The winters in this subtropical-Mediterranean climate are very mild due to the Northern Malaga mountains which block most of the northern cold from reaching the coast. The city has only seen snow once in the 20th century on a February night in 1954. Malaga is touted for being “green” all year round making it a joy to visit any time of year. June, July, and August- the hottest months- usually peak out around 87° Fahrenheit. Many British and German ex-nationals have moved to the area since the 1970’s for the pleasant weather.

Where to stay: Click here to see all properties in the Malaga area.

cyprus beach vacations


Climate: Temperature is typically between 43°F to 92°F (6°C-33°C). Rarely below 36°F (2°C) or above 96°F (35°C)

Another subtropical-Mediterranean climate, the island of Cyprus has one of the warmest climates in the Mediterranean Sea. The climate does shift dramatically the more you travel inland, reflected by the snow covered Troodos Mountains, but the coast is a sunny delight. The coast of Cyprus receives 3,200 hours of sunlight per year compared to foggy London’s 1,540 hours per year. So plan your trip to Cyprus today, and play on the sun-drenched beaches of Nissi.

Where to stay: Click here to see all properties in the Cyprus area.

marseille beach vacations

Marseille, France

Climate: Temperature is typically between 39°F to 84°F (4°C-29°C). Rarely below 30°F (-1°C) or above 90°F (32°C)

Not quite as sunny as Cyprus, but sunnier than the rest of France, Marseille is the perfect mix of beachside fun and French culture. The coastline is spotted with old fortifications and buildings. If you look out into the Bay of Marseille you can see the Frioul Archipelago, which was made famous in the Dumas novel The Count of Monte Cristo. Dry summers and mild humid winters paired with the Mediterranean breeze makes Marseille, and the surrounding coastal region, a delightful holiday destination year-round.

Where to stay: Click here to see all properties in the Marseille area or stay in nearby St. Tropez or Nice.

mykonos beach vacations

Mykonos, Greece

Climate: Temperature is typically between 48°F to 82°F (9°C-28°C). Rarely below 41°F (5°C) or above 86°F (30°C)

Mykonos and the other Cyclades islands of the Aegean all share bright and temperate springs and summers. But many tourists have the misconception that the islands completely shut down in winter. It is true that many of the big resorts and tourist based restaurants are closed in the off-season, but this can work to your advantage. Traveling off-season can help you avoid the tourist traps that would deprive you of a completely immersive island experience. The waters do get cold during the winter months, but the rocky coast is just as beautiful and the views are fabulous. Mykonos itself is too popular to be abandoned during the off-season so most amenities remain open and operational. Several beachside properties in these areas feature hot Jacuzzis as well.

Where to stay: Click here to see all properties in the Mykonos area or stay at Villa Deep Blue in October.

aruba beach vacations


Climate: Temperature is typically between 77°F to 91°F (19°C-31°C). Rarely below 74°F (16°C) or above 93°F (33°C)

Want all of the thrills of the Caribbean without the unpredictable weather? Visit Aruba! Around 20 miles north of the coast of Venezuela, this Dutch island sits right outside the hurricane zone and receives a constant stream of refreshing trade winds from the north. Cactuses thrive in the semi-arid climate though the island is not uncomfortably dry. The predictability in weather has made Aruba a go-to vacation spot for Americans- so much so that three-quarters of Aruba’s gross national product is made up by tourism and tourism related activities. The other ABC Islands (Curaçao, and Bonaire) also have similar climates.

Where to stay: Click here to see all properties in the Aruba area or stay at the Marriott Aruba Surf Club in December.

Explore any of these prime spots for beach vacations on ThirdHome’s website, and book today!

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