Long Stay Vacations: The Best Caribbean Islands for Snowbirds

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Have you ever thought of spending a few weeks or even the entire winter in a warmer climate? That’s exactly what “snowbirds” do. If you’re considering long stay vacations some place warm, you’ll love this list of the best Caribbean islands for a winter getaway.

The only trouble you may have with these options is picking which one is right for you.

So, read on for information that will help you decide where to take a warm winter vacation. Do not forget to get health insurance for your trip.

Editor’s Note: This article was updated in July 2022 to keep it fresh and up to date.

long stay vacations: the best Caribbean Islands for snowbirds
Find out what destinations are best for long stay vacations.

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CONTENTS: In this article, you will learn about 15 Caribbean Islands that make good candidates for long stay vacations, including:

What is a Snowbird?

A snowbird is someone, usually an empty-nester or retired person, who travels to someplace warm for an extended stay during the winter months.

How To Pick The Best Destination for Long Stay Vacations

Some of the top destinations for snowbirds include Arizona, Florida, Hawaii, Mexico, Spain–and our favorite, the Caribbean.

That’s what we’ve focused on here. You might consider these factors when you pick a snowbird destination:

  1. Warm Weather: What is the average temperature between late December and early March when most snowbirds are looking to get away?
  2. Affordability: Is this island paradise affordable?
  3. Attractions: What is there to do on long stay vacations?

In this guide, we’ve addressed these questions as they relate to wintering over on a Caribbean Island.

You’ll find the average temperature range from December to March listed in Fahrenheit and Celsius.

Affordability is a relative term and prices are always changing, so you’ll find we’ve rated affordability in relative terms.

For instance, the most affordable island destinations have a single ‘$’, while pricier destinations are shown as ‘$$$’.

You can see we’ve also highlighted some main attractions and activities you might enjoy that might help you decide whether this destination is a good fit for you.

After you are done exploring you might come to find out that the Caribbean islands are suited to your lifestyle. The next step you should take is to secure a citizenship. One option is to get Caribbean citizenship by investment, granted by the Caribbean government to foreign investors that contribute to the economy.

Now that you know what to expect from this list of long term vacation destinations, go ahead and dive right into your options! You’ll find them listed below, alphabetically.

Important Notice: Check with each island’s travel authority for the latest information about whether you are permitted to travel from your country of origin.

1. Anguilla

Anguilla beach scene (long stay vacations)
Anguilla averages about 80-degrees Fahrenheit year round and offers near-constant sunshine.

Average Temperature in Anguilla (Dec. to Mar.): 75-82°F / 24-28°C

Anguilla’s Affordability: $$$

What to Do in Anguilla

Anguilla is famous for its gorgeous coral reefs, public sandy beaches, and laid-back atmosphere.

You’ll find it located in the Eastern Caribbean.

When you visit, you might like to tour Anguilla’s historical churches or try snorkeling in its turquoise-blue waters. You might also enjoy tasty drinks on the beach in Anguilla’s near-constant sunshine.

You’ll find a luxury golf course on the island. (Incidentally, CuisinArt Golf Resort & Spa is rated as one of the best course in the Caribbean.)

You can also tour several wildlife sanctuaries on the small offshore islands and cays that comprise Anguilla.

Check out tours in Anguilla on Viator.

If you stay until late March in Anguilla, you can experience a two-day fun-filled “celebration of the sea” known as Festival Del Mar.

And one of the best bed and breakfasts on the entire island is La Vue Boutique Inn.

Not only do the luxurious rooms here overlook the Caribbean Sea, but they start at $220 per night (children under 12 can stay for free).

They come fully outfitted with private balconies or patios, kitchenettes, and spacious living and dining room areas.

Free WIFI and flat-screen TVs (with premium movie channels) are also available inside all of the guest rooms here.

Additionally, the hotel is well-located near both the historic Wallblake House plantation and the Devonish Art Gallery.

However, when you’re not out exploring all that this amazing island has to offer, you can either enjoy a delicious meal at the onsite Caribbean fusion restaurant or go for a dip in the inn’s outdoor pool and hot tub.

Related: Read about a tropical getaway to The Bahamas Out Islands here.

2. Aruba

Architecture in Oranjstad, Aruba (best snowbird destinations in the Caribbean)
Aruba is one of the safest Caribbean destinations.

Average Temperature in Aruba (Dec. to Mar.): 77-88°F / 25-31°C

Aruba’s Affordability: $$$

Things to Do in Aruba

Aruba is best known for its breathtaking white sand beaches, rich culture, and consistently beautiful weather.

In fact, it’s known to have the lowest rainfall of any island in the Southern Caribbean.

Even though it’s in the Caribbean, Aruba is a constituent country of the Kingdom of the Netherlands. With Bonaire and Curaçao, it’s considered one of the “ABC” islands and is part of the Dutch Caribbean.

The island measures about 20 mi. long by 6 mi. at its widest point, but much of the tourism is in one place.

When you’re not enjoying the gentle trade winds at the beach, you’ll want to visit Aruba’s capital, Oranjestad. There, you’ll see bright and beautiful architecture, plenty of shops, and museums. 

Aruba also offers spectacular opportunities for golf as well as a line of casinos on Palm Beach.

And in January, you won’t want to miss the festival of Carnaval.

Plus, it’s good to know it’s one of the safest destinations in the Caribbean.

Now, for an exceptional stay on this amazing island, try booking a room at Wonders Boutique Hotel in the residential area of Oranjestad.

It’s a casual, well-priced, and rooms here are less than $100 per night. This adult-only hotel is just 5 km away from the local airport and 4 km away from the stunning, Manchebo Beach.

Highly rated rooms here also include internet, flat-screen TVs, mini-fridges, in-room coffee/tea making facilities, and some private balconies.

You’ll also enjoy a complimentary welcome drink upon arrival.

Then, you can can board a free shuttle to the beach, and rent any essential beach equipment that you might need for the day.

Do be aware that although breakfast is available, it is not included in the price of your room.

That being said, it’s a purchase you may want to consider making since you can enjoy terrace-side dining within the resort’s lush palm tree garden.

Additionally, there’s an outdoor pool available for you to use, as well as a casual communal lounge and a bike storage area.

3. Barbados

Long stay vacations: Barbados underwater scuba diving scene with three divers, coral, and red fish
Barbados’ beautiful reefs attracts scuba divers from around the world.

Average Temperature in Barbados (Dec. to Mar.): 74-85°F / 23-29°C

Barbados’ Affordability: $$$

Things to Do in Barbados

You’ll find Barbados is a perfect winter getaway for active and laid-back travelers alike.

This small Caribbean island is about 166 square miles—which makes it perfect for exploring by land or sea.

The most easterly island of the Caribbean, Barbados offers a mix of surfable waves and calm waters.

Here’, you’ll find natural wonders, like Harrison’s Cave and Hunte’s Gardens, along with beautiful reefs that attract scuba divers from near and far.

Look for the most gorgeous beaches on Barbados’ southern and western shores.

You’ll find the rum is fine and the people are friendly on this island country located in the Lesser Antilles of the West Indies.

Foodies will be happy to find their share of Zagat rated restaurants and excellent street food.

Plus, there are plenty of festivals throughout the year in Barbados, too!

So, if you want the best stay possible, try booking a room at the Yellow Bird Hotel in Christ Church.

Guest rooms here are well-priced at around $100 per night. They offer stunning panoramas of the ocean from private balconies.

Even better, it’s just a short, 11-minute walk away from Worthing Beach.

Additionally, the historic George Washing House is a mere 4 kilometers away. This is a fantastic place to visit after savoring a sumptuous complimentary breakfast beside the onsite pool and garden.

And after a full day of exploring, relax in one of the hotel’s well-appointed studios or suites.

Children under 11 are allowed to stay for free (but if you’re empty-nesting, it’s likely you’re footloose!)

All of these gorgeous spaces include free WIFI, flat-screen TVs, sofa beds, kitchenettes, and anything else you might need for a beautiful long-term stay.

Related: Ultimate Thrills of Barbados Snorkeling: Plunge into Paradise

4. British Virgin Islands

British Virgin Islands scenic overlook with lush mountains and aqua water make it a perfect candidate for long stay vacations
The British Virgin Islands (BVI) include four main islands and 50 smaller islands and cays you can explore.

Temperature in BVI (Dec. to Mar.): 72-85°F / 22-29°C           

BVI’s Affordability: $$$

Things to Do in the British Virgin Islands

With its lush green landscapes, colorful coral reefs, and many beautiful beaches, the British Virgin Islands (BVI) is a perfect snowbird destination.

You can enjoy adventure and soak up the sun.

This 60-isle paradise is well known for its boating scene, so take a day trip around the area on a luxurious yacht!

You might not know that BVI includes the main islands of Tortola, Virgin Gorda, Anegada, and Jost Van Dyke, as well as 50 smaller islands and cays.

Tortola hosts the capital (Road Town) and is the largest of the islands in this volcanic archipelago. It measures about 12 mi. long and 3 mi. across at its widest point.

The temperature remains fairly constant here year-round, as Barbados has a tropical climate soothed by trade-winds.

Garden lovers will love the J.R. O’Neal Botanical Garden, a well landscaped park with tropical plants including some rare varieties.

In Wreck Alley, you’ll find purposely-sunken vessels which make for an incredible diving experience!

And for an amazing, well-priced stay, reserve a suite at the Wyndham Tortola BVI Lambert Beach Resort.

It’s a truly stunning resort on the island of Tortola that overlooks scenic Lambert Bay and that is a short drive away from Josiah’s Bay plantation gallery and museum.

One and two-bedroom suites here start at $145 per night. They feature exquisite wood furnishings, colorful decor, full kitchen, spacious living room area, and a flat-screen TV.

There’s even a beachside restaurant serving up delicious local fare.

Guests also enjoy an onsite tennis court, a children’s water play area, and an awesome outdoor pool with a swim-up bar.

5. Cuba

Cuba for snowbirds | Enjoy Travel Life
A visit to Cuba can feel like stepping back in time.

Average Temperature in Cuba (Dec. to Mar.): 77-81°F / 25-28°C           

Cuba’s Affordability: $

Things to Do in Cuba

Cuba is known for its rhythmic music, rich Latin American culture, and friendly locals.

Cuba was once restricted to visitors but is now is more open to snowbirds and other travelers.

Your visit to Cuba can feel like stepping back in time with its 1950s style cars and colorful colonial architecture. You’ll find sunshine and beaches and a number of cultural influences.

You’ll probably also have the chance to try some Cuban cigars!

Among the most popular ones are Camacho cigars, which are world-renowned for their exceptional quality and flavor.

Hailing from Cuba, Camacho cigars are handcrafted with only the finest tobaccos. The result is a smooth, rich smoking experience that is truly unforgettable.

Camacho cigars are available in a variety of sizes and styles, so there is sure to be one that suits your taste. So, whenever you are in Cuba, don’t forget to taste one.

Whether you are a seasoned cigar aficionado or just getting started, Camacho cigars are the perfect way to indulge in a truly luxurious smoking experience.

And did you know Cuba is home to 9 UNESCO heritage sites? That’s more than any other Caribbean island!

In fact, there’s a lot about Cuba that might surprise you.

For instance, it’s made up of the larger island of Cuba as well as several smaller archipelagos and the Isla de la Juventud.

From cruising along Havana’s iconic Malecón to embarking on scenic road trips through the countryside, when you rent a car in Cuba you’ll have the flexibility and the freedom to create unforgettable experiences.

While you’re there, you’ll want to visit Cuba’s capital, Havana, to experience some of the best of what Cuba has to offer. That includes some quirky establishments and a very active nightlife.

Or, plan a visit to Baracoa, the oldest city in the country.

If it’s a white sand beach you’d love, look to Playa Paraíso.

Wherever you go, you’ll discover that Cuba has a culture rich in music, food, culture, and traditions that’s hard to beat.

And to enhance your visit, book a room at the exquisite Art Boutique Havana – a beautifully decorated bed-and-breakfast that quietly sits in the heart of Old Havana.

Individually decorated rooms here start at $180 per night.

Your stay includes a top of the line memory foam mattresses, iPod docks, premium down comforters, air conditioning, minibars, complimentary toiletries, and in-house room service (for a nominal fee).

Other premium amenities include access to a rooftop terrace, use of a communal coffee area, concierge services, laundry facilities, free WIFI, and so much more.

6. Curaçao

curacao long stay vacation 1 | Enjoy Travel Life
Curaçao is just off the coast of Venezuela and outside “the hurricane zone.”

Average Temperature in Curaçao (Dec. to Mar.): 76-88°F / 24-31°C

Curaçao’s Affordability: $$$

Things to Do in Curaçao

Curaçao is best known for its stunning cove beaches and warm, aqua blue waters.

You’ll enjoy warm weather as you gaze at the vibrant, dutch-inspired architecture or attend one of the many festivals that occur frequently throughout the year.

This is one of the Dutch Caribbean islands (and the “C” of the “ABC” islands). It’s just 37 miles off the coast of Venezuela.

This island has its fair share of tourists, but is largely residential. This makes it especially attractive for long stay vacations.

For amazing accommodations, try the Avila Beach Hotel in Willemstad. It’s the oldest hotel in Curaçao and has a reputation for excellence that is hard to beat.

It’s also a beachside property that is within close proximity to the airport, the Swinging Queen Emma Bridge, and the Curaçao Sea Aquarium.

Light and bright rooms here start at $200 per night. They are spread throughout several well-maintained buildings, and feature free Wi-Fi, flat-screen TVs, mini-fridges, and coffeemakers.

As a guest, you’ll also enjoy access to free shuttle services.

You can make use of an outdoor pool, an onsite spa, an impressive gym, two private beaches, dine at three on-site restaurants, sample drinks at two different bars, and partake in daily breakfast (for an additional fee).

While you’re there, you’ll want to check out the Handelskade, which are the colorful buildings along the waterfront in Punda.

You’ll also find opportunities to swim with the dolphins along with water sports like:

  • Scuba diving
  • Snorkeling
  • Surfing
  • Windsurfing
  • Kitesurfing

Tip: If you want to learn about water sports and more, head over to Globo Surf.

Plus, you’ll find lots of budget-friendly places to eat a range of cuisines, including small bars called “Snacks,” which serve Chinese food.

If tropical storms and hurricanes worry you, you’ll be glad to hear that Curaçao is outside what’s known as “the hurricane zone.”

7. Dominican Republic 

Dominican Republic beach scene with cabanas
The Dominican Republic is one of the most affordable and diverse places for long stay vacations.

Average Temperature in the Dominican Republic (Dec. to Mar.): 72-88°F / 22-31°C

Dominican Republic’s Affordability: $

Things To Do in The Dominican Republic

One of the most visited islands in the Caribbean, the Dominican Republic (DR).

It’s located on the Hispaniola Island in the Greater Antilles archipelago, which it shares with Haiti.

It is home to stunning white sand beaches, world heritage sites, and of course, baseball. 

The Dominican Republic is the second largest island in the Caribbean and just two hours from the coast of Miami. It’s also a top destination for snowbirds.

Here, you’ll discover nearly 1,000 miles of coastline along the Atlantic and Caribbean.

Every Sunday in February, you’ll find a different Carnival featuring:

  • Festive parades
  • Colorful masks
  • Fun music
  • Lively dancing, and
  • Delicious food!

Related Article: Check out this world-famous Carnevale in Venice, Italy.

Most of the bigger resorts of the Dominican Republic are located in Punta Cana. But, there are some hidden gems you’ll want to explore:

  • Azua, where you’ll find ocean vineyards and wine tours
  • La Romana, if you’re looking for great golf courses
  • Samana, where you may see hundreds of humpback whales off the coast

You might also love a visit to Damajaqua cascades, where you’ll see over 27 waterfalls and can swim in the natural limestone pools.

There’s so many things to do in the Dominican Republic that these ideas only scratch the surface.

And for a magical stay on this island paradise, check out the marvelous Hodelpa Nicolás de Ovando in Santo Domingo.

It’s a beautifully renovated, 16th-century, heritage hotel in the city’s colonial quarter.

These accommodations come complete with a riverside pool, a fine dining restaurant, and stone courtyards filled with tropical plants.

Rooms here start at $170 per night. Each features chic colonial-style decor with exposed stone walls, and offers modern amenities like WIFI, expansive sitting areas, in-room safes, flat-screen TVs, and Nespresso machines.

Room service is also available upon request.

Although, you may prefer to sip on an artisanal drink at the lobby bar or savor a decadent meal at the restaurant terrace.

And when you’re not enjoying the modern convenience of your spacious room, you can make use of the outdoor pool and the communal fitness center.

More on Visiting the Dominican Republic

To make the Dominican Republic even more attractive, the cost of living is quite affordable.

If you’re looking to rent an apartment for your long stay vacation in the DR, you’ll want to look to Sosua and smaller towns near the Santo Domingo

Finally, you won’t need a Visitor Visa or Tourist Visa for your long stay vacations to the Dominican Republic.

You’ll just need to purchase a Tourist Card on arrival, which is good for 60 days, and then pay a small extension fee for longer stays. (For the most up-to-date information on visa requirements, check here.

8. Grenada 

Colorful houses on the hillside in Granada overlooking an aqua harbor with boats - best Caribbean long-stay vacation spot
Grenada is known as “Spice Island.”

Average Temperature in Grenada (Dec. to Mar.): 74-86°F / 23-30°C

Grenada’s Affordability: $$

Things to Do in Grenada

Known as the Isle of Spice, Grenada is home to numerous diving sites, lush rainforests, breathtaking waterfalls and, of course, spices.

It consists of the island of Grenada plus six smaller islands north of the main island. Grenada is about 133 square miles in size.

In the capital city of St. George, you’ll see colorful houses that climb the hillside from the waterfront. This harbor is the yachting center of the eastern Caribbean.

If you’re a cricket fan, be sure to plan a visit to The Grenada National Cricket Stadium.

On Friday nights from 6pm, you can enjoy Fish Fridays, where you’ll find an abundance of all tasty things from the sea, lamb dishes, and tin-pan music.

In addition, you’ll find a variety of other festivals in Grenada throughout the year, like the Sting Band Festival and the Grenada Music Festival.

Don’t be surprised if you detect the scent of nutmeg and vanilla in Market Square and the spice plantations.

In fact, make sure to take a tour of the Nutmeg Plant while you are there; there’s a reason it’s known as the Isle of Spice!

Do you love sweets? Then you’ll want to make a stop at the House of Chocolates.

You might also brave a sample of River Antoine Distillery‘s 150-proof rum!

After your rum tasting though, you’ll want to relax in one of the 32 amazing rooms at the Blue Horizon’s Garden Resort. It sits inside St. George’s and offers visitors a selection of well-appointed rooms.

They have free Wi-Fi, flat-screen TVs, kitchenettes; and living rooms with pull-out sofas in larger suites.

Other fantastic features for you to enjoy throughout your stay are an outdoor pool and a children’s playground.

You’ll also discover well-manicured gardens that are home to a dazzling array of native birds, and a fantastic restaurant serving traditional West Indian fare.

9. Jamaica

Colorful towels hang to dry on the beach in Jamaica (Caribbean long stay vacations)
Jamaica is known for its Reggae music, golden sand beaches, and its everlasting sunshine.

Average Temperature in Jamaica (Dec. to Mar.): 72-88°F / 22-31°C

Jamaica’s Affordability: $

Things to Do in Jamaica

One of the most popular Caribbean Islands, Jamaica is known for its Reggae music, golden sand beaches, and its everlasting sunshine.

It’s located off the North American Coast and is part of the great Antilles. It’s the third largest Caribbean island, behind Hispaniola and Cuba.

Jamaica is quite affordable.

You’ll find no shortage of beautiful resorts as well as great accommodations in some of the smaller hotels and villas.

If you’re looking to connect with other snowbirds, you’ll most likely find them in Montego Bay, Ocho Rios, Negril, and Kingston. (If you favor white sand beaches and pristine water, look to Negril.)

You’ll find nature trails and island jungles at Port Antonio.

Foodies will find plenty of delicious dining options in Jamaica. But for the most authentic cuisine, you’ll want to have a taste of the goat curry with rice and peas.

While you’re in Jamaica, be sure to enjoy a boat tour in Blue Lagoon, sunbathe on Seven Mile Beach, or go for a hike in the Blue Mountains National Park.

And of course, you must visit the Bob Marley Museum!

Afterward, enjoy an idyllic stay in the Catcha Falling Star Hotel in Negril.

It’s a quaint little independent hotel that has an array of charming wooden cabins that overlook the nearby cliff-side gardens.

Stays in the cozy but casual feeling rooms here start at $110 per night.

Accommodations include cable TV, four-poster beds, microwaves, and mini-fridges. Opt for a slightly more luxurious cabin and you’ll have a kitchenette, a living room, a furnished veranda, and more.

Snorkeling equipment is complimentary. Amenities include an outdoor oceanfront pool and a hot tub.

There’s also a laid-back international restaurant offering terrace seating. Kids age 16 and older are welcome.

However, when you’re not enjoying the many comforts of your guest room, there’s plenty to enjoy.

You can talk a walk along the property’s well-maintained limestone paths. Have a meal in the thatched roof dining room or sample a drink at Ivan’s bar.

Take a swim in the cliff-side pool or relax in the hot tub. Use some complimentary snorkeling gear, or wile the day away in one of the property’s pristine sunning areas.

10. Martinique

beach long stay vacation | Enjoy Travel Life
Martinique offers a great beach getaway for your long stay vacations.

Average Temperature in Martinique (Dec. to Mar.): 71-85°F / 22-29°C

Martinique’s Affordability: $$

Things to Do in Martinique

This French-owned island is home to some incredible natural landscapes and a rich history.

From its capital, Fort-de-France to Les Trois-llets, you will find a mix of lush gardens, delicious French and Creole cuisine, and stunning white-sand beaches in Martinique.

If you’ve never seen black sand, you can find it on Martinique at Grand’Rivière, a small fishing village located in northern Martinique.

Martinique has a rugged beauty and a unique blend of West Indian and French influence. It’s especially suited to nature-lovers, foodies, and francophiles.

The markets also hold loads of spices, exotic fruits, and medicinal herbs. Look for Martinique’s ubiquitous “ignames” or yams.

You’ll find fine dining in Fort-de-France, where restaurants combine fish and local cuisines with a French flair.

This island in the lesser Antilles relies heavily on France for imports.

That’s part of the reason why you’ll find boutiques, artwork, and the latest French fashion in the markets. Martinique may be one of the best shopping destinations in the Caribbean!

And for the perfect stay during your trip, try the Domaine de Robinson.

The casual studios and bamboo beach bungalows here are well-priced at $127 per night. They offer stellar ocean views, and you’ll be surrounded by lush, tropical greenery.

All of the facilities here also come fully outfitted with kitchenettes, dining areas, private bathrooms, mosquito nets, and verandas with seaside views. That’s everything you need for an amazing long-term stay in the Caribbean.

Additionally, the property is exceptionally well-located on the island.

This gives visitors access to a host of fun activities like horseback riding, snorkeling, and scuba diving.

Wouldn’t these be fun activities for long stay vacations?

11. Nassau

Pink building with white statues in Nassau, a great winter getaway
You’ll find charming pastel colored houses and government buildings in Nassau.

Average Temperature in Nassau (Dec. to Mar.): 66-81°F / 19-27°C

Nassau’s Affordability: $$

Things to Do in Nassau

As the capital of the Bahamas, Nassau is an extremely popular spot for tourists with its cruise ship port and countless attractions.

Experience its modern resorts on Paradise Island, shop duty-free at the downtown markets, or take in the beauty of the old, brightly colored colonial buildings. This is a great destination for long stay vacations.

Nassau is the capital city and the largest and most populous island in the Bahamas.

Located on the island of New Providence, it offers easy access to Paradise Island via the Nassau Harbor bridges.

When you visit, you can’t miss the pastel-colored houses and government buildings that are so typical of the Bahamas.

In addition to the beaches, diving excursions, and snorkeling along the offshore coral reefs, you’ll find countless things to do in Nassau.

From city tours to jeep adventures to the Heritage Museum of The Bahamas, it’s safe to say you’re unlikely to run out of things to do in this urban setting.

Like many urban settings, Nassau has its share of crime, but this hardly offsets this vibrant destination. In any case, check with the US Department of State for travel advisories before you go.

It’s also important to plan a stay in a safe and secure hotel like the British Colonial Hilton Nassau.

Not only can you sometimes find rooms here for as little as $105 per night, but this chic, Colonial-inspired accommodation sits by the bay.

It’s a short drive away from top attractions like Ardastra Gardens and Fort Fincastle.

Additionally, all the upscale rooms here ooze historic appeal and come outfitted with flat-screen TVs, wifi, mini-fridges, and coffee making facilities.

You can also upgrade your room and enjoy premium features like free breakfast and private lounge access to complimentary drinks and snacks.

In terms of amenities, there are also three separate restaurants on the property and a vintage-style bar.

Enjoy the fitness room, a private beach, an outdoor pool, and room service upon request,

12. Puerto Rico

San Juan Puerto Rico, red dome and historic fort overlooking water
Fort San Cristobel is the largest Spanish Forts in the New World.

Average Temperature in Puerto Rico (Dec. to Mar.): 72-85°F / 22-29°C

Puerto Rico’s Affordability: $$

Things to Do in Puerto Rico

Puerto Rico is known for having it all.

Its Spanish Caribbean culture, vibrant colonial architecture, lush vegetation, golden-sand beaches and surfable waves are only a few things that draw tourists to the island.

When you visit, visit the sunny capital San Juan for dining and shopping by day and experience the magic of Bioluminescent Bay by night.

You’ll also want to spend some time exploring Old San Juan, where you’ll find interesting art galleries, historic churches, and museums.

When you’re planning long stay vacations, you certainly won’t run out of things to do here.

By visiting during the winter, you’ll be glad to know you’ll miss a lot of the rain.

And, even though it’s a little cooler than other tropical destinations at this time of year, it’s still a great destination for sun-lovers.

Plus, the food is phenomenal and English is widely understood.

If you love whale-watching, head over to the Rincón Lighthouse in February and March. Then, you’ll see migrating humpback whales on their way back to North America.

Finally, one of the significant advantages of wintering in Puerto Rico is that since it is a US territory, you won’t need a visa.

You’ll enjoy all the liberties and protections of the US Constitution while you visit Puerto Rico for the winter (or any time).

And if you want to be at the center of all the action, then plan a stay at the Villa Herencia Hotel in Old San Juan.

This property is a short walk away from the Cathedral of San Juan Bautista. Select from one of eight historic rooms that start at $130 per night.

All of these beautiful spaces are adorned with wonderfully eclectic artwork and feature plush beds, Spanish tiled floors, free WIFI, flat-screen TVs, and private balconies (suites include additional seating areas and access to a shared sundeck).

You’ll also love their lavish complimentary breakfast and can access an onsite library, bar, rooftop sundeck and private dining terrace.

13. Roatan, Honduras

Colorful buildings on the harbor in Roatan Honduras, makes for a great snowbird destination
Roatan is a hidden tropical gem off the coast of Honduras. This is great option for affordable long stay vacations.

Average Temperature in Roatan (Dec. to Mar.): 72-85°F / 22-29°C

Roatan’s Affordability: $

Things to Do in Roatan

Just off the northern coast of Honduras, Roatan is an island paradise that offers a mix of adventure and serenity.

While you’re there, you might encounter some of the island’s exotic animals. This includes monkeys, sloths, and iguanas. Or try snorkeling and scuba diving in its beautiful reef-lined waters. 

Plus, it’s easy to find monthly leases on properties in Roatan, whether you’re looking for a condo, house, or apartment.

Real estate is so affordable for a winter stay!

In addition to beachfront properties, you’ll find properties with hillside views and lush green landscapes. Roatan is one place where nature reigns supreme!

In fact, Roatan has several popular expat communities from West Bay to Camp Bay, to Port Royal.

Here are some other experiences in Roatan you might enjoy:

  • Take a glass-bottom boat tour
  • Paddle through the mangroves, or
  • Dive into Mayatlantis, an underwater museum replicating Mayan civilization.

If safety is a concern, you’ll like to know that this beautiful island paradise about 40 miles off the coast of Honduras is very separate from—and much safer than—the Honduras mainland.

Instead, you’ll find magnificent white-sand beaches, pristine water, and beautiful sunsets!

For a fantastic stay on this amazing island, try Hotel Posada Seremein Roatan. It’s a well-reviewed property that sits right on West Bay Beach.

Step inside and you’ll find a wealth of spacious, modern studios that are priced at $130 per night.

They come fully outfitted with air conditioning, seaside views, flat-screen TVs, Wi-Fi, ensuite bathrooms with complimentary toiletries, and a kitchenette with a microwave and refrigerator.

A complimentary daily breakfast is also included with your stay. You’ll enjoy it at the lovely onsite restaurant, which serves a delicious array of Argentinian inspired cuisines.

Related Articles: Read about more the best islands for wildlife vacations.

14. St. Barts

A deck overlooking St. Barts waterfront with palm trees (Caribbean getaway)
St. Barts ranks as one of the safest destinations in the world. It’s perfect for long stay vacations!

Average Temperature in St. Barts (Dec. to Mar.): 75-85°F / 24-29°C

St. Barts Affordability: $$$

Things to Do in St. Barts

St. Barts is a prime spot for the rich and famous.

While you bask in the sun among the world’s top A-listers, you can also enjoy duty-free shopping, ride a jet-ski on the glistening waters, or enjoy-fine dining by the sea.

You’ll find a celebrity hideaway at the Hotel Isle de France, which also holds a popular weekly fashion show on the beach.

The tiny volcanic island surrounded by shallow reefs is more formally known as Saint Barthélemy, and it belongs to France. It offers an expansive shoreline and is not nearly as crowded as other party-islands.

Check here to find out about other villas you can rent.

You might get some afternoon thunderstorms in “The Lent” as they call the winter season.

As a winter snowbird, you’ll find it’s a cooler climate, averaging 73°F. But some might find that pleasantly refreshing!

A few points of interest in St. Barts:

  • One of the prettiest beaches on the island might be Flamands Beach.
  • Nature lovers can see a collection of over 9,000 seashells at the Inter oceans museum.
  • A visit to the 18th-century fort, Fort Gustave will give you the best view of the harbor.

The St. Bart’s Film Festival takes place at the end of April, if you’re still on the island. And if not, there are plenty of festivals throughout the year, including the February Carneval.

Plus, St. Barts ranks as one of the safest destinations in the world!

This is why you’ll thoroughly enjoy your time at Villa Etoile du Nord.

Yes, a stay at this luxurious resort will be a bit pricey. But beach enthusiasts will love that the resort is within walking distance of Flamands Beach.

Rooms here are also contemporary in style and utilize space well with high-end features. Some of them include French king beds, spacious living rooms, apple TVs, full kitchens with bars, modern en-suite bathrooms, and more.

And when you’re not recharging your batteries in your room, you can do bit of of al fresco dining by the heated outdoor pool

15. St. Lucia

Soaring twin mountains arise from the water in St. Lucia, Caribbean vacation for warm winter getaway
The twin Piton Mountains of St. Lucia.

Average Temperature in St Lucia (Dec. to Mar.): 73-84°F / 23-29°C

St. Lucia’s Affordability: $$

Things to Do in St. Lucia

With its twin Piton Mountains setting it apart from other Caribbean islands, St. Lucia is home to some of the Caribbean’s most stunning views.

Set in the lower Antilles, this 238-square-mile island may just be the most low-key destination for snowbirds.

In St. Lucia, you will find vibrant sunsets, fresh coconuts (expertly split and prepared for drinking for a small fee), and the most dramatic landscapes.

It’s one of the best places for long stay vacations!

You’ll also find some of the best snorkeling, especially at Anse Chastanet Coral Reef.

While visiting, make sure to grab a kayak to visit Pigeon Island, bike through the lush forest, or scuba dive in the crystal clear waters.

At the Sulfur Springs Park, you’ll discover steaming hot geo thermic springs, and you might even take a soak in the nearby therapeutic springs.

You can also take a drive to La Soufriere. That’s a volcano which hasn’t erupted in years, but you can still see the boiling pools and sulfur springs.

Finally, garden lovers might like to tour the botanical gardens, which offer tropical beauty along the trail to the diamond falls.

Though the official language is English, the locals also speak speak a Creole dialect—a further confirmation that you’re on a faraway vacation!

And for the perfect stay in this tropical paradise, book a room at the Harbor Club St. Lucia. This Curio Collection Hilton Hotel offers rooms that start at just $105 per night.

Plus, with a high-quality name like Hilton, you know that all the rooms here have premium amenities.

You’ll have Wi-Fi, a flat-screen TV, a private balcony with ocean views of Rodney Bay Marina, a mini-fridge, coffeemaker, and more.

Room service is also available upon request, as are premium suites with additional seating areas and access to private pools with swim-up access.

Additionally, a complimentary breakfast is also included with the price of your stay.

Also, you’ll enjoy complimentary boat transfers from Pigeon Island and access to four on-site eateries, four outdoor pools (one with a swim-up bar), sundecks, a spa, and a fitness center.

Final Thoughts on Long Stay Vacations in the Caribbean

Aren’t each of these topical islands perfect for a warm winter getaway? You can see now why it might be so hard to pick just one from these 15 best Caribbean islands for snowbirds.

If you can’t decide, we think the best plan of action as a snowbird is to line up several long stay vacations, perhaps with a new one each year. 😉

That way, if you decide to call one of them your permanent home, you’ll know what to expect as an expat.

Which of these best Caribbean Islands would be the perfect winter getaway for you? Which have you been to? Are some of these snowbird destinations high on your bucket list? Let us know in the comments below.

Jackie Gately at the beach

About Jackie Gately, editor-IN-CHIEF

I'm Jackie Gately, your travel confidante and the creative force behind Enjoy Travel Life, awarded the "Best Casual-Luxury Lifestyle Blog (USA)" in Travel and Tourism by LUXlife Magazine for four consecutive years.

With 25 years of published expertise, I'm a seasoned writer, editor, and photographer curating inspiring travel guides and lifestyle tips for empty nesters. I hope to kindle your spirit of exploration, encouraging you to overcome obstacles and turn your dreams into reality.

Learn to minimize your pre-travel angst and maximize the joy of exploration with insights from my experiences. Let's make every adventure a celebration of this exciting phase of life! 

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Next Steps

Now that you’ve picked the best island for your long stay vacation, it’s time to get planning! Read the following articles next:

Contributors: Michaela Shimkus contributed to this story.

Photo Credits: Angilla – jaegeranna1; Aruba – falco; BVI, Granada – Richard Todd; Cuba – ?; Curaçao – Steven Bol; DR – Martin Str; Jamaica – Peggy und Marco Lachmann-Anke;  Martinique, Nassau – skeeze;  PR – AndPon; Roatan – Michelle Maria; St. Barts – franckchisinau; St. Lucia – mimics (all courtesy of Pixabay); Barbados – VisionPic.net (via Pexels);

18 thoughts on “Long Stay Vacations: The Best Caribbean Islands for Snowbirds”

  1. We have visited several islands during cruise vacations and are thinking of becoming a snowbird this winter. What is the best resource for finding long term accommodations? Real estate agents? Internet sites? Your guide was most helpful in narrowing down some islands.

    • I’m glad you found my guide helpful, Erika. I would check several sources to find long term rentals, including real estate agents, online search engines, booking sites like AirBnb and Booking.com, maybe even craigslist. But your best source might be word of mouth. If you know someone who is already at the island you’re interested in, or are snowbirds elsewhere, see if they can make recommendations or know someone there who might be looking to lease their place. Also, put it out in your online circles, like Facebook and IG. You never know who has a connection until you ask. A referral would be ideal. Good luck! So exciting!

  2. What a great list! I’m such a proponent of the snowbird and slow-travel style. We did a winter in Roatan, Honduras and it as delightful! We also love the DR, but now you’re making me want to go to St. Lucia!

    • Roatan sounds wonderful, Anne – a friend of mine just returned from a yoga retreat in Roatan! Glad you enjoyed this list and feel inspired to visit St. Lucia. Let me know how it goes, when you do!

  3. Such a great list of warm getaway places for snow birds. Being Canadian, this is often something that people do to escape our cold winters. I’ve been to many of these destinations, but the one that I want to go to is Curaçao. I find it interesting that it’s part of the Netherlands. I’d love to see those colourful houses.

    • I’m not far from you in Boston, so I share that sentiment, Renee! Curaçao is a great (and colorful) destination for your next winter trip!

  4. Ahhh so many of these places are on my bucket list! This past winter we spent Jan-March away from NYC in SoCal, but this looks so magical! My parents have visited Roatan and really loved it!

    • Hard to beat the Southern California sunshine and dry climate, but these islands just might tempt you. I’m hearing a lot about how much people love Roatan lately! (But any place warm is a good candidate for winter travel, as far as I’m concerned.)

  5. With the gas prices going up in Europe moving to somewhere warmer in winter is definitely an option we consider. The Carribean are interesting for sure – we will have to check the prices of accomodations there. Cuba might be actually an option.

    • You might be surprised at prices in some of the islands, especially the lesser-travelled ones. Cuba would be a wonderful way to spend a winter getaway!

  6. This is such a great guide for long stay vacations. I would personally love to spend winter in a hot, exotic location, on as island. I have actually visited Cuba in December, for three weeks, and I loved that I could combine the culture and sightseeing with some time spent at the beach. I would have loved to stay for longer.

    • Cuba definitely tops my list, especially with the cultural considerations. Glad you got to spend a good chunk of time there! I’m with you – any island destination that’s hot and beach-y works for me.

  7. I hope one day I’ll get to my dream of becoming a ‘snowbird’ and hopefully always get the sun all year round, preferably at the beach! Most of these caribbean islands are on my bycket list so this is a super useful travel guide to visit one day 🙂

  8. I learned a new word today. It is snowbirds. In fact, it could be anyone’s dream come true to travel to a warmer climate. I know some people prefer winter, but for me, I am more into a warmer climate. I can see this article referring to me. I went to Hawaii during winter, and it was warm. I would love to visit it someday again during this time. Winter makes me lazy and wants to stay home where it is warm. Thus, I would prefer warmer climate places. I want to especially Kayak at Pigeon Island, see coral reefs (scuba dive at Aruba), and see the black sand at the Grand’Rivière, and visit cuba. So much places to discover.

    • Happy to introduce you to the word “snowbird,” Ossama! You are correct, these island getaways would be perfect for anyone looking to spend an extended time in a warmer climate. Hawaii in winter sounds wonderful!

  9. What a fantastic guide and so comprehensive. It would be hard to choose a location here with every island having it’s own appeal, amenities, events and things to do. But I guess that is also part of the process to enjoy during your discovery time to visit some before deciding on something more permanent.

    • Indeed, that is the best part of “trying on” a new place before moving. Thank you for your kind words, Noel! I’m glad you found this guide helpful. 🙂

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