In the past, visions of people taking work calls with a cool lemonade in their hands and their feet in the sand would only be featured in infomercials for the latest “get rich quick” scheme. According to current studies, however, a whopping 1 in 4 Americans are now working remotely. While many opt to work from a home office, others are now seizing the opportunity to work remotely from paradise.
Whether your dreams of paradise include beach houses in Florida or villas on an island like Curacao, secluded cabins, or walking on palm tree-lined beaches, there are endless opportunities for remote workers looking for a change of scenery. If a permanent move is out of the question, why not try exploring these seven tips for long-term vacation rentals.

1. Consider What You Need
A long-term vacation rental is drastically different than booking a hotel for a few nights. The features that you may find charming on a weekend trip may not be ideal if you are staying in a location for several weeks or months. For instance, a community pool right outside of your window may be fun for an overnight trip, but the noise from others may be distracting while you are attempting to work remotely.
Likewise, you may find it inconvenient not to have a washer and dryer on premises for weeks, whereas you might not mind it for a weekend. Think about the comforts of home and then decide which amenities are must-haves and which you can do without. This may also help to determine the type of property you are looking for, whether these are resorts in Curacao or condos in Miami.
2. Explore Different Areas
Whether you have your heart set on lounging on an island in the Caribbean, a mountain in Colorado, or a bustling city in Florida, be sure to do your research on the area before booking. This will help you gain a better understanding of the area if it is what you are looking for and if it’s conducive to remote working.
For example, an all-inclusive resort in Curacao may include Wi-Fi, whereas a cabin in the mountains may not have any internet access. It is also important to consider the proximity of attractions, grocery stores, restaurants, pharmacies, or doctors’ offices when booking a long-term vacation rental. This can help you determine if there is access to public transportation or if you will need to rent a vehicle (or bring yours along, if feasible).
3. Rent Through a Reliable Source
Unfortunately, there are several scams related to long-term vacation rentals online. You should avoid renting directly from an individual who posts ads on platforms like Craigslist. These platforms are notorious for attracting scams. Instead, turn to a reliable source such as a property management company or a reputable travel platform like Florida Rental By Owners. These companies have verified track records to verify their hosts and properties.
4. Read Reviews
Most short-term, mid-term and long-term vacation rental properties have a fair number of reviews left by visitors. Dive into these reviews and take note of any aspects that may be concerning. You can address these concerns specifically with the property management company or host. If you are concerned at all move on to the next property. In either case, be sure to focus on the most recent reviews for an accurate depiction of experiences by previous guests.
5. Don’t Rely on Pictures Alone
Viewing photographs of a property is immensely helpful when searching for a long-term vacation rental, but it is equally important to read the property listing description. This may reveal information that is not immediately noticeable through pictures alone. For example, there may be photos of a large parking lot in front of a building, but the listing may state that the parking lot is off-limits. It may also include updates that may not be reflected in photos, such as the pool is no longer working or the size of the bed has changed from a king to a queen.
6. Understand the Rules of the Rental
Both long-term and short-term properties typically come along with a set of rules that tenants/guests must abide by during their stay. These rules can run the gamut from no noise after 9 PM to no pets or other overnight guests allowed. Breaking these rules can result in losing a security deposit or being evicted from the property before you anticipated it. If you are unsure of the rules of a property you are considering, be sure to have the property management company or owner verify them before you book.
7. Book in Advance
Long-term vacation rentals are becoming more popular as the number of remote workers increases. Be sure to book your rental property well in advance to avoid higher rates or limited options. This is especially true if you are planning to visit during peak travel times, during a holiday or when a local event or festival is scheduled. If you are considering a long-term vacation rental in Florida, keep in mind that big cities like Orlando and Miami may require you to book much sooner than more rural regions, like Monroe County. You should also be prepared to wait longer for ocean-front properties or those with direct access to a beach in areas like Palm Beach.
By booking a long-term vacation rental, remote workers can take advantage of their ability to work from anywhere in the world. From all-inclusive resorts in the Caribbean to the balmy beaches of Florida, taking these steps will ensure that working remotely from paradise allows you to relax and be productive.
Author: Tom English is the director of Outreach for Sandals Resorts since 2017
