Search multiple agencies. Owners often list a property with several rental booking sites that use different names for the same unit. To confirm it’s the same place, compare the descriptions and photos of the furnishings posted on each source. Sometimes, prices are different from site to site, and often there will be one winner that offers the best deal.
Compare resort and rental agency prices. Even when a condo or villa is part of a named resort, an agency or booking site might offer it for a different price. Recently, I found a 5-night stay in a 4-bedroom villa in Jamaica through an agency that cost $4,300 more on the website of the resort it was part of.
Negotiate security deposits. When a surprise $2,500 security deposit recently appeared on my bill for a 5-night stay at a Barbados condo, I complained to the rental agent. She went back to the owner, who cut it to $1,000. The agency’s manager later claimed the $2,500 figure was inaccurate—yet months later, it still appears as the required deposit amount on the listing.
Use a credit card hold for the security deposit. Some agencies insist on cash, but no matter what, ask how long it will take to get your money back at the end of the rental. Some agencies take months to return your money, and that’s not a favorable arrangement for you.
Read the listing description and contract carefully. On one recent rental, the website for my unit’s development said the services of a cook would be included. When I double-checked with my agent, they said I could have a cook—for an extra $200 a day. Armed with this information, I went back to negotiate, and the owner agreed to split the cost of a cook with me—but it only happened because I did my research and learned that the service was supposed to be included at the development.
Double-check all the rules. Once, a rental agent told me that I had to buy trip cancellation insurance and pre-existing conditions wouldn’t be covered. But after checking with the insurance company the agency used, I learned I actually had 14 days from the date of my deposit to cancel without penalty.
Understand when concierge service is truly available. Some agencies that offer concierge services use that perk to justify their often higher prices on rental units. But these days, agencies are often overbooked, and customers are finding that the promised concierge service is not accessible when they need it. It may save you money to look for the same unit at a lower price from an agency that does not offer personalized assistance.