I know three things about Barbados: it has the coolest flag on earth, it’s where Rihanna grew up, and it’s one of the best places to head during the holidays.
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Travelers from around the world jet-set to the tropical island of Barbados when the weather turns cold. They’re looking for the warm caress offered by an equatorial paradise, along with pristine beaches, historic sites, cultural experiences, and delicious eats.
I think that’s the case with just about any Caribbean destination—but Barbados has a few other allures.
For example, it’s becoming a premier spot for remote workers who want to leave home for a while thanks to its Welcome Stamp program. It’s also home conferences like Fix 25, an up-and-coming FinTech event.
I’m not suggesting that you bundle in a little work trip with your holiday adventure in Barbados; I’m suggesting that you might have a reason to come back sooner than you thought.
Ready to take a closer look at the best rentals in Barbados for your winter getaway? Start with these.
Shortcut to the best rentals in Barbados
- Perfect for couples: Coralita No. 5
- Great for dropping off the map: Talking Trees House
- Ideal for families: West Coast Family Villa Near Holetown
- Top luxury pick: Ocean Reef 101
- Premier budget pick: Leeton-on-Sea
- Best beachfront rental: Beachside 1 Bedroom Apt
Best rentals in Barbados for the holidays
Best for dropping off the map: Talking Trees House
When I think about Barbados, my mind jumps to the seaside—but this tropical island is also home to forested hills. Enter the Talking Trees House, a full cottage located in Foster Hall.
This non-touristy area lets you take a birds-eye-view of nearby seaside towns like Bathsheba without losing site of the gorgeous hills of Barbados. Toss in the cottage’s stunning dark wood features and you’ll feel like you’ve left behind the wintery madness for an unspoiled paradise.
Just beware: you’ll need the mosquito nets to protect from bugs.
Best for families: West Coast Family Villa Near Holetown
This family-friendly rental is really something to behold. From its small pool (surrounded by palm trees) to its clean and simple design, it feels like a private resort.
But with five bedrooms that sleep ten guests and three lounging areas, you’ll get the best of both worlds: luxury amenities with enough room for a whole family to enjoy them.
Best luxury pick: Ocean Reef 101
Speaking of luxury, this condo in Bridgetown is a truly opulent way to get to know Barbados. Though located on the seaside only a short walk from the beach, you can also swim in the infinity pool that overlooks the water.
Or have a little workout in the building’s gymnasium. With private bathrooms for all three bedrooms, you can also bring along a small crew without feeling cramped at all.
Christmas dip in the pool, anyone?
Best for couples: Coralita No. 5
This seaside apartment is located on a rocky, romantic coastline in Prospect.
Though you don’t have the benefit of stepping out onto a soft-sand beach right when you wake up, I’m in love with the views and atmosphere.
The patio lets you lounge in the sun while you enjoy the lapping waves and views. The apartment’s design is also worth noting. It’s cozy, beachy, and chic. You can also walk to hotspots close by, including popular beachside restaurants, bars, and shops.
Best budget pick: Leeton-on-Sea
Flights to and from Barbados might cost you a pretty penny… but you can enjoy all it has to offer without forking over thousands for lodging.
That’s the case with this Oistins rental unit.
Though it’s very basic, it’s located right on the beach… with a private yard overlooking the sand. Despite the humble setup, it’s a Guest Favorite on Airbnb—one that many guests are excited to come back to in the coming years.
Best beachfront rental: Beachside 1 Bedroom Apt
The Leeton-on-Sea studio is an impressive beachfront property… but this location has the best views I’ve seen in Barbados.
The windows open straight onto the cerulean beach in the town of Clinketts.
In other words, not only do you have access to the beach straight from the rental’s back door, but the living room windows also showcase the view—meaning you’re always in sight of the ocean.
This is hands-down my top pick amongst the best holiday rentals in Barbados.
