From sugar-white sands and cerulean seas to thrilling adventures and fruity rum punches, the Caribbean is a tried-and-tested destination for relaxation. Now that school’s out for the summer, treat your family to the ultimate island getaway.
To make your trip even more enjoyable, consider staying in a FlipKey vacation rental. It’s no surprise that vacation homes are ideal for families—the extra living space, a full kitchen, and private outdoor area, plus amenities like laundry or a grill.
We’ve rounded up nine Caribbean destinations your family will love, each boasting some of the best vacation rental guest review scores in all of the Caribbean. From the mountains of St. Lucia to the sun-kissed shores of Turks & Caicos, choose a rental in one of these tropical hot spots and enjoy an authentic island experience.
Ratings are based on the lifetime average vacation rental review score for that destination (for stays during summer months), according to TripAdvisor reviewers. FlipKey is a subsidiary of TripAdvisor.
Average Vacation Rental Rating: 4.96/5.00
“Peace and tranquility by the sea. Everything you need, and some things you didn’t know you needed, are available in this cottage.” – FlipKey Traveler
Ringed by silky sands and blue-green waters, Cayman Brac is an island paradise situated in the Caribbean Sea. Here, you can slip into relaxation mode while lounging along the 12 miles of golden beaches, or explore the rocky bluffs and pockets of caves lining the shore. Venture off the beaten path to discover the island’s natural beauty, or plunge into the surrounding sea for spectacular diving. Known for its stunning scenery and laid-back beach vibes, one thing’s certain: chilling with your family in Cayman Brac will never get old.
Average Vacation Rental Rating: 4.93/5.00
“Perfect place in Marigot Bay. We kept pinching ourselves as we stayed in this clean, light, beautiful apartment overlooking the bay.” – FlipKey Traveler
Home to the legendary Pitons and lush Pigeon Island National Park, St. Lucia is one of the most beautiful and mountainous islands in the Caribbean. Wake to the sound of birds chirping outside your window and ease into your day on the balcony of your Marigot Bay rental. When you’re ready for an adventure, drive into the depths of the La Soufrière volcano past steaming hot springs and therapeutic mud baths, or hop in a water taxi to explore the island’s secrets. Marigot Bay is perfect for families looking to add an unforgettable excursion (or two!) to their Caribbean getaway.
Average Vacation Rental Rating: 4.87/5.00
“Everything was perfect! We are beach sloths and seafood piggies and this was the best condo for our family at an unbelievably affordable price.” – FlipKey Traveler
Dig your toes into the sand and let your worries wash away while on vacation in St. Thomas’s picturesque East End. This part of the island is where you’ll find Red Hook—a delightful community characterized by its red-tiled roof homes—as well as a bustling port that makes island hopping a cinch. Prefer to relax? Unfurl your towel at Sapphire Beach and enjoy a day of sunbathing and snorkeling with your family. No matter how you choose to spend your time, East End is a top-rated Caribbean destination that won’t disappoint!
Average Vacation Rental Rating: 4.81/5.00
“The lovely environment of the villa with its lovely pool and outdoor areas provided a welcome respite and gathering place for our family.” – FlipKey Traveler
Wide, sandy beaches, crystal clear waters, and dazzling coral reefs grace the shores of Bequia, a lush island in the Grenadines. At only seven square miles, everyone knows everyone here, and it’s the perfect destination for travelers searching for a friendly atmosphere and inviting, small-town feel. Lounge in the sun at Princess Margaret Beach or Lower Bay Beach, or go for a stroll around the village of Port Elizabeth—just don’t be startled by friendly chickens strutting at your feet. As the sun starts to fade on the horizon, head home to your waterfront rental, and pass the time guessing which celebrities are aboard the massive yachts anchored out your window in Admiralty Bay.
Average Vacation Rental Rating: 4.80/5.00
“Perfect piece of paradise on Chalk Sound. Our 3-generation family was so happy… Every night was perfect in its own way.” – FlipKey Traveler
In Providenciales (“Provo” to the locals), enjoy a breathtaking panorama of blue skies and turquoise surf, right from your seat in the sand. This sun-drenched destination is home to the TripAdvisor Travelers’ Choice award-winning beach, Grace Bay, and is the ultimate place to escape the day-to-day. Dive into the crystal clear waters and explore the miles of coral reef just offshore, or start happy hour early and indulge in some of the island’s signature Rum Punch.
Average Vacation Rental Rating: 4.70/5.00
“Loved it!!!!! The whole trip was awesome. Right from the booking to the day we went home!” – FlipKey Traveler
The capital of Curaçao, Willemstad boasts a lively downtown that bursts with colorful colonial architecture, Dutch-inspired landmarks, and a vast array of beach attractions. Float down the city’s winding waterways or stroll down the streets of the Punda and Otrobanda neighborhoods, taking in all that makes Willemstad a UNESCO World Heritage Site. When you’re not browsing the packed art galleries or sampling cocktails mixed with the island’s famed Blue Curaçao, retreat to your pastel-colored condo to relax on your balcony. From its historic charm and beautiful beaches to its year-round flawless weather, it’s no surprise that Willemstad ranks on our list of top-rated Caribbean destinations.
Average Vacation Rental Rating: 4.65/5.00
“Sooo AMAZING that we requested to book a second stay <24 hours after returning home!!!” – FlipKey Traveler
As soon as you set foot in Punta Cana, you’ll be on island time. Experience the thrill of zip-lining through the jungle, discover the hidden lagoons of Hoyo Azul, or dive into a colorful new world under the water. Up for a challenge? Punta Cana has several world-class golf courses with rolling fairways and contoured greens that are sure to provide a golf outing unlike any other. Whether you spend your days rocking in the hammock at your rental or playing in the surf, you’ll leave Punta Cana absolutely rejuvenated.
Average Vacation Rental Rating: 4.61/5.00
“The best time ever!!! Maurice (the caretaker) had that reggae music pumping for us and we loved it…dancing and singing around the villa! Yea Mon!” – FlipKey Traveler
Leaping from Blue Hole waterfall, floating down the White River, and swimming at Bamboo Beach… there are so many ways to make a splash in Ocho Rios. From thrilling adventures to laid-back happy hours, this island oasis will keep you busy for days on end. After a day of fun in the sun, let your mind wander as the breeze carries the rhythmic sound of steel drums through the air. Book a sprawling beach villa right on the water and start counting down the days until your blissful beach getaway.
Average Vacation Rental Rating: 4.58/5.00
“Our experience was A+! We absolutely LOVED the property, the town and the people we worked with.” – FlipKey Traveler
Among the top beach spots in the world, Nassau is the picture of tranquility. Here you’ll find calm, turquoise waters lapping the pristine shores, refreshing Sky Juice (a local favorite) flowing freely, and delectable conch fritters always available. In other words, Nassau offers the ultimate recipe for vacation perfection. Cut through the waves in a catamaran, snorkel with a school of fish, or laze under the sun—the possibilities are endless at this top-rated Caribbean destination!
Best Caribbean Destinations To Rent A Vacation Home
- Cayman Brac, Cayman Islands
- Marigot Bay, St. Lucia
- East End, St. Thomas
- Bequia, St. Vincent and the Grenadines
- Providenciales, Turks and Caicos
- Willemstad, Curaçao
- Punta Cana, Dominican Republic
- Ocho Rios, Jamaica
- Nassau, Bahamas