Destination guide

Is this heaven on earth? No, it's just the Caribbean!

Feel the need to unwind in an island paradise? Book a Caribbean vacation rental and you can soak up the sun in a tropical landscape dotted with more than 700 islands, islets, reefs, and cays. It's the perfect location to simply relax on the sandy shores of a beach with a cocktail in 1 hand and a book in the other, or cool off in the warm, clear waters of the Caribbean Sea. If you long for a bit more action, spend your days swimming through coral reefs and exploring old colonial towns, before dancing until dawn in trendy nightclubs.

Things to do

Citadels, cathedrals, and culture in the Caribbean

History is alive and well in the Caribbean, where you can tour such storied sites as colonial plantation houses, sugar mills, and rum distilleries. You'll find even more history at the Brimstone Hill Fortress, St Kitts, a massive 18th-century hilltop citadel, and the Cathedral of San Juan Bautista, a 1540 church where famed explorer Ponce de Leon is entombed. Culture vultures can quench their thirst for the arts at the National Museum of Fine Arts in Havana. If you have kids staying in the Caribbean vacation rental, they'll enjoy a trip to the Bermuda Aquarium, Natural History Museum, and Zoo.


Splish splash, you'll be having some fun

Most activities in the Caribbean take place in the water, including such popular pastimes as scuba diving, snorkeling, sailing, windsurfing, and deep-sea fishing. If you haven't earned your sea legs yet, try your hand at golfing, hiking, cycling, and horseback riding, or sunbathe on 1 of the Caribbean's countless beaches. Embrace local cultures with a reggae concert at a Jamaican dancehall or by pausing to listen to steel-pan street musicians in Trinidad and Tobago. True thrill seekers can tour the region in a helicopter or swoop through the air over Puerto Rico's Central Mountains on the world's longest zip line.


Come on in, the water (and the weather) is fine!

No matter what time of year you book your Caribbean vacation rental, you're almost guaranteed to enjoy sunshine and warm weather. Temperatures range from the 80s and 90s throughout the year, with northern islands, like the Bahamas, Cuba, Puerto Rico, and the Dominican Republic, more likely to experience "cold fronts" that bring temperatures in the 70s. You'll want to make sure you always pack your swimsuit as the water temperatures hover between 88 and 72 degrees throughout the year. The second-half of the year receives more rain than the first half and hurricane season typically lasts from June to November.

Natural features

From valleys to volcanoes, and everything in between

While you might picture nothing but white sand beaches and aqua sea waters, the Caribbean offers a remarkably diverse terrain. For starters, on land, you'll see dormant volcanoes, lush valleys, majestic waterfalls, palm trees, and tropical flowers as far as the eye can see. In the water, coral reefs and seagrass meadows dot the landscape, while sharks, stingrays, and sea turtles swim about. Bird watchers should carve out time to visit Codrington Lagoon National Park, home to 1 of the world's largest colonies of frigate birds, as well as a host of pelicans, terns, and gulls.

Where to stay around Caribbean?

Our 2019 property listings offer a large selection of 35,708 vacation rentals near Caribbean. From 6,587 Houses to 11,906 Villas, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Caribbean for a holiday or a weekend are on HomeAway.

What are the most popular destinations to visit in Caribbean?

There are many lovely places to stay for a holiday trip or just for a weekend in Caribbean. From HomeAway travelers, the most popular destinations to visit are:

  • Providenciales: 851 vacation rentals
  • Turks and Caicos Islands: 937 vacation rentals
  • St. Thomas: 1,033 vacation rentals
  • Aruba: 1,586 vacation rentals
  • Puerto Rico: 2,699 vacation rentals

And HomeAway offers you the chance to discover many other popular destinations in Caribbean! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Caribbean?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Caribbean:

  • Governor's Harbour, The Bahamas: 284 rentals
  • Nassau: 716 rentals
  • Punta Cana: 1,524 rentals
  • Rincón: 373 rentals
  • Montego Bay: 882 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Caribbean?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Caribbean are:

  • Princess Juliana International Airport (SXM): 762 vacation rentals
  • Cyril E King Airport (STT): 1,900 vacation rentals
  • Providenciales Airport (PLS): 861 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Caribbean?

HomeAway offers a large selection of rentals near lovely places in Caribbean. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Rum Point: 172 rentals
  • Dunmore Town: 239 rentals
  • Sapphire Beach: 1,917 rentals
  • Guana Cay Beach: 408 rentals
  • Buye Beach: 260 rentals

But there are many other points of interest around Caribbean listed on HomeAway where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Caribbean

St. Thomas
1,033 vacation rentals
San Juan
497 vacation rentals
St. Croix
388 vacation rentals
373 vacation rentals
Saint John
839 vacation rentals
300 vacation rentals
453 vacation rentals
154 vacation rentals
80 vacation rentals
Vieques Island
191 vacation rentals
220 vacation rentals
Spanish Wells
81 vacation rentals
Harbour Island
190 vacation rentals
Green Turtle Cay
237 vacation rentals
96 vacation rentals
91 vacation rentals
Virgin Gorda
72 vacation rentals
503 vacation rentals
452 vacation rentals
59 vacation rentals