Caribbean Islands vacation rentals

Search hundreds of travel sites at once for vacation home deals in Caribbean Islands

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Latest Caribbean Islands vacation rental deals

MOST POPULARMontego Bay
Vacation homes from $23
Nassau
Vacation homes from $44
San Juan
Vacation homes from $41
Oranjestad
Vacation homes from $54
Punta Cana
Vacation homes from $34
Providenciales
Vacation homes from $156

Best Caribbean Islands vacation rentals

Most recommended vacation rentals in Caribbean Islands

Show all
Skycastle Oasis - Ocho Rios
Parking
Free Wi-Fi
Pool
Naütik, Ocean Front! Great View - Fajardo
Parking
Free Wi-Fi
Pool
Pet friendly
Suenos del Mar - Fajardo - Beach
Parking
Free Wi-Fi
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

August
December
$393
$352
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 66% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Caribbean Islands vacation rental

  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Caribbean Islands for 6 days.
  • The cheapest Caribbean Islands vacation rental found on KAYAK in the last 2 weeks was $46, while the most expensive was $522.
  • Vacation rentals in Caribbean Islands are around 42% cheaper than hotels on average. Search here to compare prices for all accommodation types in Caribbean Islands.
  • The city in Caribbean Islands with the most affordable vacation homes is Negril, with around 276 properties and an average price of $54. The most popular vacation rentals in Caribbean Islands among KAYAK users are Villas Sur Mer, Bak A Yaad, and Idle Awhile The Cliffs.

FAQs when booking a vacation home in Caribbean Islands

  • How much is a vacation rental in Caribbean Islands for tonight?

    In the last 72 hours, users have found Caribbean Islands vacation rentals for tonight for as low as $32. Search here for similar prices

  • How much is a vacation rental for a week in Caribbean Islands?

    The average price for a weekly Caribbean Islands vacation rental found by KAYAK users in the last 2 weeks is $2,121.

  • How much is a vacation rental for a month in Caribbean Islands?

    The average price for a monthly Caribbean Islands vacation rental found by KAYAK users in the last 2 weeks is $9,091.

  • What types of vacation rentals are available in Caribbean Islands?

    There are loads of different property types that you can make your vacation home in Caribbean Islands. You’ll find apartments, campgrounds, condos, farm stays, houses, homestays, lodges, towers, villas, cabins, cottages, holiday parks, luxury tents, agritourism, houseboats, treehouses, barns, chalets, recreational vehicles, bungalows, caravans, boats, castles and studios.

  • What are some of the most-loved vacation rentals available in Caribbean Islands?

    There are many types of properties available for Caribbean Islands vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Perle d'Or City Apartments and Viking Hill Oceanfront Hostel & Resort.

  • What are the most popular Caribbean Islands vacation rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated vacation homes that can sleep 6 people or more by KAYAK users are Rhyne Park Inn, Luxury 2BR Home facing Beach w/Pool Montego Bay #3 and Royal Hideaway.

  • Are there any pet-friendly vacation rentals in Caribbean Islands?

    There are a number of dog and pet-friendly Caribbean Islands vacation rentals, with around 10% allowing you to bring your pet along with you.

Where to stay in Caribbean Islands?

Our map will help you find the perfect place to stay in Caribbean Islands by showing you the exact location of each vacation home.

What Caribbean Islands vacation rental guests are talking about

Show all

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.