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Caribbean beach vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Caribbean

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

  1. Entire loft
  2. Heredia
Alianz Loft

Insta @ alianzloft. 20 minutes from San Jose airport. First loft built by Alianz.cr. It contains a decked terrace, jacuzzi, firepit, rabbits garden, two rooms, two balconies, entrance gate, private garden, private parking, BBQ area, AC in each bedroom, basketball court, luxury beds, and mountain views. Ideal for architecture lovers, romantic dates, or having a good time. It is a unique space of his kind. Only pets that do not harm rabbits are allowed.

R4,853 ZAR per night
SUPERHOST
  1. Entire cottage
  2. Central Eleuthera
Bird of Paradise, Golden Chalice

Located on the tinted pink sand of Bird Point Beach, only a few steps away from the famous Tippy's Restaurant, "Bird of Paradise Beachfront Cottages" are the perfect getaway. The "Golden Chalice" is modern and unique with all the comforts of home. Beachfront deck, private pool, direct beach access, free WiFi, and time standing still are what you'll find here.

R6,396 ZAR per night
  1. Hotel room
  2. Rincon
Tres Sirenas Boutique Hotel Oceanfront Suite

Located in the 5/5 Tripadvisor rated Tres Sirenas Beach B&B, this breakfast included Oceanfront Studio is a beautiful contemporary full apartment boasting direct oceanfront views from both the interior and private balcony area this unit offers. Located on the first level of the villa, this accommodation offers breathtaking ocean views, ideal to enjoy the magnificent Rincon sunsets. Tres Sirenas Beach Hotel is a world renowned B&B situated in front of the beautiful Rincon beach in Puerto Rico.

R5,131 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

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Caribbean vacation rentals

SUPERHOST
  1. Entire villa
  2. Treasure Beach
Villa Elia~Private Seafront Tropical Paradise
R11,510 ZAR per night
SUPERHOST
  1. Treehouse
  2. Monteverde
NATURAVE - Into the woods
R2,542 ZAR per night
  1. Entire home
  2. Grand Cayman
Pools of the Kai #3 by Grand Cayman Villas
R7,907 ZAR per night
SUPERHOST
  1. Private room
  2. La Habana
Fauria Colonial House (Room 3)
R498 ZAR per night
PLUS
  1. Tiny home
  2. Villalba
Rancho Esto Es Vida !Una estadía de película!
R4,288 ZAR per night
SUPERHOST
  1. Dome
  2. Ponce
Bubble Puerto Rico Eternal
R4,732 ZAR per night
SUPERHOST
  1. Entire home
  2. Tower Isle
Tranquil Times Villa Jamaica
R7,350 ZAR per night
SUPERHOST
  1. Entire villa
  2. Philipsburg
Villa Dream View Belair Sint Maarten SXM
R6,479 ZAR per night
SUPERHOST
  1. Entire condo
  2. Santo Domingo
HEART of the City❤️📍 Rooftop POOL🏊‍♀️ ➕ Balcony ➕ GYM🏋🏼‍♀️
R1,445 ZAR per night
SUPERHOST
  1. Private room
  2. La Habana
Casa Blanca B&B with beautiful terrace &sea views
R545 ZAR per night
SUPERHOST
  1. Farm stay
  2. Monteverde
Monteverde Mountain View (see calendar 4 discount)
R1,519 ZAR per night
SUPERHOST
  1. Entire home
  2. Borinquen
The Nest at Crash Boat. Only waterfront on Beach
R4,924 ZAR per night

Caribbean house rentals

  1. Entire home
  2. North Side
Ocean's Edge: Beachfront Home with Rooftop Views
R6,911 ZAR per night
  1. Entire home
  2. Stake Bay
Modern Oceanfront, 2Primary Suites, sleeps 6, pool
R6,229 ZAR per night
SUPERHOST
  1. Entire home
  2. Key West
Grand Home/Heated, Salt Water Pool/Dog Friendly
R5,012 ZAR per night
SUPERHOST
  1. Entire home
  2. Fort Lauderdale
★Near Downtown & Beach- Luxury House /Heated spa★
R6,436 ZAR per night
  1. Entire home
  2. Grand Cayman
Lone Palm by Grand Cayman Villas
R13,954 ZAR per night
  1. Entire home
  2. Grand Cayman
Kai Tana by Grand Cayman Villas
R8,372 ZAR per night
  1. Entire home
  2. Placida
Camp GoodNow: Stunning new beachfront home, private balcony off master!
R7,558 ZAR per night
SUPERHOST
  1. Entire home
  2. Miami
ULTRA LUXURIOUS VILLA 4/3 LARGE POOL PFCT GETAWAY
R5,233 ZAR per night
SUPERHOST
  1. Entire home
  2. Cape Coral
Completely Remodeled 3 Bedroom Home With A Pool
R2,907 ZAR per night
  1. Entire home
  2. Cape Coral
NEW! Waterfront Cape Coral Oasis w/ Private Pool!
R5,532 ZAR per night
SUPERHOST
  1. Entire home
  2. Guayama
Completely private, for couples.
R1,739 ZAR per night
  1. Entire home
  2. Aguadilla Pueblo
Ta-Vera Oasis
R3,180 ZAR per night

Beach house rentals in Caribbean

SUPERHOST
  1. Entire home
  2. Fort Myers Beach
Onda Dolce Blue. Beachfront house with ocean views
R2,741 ZAR per night
SUPERHOST
  1. Entire home
  2. Siesta Key
Beachfront Getaway in Siesta Key
R4,592 ZAR per night
  1. Entire home
  2. St. Thomas
Stunning Water Views
R8,294 ZAR per night
SUPERHOST
  1. Entire home
  2. Marco Island
Luxury 4 Bedroom House ⭐️ Heated Pool ⭐️ Near Beach
R6,562 ZAR per night
  1. Entire home
  2. Luquillo
La orilla beach house
R15,402 ZAR per night
SUPERHOST
  1. Entire home
  2. Miami
Brickell View | Spacious Rooftop | Luxe 4B/3.5B
R8,764 ZAR per night
SUPERHOST
  1. Private room
  2. Cruz Bay
Hawk's Rest
R2,243 ZAR per night
  1. Entire home
  2. Torrecilla Baja
OceanView & Pool in your Backyard ✦ 8 Guests ✦ 4/2
R6,585 ZAR per night
  1. Entire home
  2. Captiva
Captiva Charm - Gulf front Olde Captiva style cottage
R9,989 ZAR per night
  1. Entire home
  2. Naples
VILLA CASCATA - Tropical Oasis, Ideal Location!
R8,555 ZAR per night
  1. Entire home
  2. Cape Coral
Roelens Vacations - Villa Carpe Diem - Cape Coral
R3,396 ZAR per night
SUPERHOST
  1. Entire home
  2. George Town
Eden Hill / Extraordinary Views / Great Location
R5,731 ZAR per night

Your guide to Caribbean

All About the Caribbean

The Caribbean is made up of 26 island countries surrounded by bejeweled blue and green waters and is known around the world as a holiday paradise. People flock here, especially in the winter, for warm sands, golden sunshine, and that sense of island time abandon — plus, the fruity drinks under towering palm trees. The Dominican Republic is the most visited of all the islands due to its vibrant city and cultural life and postcard-perfect beaches. West of that is Cuba, famous for its Old World architecture, rich jazz and music scenes, and several UNESCO World Heritage Sites. Closer to South America is little St. Lucia, known for its rainforests, colorful coral reefs (perfect for diving and snorkeling), and, of course, pristine beaches surrounded by the island’s volcanic peaks.

The countries in the Caribbean are extremely diverse, not only in their histories, cultures, and languages, but their landscapes and topographies. For example, vibrant Jamaica could not be more different from super-chill Aruba and swanky St. Barts. So whether you’re seeking an island that’s large or small, glitzy or low-key, in the Caribbean there is a sanctuary for everyone.


When is the best time to stay in a vacation rental in Caribbean?

Thanks to trade winds, the weather in the Caribbean is sunny and pleasant all year round. The only caveat is that tropical storms and hurricanes occur to varying degrees of intensity here, and their likelihood increases from about July to November. But it’s the dry season from December through March that makes the region so popular. Villas to rent in the Caribbean are in demand during the winter, as many feel the urge to escape the colder weather up north and take in the sun, fun, and the many festivals — like Trinidad’s Carnival, the biggest of the Caribbean’s carnivals, and the Bahamas’ Junkanoo, a cultural street festival and celebration dating back centuries that takes place between Boxing and New Year’s Day. There are also plenty of Caribbean rentals in May and June, if you don’t mind the chance of a little rain.


What are the top things to do in Caribbean?

Santo Domingo

Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited colonial settlement in the Western Hemisphere and was founded in 1496. The historic city center, Zona Colonial, is a UNESCO World Heritage Site, with cobblestone streets, colorful houses, and colonial-style architecture and structures like the 16th-century Basilica Cathedral of Santa María la Menor, the oldest surviving cathedral in the Americas.

Curaçao

Sitting off the coast of Venezuela is the Dutch island of Curaçao, lesser known than its neighbors, but with just as much to offer — including its lack of hurricane seasons. Willemstad, the capital, is one of the few UNESCO World Heritage cities in the Caribbean, and it’s pulsing with nightlife and festivals like Carnival and King’s Day. The diving here is top-notch, there are dozens of stunning beaches to choose from, and the lodging ranges from hostels to five-star resorts — so there’s something here for everyone.

Reggae in Jamaica

Jamaica is the birthplace of reggae. The music took off in the late 1960s, and by the 1970s, with the superstardom of Bob Marley and the Wailers, it became known throughout the world. If you’re in Kingston, check out the clubs, still playing the dub style that made the genre so popular. The best of the best musicians have been known to play at the annual reggae festival held in June.