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Caribbean Vacation Rentals

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Caribbean
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Up to $100
$100 - $199
From $200
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Enjoy Calypso Life With Your Very Own Caribbean Vacation Home

The Caribbean islands have something to offer everyone: luxurious destinations, adventurous activities, beautiful beaches, and incredible nature. Accommodations include short-term and monthly rentals, ranging from small apartments and self-contained units to stunning villa rentals with sea views.

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Best Vacation Home Deals in Caribbean

Save up to 33%

Villa Freshwater Pond
Oct 21 - Oct 28
-20%
$314
$250 per night
Villa ∙ 2 guests ∙ 1 bedroom
Comfortable Villa in Freshwater Pond with Grill + Island View
4.9
"Outstanding" (66 ratings)
Freshwater Pond, Tortola, British Virgin Islands
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Condo Grand Case
Sept 16 - Sept 23
-33%
$286
$192 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Grand Case with Patio + Panoramic View
5.0
"Outstanding" (67 ratings)
Grand Case, Collectivity of Saint Martin, Saint Martin
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Condo George Town
Oct 14 - Oct 21
-31%
$1,058
$727 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in George Town with Private Balcony
4.9
"Outstanding" (132 ratings)
George Town, Cayman Islands
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Search and compare the 108,635 properties available in Caribbean and discover the ideal one for a relaxing vacation. By comparing these properties, HomeToGo brings you the best deals as well as the highest rated properties in Caribbean.

Top-Rated Offers and Accommodations in Caribbean

Book Vacation Rentals with the Highest User Rating

Condo George Town
Jun 29 - Jul 6
$642 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Charming Condo in George Town with Private Patio + Ocean View + Close to Beach
5.0
"Outstanding" (92 ratings)
George Town, Cayman Islands
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Condo George Town
Jun 29 - Jul 6
$659 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in George Town with Tropical Pool + Ocean Views
5.0
"Outstanding" (92 ratings)
George Town, Cayman Islands
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House North Palmetto Point
Jan 20 - Jan 27
$870 per night
House ∙ 8 guests ∙ 4 bedrooms
Whole Vacation Home in North Palmetto Point with Front Pool + Garden Views
4.8
"Outstanding" (55 ratings)
North Palmetto Point, Central Eleuthera, The Bahamas
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Recommended Vacation Rentals in Caribbean

Find your perfect vacation rental in Caribbean: from $57 per night

Villa Rum Point
Sept 9 - Sept 16
-28%
$434
$315 per night
Villa ∙ 2 guests ∙ 1 bedroom
Villa in Rum Point with Pool & Grill + Pristine Views
4.9
"Outstanding" (178 ratings)
Rum Point, North Side, Cayman Islands
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Condo West Bay
Apr 27 - May 4
$749 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in West Bay with Large Pool
5.0
"Outstanding" (63 ratings)
West Bay, Cayman Islands
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Condo Rum Point
Oct 28 - Nov 4
-40%
$510
$305 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in Rum Point with Grill + Picturesque View
5.0
"Outstanding" (47 ratings)
Rum Point, North Side, Cayman Islands
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Condo George Town
Oct 14 - Oct 21
-46%
$840
$456 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Lovely Condo in George Town with Free Parking + Garden View + Beach Nearby
4.9
"Outstanding" (91 ratings)
George Town, Cayman Islands
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Condo Bodden Town
Sept 16 - Sept 23
$372 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Bodden Town with Private Pool
4.9
"Outstanding" (76 ratings)
Bodden Town, Cayman Islands
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Apartment Bodden Town
Apr 27 - May 4
-32%
$446
$305 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Wonderful Apartment in Bodden Town with Grill & Pool
5.0
"Outstanding" (86 ratings)
Bodden Town, Cayman Islands
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Villa New Castle
Jun 29 - Jul 6
$287 per night
Villa ∙ 4 guests ∙ 2 bedrooms
Nice Villa in New Castle with Private Pool + Endless Views + Beach Nearby
4.9
"Outstanding" (23 ratings)
New Castle, Saint James Windward Parish, Saint Kitts and Nevis
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Condo North Side
Aug 26 - Sept 2
$329 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in North Side with Shallow Pool + Oceanfront Views
4.9
"Outstanding" (99 ratings)
North Side, Cayman Islands
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Condo Rum Point
Sept 2 - Sept 9
-60%
$688
$277 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Rum Point with Pool, Grill & Yard + Garden View
5.0
"Outstanding" (68 ratings)
Rum Point, North Side, Cayman Islands
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Budget-friendly Rentals in Caribbean

Find Fantastic yet Inexpensive Rentals

House Rum Point
Jun 29 - Jul 6
$1,115 per night
House ∙ 8 guests ∙ 4 bedrooms
Wonderful House in Rum Point with Private Pool + Water Views
5.0
"Outstanding" (3 ratings)
Rum Point, North Side, Cayman Islands
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House Rum Point
Apr 6 - Apr 13
$934 per night
House ∙ 6 guests ∙ 3 bedrooms
Private House in Rum Point with Private Pool + Magnificent Views
4.8
"Outstanding" (103 ratings)
Rum Point, North Side, Cayman Islands
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Villa Cul-de-Sac
Sept 2 - Sept 9
-52%
$1,601
$772 per night
Villa ∙ 8 guests ∙ 3 bedrooms
Villa in Cul-De-Sac with Yard, Grill & Pool
5.0
"Outstanding" (77 ratings)
Cul-de-Sac, Collectivity of Saint Martin, Saint Martin
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Caribbean rental with full kitchen.

House Kitchen Sainte-Anne
Aug 26 - Sept 2
$225 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sainte-Anne with Pool, Yard & Patio + Garden View
4.8
"Outstanding" (51 ratings)
Sainte-Anne, Grande-Terre, Guadeloupe
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House Kitchen Stake Bay
Aug 26 - Sept 2
$300 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Stake Bay with Grill + Endless Views
5.0
"Outstanding" (50 ratings)
Stake Bay, Cayman Brac, Cayman Islands
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House Kitchen Saint James
Sept 2 - Sept 9
-16%
$285
$239 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Saint James with Grill & Pool
4.6
"Excellent" (39 ratings)
Saint James, Barbados
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Caribbean with private yards.

House Yard North Side
Sept 2 - Sept 9
-50%
$2,082
$1,048 per night
House ∙ 14 guests ∙ 5 bedrooms
Vacation Home in North Side with Spacious Patio + Panoramic View
5.0
"Outstanding" (55 ratings)
North Side, Cayman Islands
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House Yard Stake Bay
Sept 2 - Sept 9
$639 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Stake Bay with Large Pool
5.0
"Outstanding" (58 ratings)
Stake Bay, Cayman Brac, Cayman Islands
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House Yard Rum Point
Jun 29 - Jul 6
$1,724 per night
House ∙ 14 guests ∙ 6 bedrooms
House in Rum Point with Private Pool + Ocean Views
5.0
"Outstanding" (56 ratings)
Rum Point, North Side, Cayman Islands
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Cabins with a sauna

Relax and enjoy yourself in one of these Caribbean vacation rentals with saunas.

Villa Sauna Emmaus
Nov 18 - Nov 25
$558 per night
Villa ∙ 2 guests ∙ 1 bedroom
Villa in Emmaus with Yard, Pool & Sauna + Stellar Views
5.0
"Outstanding" (71 ratings)
Emmaus, Coral Bay, U.S. Virgin Islands
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Apartment Sauna Greenwich Park
Dec 9 - Dec 16
$99 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Apartment in Greenwich Park with Beautiful Garden
4.7
"Excellent" (31 ratings)
Greenwich Park, St. Ann Parish, Jamaica
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House Sauna Michelson
Oct 28 - Nov 4
$1,040 per night
House ∙ 7 guests ∙ 3 bedrooms
Pleasant House in Michelson with Yard, Grill & Pool + Amazing Views
5.0
"Outstanding" (77 ratings)
Michelson, Exuma, The Bahamas
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Popular Rental Amenities in Caribbean

  • Pool (73,240)
  • WiFi (105,869)
  • Air conditioning (98,591)
  • Pet-friendly (7,982)
  • Balcony/patio (57,054)
  • Kitchen (86,336)
  • TV (95,433)
  • Grill (42,798)
  • Washing machine (61,760)
  • Parking (5,132)
  • Yard (67,963)
  • Dishwasher (28,564)

Caribbean is a great vacation destination if you want a rental with a pool, as 65% of the accommodations there have one. Also, properties with pools in Caribbean cost, on average, $1,084 a night. Most of the available rentals with pools are apartment rental. You can also compare and find an accommodation with a pool near the water, which is the case for many of the rentals in this destination.

Price and Availability Index in Caribbean

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Vacation Rental Price Information in Caribbean

The graph shows average prices of rentals in Caribbean for the next twelve months. The most expensive week of the next 12 months is in May (5/25 - 6/1), where prices hit an average of $494 a night. You can find some of the best deals during a week of December (12/23 - 12/30). It is the cheapest week of the next 12 months.

Rental availability information in Caribbean

Our availability graph helps you identify the busiest months in Caribbean. The week with the highest booking rate in the next 12 months is in August (8/31 - 9/7), where 88% of the vacation rentals are booked. It will be easy to find a rental that suits you in a week of June (6/15 - 6/22), as 71% of the rentals are still available.

7-Day Weather Forecast in Caribbean

Sun., 24 Sep.
32°
24°

15%

6 h

11 km/h

Mon., 25 Sep.
31°
26°

10%

4 h

9 km/h

Tue., 26 Sep.
31°
26°

10%

6 h

13 km/h

Wed., 27 Sep.
31°
27°

10%

9 h

13 km/h

Thu., 28 Sep.
31°
27°

10%

7 h

15 km/h

Fri., 29 Sep.
31°
27°

15%

5 h

22 km/h

Sat., 30 Sep.
33°
25°

15%

2 h

10 km/h

What are the best nightlife spots in Caribbean?

Enjoy the Caribbean’s Lively Nightlife

Caribbean culture is famous for its upbeat music and lively parties. Throughout the islands – particularly Puerto Rico, the Dominican Republic, Aruba, and Curacao – you'll find plenty of opportunities to party. In the Dominican Republic, head to Santo Domingo's many bars and nightclubs to catch live music performances or east to the beachside town of Punta Cana. Head to the Dutch islands of Aruba and Curacao for sandy beach bars, nightclubs, and swim-up bars.

Where are the unique attractions in Caribbean?

Outdoor Activities and Adventure in the Caribbean

The Caribbean offers a wealth of outdoor activities. As the islands are legendary for their white sand and bright turquoise water, no visit would be complete without heading to the beach. Go island hopping tour by boat to explore the smaller, more remote beaches. You'll find some of the world's best snorkelling and scuba diving in the Caribbean, especially around the islands of Grenada, Saba, and St. Maarten. Discover spectacular coral reefs, sea turtles, sharks, and other underwater creatures. On land, the Caribbean also offers some great hiking, such as the El Yunque National Forest in Puerto Rico, with lush rainforest and waterfalls.

What are the best events and festivals in Caribbean?

Take Part in the Caribbean’s Famous Carnival Festivals

Every year, each Caribbean island lights up with its own Carnival festival. Although the festivals are mostly held around Ash Wednesday, their dates tend to vary year-to-year and between islands. Festivities typically involve bright and colourful parades, dancing, music, and lots of food and drink. The Carnival celebrations in Trinidad and Tobago are particularly well known, and along with traditional parades, they feature stick-fighting and limbo competitions.

Information about vacation rentals in Caribbean

🏡 Vacation rentals available 108,635 homes
💳 Possible discounts up to 33%
🌙 Nightly prices starting at $58
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 7,576 homes
🏊 Vacation rentals with pools 71,130 homes

Frequently Asked Questions

What is the typical price of a vacation home in Caribbean?

The nightly price for accommodation in Caribbean starts at $58.

What is the typical availability of Apartment rental in Caribbean?

September has the highest availability of Apartment rental in Caribbean, so you can expect plenty of selection, even for last-minute bookings.

What are the most popular vacation home amenities in Caribbean?

The most popular amenities for rentals in Caribbean include vacation homes with Pool, Internet, or Air conditioning.

How many Apartment rental and Villa can I find in Caribbean?

Caribbean has 108,635 Apartment rental and Villa available to book.

What's the best month to visit Caribbean?

If you're looking for balmy weather, June and July are typically the hottest months in Caribbean with temperatures around 33 °C. January and February in Caribbean are the coldest, with 19 °C on average.

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