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Caribbean Vacation Rentals
487 Caribbean Vacation Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Caribbean.
Select a country to narrow your vacation rental search or browse listings below:
- Anguilla (10)
- Bahamas (44)
- Barbados (21)
- British VIrgin Islands (3)
- Cayman Islands (78)
- Dominican Republic (22)
- Jamaica (53)
- Netherlands Antilles (11)
- Puerto Rico (38)
- St. Barths - St. Barts (147)
- St. Kitts and Nevis (1)
- St. Lucia (14)
- St. Maarten - St. Martin (9)
- Turks and Caicos Islands (8)
- US Virgin Islands (28)
Top Cities
Villa:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Lorient, St. Barts, St. Barths - St. Barts
Description: Overlooking the water, this two bedroom, two bathroom deluxe seaside villa is within walking distance to beautiful Lorient Beach. The equal king b... Learn More
Location: Lorient, St. Barts, St. Barths - St. Barts
Description: Overlooking the water, this two bedroom, two bathroom deluxe seaside villa is within walking distance to beautiful Lorient Beach. The equal king b... Learn More
Rates
$4066 - $9012 week
$4066 - $9012 week
Featured
Condo:
1 Bedroom, 2 Bathroom, Sleeps 2
Location: Cupecoy, St. Maarten, Netherlands Antilles
Description: 2 Bedroom, 2.5 Baths Oceanfront Condominium, on the 6th floor,with view of the ocean, lush garden, Simpson Bay lagoon, Anguilla, and the French Low... Learn More
Location: Cupecoy, St. Maarten, Netherlands Antilles
Description: 2 Bedroom, 2.5 Baths Oceanfront Condominium, on the 6th floor,with view of the ocean, lush garden, Simpson Bay lagoon, Anguilla, and the French Low... Learn More
Rates
$405 - $575 night
$2835 - $5250 week
$405 - $575 night
$2835 - $5250 week
Featured
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Marsh Harbour, Central Abaco, Bahamas
Description: Regatta condo #203 consists of 2 bedrooms and 2 bathrooms and is approximately 1,200 sq. ft. The condo is fully equipped and tastefully furnished ... Learn More
Location: Marsh Harbour, Central Abaco, Bahamas
Description: Regatta condo #203 consists of 2 bedrooms and 2 bathrooms and is approximately 1,200 sq. ft. The condo is fully equipped and tastefully furnished ... Learn More
Rates
$225 - $225 night
$1575 - $1575 week
$225 - $225 night
$1575 - $1575 week
Featured
Home:
1 Bedroom, 1 Bathroom, Sleeps 2
Location: Cayman Kai, Grand Cayman, Cayman Islands
Description: These two cozy side-by-side apartments are situated in a peaceful little sandy cove right across from famous Rum Point where there is a restaurant,... Learn More
Location: Cayman Kai, Grand Cayman, Cayman Islands
Description: These two cozy side-by-side apartments are situated in a peaceful little sandy cove right across from famous Rum Point where there is a restaurant,... Learn More
Rates
$140 - $190 night
$980 - $1330 week
$140 - $190 night
$980 - $1330 week
Featured
Villa:
1 Bedroom, 1 Bathroom, Sleeps 2
Location: Gouverneur, St. Barts, St. Barths - St. Barts
Description: The views from this cute one bedroom one bathroom hillside villa are spectacular as is the location which is only minutes from beautiful, unspoiled... Learn More
Location: Gouverneur, St. Barts, St. Barths - St. Barts
Description: The views from this cute one bedroom one bathroom hillside villa are spectacular as is the location which is only minutes from beautiful, unspoiled... Learn More
Rates
$2515 - $5781 week
$2515 - $5781 week
Featured
Villa:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Marsh Harbour, Central Abaco, Bahamas
Description: Luxurious and exquisite! Mermaid Reef Villas are perfect for the discerning vacationer that appreciates the finer things in life! In the heart of ... Learn More
Location: Marsh Harbour, Central Abaco, Bahamas
Description: Luxurious and exquisite! Mermaid Reef Villas are perfect for the discerning vacationer that appreciates the finer things in life! In the heart of ... Learn More
Rates
$400 - $500 night
$2800 - $3000 week
$400 - $500 night
$2800 - $3000 week
Featured
Home:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: St. John, St. John, US Virgin Islands
Description: Overlooking the incredible Caribbean Sea and within a mile of Cruz Bay, SeaCruz has a secluded and unparalleled view. By day, sunset, or night the... Learn More
Location: St. John, St. John, US Virgin Islands
Description: Overlooking the incredible Caribbean Sea and within a mile of Cruz Bay, SeaCruz has a secluded and unparalleled view. By day, sunset, or night the... Learn More
Rates
$2600 - $4300 week
$2600 - $4300 week
Featured
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Grand Cayman, Grand Cayman, Cayman Islands
Description: Ocean Front condo unit Bed configuration Bedroom 1: King Bedroom 2: 1Queen & 1Twin Living Room: Pull-out Queen Additional Features: Second Floor, ... Learn More
Location: Grand Cayman, Grand Cayman, Cayman Islands
Description: Ocean Front condo unit Bed configuration Bedroom 1: King Bedroom 2: 1Queen & 1Twin Living Room: Pull-out Queen Additional Features: Second Floor, ... Learn More
Rates
$325 - $675 night
$2275 - $4725 week
$325 - $675 night
$2275 - $4725 week
Featured
Home:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Grand Cayman, Grand Cayman, Cayman Islands
Description: This tastefully decorated 2 bedroom oceanfront unit has it all. Direct walk out to the beach, bright and spacious kitchen, dinning and living area ... Learn More
Location: Grand Cayman, Grand Cayman, Cayman Islands
Description: This tastefully decorated 2 bedroom oceanfront unit has it all. Direct walk out to the beach, bright and spacious kitchen, dinning and living area ... Learn More
Rates
$325 - $675 night
$2275 - $4725 week
$325 - $675 night
$2275 - $4725 week
Featured
Villa:
5 Bedroom, 5 Bathroom, Sleeps 12
Location: Seven Mile Beach, Grand Cayman, Cayman Islands
Description: This spacious, deluxe private beach front villa could be considered as one of the most sought after in the Cayman Islands! Situated directly on one... Learn More
Location: Seven Mile Beach, Grand Cayman, Cayman Islands
Description: This spacious, deluxe private beach front villa could be considered as one of the most sought after in the Cayman Islands! Situated directly on one... Learn More
Rates
$1100 - $1540 night
$7700 - $10780 week
$1100 - $1540 night
$7700 - $10780 week
Featured
Home:
2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: St. John, St. John, US Virgin Islands
Description: High up on the hill overlooking beautiful Fish Bay, is a lovely yellow villa with light purple shutters. Welcome to Daffodil Villa, a lovely two b... Learn More
Location: St. John, St. John, US Virgin Islands
Description: High up on the hill overlooking beautiful Fish Bay, is a lovely yellow villa with light purple shutters. Welcome to Daffodil Villa, a lovely two b... Learn More
Rates
$2400 - $3800 week
$2400 - $3800 week
Featured
Home:
Studio, 1 Bathroom, Sleeps 2
Location: Christ Church, Christ Church, Barbados
Description: Butterfly Beach Hotel Superior island view studio Bedding Configuration: Unit bedding varies. Unit sleeps 2. Unit Description: These superior isl... Learn More
Location: Christ Church, Christ Church, Barbados
Description: Butterfly Beach Hotel Superior island view studio Bedding Configuration: Unit bedding varies. Unit sleeps 2. Unit Description: These superior isl... Learn More
Rates
$102 - $155 night
$102 - $155 night
Featured
Condo:
3 Bedroom, 4 Bathroom, Sleeps 6
Location: Cupecoy, St. Maarten, Netherlands Antilles
Description: 3 Bedroom, 3.5 Baths Oceanfront Condominium, located on the 4th floor, with view of the ocean, lush garden. This 3 Bedroom offers a more spacious l... Learn More
Location: Cupecoy, St. Maarten, Netherlands Antilles
Description: 3 Bedroom, 3.5 Baths Oceanfront Condominium, located on the 4th floor, with view of the ocean, lush garden. This 3 Bedroom offers a more spacious l... Learn More
Rates
$605 - $860 night
$4235 - $7875 week
$605 - $860 night
$4235 - $7875 week
Featured
Condo:
1 Bedroom, 1 Bathroom, Sleeps 4
Location: Condado, North, Puerto Rico
Description: Converted one bedroom condo in Condado area of San Juan, Puerto Rico. 24 hr. security, in-ground pool, wireless internet access in common areas, un... Learn More
Location: Condado, North, Puerto Rico
Description: Converted one bedroom condo in Condado area of San Juan, Puerto Rico. 24 hr. security, in-ground pool, wireless internet access in common areas, un... Learn More
Rates
$500 - $525 week
$500 - $525 week
Apartment:
2 Bedroom, 1 Bathroom, Sleeps 4
Location: Bottle Creek, North Caicos, Turks and Caicos Islands
Description: Laughland Villa is a group of homes for visiters who want to relax away from the town. It is located to the south end of the island on the water fr... Learn More
Location: Bottle Creek, North Caicos, Turks and Caicos Islands
Description: Laughland Villa is a group of homes for visiters who want to relax away from the town. It is located to the south end of the island on the water fr... Learn More
Rates
$125 - $125 night
$775 - $775 week
$125 - $125 night
$775 - $775 week
Home:
4 Bedroom, 4 Bathroom, Sleeps 8
Location: St. John, St. John, US Virgin Islands
Description: Under new management and extensively renovated, this affordable and awesome villa, located at the water's edge overlooking the big blue sea is avai... Learn More
Location: St. John, St. John, US Virgin Islands
Description: Under new management and extensively renovated, this affordable and awesome villa, located at the water's edge overlooking the big blue sea is avai... Learn More
Rates
$1900 - $4200 week
$1900 - $4200 week
Villa:
7 Bedroom, 7.5 Bathroom, Sleeps 14
Location: St. John, Virgin Islands, US Virgin Islands
Description: Great Expectations is different than most private villas which usually have one Master bedroom for the owners with the best amenities and view, plu... Learn More
Location: St. John, Virgin Islands, US Virgin Islands
Description: Great Expectations is different than most private villas which usually have one Master bedroom for the owners with the best amenities and view, plu... Learn More
Rates
$2375 - $15000 week
$2375 - $15000 week
Apartment:
3 Bedroom, 2 Bathroom, Sleeps 8
Location: Loiza, East, Puerto Rico
Description: THE Best and most complete family Resort in Puerto Rico, 30 minutes from the Airport, 6 swimming pools, water slides, Lazy River Pool, Heated Pool,... Learn More
Location: Loiza, East, Puerto Rico
Description: THE Best and most complete family Resort in Puerto Rico, 30 minutes from the Airport, 6 swimming pools, water slides, Lazy River Pool, Heated Pool,... Learn More
Rates
$175 - $200 night
$1200 - $1500 week
$175 - $200 night
$1200 - $1500 week
Cottage:
1 Bedroom, 1 Bathroom, Sleeps 2
Location: Leverick Bay - North Sound, Virgin Gorda, British Virgin Islands
Description: "Tea & Coffee" cottages are absolutely beachfront but budget priced; the most charming holiday retreat adjacent to our private coconut grove & secl... Learn More
Location: Leverick Bay - North Sound, Virgin Gorda, British Virgin Islands
Description: "Tea & Coffee" cottages are absolutely beachfront but budget priced; the most charming holiday retreat adjacent to our private coconut grove & secl... Learn More
Rates
$1100 - $1600 week
$1100 - $1600 week
Villa:
4 Bedroom, 4.5 Bathroom, Sleeps 8
Location: Rendezvous Bay, Anguilla, Anguilla
Description: Brand new to the villa scene, Seabird Villa was designed by architect Lee Skolnick. Seabird is situated less than a minute drive to the sands of R... Learn More
Location: Rendezvous Bay, Anguilla, Anguilla
Description: Brand new to the villa scene, Seabird Villa was designed by architect Lee Skolnick. Seabird is situated less than a minute drive to the sands of R... Learn More
Rates
$650 - $3100 night
$650 - $3100 night
Special Offer Feb 29 - Jun 1 Whisk your wife away to Àni Villas and we will spo ...
Villa:
10 Bedroom, 10 Bathroom, Sleeps 20
Location: Little Bay, British West Indies, Anguilla
Description: Ani Villas Anguilla is a 10 bedroom estate with 2 fully serviced villas making it perfect for hosting larger groups and families of 20+ guests. E... Learn More
Location: Little Bay, British West Indies, Anguilla
Description: Ani Villas Anguilla is a 10 bedroom estate with 2 fully serviced villas making it perfect for hosting larger groups and families of 20+ guests. E... Learn More
Rates
$4286 - $13358 night
$30000 - $93500 week
$4286 - $13358 night
$30000 - $93500 week
Apartment:
Studio, 1 Bathroom, Sleeps 2
Location: San Juan, North, Puerto Rico
Description: Studio apartment 4 blocks from the Ocean Park beach, located in a residential street. The adjacent Loiza Street has restaurants, shops, supermarket... Learn More
Location: San Juan, North, Puerto Rico
Description: Studio apartment 4 blocks from the Ocean Park beach, located in a residential street. The adjacent Loiza Street has restaurants, shops, supermarket... Learn More
Rates
$75 - $85 night
$490 - $540 week
$75 - $85 night
$490 - $540 week
Home:
3 Bedroom, 3 Bathroom, Sleeps 8
Location: North Side, Grand Cayman, Cayman Islands
Description: Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat, Ocean Paradise offers luxury a... Learn More
Location: North Side, Grand Cayman, Cayman Islands
Description: Perfectly located on the tranquil north side of Grand Cayman for those who prefer an almost secluded island retreat, Ocean Paradise offers luxury a... Learn More
Rates
$199 - $750 night
$1350 - $4950 week
$199 - $750 night
$1350 - $4950 week
Home:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Sosua, Sosua, Dominican Republic
Description: Spacious, ocean-view apartment in Sosua's finest condominium. Located in a quiet, upscale neighborhood, but just a few minutes walk from Playa Sosu... Learn More
Location: Sosua, Sosua, Dominican Republic
Description: Spacious, ocean-view apartment in Sosua's finest condominium. Located in a quiet, upscale neighborhood, but just a few minutes walk from Playa Sosu... Learn More
Rates
$500 - $700 week
$500 - $700 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Sosua, Puerto Plata, Dominican Republic
Description: Blue Fish is a luxury, oceanfront condominium complex located in the secure, gated community of Perla Marina. Guests need only step outside to expe... Learn More
Location: Sosua, Puerto Plata, Dominican Republic
Description: Blue Fish is a luxury, oceanfront condominium complex located in the secure, gated community of Perla Marina. Guests need only step outside to expe... Learn More
Rates
$100 - $150 night
$700 - $875 week
$100 - $150 night
$700 - $875 week
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