Winter sun holidays in the Caribbean

Ditch the cold this winter: jet off to the Caribbean!

When the British weather is at its very worst, where better to escape to than the Caribbean? Amidst the 7,000 islands you have to choose from, you’ll find swaying palm trees, white, soft-sand beaches and warm, turquoise waters throughout: just what you need to cure those winter blues. Of course, while all Caribbean islands offer beautiful landscapes and sunny winter weather, each has a unique charm and character. In the Bahamas, you’ll find perfect visibility for scuba diving, while in Jamaica, you can learn about the origins of Reggae. Tobago boasts amazing pink sand shores, while Antigua is home to a number of rare bird colonies.

Wherever you choose to holiday in the Caribbean, consider booking private accommodation through HomeAway. Not only do our Caribbean villas offer a supreme level of privacy and space, but greater value for money, so you can enjoy your holiday to the fullest. You could go paragliding, snorkelling or deep sea fishing: with HomeAway Holiday Rentals, you can afford to! Because we have thousands of properties with unique locations and facilities, you know you’ll find the perfect home in the destination you’ve always dreamed of. So why wait? Simply read on for a rundown of our favourite Caribbean islands.


Top destinations in the Caribbean


Puerto Rico Puerto Rico

When looking for the tropical getaway of a lifetime, consider stunning Puerto Rico. An island lying to the east of the Dominican Republic, it’s known for its friendly people, amazing landscapes and gloriously clean, white beaches. Unlike some of the other Caribbean islands, there’s a strong Spanish influence in Puerto Rico: over four centuries of Spanish colonial rule have certainly left their mark! As well as trekking through rainforests and exploring magnificent coral reefs, expect spectacular architecture, and lively, Latin-inspired nightlife come sundown. For an activity-packed winter sun break, there’s no better choice than Puerto Rico.

View villas in Puerto Rico



Martinique Martinique

Martinique is a fantastic choice when you want some winter sun: boasting both French and Caribbean heritage, it’s an exciting destination with an elegant, unique atmosphere. Many tourists head for the south, where calm, clear waters are ideal for snorkelling, and soft, white beaches are postcard perfection, but the northern coast is no less promising. Here, black, volcanic sands are overlooked by towering peaks like Mount Pelee, located just steps from tumbling, inland waterfalls. Whether you want to see shipwrecks off the coast of Saint Pierre, or learn about Martinique’s history at Saint Louis, you’re ensured a spectacular break.

View holiday properties in Martinique



Barbados Barbados

When nothing but blissful 28°C temperatures will do, look no further than Barbados. It may be called ‘Little Britain’ by many, but it’s pleasantly removed when it comes to climate! Indeed, there’s so much to see on this beautiful, tropical haven, you’ll be hard-pushed to fit it all in! You can spend your days on paradisiacal shores, sunbathing and enjoying water sports, or head for an inland city like Bridgetown, to shop at markets and do some sightseeing. There are plenty of exciting attractions to peruse: from the fascinating Sunbury Plantation House, to the diverse Barbados Wildlife Reserve, you’ll find no shortage of things to see or do.

View holiday villas in Barbados



Guadeloupe Guadeloupe

Guadeloupe is often referred to as the ‘Emerald Isle’, and once you’ve seen its lush flora and fauna, you’ll certainly understand why. A magnificent island bursting with colour and beauty, it’s a fantastic destination - whatever your interests. You could stay in Basse-Terre, an area of spectacular rainforest, where you can hike through mountains, waterfalls and springs, or head for Grand-Terre, home to Guadeloupe’s best beaches.  Scuba divers will find themselves surrounded by some of the best coral reefs on earth, while water sports enthusiasts can enjoy a number of activities, including windsurfing, water-skiing, and sailing.

View holiday rentals in Guadeloupe



St Maarten-Saint Martin St Maarten-Saint Martin

St Maarten-Saint Martin is a tiny, but spectacular island shared between the Netherlands and France. Surrounded by warm, clear waters and boasting a reputation for lively nightlife, it’s one of the premier destinations in the Caribbean, despite its small size! Indeed, while the Netherlandish area of St Maarten is just 36km square, it’s home to the largest lake in the Caribbean, Simpson Bay. Yet while its luxury yachts and pretty streets are a beautiful sight to behold, the larger French area of Saint Martin is equally lovely: with a number of secluded coves spilling out to sparkling waters, it’s the ideal spot for a relaxing winter break.

View holiday villas in St Maarten-Saint Martin


View more properties in the Caribbean

Blue Serenity - Spacious 1 level villa with gym, pool & panoramic ocean vistas.

Blue Serenity's Main Villa is built all on one level and is fully air-conditioned, with a high-ceilinged, spacious Great Room serving as the central gathering spot. On the east side of the Great Room are two king bedrooms and the west wing compr...

New Luxurious 2BR Barbados Condo Apt on Gorgeous Dover Beach

Located on a very large, sugar-white south coast beach, this luxurious 2BR apartment offers easy access directly to the beach. Stunning, comfortable, and serene in decor and located smack-dab on beautiful sugar-white Dover Beach in Barbados, Sapp...

Sade - Conveniently located villa offers guest cottage, pool, seclusion & comfort.

Walk just 200 yards from Sade to the white sands of famous Smugglers Cove Beach! Sade offers seclusion behind groves of tall shady trees, but is just a quick walk to the beach. Sade consists of the two-story Main House and the Guest Cottage next ...

Sade - Conveniently located villa offers guest cottage, pool, seclusion & comfort.

Walk just 200 yards from Sade to the white sands of famous Smugglers Cove Beach! Sade offers seclusion behind groves of tall shady trees, but is just a quick walk to the beach. Sade consists of the two-story Main House and the Guest Cottage next ...

Gorgeous Beach Condo Apt in St Lawrence Gap, Barbados

Are you looking for superior value and drop-dead-gorgeous Caribbean Sea views? 'Sea Breeze' in the St Lawrence Beach Condos on the south coast of Barbados is a new vacation rental property, welcoming guests who wish to vacation on the island with...

MapCroatia Slovakia Russia Finland Greece Greece Cyprus Turkey Albania Bulgaria Montenegro Serbia Bosnia Hercegovina Slovenia Austria Czech Republic Hungary Romania Poland Belarus Lithuania Latvia Estonia Afrika Luxembourg Andorra Monaco Malta Italy Italy Sweden Norway Denmark Germany Netherlands Belgium France Portugal Spanien Gibraltar Switzerland Iceland UK Ireland Channel Islands World USA UK

Search for holiday rentals

Search for holiday ideas

Cheap Rentals & special Deals in Europe

More inspiration

Short Breaks Short Breaks
Summer Holidays Summer Holidays
Family Holidays


Sign up to our newsletter

Our latest updates and special offers, direct to your inbox