Caribbean Holidays
Enduring laidback charm
From family escapes to couples retreats and adults only hideaways, each handpicked hotel in our Caribbean portfolio has something for all. Picture endless white beaches, warm shallow waters and untouched rainforests, all wrapped up in a carnival atmosphere with smiling hospitality that welcomes you in.
Caribbean Islands
Caribbean Holidays
The white sandy beaches, lush tropical forests, crystal blue seas and friendly atmosphere of the Caribbean are the ideal combination for a relaxing and luxurious escape. Throughout the many Caribbean islands, there really is something for everyone. Whether it's the sun-soaked shores of Barbados, the sizzling cuisine of Antigua or the laid-back atmosphere of Jamaica, you will surely find the ideal spot for your holiday this year. You'll also find a great range of accommodation. Along with our all-inclusive resorts and intimate boutique hotels, we offer everything from private villas with maid service and cooking to barefoot beach huts.
Luxury Holidays to the Caribbean
If it's a luxury Caribbean holiday you're looking for, our destination experts offer a superb range of hotels to match your style. Whether you want a romantic honeymoon destination, an all-inclusive holiday for the family or a tranquil solo break, talk to our Caribbean travel team and plan a tropical getaway you'll never forget. Book now to take advantage of our range of direct deals with the area's best hotels, including Sandy Lane in Barbados, and Jade Mountain and Coconut Bay Beach Resort & Spa in St Lucia. And don’t miss the special prices our experts have arranged with our preferred hotel partners in the Caribbean, such as the popular Sandals Resorts in Antigua, Barbados, Grenada, Jamaica, St Lucia, The Bahamas and Turks & Caicos.
School Holidays in the Caribbean
We have limited availability to the Caribbean over the Christmas & New Year school holidays. Our Christmas special offers are exclusive to us, with early January inbounds available. We have holidays to Barbados, Antigua, Jamaica, and St Lucia, all with discounts for children and savings of up to 30%. Escape this winter and jet off to the sunny Caribbean for Christmas & New Year, plus find a host of other school holiday dates as far as Barbados, St Lucia, Cancun, and Antigua that let you beat the rush for places during peak times.
Book Early to Guarantee Your Caribbean Holiday Deals for 2025 & 2026
We have some great Caribbean holidays for 2025 & 2026 available with up to 60% savings on some hotels and generous early booking discounts on our flights. Look for deals using our onsite Holiday Search facility or call the Kenwood team. Our flights are booked with our preferred partners Virgin Atlantic and British Airways. For pre-booked seats, teen discounts and any tailor-made requirement for your holiday, call our advisors now and let us take care of the details.
Caribbean Weather
Even from space, the Caribbean’s shallow cays and coral lagoons loom impossibly blue – a testament to the archipelago’s invitingly warm waters – and illustrate the hot weather these islands are blessed with year-round. Welcome to one of the finest climates in the Americas. Cooling north-easterly trade winds moderate the Caribbean’s on-land temperatures to a tropical 24°C to 32°C at sea level, and these readings will tend not to fluctuate regardless of the time of day, month or season. Pretty predictable, but variations in temperature do occur at higher altitudes, with hilly regions being slightly cooler.
Rather than use a conventional four-season model to explain any meteorological variances, an understanding of the Caribbean’s weather patterns is probably best divided neatly into two: the rainy season – May to October – and the dry season, which corresponds to our winter. Don’t be discouraged though – even during the so-called rainy season, wet conditions fluctuate and showers can be short-lived. Leeward sides of mountainous islands are known to remain dry throughout. So, if you’re beach-ready and aching for some fun in the sun, the Caribbean is waiting to grace you with its gorgeous weather. The boxes are ticked for blue skies, clear waters and summer heat.
Special offers
The Verandah Antigua
- Up to 53% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,677 per person
Sea Breeze Beach House
- Up to 50% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,872 per person
Hard Rock Hotel & Casino Punta Cana
- Up to 55% saving
- Resort credit US$200 per room per night
- Kids Stay Free
7 nights All Inclusive including British Airways flights from £1,853 per person
Calabash Hotel
- Complimentary Private Dinner on the New Jetty & Airport Transfers
- Complimentary upgrade to Half Board
7 nights Half Board including Virgin Atlantic flights from £2,886 per person
Royalton Grenada, An Autograph Collection All-Inclusive Resort
- 30% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,842 per person
Casa de Campo Resort & Villas
- Up to 62% saving
- Complimentary Room Upgrade*
- One Free Child*
7 nights Room Only including British Airways flights from £1,746 per person
Spice Island Beach Resort
- 14% saving
7 nights All Inclusive including Virgin Atlantic flights from £3,237 per person
Blue Waters Resort and Spa
- 25% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £2,157 per person
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Carlisle Bay
- Complimentary Half Board
- 30% Saving
7 nights Half Board including Virgin Atlantic flights from £2,367 per person
Sandals Grande Antigua
- Up to 55% saving
- Up to £725 off booking bonus
- Complimentary Airport Transfers
7 nights All Inclusive including Virgin Atlantic flights from £2,117 per person
St James’s Club & Villas
- Up to 20% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,476 per person
Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort
- 30% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,850 per person
The Rockley
- Up to 40% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £1,216 per person
The Club Barbados Resort & Spa
- Up to 15% saving
7 nights All Inclusive including Virgin Atlantic flights from £1,544 per person
The Crane Resort
- Resort credit US$80 per room per stay
- Up to 35% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £1,503 per person
Margaritaville Beach Resort
Right in the heart of Nassau, this gorgeous resort is a perfect destination to appreciate the wonders of the Caribbean.
7 nights Room Only including British Airways flights from £2,224 per person
British Colonial Nassau
- 15% saving
7 nights Room Only including British Airways flights from £1,769 per person
Grand Isle Resort & Residences
- Stay 5 Pay 4
7 nights Room Only including British Airways flights from £3,047 per person
AVA Resort Cancun
- Resort credit US$200 per room per stay
- Up to 45% saving
7 nights All Inclusive including British Airways flights from £2,030 per person
Secrets Moxche Playa Del Carmen
- Up to 40% saving
7 nights All Inclusive including British Airways flights from £1,954 per person
Dreams Tulum Resort & Spa
- Up to 40% saving
- Kids Stay Free
7 nights All Inclusive including British Airways flights from £1,352 per person
Hard Rock Hotel Riviera Maya
- Up to 55% saving
- Resort credit US$200 per room per night
- Kids Stay Free
7 nights All Inclusive including British Airways flights from £1,869 per person
The Fives Oceanfront
- Up to 61% saving
- Resort credit Coupon US$555 per room per stay
7 nights Room Only including British Airways flights from £1,265 per person
Hard Rock Cancun
- Up to 55% saving
- Resort credit US$200 per room per night
- Kids Stay Free
7 nights All Inclusive including British Airways flights from £1,797 per person
Zoëtry Agua Punta Cana
- Up to 45% saving
7 nights All Inclusive including British Airways flights from £2,028 per person
Dreams Royal Beach Punta Cana
- Up to 32% saving
7 nights All Inclusive including British Airways flights from £1,449 per person
Dreams Macao Beach Punta Cana Resort & Spa
- Up to 36% saving
7 nights All Inclusive including British Airways flights from £1,487 per person
Dreams Dominicus La Romana
- Up to 20% saving
7 nights All Inclusive including British Airways flights from £1,337 per person
Couples Swept Away
- Up to 46% saving
- Complimentary Standard Transfers (Montego Bay Airport Only)
7 nights All Inclusive including British Airways flights from £2,009 per person
Moon Palace Jamaica
- Complimentary Return Airport Transfers from Montego Bay
- Kids & Teens Stay Free
- $250 Spa Credit
7 nights All Inclusive including British Airways flights from £1,700 per person
S Hotel Montego Bay
- US$100 Resort Credit Per Room Per Stay
- 20% saving
7 nights All Inclusive including British Airways flights from £2,100 per person
The Landings Resort and Spa
- Up to 40% Saving
7 nights Bed and Breakfast including British Airways flights from £1,753 per person
Coconut Bay Beach Resort & Spa
- Up to 65% saving
- Standard Transfers
7 nights All Inclusive including Virgin Atlantic flights from £1,907 per person
Bequia Beach Hotel
- Up to 40% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £2,135 per person
Coco Reef Resort & Spa
- Up to 40% saving
7 nights Bed and Breakfast including Virgin Atlantic flights from £1,216 per person
Zoëtry Curaçao Resort & Spa
An oasis of peace and tranquillity set on the beautiful island of Curaçao. Enjoy luxurious suites, a la carte restaurants, and fantastic spa facilities.
7 nights All Inclusive including American Airlines flights from £2,328 per person
Sunscape Curaçao Resort, Spa & Casino
Enjoy stunning rooms and suites, unlimited dining and drinking, and endless activities at all-inclusive, family-friendly Sunscape Curaçao Resort, Spa & Casino.
7 nights All Inclusive including American Airlines flights from £1,455 per person
Dreams Curaçao Resort Spa & Casino
- Up to 40% saving
7 nights All Inclusive including American Airlines flights from £1,537 per person
Caribbean Holiday Types
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