Caribbean Islands Luxury Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Casa de Campo Resort and Villas
Majestic Mirage Punta Cana - All inclusive
Excellence El Carmen - Adults Only All Inclusive
Excellence Punta Cana - Adults Only All Inclusive
Zel Punta Cana – All Inclusive
Don't see what you're looking for?
See all available trips from Lisbon to Caribbean Islands
View all trips
Price found within the past 48 hours. Click for updated prices.
Casa de Campo Resort and Villas
Majestic Mirage Punta Cana - All inclusive
Excellence El Carmen - Adults Only All Inclusive
Don't see what you're looking for?
See all available trips from Lisbon to Caribbean Islands
View all trips
Price found within the past 48 hours. Click for updated prices.
The Crane Resort
Colony Club, a Luxury Collection Resort, Barbados
Don't see what you're looking for?
See all available trips from Philadelphia to Caribbean Islands
View all trips
Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
1055 Ashford Avenue, San Juan
  • 17 hours drive from Windward Islands
Stay at this 5-star luxury hotel in San Juan. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,539 reviews)
"Classic hotel with a great bar."

Reviewed on 31 Jul 2025

Condado Vanderbilt Hotel
Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive

Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive

4.5 out of 5
Salt Coppers, Runaway Bay, Saint Ann
  • 36 hours drive from Windward Islands
Stay at this 4.5-star luxury property in Runaway Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in ...
8.2/10 Very Good! (2,568 reviews)
"Cleaned. At some point food was cold..and rhe mostly frustrated problem was No Tv for 3 days .yes the bedding was nice and clean..transport was great"

Reviewed on 30 Jul 2025

Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive
Majestic Elegance Punta Cana - All Inclusive

Majestic Elegance Punta Cana - All Inclusive

4.5 out of 5
Playa Bavaro - Punta Cana, Punta Cana, La Altagracia
  • 21 hours drive from Windward Islands
Stay at this 4.5-star luxury property in Punta Cana. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our ...
8.8/10 Excellent! (4,178 reviews)
"We always come back to majestic, it’s always a great time, amazing staff, the rooms are clean, the pool is great with multiple bars throughout. THE STAFF IS AMAZING!!! The restaurants always have great food including the buffets. The beach had some seaweed but that’s normal for this time of year ..."

Reviewed on 31 Jul 2025

Majestic Elegance Punta Cana - All Inclusive
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.