Caribbean
Luxury Hotels in Caribbean
The luxury hotels across Caribbean our specialists handpick for their clients, from the Caribbean to Mexico.
All Luxury Hotels in Caribbean
Showing 37–48 of 51
Hotel Christopher Saint-Barth
St Barth's
SailRock, Turks & Caicos
Turks and Caicos
Amanyara, Turks & Caicos
Turks and Caicos
Grace Bay Club, Turks & Caicos
Turks and Caicos
Como Parrot Cay, Turks & Caicos
Turks and Caicos
Ambergris Cay Private Resort, Turks & Caicos
Turks and Caicos
Secrets Baby Beach Aruba
Aruba
Bucuti & Tara Beach Resort
Aruba
Four Seasons Resort
Anguilla
Manchebo Beach Resort & Spa
Aruba
Amanyara, Turks & Caicos
The Caribbean
Cap Juluca, A Belmond Hotel
AnguillaTrips through Caribbean
Ultimate Luxury Mexico: Punta Mita, Los Cabos & Riviera Maya
Tailor-made VacationThree coastlines, one itinerary, entirely shaped around you. Move between three of Mexico's most distinct coastal regions, each with its own rhythm. From the private peninsula of Punta Mita to the dramatic cliffs of Los Cabos and the reef-lined shore of the Riviera Maya, the trip is built entirely around the version of Mexico you want to see.
9 days tailor-made from $8,900 per person View trip
Classic Caribbean: Aruba and Curacao
Tailor-made VacationRenowned for offering the quintessential Caribbean experience – white sands, swaying palm trees, and crystal-clear waters – Classic Caribbean: Aruba and Curacao forms one of our favorite twin-center vacations. These islands invite you to immerse yourself in natural beauty while indulging in world-class hospitality, all set against the stunning backdrop of the Caribbean Sea. Aruba and Curacao are incredibly LGBTQ+ friendly, making them standout destinations for inclusive travel.
7 days tailor-made from $4,435 per person View trip
Miami & Caribbean Cruise
Tailor-made VacationExperience Miami's welcoming energy, Caribbean sailing, and island time in the Bahamas, all in one luxury trip. This nine-day trip opens in Miami, a city whose LGBTQ+ history runs deep along South Beach and Ocean Drive, where Art Deco facades and an easy, sun-soaked pace set the tone for the days ahead.
9 days tailor-made from $7,345 per person View tripMoments in Caribbean
Casa Azul
Frida Kahlo's former home is a treasure trove of art history and a must-visit spot in Mexico City.
How to Visit Flamingo Island in Aruba
Izta-Popo National Park
Acres of awe-inspiring natural landscapes waiting to be explored.
Diving in the Caribbean
Discover some of the best dive sites on the planetStellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.