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Top Holidays
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- Caribbean
- Luxury Hotels
We found 77 luxury hotels for you
Destinations in Caribbean
- Get direct access to Eagle Beach, one of the best beaches in the world
- Enjoy tailored romance packages and a personal concierge service
- Feel the restorative power of the Caribbean through tailored wellness classes
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Private island resort in the heart of the Grenadines
- Beautifully appointed accommodations including private pool villas
- Excellent evening events and onsite facilities for everyone to enjoy
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Located near the quaint city of Gustavia on St. Barth’s glorious coast
- Discover delicious gastronomy at the restaurant and fabulous cocktail bar
- Access to two beautiful beaches plus a variety of activities for all ages
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Stay in a luxury treetop villa with private plunge pool
- Make the most of the dedicated villa host there to make anything happen
- Indulge in authentic and sustainable ingredients at the on-site restaurant
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Six exquisite bars and restaurants with extensive menus
- An on-site luxury Swiss spa
- Family friendly programme to educate guests on local culture
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Located on the pristine Long Bay Beach in Turks & Caicos
- Excellent onsite facilities including four swimming pools
- Four delectable restaurants and five bars
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Choose to stay in a variety of cottages, bungalows and suites
- Delve into traditional Jamaican cuisine at the stunning on-site restaurant, bar and lounge
- Keep busy with the resort’s included activities
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Stay in a choice of bright, contemporary guestrooms or suites
- Enjoy the best of Anguilla’s culinary scene at Celeste restaurant
- Make a splash in the beautiful infinity pool
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
- Choose from a collection of 13 private villas and beach houses
- Enjoy flexible dining options that will meet your every culinary need
- Experience more of the Caribbean with a vast choice of fantastic activities
Call us on 0203 816 0985
to start planning your holiday
VIEW THIS HOTELto start planning your holiday
Get in touch with our team of personal travel managers to start planning your trip
- The human touch
- Complete concierge service
- 24/7 out of hours contact
Extra Mile Guarantee
Our Extra Mile Guarantee
Our Extra Mile Guarantee
We appreciate every Winged Boots customer and to prove this we want you all to receive a very high standard of customer service when booking with us. Our Extra Mile Guarantee is just that. A promise that no matter the destination, whether it is your first or your hundredth time using Winged Boots, you will be treated like a VIP from enquiry through to departure and even when you return home.
David Ox, managing director- Dedicated personal travel managers
Each with a minimum of 10-years’ experience
- Covid regulations, simplified
We explain complicated travel requirements
- Complimentary event invitations
Meet the team at our annual shoot day, O2 London, a private dinner and more
- Transparent price
No hidden fees, quotation costs or admin charges
- The human touch
Just honest conversations with real people
- Out of hours contact
Via email, direct dial and even on Whats’App
- Concierge service
Celebrating? Let us know and we may surprise you
- Your holiday is protected
We’re licensed by ATOL and TTA
- We make it happen
Wherever, whenever, however and every time
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Get in touch with our team of personal travel managers to start planning your trip
- The human touch
- Complete concierge service
- 24/7 out of hours contact