Windward Islands Holidays from £351
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Top Windward Islands Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
£10,600
per person
10 Dec - 17 Dec
found 1 day ago
Return flight included
London (LHR) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on 22 Jun 2016
Top hotels in Windward Islands
Siesta Hotel
Morne Rouge Street St. George's
£76
13 Oct - 14 Oct
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Lovely views, warm staff"
Reviewed on 28 Sept 2026
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
1 Choc Bay Gros Islet
Fully refundableReserve now, pay when you stay
£602
5 Oct - 6 Oct
includes taxes & fees
8.8/10 Excellent! (267 reviews)
"Amazing"
Reviewed on 29 Sept 2026
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,169 reviews)
"Friendly staff"
Reviewed on 30 Sept 2026
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.
Stay near popular Windward Islands attractions
Photo by Catherine Carroll
Grand Anse Beach
9.6/10 (1,447 reviews)
If a restful holiday is part of your travel plans, Grand Anse Beach might be the perfect place to visit during your trip to Grand Anse. Make time to visit the area's shops or simply enjoy its top-notch restaurants.
Gros Piton
9.6/10 (803 reviews)
Explore one of the most famous sites in Soufrière, a gigantic volcanic peak rising from the sea that attracts visitors from all over the world.
Reduit Beach
9.0/10 (1,288 reviews)
Ride a Jet Ski, laze on the sand and enjoy a cool drink at the bar on this scenic beach set against a backdrop of verdant hills.
Anse Chastanet Beach
9.2/10 (538 reviews)
Enjoy a pleasant Caribbean beach day surrounded by abundant natural beauty. Relax sunbathing on dark sand and snorkeling in crystal-clear waters.
Photo by Davz
Sandy Beach
7.8/10 (211 reviews)
If a restful holiday is part of your travel plans, Sandy Beach might be the perfect place to visit during your trip to Vieux Fort. While in this romantic area, you can savour the top-notch restaurants.
Marigot Bay
8.8/10 (598 reviews)
Commune with nature and explore the great outdoors at Marigot Bay during your travels in Marigot Bay. While in this relaxing area, you can savour the top-notch restaurants.
Pointe du Bout Beach
8.4/10 (376 reviews)
If a restful holiday is part of your travel plans, Pointe du Bout Beach might be the perfect place to visit during your trip to Pointe du Bout.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
