Windward Islands Holidays

Top Flight + Hotel Deals in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Hotel Delle Civette

Hotel Delle Civette

Nomentano
€593
per person
1 Oct - 4 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Rome (FCO)
9.6/10 Exceptional! (316 reviews)
Staff goes above and beyond to help guests. Every single aspect of the hotel was excellent. We plan to stay there again.

Reviewed on 16 Aug 2026

Hotiday Roma Trevi

Hotiday Roma Trevi

Rome City Centre
€1,847
per person
19 Sept - 26 Sept
found 6 hours ago
Return flight included
Shannon (SNN) to Rome (FCO)
No reviews
Relais de la Poste

Relais de la Poste

Rome City Centre
€1,145
per person
25 Oct - 1 Nov
found 20 hours ago
Return flight included
Dublin (DUB) to Rome (FCO)
9.2/10 Wonderful! (707 reviews)
Customer service was top tier. Very family and welcoming. They knew we was leaving before they arrive for work and made me a box of breakfast food to take with me. Location was everything all the major attractions is within walking distance.

Reviewed on 16 Aug 2026

Palazzo Nainer

Palazzo Nainer

Rome City Centre
€3,995
per person
19 Sept - 26 Sept
found 7 hours ago
Return flight included
Shannon (SNN) to Rome (FCO)
9.4/10 Exceptional! (241 reviews)
Amazing service, very clean hotel and rooms. Best location with friends and attentive staff.

Reviewed on 14 Aug 2026

Hotel Caravita

Hotel Caravita

Rome City Centre
€637
per person
13 Oct - 16 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Rome (FCO)
8.8/10 Excellent! (402 reviews)

Top hotels in Windward Islands

Coconut Bay Beach Resort & Spa All Inclusive

Coconut Bay Beach Resort & Spa All Inclusive

Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,118 reviews)
"Very relaxing family vacation"

Reviewed on 15 Aug 2026

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Coconut Bay Beach Resort & Spa All Inclusive
Siesta Hotel

Siesta Hotel

Morne Rouge Street St. George's
€123
8 Sept - 9 Sept
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Hotel is fine, a little outdated, also pricey, but hotel is functional"

Reviewed on 16 Aug 2026

Siesta Hotel
Secrets St. Lucia Resort & Spa All Inclusive Adults Only

Secrets St. Lucia Resort & Spa All Inclusive Adults Only

1 Choc Bay Gros Islet
Fully refundableReserve now, pay when you stay
€518
8 Sept - 9 Sept
includes taxes & fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
See all 6,874 properties in Windward Islands
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

A lifeguard tower on a beach with turquoise water and a white picket fence.

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.
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A coastal town with colorful houses, a mountain, and a rainbow over the sea.

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.
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A beach at sunset with waves, palm trees, and a silhouette of a person walking.
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.
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A beach with clear turquoise water, boats, and a distant mountain.

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.
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A coastal landscape with a prominent mountain peak, lush green hills, and calm blue waters.

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.
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A beach with clear turquoise water, sandy shore, and a hill with buildings in the background.
Photo by Amir

Morne Rouge Beach

9.0/10 (550 reviews)
Why not spend a care-free afternoon at Morne Rouge Beach during your travels in Grand Anse? Make time to visit the area's shops or simply enjoy its top-notch restaurants.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.