Windward Islands Trip

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Top Windward Islands Flight + Hotel Deals

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

President Hotel

South Beach
Save 100% on your flight
₹60,924
per person
20 Oct - 25 Oct
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
8.4/10 Very good! (2,655 reviews)
Seriously look no further. This place is as good as it looks online. Pool facing room 🙌great staff. Great gym. Great rooms. So impressed with this place.

Reviewed on 12 Aug 2026

Pelican Hotel

Pelican Hotel

South Beach
Save 100% on your flight
₹71,376
per person
20 Oct - 25 Oct
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (492 reviews)
I don’t recommend this place to anyone Bad service Aggressive staff No smiles Party place Food not the best Pass on this one … the reception employee night shifts will not even get up to help Or will call the cops if his not in control I would not go there so many nicer places in Miami Beach

Reviewed on 12 Aug 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

Mid Beach
Save 100% on your flight
₹111,542
per person
20 Oct - 25 Oct
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
8.4/10 Very good! (8,649 reviews)
EAST Miami

EAST Miami

Brickell
Save 100% on your flight
₹134,590
per person
20 Oct - 25 Oct
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (3,992 reviews)
😍

Reviewed on 12 Aug 2026

Kimpton EPIC Hotel by IHG

Kimpton EPIC Hotel by IHG

Downtown Miami
Save 100% on your flight
₹93,597
per person
20 Oct - 25 Oct
found 1 day ago
Return direct flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (2,555 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! (1,110 reviews)
"Great"

Reviewed on 12 Aug 2026

Get rates
Coconut Bay Beach Resort & Spa All Inclusive
Siesta Hotel

Siesta Hotel

Morne Rouge Street St. George's
₹9,589
₹11,506 total
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"w"

Reviewed on 11 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
₹57,170
₹57,170 total
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.