Windward Islands Vacation Packages for 2026

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Windward Islands Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Encore Inn Inglewood

Encore Inn Inglewood

2.5 out of 5
Lockhaven
Price was $1,401, price is now $490 per person
$490
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
New York (JFK) to Los Angeles (LAX)
Stay at this motel in Inglewood. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions SoFi Stadium and Kia Forum are located nearby.

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was $2,344, price is now $1,112 per person
$1,112
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Book a stay at this luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was $1,596, price is now $767 per person
$767
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was $1,708, price is now $822 per person
$822
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,584, price is now $777 per person
$777
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Save 100% on your flight
Price was $1,046, price is now $564 per person
$564
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
New York (JFK) to Los Angeles (LAX)
Stay at this hotel in Glendale. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Dodger Stadium and Rose Bowl Stadium are located nearby.

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Top Hotel Deals

Coconut Bay Beach Resort & Spa All Inclusive

Coconut Bay Beach Resort & Spa All Inclusive

4 out of 5
Eau Piquant Vieux Fort
44.41 km from city center
Book a stay at this beach property in Vieux Fort. Enjoy free WiFi, free parking, and 5 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Radisson Grenada Beach Resort

Radisson Grenada Beach Resort

4 out of 5
Grand Anse St. George's
170.95 km from city center
Book a stay at this beach hotel in St. George's. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Siesta Hotel

Siesta Hotel

3 out of 5
Morne Rouge Street St. George's
171.67 km from city center
Book a stay at this family-friendly hotel in St. George's. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Sugar Beach, A Viceroy Resort

Sugar Beach, A Viceroy Resort

5 out of 5
Val des Pitons Soufrière
43.73 km from city center
Book a stay at this luxury resort in Soufrière. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Zoetry Marigot Bay - All Inclusive

Zoetry Marigot Bay - All Inclusive

5 out of 5
Marigot Bay Marigot Bay Castries
59.11 km from city center
Book a stay at this luxury property in Castries. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...
Royalton Grenada, An Autograph Collection All-Inclusive Resort

Royalton Grenada, An Autograph Collection All-Inclusive Resort

4.5 out of 5
Magazine Beach Point Seline St. George's St George's
173.41 km from city center
Book a stay at this luxury hotel in St. George's. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

4.5 out of 5
Gros Islet Gros Islet
75.83 km from city center
Book a stay at this luxury property in Gros Islet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Bay Gardens Hotel

Bay Gardens Hotel

3.5 out of 5
Rodney Bay Village Gros Islet
72.83 km from city center
Book a stay at this beach hotel in Gros Islet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Windjammer Landing Resort and Residences

Windjammer Landing Resort and Residences

5 out of 5
Labrelotte Bay Gros Islet
70.96 km from city center
Book a stay at this luxury resort in Gros Islet. Enjoy 6 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the helpful staff in our reviews. ...
Bel Jou Hotel – Adults Only – All Inclusive

Bel Jou Hotel – Adults Only – All Inclusive

3.5 out of 5
La Pansee Castries
66.02 km from city center
Book a stay at this spa property in Castries. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Harbor Club St. Lucia, Curio Collection by Hilton

Harbor Club St. Lucia, Curio Collection by Hilton

4.5 out of 5
Rodney Bay, Gros Islet Hwy Gros Islet
73.58 km from city center
Book a stay at this luxury resort in Gros Islet. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Jade Mountain Resort

Jade Mountain Resort

5 out of 5
1000 Anse Chastanet Road Soufrière
46.63 km from city center
Book a stay at this luxury resort in Soufrière. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Anse Chastanet Beach and Turtle Reef ...
Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

4.5 out of 5
Gros Islet Gros Islet Gros Islet
75.83 km from city center
Book a stay at this luxury property in Gros Islet. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
True Blue Bay Resort

True Blue Bay Resort

4 out of 5
19 Old Mill Avenue St. George's
173.88 km from city center
Book a stay at this spa resort in St. George's. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff and the property condition ...
Fond Doux Eco Resort

Fond Doux Eco Resort

3.5 out of 5
Soufriere Soufrière
44.59 km from city center
Book a stay at this spa hotel in Soufrière. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
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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.