Search Deals onWindward Islands Vacation Packages
Windward Islands Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. 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 Harbor Front Inn
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, an outdoor pool, and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenport Carousel and Camera Obscura are located nearby.
The Penguin Hotel
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy a beach locale, breakfast (surcharge), 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 Retreat Collection at 1 Hotel & Homes South Beach
per person
Aug 28 - Sep 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
President Villa
Save 100% on your flight
per person
Aug 28 - Sep 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free breakfast, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Cavalier Hotel South Beach
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3.5-star beach hotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
SIRTAJ - Beverly Hills
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
Stay at this 4-star hotel in Beverly Hills. Enjoy parking (surcharge), a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions The Grove and Hollywood Boulevard are located nearby.
Esmé Miami Beach
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star luxury hotel in Miami Beach. Enjoy free WiFi, 4 restaurants, and 4 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Landon Bay Harbor - Miami Beach
Save 100% on your flight
per person
Sep 8 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
Stay at this 3.5-star business-friendly hotel in Bay Harbor Islands. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Aventura Mall and Miami Beach Boardwalk are located nearby.
B Ocean Resort Fort Lauderdale Beach
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Las Olas Beach and Port Everglades are located nearby.
Hollywood Inn Suites Hotel
Save 100% on your flight
per person
Aug 23 - Aug 30
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Los Angeles (LAX)
Stay at this hotel in Gardena. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SoFi Stadium and Kia Forum are located nearby.
Beacon Hotel South Beach
Save 100% on your flight
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3.5-star beach hotel in Miami Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
3-4 Night Vacations in Windward Islands
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Windward Islands
Price found within the past 48 hours. Click for updated prices.
Windward Islands Last Minute Hotel Deals
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant, Vieux Fort
Stay at this 4-star 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 ...
Sugar Beach, A Viceroy Resort
Val des Pitons, Soufrière
Stay at this 5-star luxury resort in Soufrière. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Sandals St. Vincent and the Grenadines Couples Only
Buccament Bay Valley, Kingstown, Saint Andrew
Stay at this 4-star all-inclusive resort in Kingstown. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Fort Charlotte and Barrouallie ...
Beachcombers Hotel
Villa beach, Villa
Stay at this 3.5-star family-friendly resort in Villa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
Ladera Resort - Adults Only
Rabot Estate, Soufrière
Book a stay at this beach resort in Soufrière. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Buccament BAY ALL Inclusive
Buccament Bay, PO Box LY39 Layou, Kingstown
Book a stay at this all-inclusive property in Kingstown. Enjoy a health club, spa treatment rooms, and a conference center. Our guests praise the property condition ...
Sunset Shores Beach Hotel
Windward Highway, Villa Beach, Villa
Stay at this 3-star beach hotel in Villa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the restaurant and the helpful staff in our reviews. ...
Grenadine House
Kingstown Park, P.O. Box 2523, Kingstown
Stay at this 4-star spa hotel in Kingstown. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
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.
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