Search Deals onWindward Islands Vacation Packages
Windward Islands Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Boulder Station Hotel and Casino
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Las Vegas (LAS)
Stay at this 3.5-star business-friendly resort in Las Vegas. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fremont Street and Fremont Street Experience are located nearby.
Pelican Hotel
Save 100% on your flight
per person
Jun 15 - Jun 22
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Stay at this 4-star beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
May-Dee Suites
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Stay at this hotel in Hollywood. Enjoy free WiFi, free parking, and a business center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Seminole Hard Rock Casino Hollywood and Hard Rock Stadium are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach
per person
May 28 - Jun 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Miami Beach Boardwalk are located nearby.
Eden Roc Miami Beach
Save 100% on your flight
per person
Jun 2 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Book a stay at this luxury resort in Miami Beach. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions Miami Beach Boardwalk and Collins Avenue Shopping Area are located nearby.
Hollywood Historic Hotel
per person
Jun 6 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Los Angeles (LAX)
Stay at this 3-star historic hotel in Los Angeles. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Hollywood Walk of Fame and Hollywood Boulevard are located nearby.
Budget Inn Hollywood
per person
Jun 6 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Los Angeles (LAX)
Stay at this hotel in Los Angeles. Enjoy free WiFi, a 24-hour front desk, and cable TV channels. Popular attractions Hollywood Boulevard and Hollywood Walk of Fame are located nearby.
B Ocean Resort Fort Lauderdale Beach
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Welcome Inn on Colorado Blvd
per person
Jun 6 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Los Angeles (LAX)
Stay at this hotel in Los Angeles. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dodger Stadium and Rose Bowl Stadium 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 ...
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. ...
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 ...
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 ...
Cobblestone Inn
Bay Street, Kingstown
Stay at this 3-star hotel in Kingstown. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
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 ...
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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Car Rentals in Windward Islands
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