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Leeward Islands Vacation Packages

Leeward Islands Flight + Hotel Packages

Conrad Los Angeles
Westgate Las Vegas Resort & Casino
The Gates Hotel South Beach - a DoubleTree by Hilton
Private Ocean Condos at Marenas Beach
The Langham, New York, Fifth Avenue
Virgin Hotels Las Vegas, Curio Collection by Hilton
JW Marriott Anaheim Resort
Costa Hollywood Beach Resort
Faena Hotel Miami Beach
Fontainebleau Miami Beach Private Luxury Suites
The Manhattan Club
Kimpton Angler's Hotel, an IHG Hotel

3-4 Night Vacations in Leeward Islands

Westgate Las Vegas Resort & Casino
Private Ocean Condos at Marenas Beach
JW Marriott Anaheim Resort
The Plaza Hotel

5-7 Night Vacations in Leeward Islands

Conrad Los Angeles
JW Marriott Anaheim Resort
Millennium Biltmore Los Angeles
The Langham, New York, Fifth Avenue

Leeward Islands Last Minute Hotel Deals

Timothy Beach Resort
Timothy Beach Resort
3 out of 5
Frigate Bay, Basseterre, St. Kitts
Stay at this 3-star beach hotel in Basseterre. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the overall value in ...
St. Kitts Marriott Resort & The Royal Beach Casino
St. Kitts Marriott Resort & The Royal Beach Casino
4.5 out of 5
858 Frigate Bay Road, Frigate Bay, Basseterre, St. Kitts
Stay at this 4.5-star luxury resort in Basseterre. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Koi Resort Saint Kitts, Curio Collection by Hilton
Koi Resort Saint Kitts, Curio Collection by Hilton
4 out of 5
100 Koi Resort Drive, Basseterre
Stay at this 4-star business-friendly hotel in Basseterre. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Greatheeds and St Kitts Royal ...
Royal St. Kitts Hotel
Royal St. Kitts Hotel
4 out of 5
406 Zenway Blvd, Frigate Bay, Basseterre, St. Kitts
Stay at this 4-star golf hotel in Basseterre. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Marriott's St. Kitts Beach Club
Marriott's St. Kitts Beach Club
3.5 out of 5
858 Frigate Bay Road, Frigate Bay, Basseterre, St. Kitts
Stay at this 3.5-star beach condo in Basseterre. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Park Hyatt St. Kitts
Park Hyatt St. Kitts
5 out of 5
Banana Bay, South East Peninsula, Parish of St. George, Basseterre, 265
Stay at this 5-star luxury hotel in Basseterre. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Four Seasons Resort - Nevis
Four Seasons Resort - Nevis
5 out of 5
Pinney's Beach,, Jessups Village, Nevis West
Stay at this 5-star luxury resort in Jessups Village. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the breakfast and the restaurant ...
Sonesta Maho Beach All Inclusive Resort Casino & Spa
Sonesta Maho Beach All Inclusive Resort Casino & Spa
4 out of 5
1 Rhine Road, Maho Bay, Lowlands
Stay at this 4-star beach property in Lowlands. Enjoy free breakfast, free WiFi, and 2 outdoor pools. 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.

Book the perfect getaway to Leeward Islands

With Hotwire, booking your next trip to Caribbean is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Leeward Islands while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Leeward Islands flight and hotel package for as low as $245.

Living it up in Caribbean means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Leeward Islands, Caribbean vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Leeward Islands for some of the best accommodations and flight deals.

FAQs about cheap Leeward Islands packages:

How to get cheap vacation deals to Leeward Islands?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $140.

How much are Leeward Islands packages?

Vacation packages to Leeward Islands vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $245.

How to find cheap car rentals near Leeward Islands?

Hotwire partners with some of the most reliable car rental companies in Caribbean to bring you the best car rental deals in Leeward Islands for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Leeward Islands now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Leeward Islands right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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