Search Deals onLeeward Islands Vacation Packages
Leeward Islands Flight + Hotel Packages
Conrad Los Angeles
Save 100% on your flightPrice was $2,286, price is now $1,317 per person
$1,317
per person
Nov 20 - Nov 26
Roundtrip non-stop flight included
Dallas (DFW) to Los Angeles (LAX)
Stay at this 5-star luxury hotel in Los Angeles. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Popular attractions Dodger Stadium and Crypto.com Arena are located nearby. Discover genuine guest reviews for Conrad Los Angeles, in Downtown Los Angeles neighborhood, along with the latest prices and availability – book now.
Westgate Las Vegas Resort & Casino
Save 100% on your flightPrice was $400, price is now $245 per person
$245
per person
Nov 6 - Nov 10
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
Stay at this 4-star spa hotel 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 Bellagio Casino and The Cosmopolitan Casino are located nearby. Discover genuine guest reviews for Westgate Las Vegas Resort & Casino along with the latest prices and availability – book now.
The Gates Hotel South Beach - a DoubleTree by Hilton
Save 100% on your flightPrice was $646, price is now $404 per person
$404
per person
Nov 14 - Nov 18
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star business-friendly hotel in Miami Beach. Enjoy free WiFi, a rooftop terrace, and breakfast. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby. Discover genuine guest reviews for The Gates Hotel South Beach - a DoubleTree by Hilton, in South Beach neighborhood, along with the latest prices and availability – book now.
Private Ocean Condos at Marenas Beach
Save 100% on your flightPrice was $849, price is now $541 per person
$541
per person
Nov 5 - Nov 9
Roundtrip flight included
Houston (IAH) to Miami (MIA)
Stay at this 4-star beach hotel in Sunny Isles Beach. Enjoy free WiFi, a beach locale, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Hollywood Beach and Aventura Mall are located nearby. Discover genuine guest reviews for Private Ocean Condos at Marenas Beach along with the latest prices and availability – book now.
The Langham, New York, Fifth Avenue
Save 100% on your flightPrice was $3,406, price is now $2,190 per person
$2,190
per person
Nov 3 - Nov 8
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 5-star luxury hotel in New York. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the helpful staff and the spacious rooms in our reviews. Popular attractions Empire State Building and Grand Central Terminal are located nearby. Discover genuine guest reviews for The Langham, New York, Fifth Avenue, in Manhattan neighborhood, along with the latest prices and availability – book now.
Virgin Hotels Las Vegas, Curio Collection by Hilton
Save 100% on your flightPrice was $484, price is now $312 per person
$312
per person
Nov 24 - Nov 29
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
Stay at this 4.5-star luxury hotel in Las Vegas. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the clean rooms in our reviews. Popular attractions Bellagio Casino and The Cosmopolitan Casino are located nearby. Discover genuine guest reviews for Virgin Hotels Las Vegas, Curio Collection by Hilton along with the latest prices and availability – book now.
JW Marriott Anaheim Resort
Save 100% on your flightPrice was $1,356, price is now $880 per person
$880
per person
Nov 9 - Nov 13
Roundtrip non-stop flight included
Atlanta (ATL) to Los Angeles (LAX)
Stay at this 4.5-star luxury hotel in Anaheim. Enjoy free WiFi, an outdoor pool, and a restaurant. Our guests praise the clean rooms in our reviews. Popular attractions Disney California Adventure® Park and Disneyland® are located nearby. Discover genuine guest reviews for JW Marriott Anaheim Resort, in Anaheim Resort neighborhood, along with the latest prices and availability – book now.
Costa Hollywood Beach Resort
Save 100% on your flightPrice was $580, price is now $377 per person
$377
per person
Nov 13 - Nov 17
Roundtrip flight included
Houston (IAH) to Miami (MIA)
Stay at this 3.5-star beach hotel in Hollywood. Enjoy a rooftop terrace, WiFi, and valet parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Hollywood Beach and Port Everglades are located nearby. Discover genuine guest reviews for Costa Hollywood Beach Resort, in Hollywood Beach neighborhood, along with the latest prices and availability – book now.
Faena Hotel Miami Beach
Save 100% on your flightPrice was $2,610, price is now $1,710 per person
$1,710
per person
Nov 21 - Nov 25
Roundtrip flight included
Houston (IAH) to Miami (MIA)
Stay at this 5-star luxury hotel in Miami Beach. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the helpful staff and the comfy beds in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby. Discover genuine guest reviews for Faena Hotel Miami Beach, in Mid Beach neighborhood, along with the latest prices and availability – book now.
Fontainebleau Miami Beach Private Luxury Suites
Save 100% on your flightPrice was $1,877, price is now $1,252 per person
$1,252
per person
Nov 27 - Dec 1
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this 4-star spa aparthotel in Miami Beach. Enjoy free WiFi, 11 outdoor pools, and 12 restaurants. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby. Discover genuine guest reviews for Fontainebleau Miami Beach Private Luxury Suites, in Mid Beach neighborhood, along with the latest prices and availability – book now.
The Manhattan Club
Save 100% on your flightPrice was $1,125, price is now $754 per person
$754
per person
Nov 6 - Nov 10
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
Stay at this 4-star business-friendly hotel in New York. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rockefeller Center and Broadway are located nearby. Discover genuine guest reviews for The Manhattan Club, in Manhattan neighborhood, along with the latest prices and availability – book now.
Kimpton Angler's Hotel, an IHG Hotel
Save 100% on your flightPrice was $652, price is now $445 per person
$445
per person
Nov 14 - Nov 18
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star boutique resort in Miami Beach. Enjoy free WiFi, breakfast, and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby. Discover genuine guest reviews for Kimpton Angler's Hotel, an IHG Hotel, in South Beach neighborhood, along with the latest prices and availability – book now.
3-4 Night Vacations in Leeward Islands
5-7 Night Vacations in Leeward Islands
Leeward Islands Last Minute Hotel Deals
Timothy Beach Resort
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
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
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
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
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
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
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
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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Hotels Near Points of Interest in Leeward Islands
Car Rentals in Leeward Islands
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