Search Deals on
Windward Islands Vacation Packages

Windward Islands Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Treasure Island - TI Las Vegas Hotel Casino, a Radisson Hotel

Treasure Island - TI Las Vegas Hotel Casino, a Radisson Hotel

4 out of 5
Save 100% on your flight
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Las Vegas (LAS)
Book a stay at this spa resort in Las Vegas. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. Popular attractions Treasure Island Casino and The Venetian Casino are located nearby.
San Clemente Inn

San Clemente Inn

3 out of 5
per person
Dec 31 - Jan 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Los Angeles (LAX)
Book a stay at this beach condo in San Clemente. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions San Clemente Pier and San Clemente Municipal Golf Course are located nearby.
AKA West Hollywood

AKA West Hollywood

4 out of 5
per person
Jan 4 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Los Angeles (LAX)
Stay at this 4-star business-friendly hotel in West Hollywood. Enjoy free WiFi, room service, and a 24-hour fitness center. Popular attractions Hollywood Boulevard and Rodeo Drive are located nearby.
Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Las Vegas (LAS)
Stay at this 4-star hotel in Las Vegas. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Casino at the Rio All-Suite Hotel and Casino at Aria are located nearby.
Fontainebleau Las Vegas

Fontainebleau Las Vegas

5 out of 5
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Las Vegas (LAS)
Stay at this 5-star luxury resort in Las Vegas. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Casino at Circus Circus and Las Vegas Festival Grounds are located nearby.
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
per person
Jan 9 - Jan 13
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.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 5-star 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.
Park Royal Miami Beach

Park Royal Miami Beach

2.5 out of 5
per person
Jan 5 - Jan 9
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Miami Beach Boardwalk and Lincoln Road Mall are located nearby.
Eurostars Winter Haven

Eurostars Winter Haven

4 out of 5
Save 100% on your flight
per person
Jan 22 - Jan 27
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star beach hotel in Miami Beach. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Stay at this 4.5-star luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Madison Square Garden and Empire State Building are located nearby.
Lux Retreat By Renzzi

Lux Retreat By Renzzi

4 out of 5
Save 100% on your flight
per person
Jan 22 - Jan 27
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star apartment in Miami. Enjoy free WiFi, rainfall showerheads, and an in-room coffeemaker. Popular attractions Brickell City Centre and Bayfront Park are located nearby.
Doral Inn & Suites Miami Airport West

Doral Inn & Suites Miami Airport West

2.5 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Miami (MIA)
Book a stay at this business-friendly hotel in Miami. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Dolphin Mall and Miami International Mall are located nearby.

Windward Islands Last Minute Hotel Deals

Coconut Bay Beach Resort & Spa All Inclusive
Coconut Bay Beach Resort & Spa All Inclusive
4 out of 5
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 ...
Coconut Bay Beach Resort & Spa All Inclusive
Sandals St. Vincent and the Grenadines Couples Only
Sandals St. Vincent and the Grenadines Couples Only
4 out of 5
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 ...
Sandals St. Vincent and the Grenadines Couples Only
Jade Mountain Resort
Jade Mountain Resort
5 out of 5
1000 Anse Chastanet Road, Soufriere
Stay at this 5-star luxury resort in Soufriere. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Anse Chastanet Beach and Gros Piton ...
Jade Mountain Resort
Grenadine House
Grenadine House
4 out of 5
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 ...
Grenadine House
Sunset Shores Beach Hotel
Sunset Shores Beach Hotel
3 out of 5
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. ...
Sunset Shores Beach Hotel
Beachcombers Hotel
Beachcombers Hotel
3.5 out of 5
Villa beach, Villa
Stay at this 3.5-star beach resort in Villa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
Beachcombers Hotel
Cobblestone Inn
Cobblestone Inn
3 out of 5
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 ...
Cobblestone Inn
Blue Lagoon Hotel & Marina
Blue Lagoon Hotel & Marina
4 out of 5
Blue Lagoon Bay, Ratho Mill
Stay at this 4-star beach hotel in Ratho Mill. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Blue Lagoon Hotel & Marina
See all 6,173 properties in Windward Islands
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 Windward 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 Windward 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 Windward Islands flight and hotel package for as low as $305.

Living it up in Caribbean means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Windward 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 Windward Islands for some of the best accommodations and flight deals.

FAQs about cheap Windward Islands packages:

How to get cheap vacation deals to Windward 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 $102.

How much are Windward Islands packages?

Vacation packages to Windward 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 $305.

How to find cheap car rentals near Windward Islands?

Hotwire partners with some of the most reliable car rental companies in Caribbean to bring you the best car rental deals in Windward 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 Windward Islands now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Windward 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.