Exclusive Windward Islands Vacation Deals

Windward Islands vacation package deals

Price found within the past 48 hours. Click for updated prices.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,238, price is now $563 per person
$563
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,901, price is now $843 per person
$843
per person
Apr 12 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $1,404, price is now $643 per person
$643
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Ocean Four
Price was $1,380, price is now $633 per person
$633
per person
Apr 12 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Enjoy the 24-hour gym and unwind at the beach bar and poolside bar.
Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

4.5 out of 5
Hollywood
Price was $2,714, price is now $1,272 per person
$1,272
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Los Angeles (LAX)
A rooftop terrace, self parking, and laundry facilities are featured at this aparthotel. A virtual front desk are provided for your convenience.
President Hotel

President Hotel

3.5 out of 5
South Beach
Price was $1,585, price is now $746 per person
$746
per person
Apr 12 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features an outdoor pool and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and a garden are also offered.

Frequently asked questions

How much are vacation packages to Windward Islands?
The perfect $563 package deal can be booked for your next visit to Windward Islands. Why not let Travelocity take all the hassle out of arranging your travel plans? The great part about bundling your flights and hotel is that it'll save you a tidy sum. And who wouldn't love a little extra cash to play with?
Where can I get the best vacation package deals for Windward Islands?
Travelocity will be able to help you snag a terrific Windward Islands package deal. With as many as 400 partner airlines and 1,000,000 properties across the globe, we know you'll be able to put together the perfect itinerary.
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Top Windward Islands hotel deals

Radisson Grenada Beach Resort

Radisson Grenada Beach Resort

4 out of 5
Grand Anse St. George's
$282 nightly
The price is $308 total per night
$308 total
Mar 5 - Mar 6
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at one of the 2 poolside bars and enjoy free perks like full breakfast and free self parking.
Pool
Breakfast included
Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort

4.5 out of 5
Gros Islet Gros Islet
$571 nightly
The price is $571 total per night
$571 total
Mar 5 - Mar 6
Total with taxes and fees
This all-inclusive property features a full-service spa, a nightclub, and 9 restaurants. Bring the family and enjoy the free kid's club, children's pool, and arcade/game room. Enjoy the 4 outdoor pools and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Windjammer Landing Resort and Residences

Windjammer Landing Resort and Residences

5 out of 5
Labrelotte Bay Gros Islet
$540 nightly
The price is $589 total per night
$589 total
Feb 26 - Feb 27
Total with taxes and fees
A full-service spa, 7 restaurants, and 6 outdoor pools are all featured at this luxury resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the free kid's club, children's pool, and playground.
Pool
Hot Tub
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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.