Exclusive Windward Islands Vacation Deals

Windward Islands vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $712, price is now $366 per person
$366
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $1,101, price is now $504 per person
$504
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
This hotel features free WiFi in public areas, concierge services, and valet parking. A terrace, a garden, and luggage storage are also on offer.
Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

4.5 out of 5
Hollywood
Price was $1,109, price is now $519 per person
$519
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,480, price is now $1,630 per person
$1,630
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.
Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was $1,823, price is now $862 per person
$862
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Price was $911, price is now $461 per person
$461
per person
Oct 1 - Oct 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Los Angeles (LAX)
This hotel includes free WiFi in public areas and a virtual front desk. Take advantage of the self parking.

Frequently asked questions

How much are vacation packages to Windward Islands?
The perfect $366 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.
Why should I book my Windward Islands vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.

Top Windward Islands hotel deals

Coconut Bay Beach Resort & Spa All Inclusive

Coconut Bay Beach Resort & Spa All Inclusive

4 out of 5
Eau Piquant, Vieux Fort
This all-inclusive property features free water park access, a full-service spa, and a nightclub. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, free kid's club, and children's pool.
Pool
All inclusive
Sugar Beach, A Viceroy Resort

Sugar Beach, A Viceroy Resort

5 out of 5
Val des Pitons, Soufrière
The price is $1,094 total per night
$1,094 total
per night
Sep 2 - Sep 3
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and enjoy a drink at one of the 2 beachside bars. There's fun for all ages with a children's club and a playground, and in-room childcare is an added bonus.
Pool
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
A private beach, 12 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Unwind with a drink at one of the 5 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. A coffee shop, a garden, and concierge services are also on offer.
On private beach
Pool
Don't see what you're looking for?
See all available properties in Windward Islands
View all properties
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.

Best Lodging Options Near Windward Islands