Search Deals on
Windward Islands Vacation Packages

Windward Islands Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Rio Hotel & Casino, a Destination by Hyatt Hotel

Rio Hotel & Casino, a Destination by Hyatt Hotel

4 out of 5
Save 100% on your flight
Price was $722, price is now $380 per person
$380
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
Book a stay at this business-friendly resort in Las Vegas. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the convenient parking in our reviews. Popular attractions Bellagio Casino and Colosseum at Caesars Palace are located nearby.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,930, price is now $840 per person
$840
per person
Mar 9 - Mar 16
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Florida Keys Dive Center and Mangrove Marina are located nearby.
Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
Price was $998, price is now $446 per person
$446
per person
Mar 2 - Mar 6
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Las Vegas (LAS)
Stay at this 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 Aria and Bellagio Casino are located nearby.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Price was $1,118, price is now $505 per person
$505
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach aparthotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and laundry facilities. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Price was $1,202, price is now $573 per person
$573
per person
Mar 9 - Mar 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Hollywood Roosevelt

The Hollywood Roosevelt

4 out of 5
Save 100% on your flight
Price was $1,358, price is now $700 per person
$700
per person
Mar 27 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Los Angeles (LAX)
Book a stay at this luxury hotel in Los Angeles. Enjoy free WiFi, 2 restaurants, and 4 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Hollywood Boulevard and Hollywood Walk of Fame are located nearby.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
Price was $2,280, price is now $1,233 per person
$1,233
per person
Mar 6 - Mar 10
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this luxury hotel in Fort Lauderdale. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort Lauderdale Beach and Las Olas Beach are located nearby.
President Hotel Villa

President Hotel Villa

3.5 out of 5
Price was $1,326, price is now $723 per person
$723
per person
Mar 9 - Mar 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
President Hotel

President Hotel

3.5 out of 5
Price was $1,326, price is now $723 per person
$723
per person
Mar 9 - Mar 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,151, price is now $631 per person
$631
per person
Mar 9 - Mar 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $18,051, price is now $10,018 per person
$10,018
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Beachcomber Resort & Club

Beachcomber Resort & Club

4 out of 5
Price was $953, price is now $533 per person
$533
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach resort in Pompano Beach. Enjoy 2 outdoor pools, a private beach, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Fort Lauderdale Beach and Pompano Beach are located nearby.

3-4 Night Vacations in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $601, price is now $300 per person
$300
per person
Mar 11 - Mar 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $857, price is now $380 per person
$380
per person
Mar 15 - Mar 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
The Hollywood Roosevelt

The Hollywood Roosevelt

4 out of 5
Hollywood
Save 100% on your flight
Price was $1,358, price is now $700 per person
$700
per person
Mar 27 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Los Angeles (LAX)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $728, price is now $385 per person
$385
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)

5-7 Night Vacations in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $1,118, price is now $505 per person
$505
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

2.5 out of 5
Price was $1,519, price is now $803 per person
$803
per person
Mar 14 - Mar 21
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Los Angeles (LAX)
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,930, price is now $840 per person
$840
per person
Mar 9 - Mar 16
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,202, price is now $573 per person
$573
per person
Mar 9 - Mar 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)

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
Book a stay at this 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
Beachcombers Hotel

Beachcombers Hotel

3.5 out of 5
Villa beach Villa
Book a stay at this family-friendly resort in Villa. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
Beachcombers Hotel
Sugar Beach, A Viceroy Resort

Sugar Beach, A Viceroy Resort

5 out of 5
Val des Pitons Soufrière
Book a stay at this luxury resort in Soufrière. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Sugar Beach, A Viceroy Resort
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
Book a stay at this 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
Sunset Shores Beach Hotel

Sunset Shores Beach Hotel

3 out of 5
Windward Highway Villa
Book a stay at this 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
Grenadine House

Grenadine House

4 out of 5
Kingstown Park Kingstown
Book a stay at this 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
Spring Gardens Resort

Spring Gardens Resort

3.5 out of 5
SPRING, BIABOU PERUVIAN VALE Biabou
Book a stay at this business-friendly hotel in Biabou. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Montreal Gardens and Argyle Beach ...
Spring Gardens Resort
Holiday Inn Express & Suites Diamond by IHG

Holiday Inn Express & Suites Diamond by IHG

3 out of 5
Windward Highway Diamond
Stay at this hotel in Diamond. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Argyle Beach and Villa Beach are located nearby.
Holiday Inn Express & Suites Diamond by IHG
See all 6,731 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.