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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

Treasure Island - TI Las Vegas Hotel & Casino

4 out of 5
Save 100% on your flight
Price was $692, price is now $281 per person
$281
per person
Feb 18 - Feb 22
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 parking, an outdoor pool, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Treasure Island Casino and The Venetian Casino are located nearby.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,172, price is now $445 per person
$445
per person
Feb 9 - Feb 13
found 13 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.
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Price was $1,037, price is now $443 per person
$443
per person
Jan 31 - Feb 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this beach hotel in Sunny Isles Beach. Enjoy a beach locale, breakfast (surcharge), and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Aventura Mall and Gulfstream Park Racing and Casino are located nearby.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Price was $1,131, price is now $500 per person
$500
per person
Feb 4 - Feb 8
found 1 day 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.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,992, price is now $887 per person
$887
per person
Feb 16 - Feb 21
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Little Conch Key and Walkers Island are located nearby.
President Hotel

President Hotel

3.5 out of 5
Price was $1,923, price is now $878 per person
$878
per person
Feb 8 - Feb 15
found 1 day 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
Price was $1,761, price is now $807 per person
$807
per person
Feb 8 - Feb 15
found 1 day 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.
President Hotel Villa

President Hotel Villa

3.5 out of 5
Price was $1,286, price is now $602 per person
$602
per person
Feb 11 - Feb 15
found 16 hours 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 Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $17,069, price is now $8,159 per person
$8,159
per person
Feb 4 - Feb 8
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.
1818 Meridian House Apartments and Suites by Eskape Collection

1818 Meridian House Apartments and Suites by Eskape Collection

3 out of 5
Save 100% on your flight
Price was $657, price is now $317 per person
$317
per person
Feb 3 - Feb 8
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this golf aparthotel in Miami Beach. Enjoy free WiFi, parking (surcharge), and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Beach Place Hotel

Beach Place Hotel

2 out of 5
Price was $1,295, price is now $632 per person
$632
per person
Feb 8 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Aventura Mall and Collins Avenue Shopping Area are located nearby.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Save 100% on your flight
Price was $807, price is now $396 per person
$396
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Los Angeles (LAX)
Stay at this hotel in Glendale. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Rose Bowl Stadium and Dodger Stadium are located nearby.

3-4 Night Vacations in Windward Islands

Price found within the past 48 hours. Click for updated prices.
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Ocean Four
Price was $1,037, price is now $443 per person
$443
per person
Jan 31 - Feb 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,172, price is now $445 per person
$445
per person
Feb 9 - Feb 13
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $2,262, price is now $991 per person
$991
per person
Feb 12 - Feb 15
found 1 day 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 $1,114, price is now $512 per person
$512
per person
Feb 12 - Feb 15
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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $693, price is now $305 per person
$305
per person
Feb 20 - Feb 25
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Price was $2,528, price is now $937 per person
$937
per person
Feb 7 - Feb 14
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,453, price is now $568 per person
$568
per person
Jan 30 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Treasure Island - TI Las Vegas Hotel & Casino

Treasure Island - TI Las Vegas Hotel & Casino

4 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $789, price is now $317 per person
$317
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Las Vegas (LAS)

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
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
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
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
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
Rabot Hotel from Hotel Chocolat

Rabot Hotel from Hotel Chocolat

4.5 out of 5
Rabot Estate Soufrière
Book a stay at this luxury hotel in Soufrière. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Rabot Hotel from Hotel Chocolat
See all 6,671 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.