Search Deals onWindward Vacation Packages
Windward Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Sunset Cove Beach Resort
Price was $934, price is now $493 per person
$493
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Book a stay at this beach hotel in Key Largo. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are located nearby.
Barcelona Studios Guesthouse
South Beach
Price was $1,110, price is now $584 per person
$584
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Stay at this guesthouse in Miami Beach. Enjoy free WiFi, a garden, and a picnic area. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $17,867, price is now $9,939 per person
$9,939
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Eden Roc Miami Beach
Mid Beach
Save 100% on your flight
Price was $998, price is now $583 per person
$583
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Book a stay at this luxury resort in Miami Beach. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
President Villa
South Beach
Save 100% on your flight
Price was $939, price is now $554 per person
$554
per person
Oct 25 - Nov 1
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free breakfast, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.
Casa Morada
Matecumbe
Save 100% on your flight
Price was $1,118, price is now $670 per person
$670
per person
Oct 19 - Oct 24
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
Fontainebleau Miami Beach
Mid Beach
Save 100% on your flight
Price was $887, price is now $533 per person
$533
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4.5-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.
Tranquility Bay Beachfront Hotel and Resort
Save 100% on your flight
Price was $1,260, price is now $762 per person
$762
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Stay at this 4-star beach hotel in Marathon. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sombrero Beach and Shady Palm Art Gallery are located nearby.
3-4 Night Vacations in Windward
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Windward
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Windward
Fontainebleau Miami Beach
4441 Collins Avenue, Miami Beach, FL
Stay at this 4.5-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 ...
citizenM Miami Worldcenter
700 NE 2ND AVENUE, Miami, FL
Stay at this 4-star business-friendly hotel in Miami. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
La Quinta Inn by Wyndham Miami Airport North
7401 Nw 36th St, Miami, FL
Stay at this 3-star business-friendly hotel in Miami. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Save an average of 15% on thousands of hotels when you're signed in
InterContinental Miami by IHG
100 Chopin Plz, Miami, FL
Stay at this 5-star luxury hotel in Miami. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the breakfast and the helpful staff in our ...
Four Points by Sheraton Fort Lauderdale Airport - Dania Beach
1900 Stirling Road, Dania Beach, FL
Stay at this 3-star business-friendly hotel in Dania Beach. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Pullman Miami Airport
5800 Waterford District Drive, Miami, FL
Stay at this 4-star business-friendly hotel in Miami. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and ...
citizenM Miami Brickell
11 SE 10th Street, Miami, FL
Stay at this 4-star business-friendly hotel in Miami. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Mondrian South Beach
1100 West Ave, Miami Beach, FL
Stay at this 4.5-star luxury hotel in Miami Beach. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Oct 4 - Sat, Oct 11
BOS
Logan Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Wed, Sep 17 - Sat, Sep 20
LGA
LaGuardia
MIA
Miami Intl.
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Tue, Sep 30 - Tue, Oct 7
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$75 Roundtrip, found 2 days ago
$75
Roundtrip
found 2 days ago
Thu, Sep 25 - Sat, Oct 4
ATL
Hartsfield-Jackson Atlanta Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
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