Windward Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Windward Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel
South Beach
Save 100% on your flight
per person
Sep 1 - Sep 8
found 4 hours ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free WiFi, 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 Ocean Drive are located nearby.
The Shelborne By Proper
South Beach
per person
Sep 1 - Sep 8
found 4 hours ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Stay at this 4-star beach hotel in Miami Beach. Enjoy free WiFi, a private beach, and 3 bars/lounges. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Cavalier Hotel South Beach
South Beach
per person
Sep 1 - Sep 8
found 4 hours ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Stay at this 3.5-star beach hotel in Miami Beach. Enjoy a beach locale, 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 Ocean Drive are located nearby.
President Hotel
South Beach
Save 100% on your flight
per person
Sep 1 - Sep 8
found 4 hours ago
Roundtrip flight included
Cleveland (CLE) 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 Ocean Drive are located nearby.
Flow Miami Hotel
Downtown Miami
per person
Sep 1 - Sep 8
found 4 hours ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Stay at this 3.5-star apartment in Miami. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Popular attractions Kaseya Center and Bayside Marketplace are located nearby.
B Ocean Resort Fort Lauderdale Beach
East Fort Lauderdale
Save 100% on your flight
per person
Aug 8 - Aug 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Las Olas Beach and Port Everglades are located nearby.
Top Hotel Deals
Fontainebleau Miami Beach
4441 Collins Avenue, Miami Beach, FL
14.39 km from Windward
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
17.44 km from Windward
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 ...
InterContinental Miami by IHG
100 Chopin Plz, Miami, FL
18.38 km from Windward
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 ...
Mondrian South Beach
1100 West Ave, Miami Beach, FL
17.68 km from Windward
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 ...
Hyatt Regency Miami
400 Se 2nd Ave, Miami, FL
18.59 km from Windward
Stay at this 4-star eco-certified hotel in Miami. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean ...
Holiday Inn Miami - International Airport by IHG
1111 S Royal Poinciana Blvd, Miami Springs, FL
16.71 km from Windward
Stay at this 3-star business-friendly hotel in Miami Springs. Enjoy free WiFi, a free airport shuttle, and room service. Our guests praise the restaurant and ...
Kimpton EPIC Hotel by IHG
270 Biscayne Blvd Way, Miami, FL
18.6 km from Windward
Stay at this 5-star luxury hotel in Miami. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
B Ocean Resort Fort Lauderdale Beach
1140 Seabreeze Blvd, Fort Lauderdale, FL
20.29 km from Windward
Stay at this 4-star beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff ...
Eden Roc Miami Beach
4525 Collins Ave, Miami Beach, FL
14.24 km from Windward
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 ...
Holiday Inn Miami West - Airport Area by IHG
7707 N.W. 103rd Street, Hialeah, FL
16.65 km from Windward
Stay at this 3-star business-friendly hotel in Hialeah. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Embassy Suites by Hilton Fort Lauderdale 17th Street
1100 SE 17th Street, Fort Lauderdale, FL
18.59 km from Windward
Book a stay at this family-friendly hotel in Fort Lauderdale. Enjoy free breakfast, room service, and a 24-hour fitness center. Our guests praise the breakfast ...
Diplomat Beach Resort Hollywood, Curio Collection by Hilton
3555 S Ocean Dr, Hollywood, FL
8.34 km from Windward
Stay at this 4.5-star luxury resort in Hollywood. Enjoy a full-service spa, 6 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
citizenM Miami Brickell
11 SE 10th Street, Miami, FL
19.28 km from Windward
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 ...
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Aug 20 - Fri, Sep 5
LGA
LaGuardia
MIA
Miami Intl.
$56 Roundtrip, found 2 days ago
$56
Roundtrip
found 2 days ago
Wed, Jul 9 - Thu, Jul 10
BOS
Logan Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$87 Roundtrip, found 4 days ago
$87
Roundtrip
found 4 days ago
Tue, Sep 9 - Tue, Sep 23
BOS
Logan Intl.
MIA
Miami Intl.
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Tue, Sep 16 - Tue, Sep 30
JFK
John F. Kennedy Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Sun, Aug 17 - Sat, Aug 23
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Best points of interest in Miami
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