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.
Clevelander Hotel – Adults Only
South Beach
Save 100% on your flight
Price was $442, price is now $245 per person
$245
per person
Nov 16 - Nov 20
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 4-star beach hotel in Miami Beach. Enjoy a beach locale, 2 bars/lounges, and a nightclub. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Bentley Hotel South Beach
South Beach
Save 100% on your flight
Price was $3,089, price is now $1,657 per person
$1,657
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a rooftop terrace, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $16,498, price is now $8,918 per person
$8,918
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Park Central South Beach
South Beach
Save 100% on your flight
Price was $2,865, price is now $1,560 per person
$1,560
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this 4-star historic resort in Miami Beach. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $456, price is now $249 per person
$249
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
Stay at this 3.5-star 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 Penguin Hotel
South Beach
Save 100% on your flight
Price was $2,164, price is now $1,217 per person
$1,217
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy a beach locale, breakfast (surcharge), and valet parking (surcharge). 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.
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 ...
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 ...
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 ...
La Quinta Inn by Wyndham Miami Airport North
7401 Nw 36th St, Miami, FL
19.89 km from Windward
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 ...
EAST Miami
788 Brickell Plaza, Miami, FL
19.06 km from Windward
Stay at this 5-star luxury hotel in Miami. Enjoy free WiFi, 4 outdoor pools, and 2 restaurants. Our guests praise the pool and the restaurant in our reviews. ...
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 ...
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 ...
Hyatt Place Miami Airport-East
3549 NW Le Jeune Road, Miami, FL
16.93 km from Windward
Stay at this 3-star business-friendly hotel in Miami. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Four Points by Sheraton Fort Lauderdale Airport - Dania Beach
1900 Stirling Road, Dania Beach, FL
12.41 km from Windward
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 ...
Clarion Inn & Suites Miami International Airport
5301 Nw 36th St, Miami Springs, FL
17.87 km from Windward
Stay at this hotel in Miami Springs. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms ...
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, 5 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
Embassy Suites by Hilton Miami International Airport
3974 NW South River Drive, Miami, FL
16.76 km from Windward
Stay at this 4-star business-friendly hotel in Miami. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and the ...
Park Central South Beach
640 Ocean Dr, Miami Beach, FL
18.49 km from Windward
Stay at this 4-star historic resort in Miami Beach. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
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.
Thu, Oct 30 - Mon, Nov 3
ATL
Hartsfield-Jackson Atlanta Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Sun, Jan 25 - Fri, Jan 30
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$68 Roundtrip, found 11 hours ago
$68
Roundtrip
found 11 hours ago
Wed, Jan 14 - Tue, Jan 20
LGA
LaGuardia
MIA
Miami Intl.
$81 Roundtrip, found 5 days ago
$81
Roundtrip
found 5 days ago
Mon, Oct 20 - Fri, Oct 24
TTN
Mercer
FLL
Fort Lauderdale - Hollywood Intl.
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago