Windward Vacation Packages

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Top Holiday Package Deals in Windward

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

Pantera Rosa

South Beach

CA $689

per person

Oct 13 - Oct 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8.8/10 Excellent! (74 reviews)

The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.

Reviewed on Jun 26, 2026

Casablanca Miami Beach

North Beach

CA $5,392

per person

Oct 25 - Oct 29

found 10 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

5.8/10 (327 reviews)

Valet parking 10/10, safety 10/10 room description not the same as what I got, dirty towels and blanket bad experience.

Reviewed on Aug 12, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

CA $18,379

per person

Oct 18 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

8/10 Very good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Nobu Hotel Miami Beach

Mid Beach

CA $1,769

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

8.6/10 Excellent! (1,447 reviews)

Omni Fort Lauderdale Hotel

East Fort Lauderdale

CA $1,446

per person

Oct 20 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

9.6/10 Exceptional! (544 reviews)

The property is beautiful, clean, and the staff is sensational!! A must stay property!!

Reviewed on Aug 12, 2026

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward

A beach with clear turquoise water, a rocky shoreline, and several high-rise buildings in the background.

South Beach

3 out of top 10 points of interest in this area

Major entertainment destination with numerous nightclubs, restaurants, and boutiques. Stroll along Lincoln Road and Ocean Drive, admire Art Deco buildings, and enjoy easy access to public transportation.

A coastal cityscape with high-rise buildings and a marina.

Brickell

A dense, high-rise residential area with upscale condos, Brickell boasts popular Miami restaurants, shops, and art galleries. Explore Mary Brickell Village or catch the Metromover for easy transportation.

A city skyline at dusk with illuminated buildings reflecting on the water.

Downtown Miami

2 out of top 10 points of interest in this area

An urban city center with a rich cultural scene, Downtown Miami offers shopping at Flagler Street, Bayside Marketplace, and Mary Brickell Village. Explore Pérez Art Museum Miami, Miami Children's Museum, and enjoy the pedestrian-friendly area with extensive public transit options.

A modern urban area with two prominent high-rise buildings, a central road, and surrounding commercial buildings.

Doral

A noteworthy feature of Doral is its popular shops. While you're in town, be sure to stop and check out CityPlace Doral and Miami International Mall.

A street with palm trees, cars, and a pedestrian crossing sign.

Flamingo/Lummus

If you're spending some time in Flamingo/Lummus, Collins Avenue Shopping Area and Miami Beach Boardwalk are top sights worth seeing.

Windward Hotel Deals

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $347

CA $490 total

Aug 16 - Aug 17

includes taxes & fees

8.4/10 Very good! (8,747 reviews)

"It’s ok"

Reviewed on Aug 13, 2026

Loews Miami Beach Hotel – South Beach

1601 Collins Ave Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $224

CA $335 total

Sep 7 - Sep 8

includes taxes & fees

9.4/10 Exceptional! (1,281 reviews)

"Great location and staff …had a great time in Miami"

Reviewed on Aug 13, 2026

B Ocean Resort Fort Lauderdale Beach

1140 Seabreeze Blvd Fort Lauderdale FL

Fully refundableReserve now, pay when you stay

CA $163

CA $255 total

Aug 26 - Aug 27

includes taxes & fees

7.6/10 Good! (4,279 reviews)

"It could use some fresh paint by the pool and the pool side chairs need to be updated or cleaned but the staff was helpful and checking in was a pleasure. This was my 2nd visit and I’d come back for sure. Just a few suggestions. Good luck! Until next time!"

Reviewed on Aug 12, 2026

See all 23,415 properties in Windward

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.