Tradewinds Vacations

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Where to stay in Tradewinds

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

Tradewinds Hotel Deals

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
The price is ₩165,399 per night from Sep 28 to Sep 29
₩165,399
₩215,756 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (1,023 reviews)
"The area is still recovering from hurricane Ian. Most places are still rebuilding. Lani Kai has come along way still has the fantastic beach nice rooms good food can't wait until the roof top bar and restaurant opens their getting close. Hopefully on our next stay. Our get-away"

Reviewed on Sep 18, 2025

Lani Kai Beachfront Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is ₩237,668 per night from Sep 28 to Sep 29
₩237,668
₩319,824 total
Sep 28 - Sep 29
includes taxes & fees
8.8/10 Excellent! (1,475 reviews)
"Great stay, accommodations, location"

Reviewed on Sep 18, 2025

Margaritaville Beach Resort Fort Myers
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr, Fort Myers, FL
Fully refundableReserve now, pay when you stay
The price is ₩162,056 per night from Oct 5 to Oct 6
₩162,056
₩180,692 total
Oct 5 - Oct 6
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
"Shower had poor pressure. I have thick hair so this is important to me. Besides that it was nice."

Reviewed on Sep 23, 2025

Hilton Garden Inn Ft Myers
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.

Frequently asked questions

How much does a Tradewinds vacation package cost?
Customize your Tradewinds vacation package from only . Pick from any combination of rental cars, flights and hotels to create the trip you've been dreaming of. Remember to add on a few activities!
How do I get a cheap travel package to Tradewinds?
Combine your bookings with Expedia to save big bucks on your next trip. With over 550 airlines and 1,000,000 hotel options across the world, your Tradewinds vacation package can be tailored exactly to suit your travel style. With all that extra money, why not include one or more awesome activities and tours? It's an easy way to unlock even more savings. That dream vacation to Tradewinds is much closer than you thought!
Where should I stay in Tradewinds?
With popular attractions like Sanibel Island Southern Beach and Bowmans Beach in this area, look for a hotel positioned near either of them. J. N. Ding Darling National Wildlife Refuge is another sight in Tradewinds that draws the crowds.
What are the top hotels in Tradewinds?
Secure a room at West End Paradise Unit 3 - One Bedroom Suite W. It's one of the neighborhood's most popular properties. Another top option in Tradewinds is West End Paradise Unit 1 - One Bedroom Suite W.
How far in advance should I book my Tradewinds vacation?
While prices fluctuate, we generally advise booking your spot as early as possible. Most international airfares can be compared on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you may still get lucky. Cheap journeys to Tradewinds sometimes occur only weeks before departure.
What does an Expedia Tradewinds travel package include?
Much of that depends on you. You can choose from a range of Tradewinds packages, such as a rental car, flight and hotel. You can also book a hotel and a flight, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your Tradewinds vacation looks like, get ready to save!
What should I know before booking a Tradewinds travel package?
Design deals to match your budget with an Expedia package. Hotels, airfares, rental cars — we have everything you need to plan your break. You'll save precious dollars just for combining your bookings. Whether you're taking off on an adventure in the snow or kicking back on a warm beach, your ideal vacation is just clicks away.
Can I choose my airline with a Tradewinds Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Simply choose your preferred carrier and craft your ideal Tradewinds getaway.
If I'm not able to travel, can I cancel my Tradewinds vacation package?
It's good to know that you can cancel your Tradewinds booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Tradewinds

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.