Tradewinds Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    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
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West End

4 out of top 10 points of interest in this area

While visiting West End, you might make a stop by sights like J. N. Ding Darling National Wildlife Refuge and Bowman's Beach.

Find hotels in West End

Tradewinds Hotel Deals

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
The price is ￥62,731 per night from Feb 12 to Feb 13
￥62,731
￥73,877 total
Feb 12 - Feb 13
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Nice room and perfect location

Reviewed on Feb 1, 2026

Marriott Sanibel Harbour Resort & Spa
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is ￥46,552 per night from Feb 10 to Feb 11
￥46,552
￥59,795 total
Feb 10 - Feb 11
includes taxes & fees
8.8/10 Excellent! (1,858 reviews)
Excellent room and location

Reviewed on Feb 7, 2026

Margaritaville Beach Resort Fort Myers
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
Fully refundableReserve now, pay when you stay
The price is ￥58,991 per night from Feb 11 to Feb 12
￥58,991
￥69,705 total
Feb 11 - Feb 12
includes taxes & fees
9/10 Wonderful! (1,592 reviews)
Room was nice. We tried to shut light off in bathroom but it stayed on impacting sleep a bit but we for used to that. Like the beach access.

Reviewed on Feb 9, 2026

Sanibel Island Beach Resort
See all 12,899 properties in Tradewinds
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.