Tradewinds Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    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

Top hotels in Tradewinds

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 S$255 per night from 15 Jun to 16 Jun
S$255
15 Jun - 16 Jun
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"It was way better than my expectations!! I had so much fun and did not want to leave!! I will definitely be back and tell others to go! The staff was extremely helpful and friendly and the room was clean and comfortable!!"

Reviewed on 6 Jun, 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 S$345 per night from 10 Jun to 11 Jun
S$345
10 Jun - 11 Jun
includes taxes & fees
8.8/10 Excellent! (1,142 reviews)
"Beautiful resort right on the beach! The pool is large and pretty. Lots of chairs and umbrellas. The interior is gorgeous and the staff are great."

Reviewed on 7 Jun, 2025

Margaritaville Beach Resort Fort Myers
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
2.5 out of 5
1538 Cape Coral Pkwy E, Cape Coral, FL
Fully refundable
The price is S$162 per night from 18 Jun to 19 Jun
S$162
18 Jun - 19 Jun
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Great hotel, clean, family friendly and location was convenient. My only observation is that pool towels are extremely small and thin. However, in spite of that I would still recommend it. Breakfast variety was very good with fresh coffee!"

Reviewed on 3 Jun, 2025

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
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 holiday package cost?
Customize your Tradewinds holiday 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 holiday 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 holiday 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 neighbourhood’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 holiday?
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 holiday 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 holiday is just clicks away.
Can I choose my airline with a Tradewinds Expedia holiday 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 holiday 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.

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.