Tradewinds Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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

Your Tradewinds Holiday

Booking a tailor-made Tradewinds holiday package is a great way to become familiar with this unique neighbourhood. From its hot spots to its little-known gems, there's plenty to discover. Kick start your trip to Tradewinds by heading to nearby attractions such as Sanibel Island Southern Beach, Bowmans Beach and J. N. Ding Darling National Wildlife Refuge. Whatever your travel plans or the size of your budget, booking your perfect Tradewinds holiday is easy with Expedia.

Our guide on where to stay in Tradewinds

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

Mid Island

3 out of top 10 points of interest in this area

If you're spending some time in Mid Island, Periwinkle Way and Sanibel Island Southern Beach are top sights worth seeing.

Find hotels in Mid Island

Our pick of the best Tradewinds Hotel Deals

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is AU$684 per night from 26 Feb to 27 Feb
AU$684
26 Feb - 27 Feb
includes taxes & fees
9/10 Wonderful! (1,902 reviews)
We had a fabulous stay! So many great amenities, restaurants, pool and beach area. The staff is so friendly and helpful. We’ll definitely return!

Reviewed on 24 Feb 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 AU$695 per night from 26 Feb to 27 Feb
AU$695
26 Feb - 27 Feb
includes taxes & fees
9.2/10 Wonderful! (1,637 reviews)
The room was very clean and we appreciated the daily room service that was provided.

Reviewed on 25 Feb 2026

Sanibel Island Beach Resort
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 refundableReserve now, pay when you stay
The price is AU$214 per night from 1 Mar to 2 Mar
AU$214
1 Mar - 2 Mar
includes taxes & fees
9.2/10 Wonderful! (1,260 reviews)
Absolutely fantastic

Reviewed on 25 Feb 2026

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
See all 12,993 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

Activities

Copacetic Day Sail

Copacetic Day Sail

AU$101
per adult
100% of travellers recommend
Copacetic Day Sail
Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

AU$92
per adult
Dolphin Wildlife Cruise Fort Myers Beach
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

AU$101
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
See all activities in Sanibel
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.