Tradewinds Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to NZ$616 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

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
Fort Myers featuring a beach

West End

3 out of top 10 points of interest in this area

If you're spending some time in West End, J. N. Ding Darling National Wildlife Refuge and Bowman's Beach are top sights worth seeing.

Find hotels in West End

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 NZ$374 per night from 20 Nov to 21 Nov
NZ$374
20 Nov - 21 Nov
includes taxes & fees
8.8/10 Excellent! (1,631 reviews)
Yes very much so.

Reviewed on 14 Nov 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 refundableReserve now, pay when you stay
The price is NZ$164 per night from 23 Nov to 24 Nov
NZ$164
23 Nov - 24 Nov
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
Room was very clean, the staff were outstanding

Reviewed on 17 Nov 2025

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
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 NZ$389 per night from 20 Nov to 21 Nov
NZ$389
20 Nov - 21 Nov
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
Clean rooms

Reviewed on 16 Nov 2025

Lani Kai Beachfront Resort
See all 12,661 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 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.

Discover the most popular places to visit in Tradewinds

Bowman's Beach

Bowman's Beach

Relax and revel in a visit to one of the area’s most beautiful beaches, great for swimming, fishing and finding special seashells.

Bowman's Beach

Sanibel and Captiva Island Visitor's Center

Sanibel and Captiva Island Visitor's Center is just one of the places to see in Sanibel, so why not enjoy the other things to explore during your travels? Stroll along the beautiful beaches or discover the breathtaking sunrises in this family-friendly area.

Sanibel and Captiva Island Visitor's Center

Activities

Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

NZ$122
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

NZ$111
per adult
Dolphin Wildlife Cruise Fort Myers Beach
Kayaking Rock Creek in the Bunche Beach Preserve

Guided Kayak Eco Tour - Bunche Beach

NZ$121
per adult
98% of travellers recommend
Guided Kayak Eco Tour - Bunche Beach
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.