Tradewinds Vacation Packages

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    Save up to CA $1,096 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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Top Holiday Package Deals in Tradewinds

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was CA $794, price is now CA $573 per person
CA $573
per person
May 28 - May 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,008 reviews)
The was a nice surprise. We will be back

Reviewed on Apr 20, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $2,332, price is now CA $1,279 per person
CA $1,279
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
From the moment we walked in staff were friendly and helpful with everything... Valet crew was also on top with scheduling Our room had Amazing views of beach and ocean. We couldn't have asked for more... Just a wonderful experience overall

Reviewed on Apr 21, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,413, price is now CA $854 per person
CA $854
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (748 reviews)
Great pools, service, food, rooftop, bedding, balcony and boat/beach access was icing on the cake! I felt all a good value for the price. Plus had a surprise on steel drum entertainment by pool on Sunday - so fun! Lots of outdoor space to take in the surrounding water and greenery. A bit of a drive to downtown Naples, but if you aren’t planning on doing that every day - The Perry is your place! Wonderful the iconic Bay House restaurant is right next door.

Reviewed on Apr 20, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was CA $966, price is now CA $695 per person
CA $695
per person
May 28 - May 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
8.6/10 Excellent! (1,001 reviews)
Likes: Pools and the beach across the road. Free coffee at marina. Our room Well, kept grounds and lots of nature Food at the pool bar was really good and very fast. Dislikes: No ice machine told it was broken Broken elevator Book in room has wrong times when places we’re open and closed not accurate No beach service even though the book says there is. Minimal first aid Door on balcony didn’t close all the way. Gap at the top of slider door Bathroom & bedroom doors squeak really bad Everyday Sewer smell on outside balcony in morning Rented cabana for half a day. No real amenities in the cabana such as a small fridge with waters in it. The only amenity was you had a server come to your cabana and ask if you wanted to order drinks or food. We saw them the first 30 minutes and then after that no service at all. The cushions on the chairs in the cabana did not fit the chairs. We went to two different restaurants while we were there and both had the same menu so really it wasn’t like two different restaurants. Just their names were different. The food was not very good at either restaurants. They have a place to order pizza and a few tables outside of it to sit to eat your pizza if you want or take back to your room. Pizza was not that good

Reviewed on Apr 19, 2026

Candlewood Suites Fort Myers Sanibel Gateway by IHG

Candlewood Suites Fort Myers Sanibel Gateway by IHG

3 out of 5
South Fort Myers
Price was CA $870, price is now CA $626 per person
CA $626
per person
Jun 5 - Jun 11
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
7.6/10 Good! (1,005 reviews)
Staff was helpful and friendly. Location was tucked away and private.

Reviewed on Apr 10, 2026

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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Mid Island

2 out of top 10 points of interest in this area

While visiting Mid Island, you might make a stop by sights like Periwinkle Way and Sanibel Island Southern Beach.

Find hotels in Mid Island

Tradewinds Hotel Deals

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 CA $138 per night from May 10 to May 11
CA $138
CA $154 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (1,411 reviews)
Rbevvevec

Reviewed on Apr 20, 2026

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is CA $305 per night from May 18 to May 19
CA $305
CA $408 total
May 18 - May 19
includes taxes & fees
9/10 Wonderful! (2,033 reviews)
Very nice but expensive

Reviewed on Apr 21, 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 CA $285 per night from May 17 to May 18
CA $285
CA $352 total
May 17 - May 18
includes taxes & fees
9.2/10 Wonderful! (1,801 reviews)
Our stay at Sanibel Island Beach Resort was absolutely exceptional from start to finish. The property perfectly captures the laid-back charm of Sanibel while still offering all the comforts you’d want for a relaxing getaway. Our room was spotless, well-appointed, and thoughtfully designed, with comfortable ...

Reviewed on Apr 20, 2026

Sanibel Island Beach Resort
See all 13,046 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Tradewinds vacation package cost?
Customize your Tradewinds vacation package from only CA $573. 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

Bowman's Beach

Bowman's Beach

4.5/5(16 reviews)

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
J. N. Ding Darling National Wildlife Refuge

J. N. Ding Darling National Wildlife Refuge

5/5(2 reviews)

See almost anything that flies, swims or crawls in Florida in this protected area. Become acquainted with wildlife while learning about varied species.

J. N. Ding Darling National Wildlife Refuge

Sanibel Island Golf Club

Enjoy a round of golf in Sanibel at Sanibel Island Golf Club. Stroll along the seaside in this family-friendly area, or check out its lively bars.

Sanibel Island Golf Club

Things to do

Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

CA $88
per adult
100% of travellers recommend
Dolphin Wildlife Cruise Fort Myers Beach
Guided Kayak Eco Tour - Bunche Beach

Guided Kayak Eco Tour - Bunche Beach

CA $96
per adult
98% of travellers recommend
Guided Kayak Eco Tour - Bunche Beach
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

CA $90
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
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.