Tradewinds Holidays

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    Save up to €185 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Fort Myers-Estero/FGCU

Hampton Inn & Suites Fort Myers-Estero/FGCU

2.5 out of 5
Price was €677, price is now €505 per person
€505
per person
2 Jan - 6 Jan
found 21 hours ago
Return flight included
Toronto (YYZ) to Fort Myers (RSW)
18.4/10 Exceptional! (1,001 reviews)
The hotel is clean. Great staff. Easy in easy out

Reviewed on 15 Nov 2025

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was €1,021, price is now €599 per person
€599
per person
2 Jan - 6 Jan
found 21 hours ago
Return flight included
Toronto (YYZ) to Fort Myers (RSW)
18.4/10 Exceptional! (1,001 reviews)
Nice room and was perfect for a 2 night stay

Reviewed on 20 Nov 2025

Flamingo Inn

Flamingo Inn

3 out of 5
Mid Island
Price was €730, price is now €519 per person
€519
per person
2 Jan - 6 Jan
found 21 hours ago
Return flight included
Toronto (YYZ) to Fort Myers (RSW)
15.6/10 Exceptional! (981 reviews)
Wonderful and cozy stay. Just right for two. Spotless, clean and updated in good taste. The bed was nice a big with crisp clean white sheets. We slept very well. The fridge and shower were a little small. Beach towels and beach chairs were a bonus. No fault to property but we were disappointed with the bugs Labor Day Weekend. Unfortunately we got eaten alive by swarms of mosquitos on the way to and back from the beach the first time. We tried going for sunset but had to run back flailing. We had to kill the ones that followed us back to the room. Literally a slapping contest. Next morning we ran to the car to find breakfast and a new beach. Ended up going to Lovers Key for the rest of the trip (no bugs there). We attempted one more cautious walk to Flamingo Beach and couldn't. Must be better in the winter. We will be back!

Reviewed on 1 Sept 2025

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was €988, price is now €735 per person
€735
per person
2 Jan - 6 Jan
found 21 hours ago
Return flight included
Toronto (YYZ) to Fort Myers (RSW)
16.8/10 Exceptional! (1,005 reviews)
Staff was great. The room smelled like poop

Reviewed on 18 Nov 2025

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

5 out of 5
Mid Island
Price was €1,314, price is now €989 per person
€989
per person
2 Jan - 6 Jan
found 21 hours ago
Return flight included
Toronto (YYZ) to Fort Myers (RSW)
17.2/10 Exceptional! (2,581 reviews)
Staff was very nice, pool was warm & clean. Mike the bartender at Turtles Was Fabulous!!!

Reviewed on 11 Nov 2025

Where to stay in Tradewinds

Find the best Tradewinds areas and neighborhoods for the activities you enjoy most. Learn more about Tradewinds
Fort Myers showing a sandy 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

Top hotels in Tradewinds

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is €208 per night from 1 Dec to 2 Dec
€208
1 Dec - 2 Dec
includes taxes & fees
8.8/10 Excellent! (1,649 reviews)
The view was nice

Reviewed on 21 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 €77 per night from 16 Dec to 17 Dec
€77
16 Dec - 17 Dec
includes taxes & fees
9.2/10 Wonderful! (1,014 reviews)
Breakfast was excellent

Reviewed on 18 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 €224 per night from 4 Dec to 5 Dec
€224
4 Dec - 5 Dec
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Breakfast was great but not included with the room price The 29 drink credit we had to ask them about it as we didn’t receive it upon check in. But they gave us a rum barrell drink ticket snd domestic beer drink ticket and he tossed in a couple of xtras. We don’t care for the rum drinks. But overall ...

Reviewed on 15 Nov 2025

Lani Kai Beachfront Resort
See all 12,694 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 €505. 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.

Popular places to visit

Sanibel Island Lighthouse

Sanibel Island Lighthouse

4/5(23 reviews)

You can find out about the history of Sanibel with a trip to Sanibel Island Lighthouse. Wander through the beautiful beaches and seaside in this family-friendly area.

Sanibel Island Lighthouse
Periwinkle Way

Periwinkle Way

The island’s spine is also its commercial hub. Drive or bike the road’s length to find attractions and discover many stores and restaurants.

Periwinkle Way

Things to do

Copacetic Day Sail

Copacetic Day Sail

€61
per adult
100% of travellers recommend
Copacetic Day Sail
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

€61
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

€55
per adult
Dolphin Wildlife Cruise Fort Myers 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.