Tradewinds Vacations
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Your Tradewinds Vacation
Booking a tailor-made Tradewinds vacation package is a great way to become familiar with this unique neighborhood. 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 vacation is easy with Expedia.
Price found within the past 48 hours. Click for updated prices.
- Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Aug 16 - Aug 21Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton + Flight
Punta Gorda5 nights9.2/10 - Wonderful (2,719 reviews)"The best in florida"Reviewed May 29, 2026Roundtrip • Minneapolis (MSP) - Fort Myers (RSW)MSP - RSW • Nonstop RSW - MSP • Nonstop - LaPlaya Beach & Golf Resort - A Noble House Resort
Aug 11 - Aug 19LaPlaya Beach & Golf Resort - A Noble House Resort + Flight
Vanderbilt Beach8 nights9.0/10 - Wonderful (1,002 reviews)"While the hotel benefits from a desirable location and distinctive Florida charm, the property currently shows signs of deferred maintenance and inconsistent operational oversight. Improvements in cleanliness, facility upkeep, responsiveness, and food service quality would greatly enhance the guest experience and better align the property with guest expectations. Summary of main issues: +guest room condition issues included a rusty bathtub, cracked sink, stained lampshades and ceiling stains...."Reviewed May 27, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop - Chadwick Cove Resort & Marina
Aug 10 - Aug 14Chadwick Cove Resort & Marina + Flight
Manasota Key4 nights9.6/10 - Exceptional (19 reviews)"The listing stated step to beach. It was not only across the street but offered no access. "Reviewed May 10, 2026Roundtrip • New York (EWR) - Fort Myers (RSW)EWR - RSW • Nonstop RSW - EWR • Nonstop$950$617found 12 hours agoper traveler - The Suites at Fishermen’s Village- 2 Bedroom Suites
Aug 16 - Aug 21The Suites at Fishermen’s Village- 2 Bedroom Suites + Flight
Punta Gorda Isles5 nights9.8/10 - Exceptional (1,219 reviews)"Great location clean and specious"Reviewed May 29, 2026Roundtrip • Minneapolis (MSP) - Fort Myers (RSW)MSP - RSW • Nonstop RSW - MSP • Nonstop - Tween Waters Island Resort & Spa
Aug 12 - Aug 16Tween Waters Island Resort & Spa + Flight
Captiva4 nights8.6/10 - Excellent (1,001 reviews)"Our view was beautiful. Our dining experiences(including poolside dining) were not the best. Ordered gluten free tacos, ended up getting flour- asked to have corn and the ingredients were scooped out and placed back into the corn. Anyone with celiac disease understands this is not okay, equates to contamination and inflammation. I am always amazed at the difference in treatment when traveling with my husband versus not. This trip was without him and when you a woman traveling with your..."Reviewed May 28, 2026Roundtrip • Boston (BOS) - Fort Myers (RSW)BOS - RSW • Nonstop RSW - PSM • Nonstop
Where to stay in Tradewinds
Find the best Tradewinds areas and neighborhoods for the activities you enjoy most. Learn more about Tradewinds
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.
Tradewinds Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$274 nightly
The price is $306 total per night from Jun 8 to Jun 9
$306 total
Jun 8 - Jun 9
Total with taxes and fees
9/10 Wonderful! (2,147 reviews)
"The Ocean view, Sunset Dj at the morning pool was Horrible They definitely need better DJ"
Reviewed on May 30, 2026
Holiday Inn Express Cape Coral-Fort Myers Area by IHG
1538 Cape Coral Pkwy E Cape Coral FL
Fully refundable
$105 nightly
The price is $117 total per night from Jun 4 to Jun 5
$117 total
Jun 4 - Jun 5
Total with taxes and fees
9.2/10 Wonderful! (1,494 reviews)
"There were vagrants everywhere, food on the floor in the hallways, and a terrible smell. If we hadn’t been the middle of the night after driving many hours, we definitely would’ve went elsewhere."
Reviewed on May 29, 2026
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $155 total per night from May 31 to Jun 1
$155 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (1,541 reviews)
"We arrived to 4 cars of cops on the property and were told they were breaking up fights on the beach and at the bar. I was instantly concerned but assured that it was only because it was memorial Day weekend and the crowds would die down after. This was true. The following days were much calmer. ..."
Reviewed on May 30, 2026
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.
Discover the most popular places to visit in Tradewinds
Sanibel Island Southern Beach
Why not spend a lazy afternoon at Sanibel Island Southern Beach during your trip to Sanibel?
Sanibel Island Lighthouse
Although nobody knows how many shipwrecks it’s prevented, this lighthouse has been a welcome beacon for over a century. Visit it on an island that’s noted for shell collecting.
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.
Things to do
Fort Myers Beach Sunset and Dolphin Watching Cruise
$70
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.