Tradewinds Vacations from $425

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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.

The Latest Tradewinds Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was $845, price is now $425 per person
$425
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,009 reviews)
Great option. Best breakfast and good lication. Showing some age now.

Reviewed on Nov 8, 2025

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,207, price is now $591 per person
$591
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,013 reviews)
Clean room, good price, fabulous staff, especially Penny, bar/restaurant, pool, location, mooring room all great perks!

Reviewed on Nov 9, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $1,411, price is now $723 per person
$723
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (666 reviews)
Rooms were super nice. Pools were amazing, the guys at the restaurant on site were all amazing but needed more than 2 people working and we waited a little while just to order take out.All in all a great weekend getaway.

Reviewed on Nov 9, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,152, price is now $677 per person
$677
per person
Jan 17 - Jan 21
found 4 hours ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
9.6/10 Exceptional! (443 reviews)
We enjoyed our walk-out patio room on the ground floor to the pool.

Reviewed on Nov 12, 2025

OYO Waterfront Hotel - Cape Coral/Fort Myers, FL

OYO Waterfront Hotel - Cape Coral/Fort Myers, FL

2.5 out of 5
Caloosahatchee
Save 100% on your flight
Price was $762, price is now $488 per person
$488
per person
Jan 15 - Jan 18
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
5.8/10 (1,004 reviews)
This hotel was close to everything which made it convenient for us. However, we found two cockroaches in the kitchen area.

Reviewed on Mar 18, 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 featuring a sandy beach

West End

3 out of top 10 points of interest in this area

While visiting West End, you might make a stop by sights like J. N. Ding Darling National Wildlife Refuge and Bowman's Beach.

Find hotels in West End

Tradewinds Hotel Deals

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
$212 nightly
The price is $237 total per night from Nov 25 to Nov 26
$237 total
Nov 25 - Nov 26
Total with taxes and fees
8.8/10 Excellent! (1,618 reviews)
Great staff and clean and comfortable room.

Reviewed on Nov 11, 2025

Margaritaville Beach Resort Fort Myers
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
$195 nightly
The price is $218 total per night from Nov 19 to Nov 20
$218 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,015 reviews)
Friendly staff, room was clean, easy to find parking (but you have to pay for parking even if you are a guest of the hotel). Parking is in addition to a resort fee. They responded to our questions right away. Great atmosphere with music. I wish the information was updated that the sunroof deck bar ...

Reviewed on Nov 9, 2025

Lani Kai Beachfront Resort
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr, Fort Myers, FL
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from Nov 23 to Nov 24
$124 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Good 👍

Reviewed on Nov 7, 2025

Hilton Garden Inn Ft Myers
See all 12,789 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Tradewinds

Sanibel Island Southern Beach

Sanibel Island Southern Beach

4.5/5(171 reviews)

Why not spend a lazy afternoon at Sanibel Island Southern Beach during your trip to Sanibel?

Sanibel Island Southern Beach
Bowman\'s Beach which includes general coastal views and a sandy beach

Bowman's Beach

4.5/5(481 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
Sanibel Island Lighthouse which includes a beach, general coastal views and a sunset

Sanibel Island Lighthouse

4.5/5(1,092 reviews)

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.

Sanibel Island Lighthouse

Things to do

Fort Myers Beach Sunset Excursion

Fort Myers Beach Sunset Excursion

$65
per adult
100% of travellers recommend
Fort Myers Beach Sunset Excursion
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

$70
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

$65
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.