Tradewinds Vacations from $306

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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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $603, price is now $306 per person
$306
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
People so helpful and friendly ~ communication very good. Room was really nice.

Reviewed on Sep 2, 2025

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 $2,502, price is now $1,090 per person
$1,090
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,004 reviews)
Ants in room-service was just okay-place needs updating-prices very high for what you get. Lack of attention to detail-Balleen was just fair-signature grouper dish highly recommended by server was warm (not hot) and risotto cake was undercooked (and for $65 per portion ????? ) overall price for value received was WAY TO HIGH).

Reviewed on Aug 29, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,319, price is now $705 per person
$705
per person
Oct 20 - Oct 25
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,001 reviews)
Location, service and amenities are excellent

Reviewed on Aug 31, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,089, price is now $586 per person
$586
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,474 reviews)
The housekeeper staff were really good. The elevator was out of order per more than 3 months and the hotel did not advertise us. Limited of parking wich is not fear after the a lot of money we paid. We have been coming more than 5 times but this time was the worse Experience. It was really sad to see the housekeeping staff carrying the stuff by stairs.

Reviewed on Sep 2, 2025

Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $978, price is now $588 per person
$588
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (85 reviews)
I had a great time there - staff was great - room was amazing on all levels . I will be back guaranteed

Reviewed on Aug 31, 2025

Where to stay in Tradewinds

Find the best Tradewinds areas and neighborhoods for the activities you enjoy most. Learn more about Tradewinds
Periwinkle Way featuring cycling as well as an individual femail

Beachview Country Club Estates

1 out of top 10 points of interest in this area

If you're spending some time in Beachview Country Club Estates, Periwinkle Way and Sanibel Island Golf Club are top sights worth seeing.

Find hotels in Beachview Country Club Estates

Tradewinds Hotel Deals

Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

Sanibel
$450 nightly
The price is $474 total per night from Sep 10 to Sep 11
$474 total
Sep 10 - Sep 11
Total with taxes and fees
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
$199 nightly
The price is $222 total per night from Sep 4 to Sep 5
$222 total
Sep 4 - Sep 5
Total with taxes and fees
Margaritaville Beach Resort Fort Myers
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
$107 nightly
The price is $119 total per night from Sep 9 to Sep 10
$119 total
Sep 9 - Sep 10
Total with taxes and fees
8.4/10 Very Good! (988 reviews)
"Safe and quiet place. Easy parking. Strongly recommend."

Reviewed on Aug 23, 2025

Hilton Garden Inn Ft Myers
See all 12,080 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

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

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

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

$60
per adult
100% of travellers recommend
Fort Myers Beach Sunset Excursion
Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

$65
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

$59
per adult
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
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.