Tradewinds Vacations

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Your Tradewinds Vacation

Reserving a tailor-made Tradewinds vacation package is a great way to know the ins and outs of this unique neighborhood. From its must-see spots to its lesser-known treasures, there's plenty to discover. Kick start your trip to Tradewinds by heading to nearby attractions such as Bowmans Beach, J. N. Ding Darling National Wildlife Refuge and JN Ding Darling National Wildlife Refuge. Whatever your travel goals or budget, booking your ideal Tradewinds vacation is simple with Expedia.

The Latest Tradewinds Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Fort Myers Airport/FGCU

Hilton Garden Inn Fort Myers Airport/FGCU

3 out of 5
Save 100% on your flight
per person
Aug 25 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,000 reviews)
The evening front desk lady on Sunday was so nice

Reviewed on Jun 4, 2024

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
per person
Aug 25 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (405 reviews)
Quiet community. Floors were very dirty. Friendly people.

Reviewed on Jun 4, 2024

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
per person
Aug 25 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,000 reviews)
The resort is extremely awesome!!! But I don’t know why the parking is an extra and is really expensive, if you are paying for staying there! And you don’t have option to parking in other sites more accesible! Is more expensive the parking than the food… I don’t get it

Reviewed on Jun 14, 2024

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Park Shore
Save 100% on your flight
per person
Aug 25 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,182 reviews)
Perfecto lugar para unas vacaciones en familia

Reviewed on Jun 14, 2024

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
per person
Aug 25 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Hotel was very elegant and the staff was amazing.

Reviewed on Jun 7, 2024

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 hotel + flight trips in Beachview Country Club Estates

Tradewinds Hotel Deals

Marriott Sanibel Harbour Resort & Spa
Marriott Sanibel Harbour Resort & Spa
4 out of 5
17260 Harbour Pointe Dr, Fort Myers, FL
Fully refundableReserve now, pay when you stay
The price is $189 per night from Jun 16 to Jun 17
$189
$239 total
includes taxes & fees
Jun 16 - Jun 17
8.4/10 Very Good! (1,003 reviews)
"Beautiful view from my balcony."

Reviewed on Jun 13, 2024

Marriott Sanibel Harbour Resort & Spa
Margaritaville Beach Resort Fort Myers
Margaritaville Beach Resort Fort Myers
4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is $269 per night from Jul 16 to Jul 17
$269
$339 total
includes taxes & fees
Jul 16 - Jul 17
8.6/10 Excellent! (346 reviews)
Great, but not for families with kids
"Great service, rooms looked like new. Very close to the beach. But just so you know I don’t think it’s a hotel for families with kids. There were a lot of people drinking in the pool and partying after a lot of margaritas so my kids felt a little uncomfortable."

Reviewed on Jun 10, 2024

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 $240 per night from Jul 7 to Jul 8
$240
$293 total
includes taxes & fees
Jul 7 - Jul 8
8.4/10 Very Good! (1,036 reviews)
"Absolutely wonderful"

Reviewed on Jun 11, 2024

Sanibel Island Beach Resort
See all 10,745 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Tradewinds vacation package cost?
Customize your Tradewinds vacation package from only $462. 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

Image for 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
Image for Bowman's 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
Image for Sanibel Island Lighthouse

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

Image for Guided Kayak Sunset Tour in Pelican Bay at Fort Myers Beach

Guided Kayak Sunset Tour in Pelican Bay at Fort Myers Beach

$70
Per adult
Guided Kayak Sunset Tour in Pelican Bay at Fort Myers Beach
See all activities in Sanibel

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.