Tradewinds Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Tradewinds

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
East Naples
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.2/10 Very Good! (1,494 reviews)
The man who checked us in was super friends and accommodating

Reviewed on Jul. 20, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Service was excellent

Reviewed on Jul. 19, 2025

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Park Shore
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,583 reviews)
This is like home away from home! Spa services are an integral part of the beauty of this resort! Food and drinks are top notch, and having been there for several visits over the years its great to see familiar faces on staff and receive the best service! Cannot wait to go back!

Reviewed on Jul. 20, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
A very nice hotel in the heart of downtown Naples. Clean modern rooms, attentive staff and a sunny pool deck. Naples’ best dining steps from your door.

Reviewed on Jul. 9, 2025

The Vistas At Eastwood Apartments By Barsala

The Vistas At Eastwood Apartments By Barsala

4 out of 5
Eastwood Village
Save 100% on your flight
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8/10 Very Good! (1 review)

Where to stay in Tradewinds

Find the best Tradewinds areas and neighborhoods for the activities you enjoy most. Learn more about Tradewinds
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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
The price is CA $273 per night from Aug 3 to Aug 4
CA $273
CA $585 total
Aug 3 - Aug 4
includes taxes & fees
9.6/10 Exceptional! (38 reviews)
Short vacation
"Nice place to go to beach and park to watched birds."

Reviewed on May 19, 2025

Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views

West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views

Sanibel
9.8/10 Exceptional! (11 reviews)
Fantastic prioerty
"Everything was amazing and so clean. Just as described in the listing. Would definitely stay again."

Reviewed on Jul. 9, 2025

Get rates
West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views
West End Paradise Unit 1 Turtle 2 - One bedroom suite w/water views

West End Paradise Unit 1 Turtle 2 - One bedroom suite w/water views

Sanibel
9/10 Wonderful! (2 reviews)
"Great location! Good beach access! Very nice"

Reviewed on Jun. 17, 2025

Get rates
West End Paradise Unit 1 Turtle 2 - One bedroom suite w/water views
See all 11,882 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Tradewinds vacation package cost?
Customize your Tradewinds vacation package from only CA $465. 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

Bowman's Beach

Bowman's Beach

4.5/5(14 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
J. N. Ding Darling National Wildlife Refuge

J. N. Ding Darling National Wildlife Refuge

5/5(2 reviews)

See almost anything that flies, swims or crawls in Florida in this protected area. Become acquainted with wildlife while learning about varied species.

J. N. Ding Darling National Wildlife Refuge

Sanibel Island Golf Club

Enjoy a round of golf in Sanibel at Sanibel Island Golf Club. Stroll along the seaside in this family-friendly area, or check out its lively bars.

Sanibel Island Golf Club

Things to do

Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

CA $84
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $89
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

CA $96
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
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.