Tradewinds Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Tradewinds

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Fort Myers Airport by IHG

Holiday Inn Express & Suites Fort Myers Airport by IHG

2.5 out of 5
Daniels Corridor
Save 100% on your flight
per person
May 29 - Jun. 5
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.6/10 Exceptional! (814 reviews)
It had very comfortable bed and pillows, staff was pleasant. Only bummer was we were looking forward to being in yhe pool but wasn't told until we got there, it's not heated.☹️

Reviewed on Mar. 24, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
per person
May 16 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,273 reviews)
The location of this property is amazing! It’s literally on the beach. The staff is also wonderful! The front desk staff was so nice and remembered our son by name. We will definitely be coming back.

Reviewed on Mar. 24, 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Jun. 16 - Jun. 19
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Fort Myers (RSW)
9.6/10 Exceptional! (2,127 reviews)
Excellent property and service. Highly recommended!

Reviewed on Mar. 24, 2025

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Save 100% on your flight
per person
May 23 - May 27
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Fort Myers (RSW)
8.4/10 Very Good! (1,022 reviews)
I really thought everything was remodeled but It was just painted. At least on the 3rd floor where I was. 2 dehumidifiers running. Not sure if that was standard. The flooring was completely Scratched up and gouged out in some areas. Room service didn’t show up unless I called I put tag out everyday for room service but they never showed. They just gave the rooms a fluff and puff! I stayed in 301 FYI

Reviewed on Mar. 26, 2025

South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
per person
Apr. 28 - May 3
found 22 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
8.4/10 Very Good! (1,002 reviews)
Have stayed in past year and room was wonderful. This condo was not updated. It was clean, but needs updating. Was missing so amenities, quickly staff replaced. (Coffee maker, toaster). This unit - Bayview 2516 did have Allan with extra table and couch area- that was a bonus. Bay view pool is a good alternative to the main pool also. Dock is closed- by can still fish.

Reviewed on Mar. 23, 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
The price is CA $428 per night from Apr. 21 to Apr. 22
CA $428
CA $797 total
includes taxes & fees
Apr 21 - Apr 22
9.6/10 Exceptional! (36 reviews)
Great Trip
"Only stayed for a few days but didn't want to leave. The cottage was very nice for the two of us, just the right size and the walk to the beach was not a problem. We did not drive (and use the beach pass) and walked it twice a day. Everything about the stay was fabulous and the beach was amazing ..."

Reviewed on Feb. 16, 2025

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
The price is CA $428 per night from Apr. 7 to Apr. 8
CA $428
CA $533 total
includes taxes & fees
Apr 7 - Apr 8
8.8/10 Excellent! (953 reviews)
"Our trip was wonderful and the resort good and the staff was very friendly. With that said the price is quite steep and the chance of us staying there again are very slim."

Reviewed on Mar. 25, 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
The price is CA $160 per night from Apr. 28 to Apr. 29
CA $160
CA $223 total
includes taxes & fees
Apr 28 - Apr 29
8.4/10 Very Good! (1,000 reviews)
"We enjoyed our stay at Lani Kai. We were in room 120 - directly above the area for nightly entertainment. It was very loud while music was playing and it was close enough to patrons to hear all their "fun" BUT, music ended by 10pm and by 10:15 it was quiet and we were able to sleep just fine. I'm ..."

Reviewed on Mar. 24, 2025

Lani Kai Beachfront Resort
See all 11,186 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 $619. 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

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $93
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
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
Tiki Boat Tours

Tiki Boat Tours

CA $72
per adult
Tiki Boat Tours
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.