Tradewinds Vacation Packages

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Top Holiday Package Deals in Tradewinds

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
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,000 reviews)
Staff was wonderful, the hotel was amazing for the price and it also had a great restaurant and outside area. Would absolutely stay here again next time for sure!

Reviewed on Apr. 7, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,273 reviews)
Edison Beach house is a wonderful place to stay! Very clean and convenient! It was perfect for our weekend getaway. It was right on the water but also has a nice pool and chairs if you don’t want to be on the sand. It was within walking distance to restaurants and stores. The only bad thing is the bed wasn’t very comfortable at all. Everything else was great!

Reviewed on Apr. 18, 2025

The Boat House

The Boat House

2 out of 5
Olde Marco
Save 100% on your flight
per person
Jun. 28 - Jul. 5
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (595 reviews)
Absolutely love this spot!!!

Reviewed on Apr. 3, 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Jun. 28 - Jul. 1
found 2 days ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.6/10 Exceptional! (2,127 reviews)
We loved our stay at Bellasera so much and can't wait to stay here again. Room was huge (895 SF) and we had a full kitchen and a washer/dryer, plus a dining room, living room, and enclosed balcony that also had a table and 4 chairs. The staff was great! The concierge got us a reservation for dinner at a "very hard to get reservations" restaurant! The free shuttle service that will take you and pick you up until 11 at night is amazing! 5-minute walk to 5th Avenue. 5 stars!

Reviewed on Apr. 15, 2025

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Save 100% on your flight
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.4/10 Very Good! (1,022 reviews)
We loved the Lani Kai!

Reviewed on Apr. 18, 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 $317 per night from May 5 to May 6
CA $317
CA $630 total
includes taxes & fees
May 5 - May 6
9.6/10 Exceptional! (37 reviews)
40th Wedding Anniversary trip
"My husband and I stayed mid-March for 7 days. The weather cooperated and it was sunny and mid-70’s all week! The Ibis cottage was perfect for the two of us and it was far enough away from the commerce area that it was peaceful and quiet. We never ran out of activities and excursions mixed in with ..."

Reviewed on Mar. 17, 2025

Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
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)
Enjoyed Stay
"Basic needs met. Thanks"

Reviewed on May 21, 2022

Get rates
West End Paradise Unit 1 Turtle 2 - One bedroom suite w/water views
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 $345 per night from May 12 to May 13
CA $345
CA $438 total
includes taxes & fees
May 12 - May 13
8.8/10 Excellent! (1,003 reviews)
"I love my stay"

Reviewed on Apr. 13, 2025

Margaritaville Beach Resort Fort Myers
See all 11,264 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 $546. 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 $93
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 $93
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
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.