Tradewinds Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Reception
    Jul 12 - Jul 17

    Fairfield Inn & Suites by Marriott Venice + Flight

    Venice
    5 nights
    3.0 star property
    9.2/10 - Wonderful (1,001 reviews)
    "We had a great stay. It was close to the beach and amenities near by. Would stay again."
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Tampa (TPA)
    DUB - TPA • 1 stop TPA - DUB • 1 stop
    €1,215
    €1,130
    per traveller
    found 1 day ago
    Fairfield Inn & Suites by Marriott Venice
  • View from property
    Jul 12 - Jul 17

    Inn at the Beach + Flight

    Venice Island
    5 nights
    3.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    "We loved everything about our stay at Inn at the Beach in Venice. Our room was perfect and we were steps away from the beach. Housekeeping is top notch. We enjoyed walking to the Venice Community Park to play tennis, we enjoyed the pool and hot tub. Great location in beautiful Venice. We will definitely be back!"
    Reviewed May 30, 2026
    Return • Dublin (DUB) - Tampa (TPA)
    DUB - TPA • 1 stop TPA - DUB • 1 stop
    €1,605
    €1,385
    per traveller
    found 1 day ago
    Inn at the Beach

Where to stay in Tradewinds

Find the best Tradewinds areas and neighborhoods for the activities you enjoy most. Learn more about Tradewinds
Sanibel Island Lighthouse in Florida

Mid Island

2 out of top 10 points of interest in this area

If you're spending some time in Mid Island, Periwinkle Way and Sanibel Island Southern Beach are top sights worth seeing.

Find hotels in Mid Island

Top hotels in Tradewinds

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 €278 per night from 7 Jun to 8 Jun
€278
7 Jun - 8 Jun
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"First of all WE WILL return. Loved the property, loved the P&Q (Stay at Captiva Tower if you want more peace). My ONE gripe, and I hope it is passed up the chain to management, is that we stayed over on a three day holiday weekend. BOTH the new evening Dinner cruise AND the Courtside Steakhouse were ..."

Reviewed on 30 May 2026

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 €240 per night from 14 Jun to 15 Jun
€240
14 Jun - 15 Jun
includes taxes & fees
9/10 Wonderful! (2,153 reviews)
"Perfect long weekend getaway"

Reviewed on 30 May 2026

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 €171 per night from 8 Jun to 9 Jun
€171
8 Jun - 9 Jun
includes taxes & fees
9/10 Wonderful! (1,547 reviews)
"This place was in the a perfect location right on the beach and walking distance to town. Lots of shops and restaurants on property!! Chairs and umbrellas on beach to rent!"

Reviewed on 31 May 2026

Lani Kai Beachfront Resort
See all 13,034 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.

Frequently asked questions

How much does a Tradewinds holiday package cost?
Customize your Tradewinds holiday package from only . 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 holiday 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 holiday 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 neighbourhood'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 holiday?
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 holiday 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 holiday is just clicks away.
Can I choose my airline with a Tradewinds Expedia holiday 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 holiday 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.

Popular places to visit

Sanibel Island Lighthouse

Sanibel Island Lighthouse

4/5(23 reviews)

You can find out about the history of Sanibel with a trip to Sanibel Island Lighthouse. Wander through the beautiful beaches and seaside in this family-friendly area.

Sanibel Island Lighthouse
Periwinkle Way

Periwinkle Way

The island’s spine is also its commercial hub. Drive or bike the road’s length to find attractions and discover many stores and restaurants.

Periwinkle Way

Things to do

Copacetic Day Sail

Copacetic Day Sail

€60
per adult
100% of travellers recommend
Copacetic Day Sail
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

€60
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

€55
per adult
100% of travellers recommend
Dolphin Wildlife Cruise Fort Myers Beach
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.