Tradewinds Holidays from £858

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Your Tradewinds Holiday

Reserving a tailor-made Tradewinds holiday package is a great way to know the ins and outs of this unique neighbourhood. 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 holiday is simple with Expedia.

Price found within the past 48 hours. Click for updated prices.
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Daniels Corridor
Price was £1,110, price is now £858 per person
£858
per person
30 Apr - 7 May
found 9 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
No reviews
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was £3,732, price is now £2,433 per person
£2,433
per person
26 Mar - 2 Apr
found 1 day ago
Return flight included
Manchester (MAN) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
The 2 room condo was huge& had everything you could ask for. The surroundings were beautiful.

Reviewed on 30 Jan 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was £1,401, price is now £934 per person
£934
per person
30 Apr - 7 May
found 9 hours ago
Return flight included
London (LON) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Very clean room with great view of estuary. Friendly staff. The only downside was that we were charged a $25 per day resort fee we were not expecting

Reviewed on 7 Feb 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was £1,838, price is now £1,327 per person
£1,327
per person
25 Apr - 2 May
found 17 hours ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
The hotel was amazing and super clean.

Reviewed on 8 Feb 2026

Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Price was £1,729, price is now £1,325 per person
£1,325
per person
25 Apr - 2 May
found 17 hours ago
Return direct flight included
Manchester (MAN) to Fort Myers (RSW)
9.6/10 Exceptional! (361 reviews)
The room was perfect for just my husband and myself, but with my elderly mother in a wheelchair, the bed was too high, toilet was too low and wobbled. She slept on the couch, and it was so low we had to both help her off of it. The view we had the condo was awesome except for someone in a wheelchair😔

Reviewed on 19 Jan 2026

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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West End

4 out of top 10 points of interest in this area

If you're spending some time in West End, J. N. Ding Darling National Wildlife Refuge and Bowman's Beach are top sights worth seeing.

Find hotels in West End

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 £345 per night from 12 Feb to 13 Feb
£345
12 Feb - 13 Feb
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Nice room and perfect location

Reviewed on 1 Feb 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 £246 per night from 10 Feb to 11 Feb
£246
10 Feb - 11 Feb
includes taxes & fees
8.8/10 Excellent! (1,851 reviews)
Very clean

Reviewed on 3 Feb 2026

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 £310 per night from 10 Feb to 11 Feb
£310
10 Feb - 11 Feb
includes taxes & fees
9/10 Wonderful! (1,586 reviews)
Great beach hotel! Room is clean and bed comfortable. All the staff are friendly and accommodating. Tiki hut fun by the pool. The restaurant is great for a lite bite and a full meal. The beach is steps from the hotel. Perfect get away even during the cold spell.

Reviewed on 4 Feb 2026

Sanibel Island Beach Resort
See all 12,899 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Tradewinds travel package cost?
Say yes to new adventures with our Tradewinds travel packages, which start from a low £858. Handpick the flights and hotels that suit your travel plans. Then, add on a few enriching experiences for an amazing escape.
If I'm not able to travel, can I cancel my Tradewinds travel package?
If your holiday plans in Tradewinds have changed, it's good to know that it's possible to amend or cancel your booking. If you booked less than 24 hours ago, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Tradewinds?
Our Tradewinds travel packages offer plenty of savings for the savvy globetrotter. For the best deal, simply bundle your hotel, flights and extras (including tours) into a budget-friendly package. But bargain prices are only the start of your next big adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotel options across the globe to pick from. No matter your budget, there's a package with your name on it.
Does Expedia offer Book Now, Pay Later Tradewinds holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a terrific getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can jet away on that well-deserved holiday now.
  • Pay in instalments holidays: If you want to pay for your getaway across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking the "book now" button is much easier with this plan. Just put down a small deposit on your holiday and then start working on your travel itinerary.

Where should I stay in Tradewinds?
A getaway to Tradewinds isn't complete without paying a visit to Bowmans Beach, Sanibel Island Southern Beach and J. N. Ding Darling National Wildlife Refuge. Spend your evenings close to these popular attractions and make sightseeing a breeze.
What are the top hotels in Tradewinds?
Get your escape off to a great start by booking a stay at Sundial Beach Resort And Spa. It's one of most popular properties in Tradewinds. Another option is Sanibel Island Beach Resort.
How far in advance should I book my Tradewinds holiday?
Reserving your seat early with Expedia means one less thing to worry about. Many air carriers display prices up to 12 months prior to departure dates. Typically, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Tradewinds are still known to appear a few weeks before departure.
What does an Expedia Tradewinds travel package include?
Packages include flights, hotels and rental cars, but you can combine any of them to create your dream Tradewinds escape. You can also add on a few activities and experiences once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll score deals you won't find anywhere else.
What should I know before booking a Tradewinds travel package?
So many places to wander around, so many things to do. With a package, you'll be able to tick more of them off your list. Bundle your hotels, rental cars and flights and see how much you save.
Can I choose my airline with a Tradewinds Expedia travel package?
Yes — that's one of the best things about an Expedia travel package. You're the boss! We have access to more than 550 partner airlines globally, so you have options galore when creating your Tradewinds getaway.

Popular places to visit

Sanibel Island Lighthouse which includes a beach, general coastal views and a sunset

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
Sunset on Sanibel Causeway. #beachtips #BVSblue

Causeway Islands Park B

If a restful holiday is part of your travel plans, Causeway Islands Park B might be the perfect place to visit during your trip to Sanibel. Wander the seaside or discover the beautiful sunsets in this family-friendly area.

Causeway Islands Park B

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 visit its lively bars.

Sanibel Island Golf Club

Things to do

Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

£47
per adult
Dolphin Wildlife Cruise Fort Myers Beach
Copacetic Day Sail

Copacetic Day Sail

£51
per adult
100% of travellers recommend
Copacetic Day Sail
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise

£33
per adult
Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
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. Flight-inclusive packages are ATOL protected.