Tradewinds Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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

2 out of top 10 points of interest in this area

While visiting Beachview Country Club Estates, you might make a stop by sights like Periwinkle Way and Sanibel Island Golf Club.

Find hotels in Beachview Country Club Estates

Top hotels in Tradewinds

Margaritaville Beach Resort Fort Myers
Margaritaville Beach Resort Fort Myers
4 out of 5
251 Crescent Street, Fort Myers Beach, FL
The price is S$391 per night from 10 Dec to 11 Dec
S$391
includes taxes & fees
10 Dec - 11 Dec
8.8/10 Excellent! (656 reviews)
"You get more here than you’re paying for ! I would choose a margaritaville over many other resorts any day."

Reviewed on 27 Nov,2024

Margaritaville Beach Resort Fort Myers
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 S$274 per night from 10 Dec to 11 Dec
S$274
includes taxes & fees
10 Dec - 11 Dec
8.2/10 Very Good! (984 reviews)
"Great place for gateway to Sanibel and Captiva. Likely my new favorite!"

Reviewed on 27 Nov,2024

Marriott Sanibel Harbour Resort & Spa
The Lighthouse Resort Inn & Suites
The Lighthouse Resort Inn & Suites
3 out of 5
1051 5th St, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
The price is S$193 per night from 2 Dec to 3 Dec
S$193
includes taxes & fees
2 Dec - 3 Dec
8.4/10 Very Good! (1,176 reviews)
"Close to the beach , food at the tiki bar is great! Would definitely come back"

Reviewed on 27 Nov,2024

The Lighthouse Resort Inn & Suites
See all 10,736 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.

Things to do

2hr Tiki Pub Fun in the Sun Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

S$60
Per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
Tiki Boat Tours

Tiki Boat Tours

S$67
Per adult
Tiki Boat Tours
Dolphin and Sightseeing Tiki Cruise

Dolphin and Sightseeing Tiki Boat Cruise

S$74
Per adult
Dolphin and Sightseeing Tiki Boat 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.