Tradewinds Holidays

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Price found within the past 48 hours. Click for updated prices.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
per person
10 Feb - 13 Feb
found 1 day ago
Return flight included
Palm Springs (PSP) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Captiva is a seriously peaceful place with some incredible sunsets. Tween makes it all that much more special. The gulf view rooms and the fresh food served daily. Friendly staff, fun property and a guaranteed relaxing vacation. Tween is always on my perfect scenery and relax mode list!

Reviewed on 8 Jan 2025

Edison Beach House

Edison Beach House

3.5 out of 5
per person
10 Feb - 13 Feb
found 1 day ago
Return flight included
Palm Springs (PSP) to Fort Myers (RSW)
9.4/10 Exceptional! (1,218 reviews)
Staff were friendly and helpful

Reviewed on 1 Jan 2025

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
per person
10 Feb - 13 Feb
found 1 day ago
Return flight included
Palm Springs (PSP) to Fort Myers (RSW)
9/10 Wonderful! (918 reviews)
Very cool location and short distance to Key West Express ferry.

Reviewed on 6 Jan 2025

Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
per person
10 Feb - 13 Feb
found 1 day ago
Return flight included
Palm Springs (PSP) to Fort Myers (RSW)
8.8/10 Excellent! (1,040 reviews)
Beach front was quiet and very nice. Had chairs that you didn't have to rent. Pool was great and very warm. Nice Tiki Bar and food was very good. BRGR had great staff, limited menu but was very good both times we ate there.

Reviewed on 8 Jan 2025

Sanibel Inn

Sanibel Inn

2 out of 5
per person
10 Feb - 13 Feb
found 1 day ago
Return flight included
Palm Springs (PSP) to Fort Myers (RSW)
8.8/10 Excellent! (1,000 reviews)
The property is rather old but the staff and their attention to details and humble approach makes this place remarkable. I have asked for some modifications in my reservation and they were very caring about it, if you are looking for peace then this is the place. It has everyone that you might need for unwinding.

Reviewed on 27 Sep 2022

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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Sanibel Isles

While Sanibel Isles isn't home to many top sights, Dunes Golf and Tennis Club and Periwinkle Way are some notable places to visit nearby.

Find hotels in Sanibel Isles

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 €357 per night from 10 Jan to 11 Jan
€357
includes taxes & fees
10 Jan - 11 Jan
8.2/10 Very Good! (1,004 reviews)
"You are right by the Sanibel bridge."

Reviewed on 19 Dec 2024

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 €307 per night from 9 Jan to 10 Jan
€307
includes taxes & fees
9 Jan - 10 Jan
8.8/10 Excellent! (740 reviews)
"Atmosphere is perfect! Very clean and fresh! Cocktails were good only thing didn’t care for was the food at lah te da not the greatest could use some more flavor. But JWB grill upstairs is excellent!"

Reviewed on 7 Jan 2025

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 €315 per night from 13 Jan to 14 Jan
€315
includes taxes & fees
13 Jan - 14 Jan
8.6/10 Excellent! (1,038 reviews)
Fint läge precis vid stranden
"Bra hotell med jättefint poolområde och fint läge precis vid stranden. Vårt rum var ganska enkelt och kanske lite trångt för fyra personer men var helt ok för en natt. Det är dock läget och utomhusområdet som gör detta hotell, poolen var jättefin med massor av stolar precis som på stranden. Kul med ..."

Reviewed on 8 Jan 2025

Sanibel Island Beach Resort
See all 10,935 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 €927. 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

Dolphin and Sightseeing Tiki Cruise

Dolphin and Sightseeing Tiki Boat Cruise

€53
per adult
Dolphin and Sightseeing Tiki Boat Cruise
Tiki Boat Tours

Tiki Boat Tours

€48
per adult
Tiki Boat Tours
Parasailing Adventure on Fort Myers Beach

Parasailing Adventure on Fort Myers Beach (400 Foot Flight)

€82
per adult
94% of travellers recommend
Parasailing Adventure on Fort Myers Beach (400 Foot Flight)
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.