Island Woods Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Holiday Package Deals in Island Woods

Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral

Quality Inn Fort Myers Cape Coral

2 out of 5
Save 100% on your flight
Price was CA $841, price is now CA $520 per person
CA $520
per person
Jan 4 - Jan 11
found 1 hour ago
Roundtrip flight included
Buffalo (BUF) to Fort Myers (RSW)
7.6/10 Good! (495 reviews)
The hotel and room was nice.

Reviewed on Nov 1, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was CA $3,002, price is now CA $1,868 per person
CA $1,868
per person
Jan 17 - Jan 24
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9.2/10 Wonderful! (3,490 reviews)

The Bay Inn at Lani Kai

The Bay Inn at Lani Kai

3 out of 5
Price was CA $1,960, price is now CA $1,261 per person
CA $1,261
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
7.8/10 Good! (531 reviews)

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was CA $2,624, price is now CA $1,749 per person
CA $1,749
per person
Jan 3 - Jan 10
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (135 reviews)
The property is absolutely gorgeous…. The rooms are extremely comfortable and the amenities are perfect. So much fun!

Reviewed on Nov 2, 2026

Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was CA $1,942, price is now CA $1,310 per person
CA $1,310
per person
Jan 4 - Jan 11
found 1 hour ago
Roundtrip flight included
Buffalo (BUF) to Fort Myers (RSW)
9.8/10 Exceptional! (31 reviews)
Amazing , safe and beautiful place to stay . I was there for over 3 weeks and it’s local to many great locations , quiet and safe and over all highly recommend.

Reviewed on Oct 30, 2026

Where to stay in Island Woods

Find the best Island Woods areas and neighborhoods for the activities you enjoy most. Learn more about Island Woods
A coastal scene with a lighthouse, beach, and ocean.

Mid Island

3 out of top 10 points of interest in this area

While visiting Mid Island, you might make a stop by sights like Periwinkle Way and Sanibel Island Southern Beach.

Find hotels in Mid Island

Island Woods Hotel Deals

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 CA $290 per night from Nov 15 to Nov 16
CA $290
CA $372 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Beautiful resort. The fitness center was well equipped and clean. The pools were wonderful. Dolphins were observed feeding just off the dock. The walking paths are nice. Even off season there were plenty of staff in restaurant and at the pool cafe. Great view off the balcony of our room. Be prepared ..."

Reviewed on Oct 30, 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 CA $236 per night from Nov 3 to Nov 4
CA $236
CA $334 total
Nov 3 - Nov 4
includes taxes & fees
9/10 Wonderful! (2,730 reviews)
"The pool is beatiful the staff are very attentive"

Reviewed on Nov 2, 2026

Margaritaville Beach Resort Fort Myers
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 CA $113 per night from Nov 8 to Nov 9
CA $113
CA $153 total
Nov 8 - Nov 9
includes taxes & fees
8.6/10 Excellent! (1,841 reviews)
"Room was old and worn out. Alarm beeped all night long from outside fire safety light.Bed was comfortable but didn’t have a blanket or cover, only two sheets. Couldn’t figure out the tv. Shower leaked into kitchen. Stove but no pans(wouldn’t have used it anyway). Nice packet of coffee but barely ..."

Reviewed on Nov 1, 2026

The Lighthouse Resort Inn & Suites
See all 15,593 properties in Island Woods
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
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Frequently asked questions

How much does an Island Woods vacation package cost?
Starting from a low CA $520, a package is your ticket to cheap travel. Build your own Island Woods getaway by selecting from our great range of airfares, hotels and rental cars.
How do I get a cheap travel package to Island Woods?
It's easy. Just bundle. Hotels, flights and rental cars — combine whatever you need into an Island Woods vacation package to save tons of cash. Score even more bargains when you add extras such as experiences or tours to your booking. But that's not the only good part. You have the flexibility to put together your vacation your own way. We offer more than 550 air carriers and 1,000,000 properties globally, so that everyone has an opportunity to travel and live out those vacation fantasies.
Where should I stay in Island Woods?
A vacation in Island Woods wouldn't be complete without visiting Sanibel and Captiva Island Visitors Center, Sanibel Island Northern Beach and Periwinkle Way. Spend your nights near these popular attractions and make sightseeing simple.
How far in advance should I book my Island Woods vacation?
Reserving your tickets early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to 12 months prior to departure dates. This is often the cheapest time to book. If circumstances have left you booking late, discount flights to Island Woods sometimes emerge just weeks before departure.
What does an Expedia Island Woods travel package include?
Expedia has everything you need to arrange your Island Woods escape, but what goes into your package is your call. Pick from any combination of flights, hotels and rental cars. After some activities to fill in your time? Once you've made your booking, you can add them on too. No matter your budget or style, there's a package deal to meet your needs.
What should I know before booking an Island Woods travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've created your package, add on fun stuff like tours and activities. Your next awesome vacation is only a few clicks away.
Can I choose my airline with an Island Woods Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're the boss! We have more than 550 partner airlines worldwide, so you have options galore when organizing your Island Woods adventure.
If I'm not able to travel, can I cancel my Island Woods vacation package?
We totally understand — unexpected stuff happens. If you've locked in an Island Woods vacation package and have to change or cancel it, we can help. We suggest visiting our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to amend or cancel your itinerary for free. If it's been longer than 24 hours, your hotel, airline or car rental company may charge a fee.

Things to do

Sunset Cruise Fort Myers Beach

Sunset Cruise Fort Myers Beach

CA $68
per adult
100% of travellers recommend
Sunset Cruise Fort Myers Beach
Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

CA $90
per adult
100% of travellers recommend
Dolphin Wildlife Cruise Fort Myers Beach
Dolphin and Shelling Cruise Tour at Fort Myers Beach

Dolphin and Shelling Cruise Tour at Fort Myers Beach

CA $105
per adult
100% of travellers recommend
Dolphin and Shelling Cruise Tour at 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.