South Island Vacation Packages

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Top Holiday Package Deals in South Island

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was CA $981, price is now CA $595 per person
CA $595
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.2/10 Very Good! (1,011 reviews)
Property was good. . Shopwer drains poorly standing in water all the time

Reviewed on Sep. 8, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $4,656, price is now CA $2,044 per person
CA $2,044
per person
Nov 29 - Dec 6
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep. 2, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was CA $1,193, price is now CA $628 per person
CA $628
per person
Nov 18 - Nov 25
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Over all a good stay and great price. Only issue would be the mattress was old lumpy , came home with back pain.

Reviewed on Sep. 8, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $3,743, price is now CA $2,140 per person
CA $2,140
per person
Nov 29 - Dec 6
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
They know how to make you feel special. The service was incredible; everyone is very, very friendly. The hotel is beautiful, very quiet, and centrally located just a few minutes from the beach. If you want a place to relax, this is the one. We will definitely be back.

Reviewed on Sep. 8, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,637, price is now CA $1,528 per person
CA $1,528
per person
Nov 29 - Dec 6
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
nice and very clean, comfortable room, quit at night around the pool feel good

Reviewed on Sep. 8, 2025

Where to stay in South Island

Find the best South Island areas and neighborhoods for the activities you enjoy most. Learn more about South Island
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Mid Island

1 out of top 10 points of interest in this area
4.5/5(4 area reviews)

While visiting Mid Island, you might make a stop by sights like Estero Boulevard Beach and Sterling Ave Beach.

Find hotels in Mid Island

South Island Hotel Deals

Pointe Estero Beach Resort

Pointe Estero Beach Resort

2 out of 5
6640 Estero Blvd, Fort Myers Beach, FL
The price is CA $275 per night from Oct 1 to Oct 2
CA $275
CA $756 total
Oct 1 - Oct 2
includes taxes & fees
Pointe Estero Beach Resort
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
6620 Estero Blvd, Fort Myers Beach, FL
The price is CA $251 per night from Sep 9 to Sep 10
CA $251
CA $776 total
Sep 9 - Sep 10
includes taxes & fees
GullWing Beach Resort
Great 9th Floor Views and Just 103 Yards from the Beach!

Great 9th Floor Views and Just 103 Yards from the Beach!

Fort Myers Beach
Get rates
Great 9th Floor Views and Just 103 Yards from the Beach!
See all 1,051 properties in South Island
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
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a South Island vacation package cost?
Get set to book, because a getaway to South Island starts from an enticing CA $595. When you bundle your flights, hotels and car rentals into a package, you'll score great deals.
How do I get a cheap travel package to South Island?
One word: bundle. Hotels, rental cars and flights — combine whatever you need into a South Island vacation package and save. Score even better deals when you add extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to tailor your trip your own way. We offer more than 550 partner airlines and 1,000,000 properties worldwide, so that everyone has a chance to travel and fulfill those vacation dreams.
How far in advance should I book my South Island vacation?
While not all airlines release ticket prices early, customers are usually able to compare international airfares on Expedia up to 12 months in advance. This is the time when you'll nab some incredible deals. If you've left everything to the last minute, you might get lucky. Low prices sometimes emerge a few weeks prior to departure.
What does an Expedia South Island travel package include?
Flights, hotels and a cool set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a few sightseeing tours and watch your savings stack up. When it comes to creating your South Island trip, you're the boss!
What should I know before booking a South Island travel package?
You can look forward to saving with an Expedia travel package. Bundle your flights, rental cars and hotels and score exciting discounts. You're not limited to hotels, however. Book with us and take your pick of beachside villas, mountain cabins and even treehouses and ranches!
Can I choose my airline with a South Island Expedia vacation package?
Yes, and with more than 550 airlines to choose from across the globe, you've got lots of choice. Take a look at the available options and find out which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my South Island vacation package?
If your vacation plans in South Island have changed, it's good to know that you can cancel or amend your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may impose a fee. To find out more, visit our Customer Service Portal.

Discover the most popular places to visit in South Island

Bunche Beach

Bunche Beach

Find a relatively obscure beach in a popular area of sand, warm water and a fascinating variety of coastal life. You’ll be thankful for the uncrowded space.

Bunche Beach
Lynn Hall Memorial Park

Lynn Hall Memorial Park

Why not spend a carefree afternoon at Lynn Hall Memorial Park during your travels in Fort Myers Beach? Amble around this family-friendly area's seaside and enjoy its top-notch restaurants.

Lynn Hall Memorial Park

Key West Express

Explore the waterfront in Fort Myers Beach with a trip to Key West Express. Discover the area's beautiful sunsets and lively bars.

Key West Express

Things to do

Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

CA $89
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise

CA $82
per adult
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $90
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
See all activities in Fort Myers Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.