South Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in South Island

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was CA $1,183, price is now CA $834 per person
CA $834
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,012 reviews)

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 $3,153, price is now CA $1,863 per person
CA $1,863
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,007 reviews)
Love it and why we keep coming back!

Reviewed on Aug 4, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,628, price is now CA $1,088 per person
CA $1,088
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.6/10 Exceptional! (970 reviews)
Great place to stay. Everything you need is on the property

Reviewed on Aug 4, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was CA $1,715, price is now CA $1,189 per person
CA $1,189
per person
Oct 22 - Oct 29
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.8/10 Exceptional! (1,276 reviews)

Casa Tiki

Casa Tiki

3 out of 5
Hancock
Price was CA $1,446, price is now CA $1,027 per person
CA $1,027
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
No reviews

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
A sunset over a calm sea with trees framing the view.

Mid Island

1 out of top 10 points of interest in this area

While visiting Mid Island, you might make a stop by sights like Castle Beach and Estero Boulevard 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 $207 per night from Aug 16 to Aug 17
CA $207
CA $687 total
Aug 16 - Aug 17
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 $225 per night from Aug 12 to Aug 13
CA $225
CA $754 total
Aug 12 - Aug 13
includes taxes & fees
GullWing Beach Resort
Beach Front Bargain at Estero Beach & Tennis Club!

Beach Front Bargain at Estero Beach & Tennis Club!

Fort Myers Beach FL
10/10 Exceptional! (93 reviews)
"Other than the noise from the balcony renovations on other balconies, (above and below me) the stay was great. Too many shells on the beach made walking difficult without shoes. July isn't the best time due to frequent rain showers, riptides and hot humid weather, but that's Florida."

Reviewed on Aug 3, 2026

Get rates
Beach Front Bargain at Estero Beach & Tennis Club!
See all 1,135 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.
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All Inclusive 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 $834. 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.

Stay near popular South Island attractions

Castle Beach

8.0/10 (7 reviews)
Why not spend a lazy afternoon at Castle Beach during your trip to Fort Myers Beach?
See properties

Things to do

Sunset Cruise Fort Myers Beach

Sunset Cruise Fort Myers Beach

CA $67
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
Guided Kayak Eco Tour - Bunche Beach

Guided Kayak Eco Tour - Bunche Beach

CA $99
per adult
98% of travellers recommend
Guided Kayak Eco Tour - Bunche Beach
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.