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

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    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.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was CA $2,290, price is now CA $1,415 per person
CA $1,415
per person
Dec 15 - Dec 22
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Fort Myers (RSW)
9.4/10 Exceptional! (135 reviews)
Beautiful location.

Reviewed on Nov 8, 2026

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 $4,954, price is now CA $3,233 per person
CA $3,233
per person
Jan 17 - Jan 21
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (1,003 reviews)
Great resort. Probably the nicest on the entire run of resorts on this beach. And that includes the Ritz-Carlton just upo the way. Obviously, the Ritz is classier, but La Playa felt more exclusive and comfortable. The beach experience is top-notch, with complimentary umbrellas and beach chairs upon request. The bar and restaurant were very good. Drinks are pricey, to be sure, which can add up if you're ordering while relaxing on the beach for days on end. About a 25 minute drive to the best restaurants and shops in Old Town Naples. This was a little far for us, since we didn't have a car and Uber'd whenever we went out. Overall, a very nice experience.

Reviewed on Nov 9, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,148, price is now CA $1,498 per person
CA $1,498
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (1,224 reviews)

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

3 out of 5
Price was CA $4,798, price is now CA $3,407 per person
CA $3,407
per person
Jan 25 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 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 $233 per night from Dec 10 to Dec 11
CA $233
CA $719 total
Dec 10 - Dec 11
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"No hay personal desp de las 5 de la tarde que te ayude con nada . Si quieres ir a un hotel que lo tienes que llevar todo este es el hotel . Tuve muy mala experiencia llegué desp de las 5 pm y estuve dos horas para que me dieran un código para acceder a mi habitación"

Reviewed on Oct 31, 2026

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 $257 per night from Dec 1 to Dec 2
CA $257
CA $793 total
Dec 1 - Dec 2
includes taxes & fees
9.6/10 Exceptional! (987 reviews)
"Beautiful property, generous size condos and all the amenities."

Reviewed on Nov 6, 2026

GullWing Beach Resort
Santa Maria Resort- Great Resort and Condo!! Large pool/Hot Tub & Tiki Hut !!

Santa Maria Resort- Great Resort and Condo!! Large pool/Hot Tub & Tiki Hut !!

Fort Myers Beach FL
8.6/10 Excellent! (18 reviews)
"It was adequate. Beach accessibility was problematic for 2 people in the party with slight mobility issues"

Reviewed on Aug 3, 2026

Get rates
Santa Maria Resort- Great Resort and Condo!! Large pool/Hot Tub & Tiki Hut !!
See all 1,154 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
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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 $1,415. 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 $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
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.