South Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
It was nice …. Good service at front desk and for the buainess center … frees snacks and drinks in the room was really nice !

Reviewed on Aug. 2, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.8/10 Excellent! (1,000 reviews)
No self parking available, forced to valet @ $44/ day Would recommend to add self parking option or reduce valet parking rate by 50%

Reviewed on Aug. 5, 2025

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,000 reviews)
Nice property, but rooms are dated, 3 star rating but paying 4-5 star prices. AC broke, we were offered another room but no help or golf cart to help move us at 10 PM to a different building.

Reviewed on Jul. 29, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.8/10 Exceptional! (500 reviews)
All was excellent. Luciana is the best

Reviewed on Aug. 3, 2025

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,049 reviews)
Staff was friendly and accommodating. Negatives 1.3 dehumidifiers in our suit, we emptied 2.TV goes blank and a shut off message is displayed when you try to tune to a channel in the guide that’s not available. Multiple times a day. 3. Concessions shut down 6:00 pm or earlier depending on the weather 4. Have a lounge that was under reconstruction along with other places in the resort. Nothing mentioned when booking it was under reconstruction 5. Shower soaps and shampoo in automatic feeds on the shower wall. Smelled old and moldy 6. Closed the pool a few times claiming weather in the area. Margaritaville pool was open. 7. Happy hour was upstairs in the dining room and not in the downstairs bars. What’s up with that? 8. Beach was under water when the tide came in, or the threat of a storm. Margaritaville’s was built up and dry. Site should have informed that the place was still under reconstruction

Reviewed on Aug. 5, 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
Default Image

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 $248 per night from Aug 12 to Aug 13
CA $248
CA $724 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Exceeded my expectations!"

Reviewed on Aug. 1, 2025

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 $274 per night from Aug 6 to Aug 7
CA $274
CA $799 total
Aug 6 - Aug 7
includes taxes & fees
9.4/10 Exceptional! (925 reviews)
"We loved the property, but I didn’t know the property was under construction. The pool view with the construction is not the best view. Aside from that everything was amazing. The apartment was so clean and comfortable."

Reviewed on Jul. 7, 2025

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
9.8/10 Exceptional! (131 reviews)
"Great place to stay!"

Reviewed on Jul. 18, 2025

Get rates
Great 9th Floor Views and Just 103 Yards from the Beach!
See all 1,028 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
Beach Vacations
Family Vacations
Family Vacations

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 $515. 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 lively bars.

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

Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

CA $96
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
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
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $89
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.