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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,000 reviews)
Front desk was so nice ! Super sweet and friendly. Thank you

Reviewed on Mar. 15, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,273 reviews)
Great place on the beach with designated parking and friendly staff

Reviewed on Mar. 30, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
per person
May 11 - May 18
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (121 reviews)
We had a great time during our Spring Break staycation. Amy in the front desk and Ralph (driver) made our stay extra special. Truly two assets to the hotel.

Reviewed on Mar. 29, 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Jun. 1 - Jun. 8
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (2,127 reviews)
My husband and two teenagers booked a last minute get away and we were so happy that we did! The welcome we received was charming, our room was spotless and The Claw Bar was delicious! We enjoyed the close location to restaurants and food. The shuttle service provided was easy to use and the drivers were friendly and helpful. Absolutely great!

Reviewed on Mar. 29, 2025

GreenLinks Golf Villas at Lely Resort

GreenLinks Golf Villas at Lely Resort

3 out of 5
Save 100% on your flight
per person
Jun. 1 - Jun. 8
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (513 reviews)
We had a wonderful time!!

Reviewed on Mar. 15, 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

GullWing Beach Resort
GullWing Beach Resort
3.5 out of 5
6620 Estero Blvd, Fort Myers Beach, FL
The price is CA $473 per night from Apr. 5 to Apr. 6
CA $473
CA $1,040 total
includes taxes & fees
Apr 5 - Apr 6
9.4/10 Exceptional! (909 reviews)
"Wonderful to just walk out the door and onto the beach! Everything was nice: well-equipped kitchen with new appliances, washer and dryer etc. Some construction still going on, but this is the case for most places in Fort Myers Beach and it never bothered us. Great place to stay."

Reviewed on Feb. 23, 2025

GullWing Beach Resort
Pointe Estero
Pointe Estero
2 out of 5
6640 Estero Blvd, Fort Myers Beach, FL
9.2/10 Wonderful! (999 reviews)
"The 2bd beachfront condo was exactly as described. The layout was perfect and the views were amazing. Thoroughly enjoyed the screened in balconies The only thing that would have made it better is if 2 chairs and an umbrella were included in the price and not rentals from a separate company. But otherwise ..."

Reviewed on Sep. 12, 2022

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Pointe Estero
Spectacular Sunsets with Direct Gulf views, Pool, 11th floor, Private Wi-Fi
Spectacular Sunsets with Direct Gulf views, Pool, 11th floor, Private Wi-Fi
Fort Myers Beach
9.8/10 Exceptional! (188 reviews)
Beautiful view
"The view of the water and sunsets were beautiful. We understand that the renewal of the beach is needed but weren't pleased that they worked all night long. Also, there was a toilet leak that was an inconvenience but those type of things happen. We were pleased with communication with Mike and also ..."

Reviewed on Mar. 25, 2025

Get rates
Spectacular Sunsets with Direct Gulf views, Pool, 11th floor, Private Wi-Fi
See all 932 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 $512. 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

Lynn Hall Memorial Park

Lynn Hall Memorial Park

4/5(20 reviews)

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
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

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

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $93
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

CA $84
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Tiki Boat Tours

Tiki Boat Tours

CA $72
per adult
Tiki Boat Tours
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.