South Island Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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(2 area reviews)

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

Find hotels in Mid Island

Top hotels in South Island

GullWing Beach Resort
GullWing Beach Resort
3.5 out of 5
6620 Estero Blvd, Fort Myers Beach, FL
The price is S$687 per night from 2 Dec to 3 Dec
S$687
includes taxes & fees
2 Dec - 3 Dec
9.4/10 Exceptional! (896 reviews)
Nice resort but some construction noises
"We liked the location and the room. There is some noisy construction work going on in the resort and in the buildings nearby. However, we decided to stay for two weeks."

Reviewed on 17 Nov,2024

GullWing Beach Resort
Estero Beach & Tennis by VTrips
Estero Beach & Tennis by VTrips
2.5 out of 5
7300 Estero Blvd., Fort Myers Beach, FL
5/10 (4 reviews)
"The views and sunsets were beautiful."

Reviewed on 10 Feb,2024

Get rates
Estero Beach & Tennis by VTrips
See all 965 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.

Frequently asked questions

How much does a South Island holiday package cost?
Get set to book, because a getaway to South Island starts from an enticing . 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 holiday 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 fulfil those holiday dreams.
How far in advance should I book my South Island holiday?
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 holiday 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 holiday package?
If your holiday 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.

Things to do

2hr Tiki Pub Fun in the Sun Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

S$59
Per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
Clear Kayak Guided Tours in Naples

Clear Kayak Guided Tours in Naples

S$104
Per adult
100% of travellers recommend
Clear Kayak Guided Tours in Naples
Tiki Boat Tours

Tiki Boat Tours

S$66
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.