South Island Holidays
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Our guide on 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
Mid Island
2 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.
TP Hill's
When in TP Hill's, you can plan a visit to Key West Express and Estero Boulevard Beach, some noteworthy sights in the nearby area.
Downtown Fort Myers Beach
1 out of top 10 points of interest in this area
If you're spending some time in Downtown Fort Myers Beach, Lynn Hall Memorial Park and Estero Boulevard Beach are top sights worth seeing.
Winklers
Winklers might not have many top sights, but Key West Express and Estero Boulevard Beach are two attractions nearby that you can check out.
Laguna Shores
While Laguna Shores may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lover's Key Beach and Santini Marina Shopping Plaza.
Our pick of the best South Island Hotel Deals
Pointe Estero Beach Resort
6640 Estero Blvd Fort Myers Beach FL
NZ$898
14 Oct - 15 Oct
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Loved this place. Down side is we spent 2 nights uncomfortable because air conditioning stopped working. It was repaired in a timely way but 2 nights with no air when it was very hot was not good. There was no one to report it to we were told at the office at about 4:45. So next day when the guy ..."
Reviewed on 9 Oct 2026
GullWing Beach Resort
6620 Estero Blvd Fort Myers Beach FL
NZ$1,002
12 Oct - 13 Oct
includes taxes & fees
Mariners Boathouse by Coolvacay
7630 Estero Blvd Fort Myers Beach FL
9.8/10 Exceptional! (15 reviews)
"Very nice place, our 2nd time here and we still love it"
Reviewed on 7 Sept 2026
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.
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?
Santini Marina Shopping Plaza
8.8/10 (527 reviews)
You can do some window-shopping at Santini Marina Shopping Plaza during your trip to Fort Myers Beach. Wander the beautiful beaches or discover the beautiful sunsets in this family-friendly area.
Activities
2.5-Hour Guided Group Kayak Tour on Big Hickory Pass
NZ$96
per adult
Sunset Cruise Fort Myers Beach
NZ$80
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.