South Island Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

  • Rest easy

    Plan, book, and manage your trip all in one place

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
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 Castle Beach and Estero Boulevard Beach.

Find hotels in Mid Island

Our pick of the best 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 NZ$813 per night from 4 Aug to 5 Aug
NZ$813
4 Aug - 5 Aug
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Spacious clean and nice condo"

Reviewed on 28 June 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 NZ$895 per night from 29 July to 30 July
NZ$895
29 July - 30 July
includes taxes & fees
9.4/10 Exceptional! (955 reviews)
"We have stayed here before. We love how big the rooms are. The pool is always clean. Their is always someone cleaning around the property"

Reviewed on 27 June 2026

GullWing Beach Resort
Beach Front Bargain at Estero Beach & Tennis Club!

Beach Front Bargain at Estero Beach & Tennis Club!

Fort Myers Beach FL
10/10 Exceptional! (91 reviews)
"Unfortunately, due to other circumstances, I was not able to go on the trip and had to cancel. The host did an excellent job of keeping posted about other balcony construction taking place long before I could check in and was fully understanding if I had to cancel at the time. Because of the owner's ..."

Reviewed on 4 June 2026

Get rates
Beach Front Bargain at Estero Beach & Tennis Club!
See all 1,122 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.

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

Activities

Copacetic Day Sail

Copacetic Day Sail

NZ$119
per adult
100% of travellers recommend
Copacetic Day Sail
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

NZ$118
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

NZ$109
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.