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
Sunset on the island of Sanibel.Florida.USA

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 Estero Boulevard Beach and Sterling Ave 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$1,082 per night from 27 Apr to 28 Apr
NZ$1,082
27 Apr - 28 Apr
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
The property was special and our stay was excellent. Spacious, clean, friendly staff and the beach was clean. Seating area at night with fire pits made for a nice way to end the day.

Reviewed on 28 Mar 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$1,168 per night from 27 Apr to 28 Apr
NZ$1,168
27 Apr - 28 Apr
includes taxes & fees
9.4/10 Exceptional! (938 reviews)
Wonderful stay

Reviewed on 26 Mar 2026

GullWing Beach Resort
Carribean Beach Club

Carribean Beach Club

2.5 out of 5
7600 Estero Blvd Fort Myers Beach FL
8.8/10 Excellent! (5 reviews)
Great and quiet location. Small room and needed updating but was clean. Pool was clean and enjoyed it. The hot tub was cloudy and questionable. The beach location was fantastic and private. If you want to see dolphins and get some shelling in, this is perfect. There are low tide pools when you walk ...

Reviewed on 23 Mar 2026

Get rates
Carribean Beach Club
See all 1,137 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.

Discover the most popular places to visit in South Island

Smugglers Cove Adventure Golf

You can take time to visit Smugglers Cove Adventure Golf during your travels to Fort Myers Beach. Discover the beautiful sunsets and lively bars in this family-friendly area.

Smugglers Cove Adventure Golf

Activities

Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

NZ$119
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
Dolphin Wildlife Cruise Fort Myers Beach
Copacetic Day Sail

Copacetic Day Sail

NZ$119
per adult
100% of travellers recommend
Copacetic Day Sail
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.