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 Castle Beach and Estero Boulevard Beach.

Find hotels in Mid Island

Our pick of the best 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 NZ$880 per night from 21 May to 22 May
NZ$880
21 May - 22 May
includes taxes & fees
9.4/10 Exceptional! (945 reviews)
The condo was clean with plenty of space. Full kitchen and great views from the balcony. The only negative is we experienced several groups of rowdy guests and after office hours there is little security and no one to contact.

Reviewed on 8 May 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! (89 reviews)
Super clean room,all the amenities you would need,clear instructions on how to use things, beach view, host is easy to contact.

Reviewed on 29 Apr 2026

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Beach Front Bargain at Estero Beach & Tennis Club!
7 Miles of Paradise! Completely Renovated Condo. Cleaning Included.

7 Miles of Paradise! Completely Renovated Condo. Cleaning Included.

Fort Myers Beach FL
9.8/10 Exceptional! (209 reviews)
The condo was great and had a really nice view. Everything was as advertised. Very close to the beach.

Reviewed on 9 May 2026

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7 Miles of Paradise! Completely Renovated Condo. Cleaning Included.
See all 1,091 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
Guided Kayak Eco Tour - Bunche Beach

Guided Kayak Eco Tour - Bunche Beach

NZ$119
per adult
98% of travellers recommend
Guided Kayak Eco Tour - Bunche Beach
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.