South Island Holidays

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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
A sunset over a calm sea with trees framing the view.

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.

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A coastal cityscape with a marina, dense housing, and a 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.

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A beach at sunset with a pink and purple sky, people walking, and a lifeguard tower in the distance.

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.

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A coastal town with a beach, buildings, and a road.

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.

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A river with a cityscape in the background.

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.

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Top hotels in South Island

Pointe Estero Beach Resort

Pointe Estero Beach Resort

6640 Estero Blvd Fort Myers Beach FL
S$659
30 Sept - 1 Oct
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Great for family vacations where you just want to relax and enjoy the beach. Close enough to the night life if that's your thing but far enough that you can sleep peacefully. Highly recommend this place, the apartment has everything you need."

Reviewed on 13 Sept, 2026

Pointe Estero Beach Resort
GullWing Beach Resort

GullWing Beach Resort

6620 Estero Blvd Fort Myers Beach FL
S$667
15 Sept - 16 Sept
includes taxes & fees
9.6/10 Exceptional! (972 reviews)
"The location was great. It was really clean. It had great amenities. The beds were comfortable. Little upset about the noise that came out of the mechanical room, but dealt with it... Would stay again."

Reviewed on 8 Sept, 2026

GullWing Beach Resort
Mariners Boathouse by Coolvacay

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

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Mariners Boathouse by Coolvacay
See all 1,134 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?
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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.
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Things to do

Sunset Dolphin Cruise with Sanibel Lighthouse Views

Sunset Dolphin Cruise with Sanibel Lighthouse Views

S$78
per adult
94% of travellers recommend
Sunset Dolphin Cruise with Sanibel Lighthouse Views
Everglades Day Safari from Fort Myers/Naples Area

Everglades Day Safari from Fort Myers/Naples Area

S$319
per adult
90% of travellers recommend
Everglades Day Safari from Fort Myers/Naples Area
Copacetic Day Sail

Copacetic Day Sail

S$89
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. 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.