South Island Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in South Island

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was CA $1,555, price is now CA $939 per person
CA $939
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,008 reviews)
We enjoyed our stay! Very convenient location, right on the water, clean with recently renovated rooms. We went for a girls weekend and loved it! The only thing I can’t rave about was they had very poor water pressure, not sure if it was because we were on an end unit, but it was a trickle out of the shower head which can be a little difficult if you have a lot of hair, no hairdryer in room, and wish they had a full sized mirror in the room. Regardless I would definitely recommend staying there! It’s a beautiful property!

Reviewed on Apr 14, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $3,104, price is now CA $1,603 per person
CA $1,603
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
Excellent location and hotel!

Reviewed on Apr 12, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $2,243, price is now CA $1,203 per person
CA $1,203
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (748 reviews)
Spectacular spot. New hotel hits all the right notes. Service was superb. The room was immaculate and had a tremendous view. The first level pool is huge. I swam laps every day. The showstopper though is the rooftop pool and bar. I watched the Masters in splendor with views east and west. Again service was great and the food was great too. Check it out.

Reviewed on Apr 17, 2026

Casa Playa Beach Resort

Casa Playa Beach Resort

2.5 out of 5
Price was CA $2,001, price is now CA $1,297 per person
CA $1,297
per person
Jun 30 - Jul 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (175 reviews)
A big plus having chairs and umbrellas available.

Reviewed on Apr 15, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $1,743, price is now CA $1,135 per person
CA $1,135
per person
Jul 8 - Jul 12
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (821 reviews)
spectacular place for a weekend!!

Reviewed on Apr 16, 2026

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
4.5/5(4 area reviews)

While visiting Mid Island, you might make a stop by sights like Estero Boulevard Beach and Sterling Ave Beach.

Find hotels in Mid Island

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 CA $184 per night from May 7 to May 8
CA $184
CA $650 total
May 7 - May 8
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Great place, carpets could be updated

Reviewed on Apr 14, 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 CA $198 per night from May 4 to May 5
CA $198
CA $712 total
May 4 - May 5
includes taxes & fees
9.4/10 Exceptional! (943 reviews)
Great location right on the beach.

Reviewed on Apr 8, 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! (88 reviews)
We stayed in this condo the first full week of April 2026. Everything from communication to check-in to departure was made easy by the promptness and thoroughness of our host. The condo was beyond well stocked from bath items, linens, towels to paper products (toilet tissue, paper towels, Kleenex) ...

Reviewed on Apr 14, 2026

Get rates
Beach Front Bargain at Estero Beach & Tennis Club!
See all 1,102 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.
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Frequently asked questions

How much does a South Island vacation package cost?
Get set to book, because a getaway to South Island starts from an enticing CA $939. 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 vacation 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 fulfill those vacation dreams.
How far in advance should I book my South Island vacation?
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 vacation 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 vacation package?
If your vacation 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

Bunche Beach

Bunche Beach

Find a relatively obscure beach in a popular area of sand, warm water and a fascinating variety of coastal life. You’ll be thankful for the uncrowded space.

Bunche Beach
Lynn Hall Memorial Park

Lynn Hall Memorial Park

4/5(20 reviews)

Why not spend a carefree afternoon at Lynn Hall Memorial Park during your travels in Fort Myers Beach? Amble around this family-friendly area's seaside and enjoy its lively bars.

Lynn Hall Memorial Park
Palm trees at Fort Myers Beach Bowditch Point Park, Florida USA

Bowditch Point Park

You can take time to visit Bowditch Point Park during your travels to Fort Myers Beach. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

Bowditch Point Park

Things to do

Dolphin Wildlife Cruise Fort Myers Beach

Dolphin Wildlife Cruise Fort Myers Beach

CA $87
per adult
Dolphin Wildlife Cruise Fort Myers Beach
Clear Kayak Guided Eco Tour in North Naples

Clear Kayak Guided Eco Tour in North Naples

CA $122
per adult
100% of travellers recommend
Clear Kayak Guided Eco Tour in North Naples
Guided Kayak Eco Tour - Bunche Beach

Guided Kayak Eco Tour - Bunche Beach

CA $96
per adult
98% of travellers recommend
Guided Kayak Eco Tour - Bunche 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.