South Island Vacation Packages

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Top Holiday Package Deals in South Island

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.2/10 Very Good! (1,001 reviews)
The room, breakfast and front desk receptionist were awesome. The one downfall was when room service opened the door to the room the morning at 10 am of us leaving and asking what time we were leaving granted check our time is 12 pm.

Reviewed on Jul. 19, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
per person
Aug 30 - Sep 6
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Service was excellent

Reviewed on Jul. 19, 2025

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Park Shore
Save 100% on your flight
per person
Aug 30 - Sep 6
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,583 reviews)
This is like home away from home! Spa services are an integral part of the beauty of this resort! Food and drinks are top notch, and having been there for several visits over the years its great to see familiar faces on staff and receive the best service! Cannot wait to go back!

Reviewed on Jul. 20, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
per person
Aug 30 - Sep 6
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
A very nice hotel in the heart of downtown Naples. Clean modern rooms, attentive staff and a sunny pool deck. Naples’ best dining steps from your door.

Reviewed on Jul. 9, 2025

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
8.6/10 Excellent! (1,020 reviews)
Beautiful views from our balcony. Food was excellent, location, beach was clean, many places on premises to eat, snack machines, etc.

Reviewed on Jul. 20, 2025

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
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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

Pointe Estero

2 out of 5
6640 Estero Blvd, Fort Myers Beach, FL
The price is CA $229 per night from Jul 21 to Jul 22
CA $229
CA $702 total
Jul 21 - Jul 22
includes taxes & fees
9.2/10 Wonderful! (999 reviews)
My favorite place to stay on FMB
"I’ve stayed there with family many years before hurricane. It’s always been my favorite. The employees were very nice. Eddie at the front desk answered all our questions and always asked if things were going okay when we would run into him. Craig was another employee that was great, always talked ..."

Reviewed on Jul. 14, 2025

Pointe Estero
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
6620 Estero Blvd, Fort Myers Beach, FL
The price is CA $241 per night from Jul 21 to Jul 22
CA $241
CA $761 total
Jul 21 - Jul 22
includes taxes & fees
9.4/10 Exceptional! (925 reviews)
"We loved the property, but I didn’t know the property was under construction. The pool view with the construction is not the best view. Aside from that everything was amazing. The apartment was so clean and comfortable."

Reviewed on Jul. 7, 2025

GullWing Beach Resort
Great 9th Floor Views and Just 103 Yards from the Beach!

Great 9th Floor Views and Just 103 Yards from the Beach!

Fort Myers Beach
9.8/10 Exceptional! (128 reviews)
Amazing time
"Beach is beautiful! The condo is completely clean. Manager is quick to reply to any and all requests. We would stay here again and recommend to all family and friends. Thank you for a great week and experience:)"

Reviewed on May 10, 2025

Get rates
Great 9th Floor Views and Just 103 Yards from the Beach!
See all 993 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $330. 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

Key West Express

Explore the waterfront in Fort Myers Beach with a trip to Key West Express. Discover the area's beautiful sunsets and top-notch restaurants.

Key West Express

Things to do

Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

CA $84
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise

CA $89
per adult
100% of travellers recommend
Fort Myers Beach: Adults only BYOB Tiki Pub Daytime Cruise
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

CA $96
per adult
100% of travellers recommend
Southwest Florida Sunset 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.