South Island Vacations from $518

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Your South Island Vacation

When it's time for your next adventure, choose a South Island vacation package. From its coastal beaches to a whole lot more, there are tons of enticing reasons to base yourself in this neighborhood. Start your trip to South Island by checking out nearby attractions such as Lovers Key Beach, Santini Marina Shopping Plaza and Mound House. No matter your travel goals or budget, booking your ideal South Island vacation is simple with Expedia.

The Latest South Island Vacation Packages

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 $1,309, price is now $518 per person
$518
per person
Jan 15 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Very nice Staff is excellent.

Reviewed on Nov 24, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,646, price is now $878 per person
$878
per person
Jan 15 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Clean room! Wonderful lazy river! Had such a great vacation there!

Reviewed on Nov 25, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,946, price is now $1,039 per person
$1,039
per person
Feb 16 - Feb 21
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
The bed was very comfortable. The shower was clean and updated. We enjoyed the fire pits at night.

Reviewed on Nov 27, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,985, price is now $1,106 per person
$1,106
per person
Feb 16 - Feb 21
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
El personal súper amable y todo muy limpio,la habitación excelente

Reviewed on Nov 24, 2025

Hilton Naples

Hilton Naples

4 out of 5
Central Naples
Save 100% on your flight
Price was $1,166, price is now $713 per person
$713
per person
Feb 1 - Feb 5
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,312 reviews)
The room was fine, my issue was customer service. We left a few things in the room by mistake when we checked out at 9am, I called the desk 20 minutes later and told them we'd swing by to pick the items up around 11. When we arrived at 11:30, it took 20 minutes to get the items from housekeeping.

Reviewed on Nov 29, 2025

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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
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Mid Island

1 out of top 10 points of interest in this area
4.5/5(108 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
$506 nightly
The price is $556 total per night from Dec 6 to Dec 7
$556 total
Dec 6 - Dec 7
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Everything was perfect.

Reviewed on Nov 16, 2025

Pointe Estero Beach Resort
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
6620 Estero Blvd Fort Myers Beach FL
$512 nightly
The price is $563 total per night from Dec 2 to Dec 3
$563 total
Dec 2 - Dec 3
Total with taxes and fees
9.4/10 Exceptional! (932 reviews)
Wonderful vacation at the Gullwing.

Reviewed on Nov 2, 2025

GullWing Beach Resort
Yachts and Villas By the Bay

Yachts and Villas By the Bay

Fort Myers Beach FL
9/10 Wonderful! (39 reviews)
Winter get away
This is a great place to relax close to shops and the beach. Most important everyone is friendly. We enjoyed the stay.

Reviewed on Jan 23, 2025

Get rates
Yachts and Villas By the Bay
See all 1,150 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in South Island

#kidsfun I wouldn't say feed the seagulls but there are so many nice restaurants and beach shops.

Castle Beach

Why not spend a lazy afternoon at Castle Beach during your trip to Fort Myers Beach?

Castle Beach
Bunche Beach featuring general coastal views and a 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
Fishing Pier Fort Myers Beach featuring a sandy beach and a bridge

Lynn Hall Memorial Park

4.5/5(786 reviews)

Walk over the water on a long pier that’s popular day and night for the breeze and fishing.

Lynn Hall Memorial Park

Things to do

Fort Myers Beach Sunset Excursion

Fort Myers Beach Sunset Excursion

$65
per adult
100% of travellers recommend
Fort Myers Beach Sunset Excursion
Southwest Florida Sunset Sail

Southwest Florida Sunset Sail

$70
per adult
100% of travellers recommend
Southwest Florida Sunset Sail
Dolphin and Sightseeing Tiki Cruise

Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included

$65
per adult
Fort Myers Beach Dolphin & Sightseeing Tour Refreshments Included
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.