South Island Vacations from $517

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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.
Lehigh Resort Club

Lehigh Resort Club

Joel
Save 100% on your flight
$517
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (115 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$972
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
$2,393,570
per person
Dec 1 - Dec 8
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing times said amenities. Prices for amenities and rentals were reasonable in my opinion. The restaurants range in price from reasonable to upscale dining. Our room was exactly as pictured. The entire property including the private beach - which was just across the road - were exceptionally clean. My only complaint was our bed was very firm for our tastes. The Gulf side beach was gorgeous. We saw many shore birds and dolphins. The bay side features a large marina and manatees in the cove. All staff we encountered were very friendly and helpful. We stayed in mid September and it appeared that most of the rooms were filled, but it was still very relaxing, quiet, and uncrowded. The location is excellent. It's easy to find off the main road through the islands and it's only a short drive to the attractions and beaches in both Sanibel and Captiva. Overall I would recommend and would stay here again.

Reviewed on Sep 20, 2026

Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

South Island
Save 100% on your flight
$869
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (13 reviews)
Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Windward Passage Resort

Windward Passage Resort

Save 100% on your flight
$835
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (11 reviews)
Wonderful view of the ocean

Reviewed on Sep 15, 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
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.

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.

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.

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

Winklers

While Winklers might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Key West Express and Estero Boulevard Beach.

A river with a cityscape in the background.

Laguna Shores

Though Laguna Shores might not have many top sights, you can venture to the surrounding area to see attractions like Lover's Key Beach and Santini Marina Shopping Plaza.

South Island Hotel Deals

Pointe Estero Beach Resort

Pointe Estero Beach Resort

6640 Estero Blvd Fort Myers Beach FL
$424 nightly
$464 total
Sep 25 - Sep 26
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"The property has everything it needs to be a 10/10, but the hotel service is a 0/10. Checkout is at 10:00 AM, which is extremely early. After checkout, you are no longer allowed to use any of the hotel facilities. You cannot use the pool, towels, beach chairs, or anything else. So, if you come for ..."

Reviewed on Sep 21, 2026

Pointe Estero Beach Resort
GullWing Beach Resort

GullWing Beach Resort

6620 Estero Blvd Fort Myers Beach FL
$499 nightly
$548 total
Sep 22 - Sep 23
Total with taxes and fees
9.6/10 Exceptional! (974 reviews)
"Everything was great. the location is perfect"

Reviewed on Sep 18, 2026

GullWing Beach Resort
Santa Maria Resort- Great Resort and Condo!!  Large pool/Hot Tub & Tiki Hut !!

Santa Maria Resort- Great Resort and Condo!! Large pool/Hot Tub & Tiki Hut !!

Fort Myers Beach FL
8.6/10 Excellent! (18 reviews)
"It was adequate. Beach accessibility was problematic for 2 people in the party with slight mobility issues"

Reviewed on Aug 3, 2026

Get rates
Santa Maria Resort- Great Resort and Condo!! Large pool/Hot Tub & Tiki Hut !!
See all 1,133 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.

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?
See properties

Santini Marina Shopping Plaza

8.8/10 (527 reviews)
You can browse for the perfect souvenirs at Santini Marina Shopping Plaza during your visit to Fort Myers Beach. Wander the beautiful beaches or discover the beautiful sunsets in this family-friendly area.
See properties

Things to do

Fort Myers Beach Sunset and Dolphin Watching Cruise

Fort Myers Beach Sunset and Dolphin Watching Cruise

$63
per adult
100% of travellers recommend
Fort Myers Beach Sunset and Dolphin Watching Cruise
2.5-Hour Guided Group Kayak Tour on Big Hickory Pass

2.5-Hour Guided Group Kayak Tour on Big Hickory Pass

$55
per adult
2.5-Hour Guided Group Kayak Tour on Big Hickory Pass
Copacetic Day Sail

Copacetic Day Sail

$70
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.