
South Island Vacations from $524
Book a Hotel + Flight or Car together to unlock savings
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.


Manasota Key Resort
Save 100% on your flight
Price was $960, price is now $553 per person
$553
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (303 reviews)
We were only on property for 10 minutes before agreeing that we needed to come back every year.
It is a little piece of paradise. We used all the things, from lawn chairs to shuffle boards, paddle boards, bikes, and pool.
It is a short drive to restaurants and stores, but the kitchenette was perfect for cooking a quick meal. The rooms are spacious and comfortable.
Reviewed on Jul 16, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Save 100% on your flight
Price was $1,573, price is now $972 per person
$972
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,006 reviews)
BEWARE IF YOU ARE PLANNING TO RENT A CAR WHILE STAYING AT LAPLAYA RESORT!!!! This resort will charge you a $44 valet parking fee and a $2.64 parking tax fee PER DAY!! That is an additional $326.48 for a week’s stay just to keep a vehicle on their property!! You do not have the option to park your vehicle yourself. Also, you will feel obligated to tip the drivers when they get your vehicle both coming and going. The resort also automatically puts a $200 PER DAY charge on your credit card for daily “incidentals.” That charge will only drop off if you choose not to eat at the resort. When I brought all of this up to the front desk, none of the staff seemed to care that it was a bait and switch situation. My husband and I will NOT be staying at this resort in the future. Expedia also needs to do a better job of making ALL hotel fees crystal clear on their website!!
Reviewed on Jul 26, 2026

Casa Ybel Resort
Mid Island
Save 100% on your flight
Price was $1,894, price is now $1,289 per person
$1,289
per person
Aug 27 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (379 reviews)
+: Room was nice. Great view. Enjoyed sitting out on the enclosed lanai in the mornings and evenings. Quiet (other than the cleaning people speaking quite loudly outside our door one afternoon). Convenient to attractions and area restaurants.
-: Way too expensive. Restaurant prices were ridiculously high (although the food and service were good). Ditto pool bar. There were no wash clothes in our room. We had to wait until the next morning to get some, and then they were cosmetic wash clothes (black) which continually ran black dye. Ugh. Apparently you had to pay to rent beach chairs/umbrella at $40 a day. Seems overkill. We didn't bother to do this.
Reviewed on Jul 24, 2026

Bellasera Resort
Old Naples
Save 100% on your flight
Price was $2,046, price is now $1,408 per person
$1,408
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,295 reviews)
We really liked the property! The pool is a little small but the rest was amazing! The food was really good!
Reviewed on Jul 26, 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

Mid Island
1 out of top 10 points of interest in this area
While visiting Mid Island, you might make a stop by sights like Castle Beach and Estero Boulevard Beach.
South Island Hotel Deals

Pointe Estero Beach Resort
6640 Estero Blvd Fort Myers Beach FL
$430 nightly
The price is $471 total per night from Aug 13 to Aug 14
$471 total
Aug 13 - Aug 14
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"Love the place"
Reviewed on Jul 24, 2026

GullWing Beach Resort
6620 Estero Blvd Fort Myers Beach FL
$478 nightly
The price is $524 total per night from Jul 27 to Jul 28
$524 total
Jul 27 - Jul 28
Total with taxes and fees
9.4/10 Exceptional! (960 reviews)
"Great location, clean , only minus the beach chairs and umbrellas."
Reviewed on Jul 22, 2026

Beach Front Bargain at Estero Beach & Tennis Club!
Fort Myers Beach FL
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
Things to do

Fort Myers Beach Sunset and Dolphin Watching Cruise
$70
per adult
100% of travellers recommend

2.5-Hour Guided Group Kayak Tour on Big Hickory Pass
$55
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.























