Gateway Vacations from $403
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Your Gateway Vacation
With all your travel plans organized before you set off, our Gateway vacation packages mean you can focus more on having fun! One place to consider staying in this vibrant city is Miromar Lakes, which is good for watersports and golfing. If taking in sights is on the to-do list during your trip to Gateway, visit popular attractions like JetBlue Park at Fenway South, Six Mile Cypress Slough Preserve and Legends Golf and Country Club. A couple of clicks is all it takes to create a tailored Gateway vacation on Expedia.
The Latest Gateway Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina
Save 100% on your flight
Price was $775, price is now $403 per person
$403
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
We loved the location. The space was very clean and large. We will definitely be staying here again.
Reviewed on Jan 16, 2026
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was $2,396, price is now $1,256 per person
$1,256
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
The place was really nice. The amenities such as several pools, jacuzzies, dry and wet saunas, adjacent to golf course, ferry shuttle to a beautiful beach made for a very relaxing time. Just what the doctor ordered. We had some problems with our room, AC in our room broke and needed to be fixed, blow dryer was broken. Lazy river was down for the week. The Concierges seemed reluctant to help at times, as if they were told not to let patrons take advantage. Ex. We missed the shuttle to the island by a minute and the concierge was like oh well your tough luck attitude rather than.... how can I make it happen for you.
Reviewed on Jan 15, 2026
Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
Price was $972, price is now $513 per person
$513
per person
Mar 12 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,004 reviews)
Great hotel
Great people and service.
Very good breakfast
Reviewed on Jan 2, 2026
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,317, price is now $739 per person
$739
per person
Mar 14 - Mar 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Beautiful property with everything one could possibly need for a get-away.
Reviewed on Jan 6, 2026
Where to stay in Gateway
Find the best Gateway areas and neighborhoods for the activities you enjoy most. Learn more about Gateway
Iona
Iona might not have many top sights, but Cape Coral Yacht Club Beach and Key West Express are two attractions nearby that you can check out.
Gateway Hotel Deals
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $218 total per night from Jan 19 to Jan 20
$218 total
Jan 19 - Jan 20
Total with taxes and fees
9/10 Wonderful! (1,097 reviews)
Great location, fun atmosphere lots of fun amenities!
Reviewed on Jan 11, 2026
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
$401 nightly
The price is $448 total per night from Jan 18 to Jan 19
$448 total
Jan 18 - Jan 19
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Our balcony had the best view of Sanibel Island and Harbour.
Reviewed on Jan 14, 2026
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$289 nightly
The price is $323 total per night from Jan 20 to Jan 21
$323 total
Jan 20 - Jan 21
Total with taxes and fees
8.8/10 Excellent! (1,787 reviews)
Everyone was so nice and the hotel was so nice and clean.
Reviewed on Jan 13, 2026
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.
Discover the most popular places to visit in Gateway
JetBlue Park at Fenway South
Catch an event at JetBlue Park at Fenway South during your trip to Fort Myers. Amble around the area's beautiful beaches or attend a baseball game.
Things to do
Historic Walking Tour of Fort Myers
$26
per adult
100% of travellers recommend
Everglades Day Safari from Sanibel, Fort Myers & Naples
$225
per adult
Self-Guided Fort Myers Scavenger Hunt: His Greatest Invention
$12
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.