Gateway Vacations from $237
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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.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $456, price is now $237 per person
$237
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
The staff at the counter are not friendly at all, the room was just clean.
Reviewed on Jan 6, 2026
Matanzas Inn Bayside Resort and Marina
Price was $709, price is now $346 per person
$346
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Erica was wonderful, she was very pleasant and very accommodating.
Reviewed on Jan 2, 2026
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,160, price is now $643 per person
$643
per person
Mar 22 - Mar 26
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
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Price was $1,828, price is now $1,017 per person
$1,017
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Wonderful staff and management, great outdoor amenities and we all agreed the NYE events were perfect for our grandchildren. Some of the rooms were a bit dated but the staff quickly responded with appropriate room changes.
Reviewed on Jan 8, 2026
Hyatt Place Fort Myers/at The Forum
The Forum
Save 100% on your flight
Price was $429, price is now $239 per person
$239
per person
Mar 23 - Mar 26
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
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
$223 nightly
The price is $249 total per night from Jan 12 to Jan 13
$249 total
Jan 12 - Jan 13
Total with taxes and fees
9/10 Wonderful! (1,082 reviews)
It was our first time there. Would go back.
Reviewed on Jan 6, 2026
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
$391 nightly
The price is $436 total per night from Jan 12 to Jan 13
$436 total
Jan 12 - Jan 13
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Staff was very nice. A problem we had was their were 4 of us in the room and trying to get 4 towels and washcloths was a hard task, also coffee in room.
Reviewed on Jan 3, 2026
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
$271 nightly
The price is $303 total per night from Jan 12 to Jan 13
$303 total
Jan 12 - Jan 13
Total with taxes and fees
8.8/10 Excellent! (1,768 reviews)
Will be back.
Reviewed on Jan 7, 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
4.5/5(394 reviews)
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.