Gateway Vacation Packages 2026 from $677

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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.

Casa Tiki

Hancock

Save 100% on your flight

$677

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

No reviews

Tween Waters Island Resort & Spa

Save 100% on your flight

$1,018

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Very nice place to enjoy and have a good time. Beach across the street, pool bar and restaurants nearby. Super quite and relaxing. We definitely recommend this place and hopefully coming back soon

Reviewed on Aug 10, 2026

South Seas

Save 100% on your flight

$984

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.4/10 Very Good! (1,004 reviews)

Manasota Key Resort

Save 100% on your flight

$927

per person

Sep 14 - Sep 19

found 2 days ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (307 reviews)

Wow! I wasn’t sure what to expect with this being our 1st trip to this part of FL! But it exceeded our expectations! The view of the ocean, clean room, amenities, and ease of laundry! Helpful staff and so welcoming! We will for sure be back! Thank you!

Reviewed on Aug 10, 2026

The Perry Hotel Naples

Save 100% on your flight

$834

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (992 reviews)

Where to stay in Gateway

Find the best Gateway areas and neighborhoods for the activities you enjoy most. Learn more about Gateway

A beach at sunset with the sun reflecting on the water, palm trees, and a clear sky.

Villas

1 out of top 10 points of interest in this area

The beaches and abundant dining options are top of the list for many visitors to Villas. A stop by Bell Tower Shops or Regal Belltower might round out your trip.

An aerial view of a coastal area with a bridge connecting two land masses, a beach, and a clear blue sky.

Iona

While visiting Iona, you might make a stop by sights like Estero Bay Preserve State Park and Tribby Arts Center.

Punta Rassa

1 out of top 10 points of interest in this area

Punta Rassa is a destination visitors seek out for is beaches, abundant dining options, and waterfront views. You might want to check out attractions like Sanibel Harbour or Sanibel Harbour Beach while you're exploring the neighborhood.

A pier extending into the water with two gazebos at the end, under a sunset sky.

South Fort Myers

While visiting South Fort Myers, you might make a stop by sights like Estero Bay Preserve State Park and Castle Golf.

Daniels Corridor

2 out of top 10 points of interest in this area

While visiting Daniels Corridor, you might make a stop by sights like Lee Health Sports Complex and JetBlue Park at Fenway South.

Gateway Hotel Deals

Margaritaville Beach Resort Fort Myers

251 Crescent Street Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$202 nightly

$226 total

Aug 31 - Sep 1

Total with taxes and fees

9/10 Wonderful! (2,423 reviews)

"Very clean, it smells really good. Many options to drink and eat."

Reviewed on Aug 12, 2026

Baymont by Wyndham Fort Myers Central

4850 S Cleveland Ave Fort Myers FL

Fully refundableReserve now, pay when you stay

$62 nightly

$69 total

Aug 31 - Sep 1

Total with taxes and fees

Lani Kai Beachfront Resort

1400 Estero Blvd Fort Myers Beach FL

Fully refundableReserve now, pay when you stay

$136 nightly

$152 total

Aug 13 - Aug 14

Total with taxes and fees

See all 14,473 properties in Gateway

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.