Gateway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Price found within the past 48 hours. Click for updated prices.
  • 2 outdoor pools, cabanas (surcharge), pool umbrellas
    Jul 29 - Aug 5

    The Perry Hotel Naples + Flight

    Naples
    7 nights
    4.5 star property
    9.6/10 - Exceptional (827 reviews)
    "I come back again"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • 1 stop RSW - YYZ • 1 stop
    CA $1,627
    CA $973
    per traveller
    found 2 days ago
    The Perry Hotel Naples
  • View from room
    Aug 12 - Aug 20

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    8 nights
    4.5 star property
    9.0/10 - Wonderful (1,000 reviews)
    "Enjoyed the bar/food access on the beach; plenty of chairs/umbrellas/towels (which were all included); all the men were quick to help you set-up your preferred location on the Beach. Food was great (with healthy options) and room service was quick. Snack and drink options provided in rooms were also a big plus."
    Reviewed May 26, 2026
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - MIA • Nonstop MIA - YUL • Nonstop
    CA $3,237
    CA $1,824
    per traveller
    found 21 hours ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • 3 outdoor pools, cabanas (surcharge), pool umbrellas
    Aug 12 - Aug 20

    Hyatt Vacation Club at Coconut Cove, Bonita Springs + Flight

    Bonita Springs
    8 nights
    4.0 star property
    9.0/10 - Wonderful (886 reviews)
    "Xx"
    Reviewed May 26, 2026
    Roundtrip • Montreal (YUL) - Miami (MIA)
    YUL - MIA • Nonstop MIA - YUL • Nonstop
    CA $2,058
    CA $1,350
    per traveller
    found 21 hours ago
    Hyatt Vacation Club at Coconut Cove, Bonita Springs
  • Exterior
    Jun 28 - Jul 11

    Chadwick Cove Resort & Marina + Flight

    Manasota Key
    13 nights
    4.0 star property
    9.6/10 - Exceptional (19 reviews)
    "The listing stated step to beach. It was not only across the street but offered no access. "
    Reviewed May 10, 2026
    Roundtrip • Toronto (YYZ) - Tampa (TPA)
    YYZ - TPA • 1 stop TPA - YYZ • 1 stop
    CA $2,149
    CA $1,430
    per traveller
    found 2 days ago
    Chadwick Cove Resort & Marina
  • In-room safe, blackout drapes, iron/ironing board, cribs/infant beds
    Aug 10 - Aug 21

    Casa Ybel Resort + Flight

    Mid Island
    11 nights
    2.5 star property
    8.8/10 - Excellent (354 reviews)
    "Absolutely loved my stay at Casa Ybel. The beach is steps away and all of the units have back doors/ porches to make accessing the beach even easier. Check in was ok. The young lady helping me even held my groceries since our room was not ready yet and then had them delivered to our room. Some of the young maintenance staff came in while I was checking in and seemed to try and start an argument with her, but she kept professional. I would absolutely stay here again."
    Reviewed May 23, 2026
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - MIA • Nonstop MIA - YYZ • Nonstop
    CA $3,750
    CA $2,587
    per traveller
    found 2 days ago
    Casa Ybel Resort

Where to stay in Gateway

Find the best Gateway areas and neighborhoods for the activities you enjoy most. Learn more about Gateway
Aerial view of the road bridge between Captiva Island and Sanibel Island in Lee County, Florida, United States

Iona

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

Find hotels in Iona

Gateway Hotel Deals

Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

2.5 out of 5
4850 S Cleveland Ave Fort Myers FL
Fully refundableReserve now, pay when you stay
The price is CA $92 per night from Jun 9 to Jun 10
CA $92
CA $102 total
Jun 9 - Jun 10
includes taxes & fees
6.8/10 (1,081 reviews)
"Its a Clean place to rest."

Reviewed on May 26, 2026

Baymont by Wyndham Fort Myers Central
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is CA $259 per night from Jun 10 to Jun 11
CA $259
CA $358 total
Jun 10 - Jun 11
includes taxes & fees
9/10 Wonderful! (2,140 reviews)
"Second trip to this resort. Clean, friendly, fun and well maintained. It is pricey for drinks however the drinks are wonderful and part of the experience. Would love to come back again!"

Reviewed on May 27, 2026

Margaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
The price is CA $189 per night from May 31 to Jun 1
CA $189
CA $242 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (1,528 reviews)
"Love that all the rooms are ocean view and hotel is centrally located"

Reviewed on May 27, 2026

Lani Kai Beachfront Resort
See all 14,223 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Gateway vacation package cost?
Be ready to book, because a trip to Gateway starts from an affordable . When you bundle your hotels, flights and car rentals into a vacation package, you'll walk away with the biggest deals.
How do I get a cheap travel package to Gateway?
Book everything in one place with our Gateway vacation packages. You'll discover bargains on hotels, flights and more that'll keep your pocket happy and adventurous side satisfied. And, with more than 550 airlines and 1,000,000 hotels throughout the world to select from, you'll have endless opportunities to mix and match all you want.
Where should I stay in Gateway?
Make sightseeing easier by staying someplace close to Gateway's big attractions. Edison and Ford Winter Estates and Manatee Park are two of the most popular.
What are the top hotels in Gateway?
Florida Pool - Home Getaway In Timber Ridge Of Gateway is one of Gateway's top properties. Check in to a room here and you'll slumber peacefully knowing you're in excellent hands.
How far in advance should I book my Gateway vacation?
It can be tricky to know when is the ideal time to book your Gateway vacation. But usually the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels nearly 12 months prior to departure. If you're considering a last-minute getaway, no need to stress! There are great deals posted on Expedia all the time.
What does an Expedia Gateway travel package include?
Hotels, flights and rental cars — you'll find them all here. With Expedia, you can create your Gateway travel package your way. All you have to do is work out just what you need. Once you've made your booking, you can add on fun things like tours and activities. The more you bundle, the more you save!
What should I know before booking a Gateway travel package?
An Expedia travel package can be customized for your budget and is a fantastic way to make your hard-earned dollars stretch further. How little or much you include is up to you. Hotels, rental cars and flights — mix and match whatever combination suits your plans.
Can I choose my airline with a Gateway Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Just pick the carrier that suits you and create your ideal Gateway trip.
If I'm not able to travel, can I cancel my Gateway vacation package?
Your situation can change in the blink of an eye, so yes. You may be able to amend or cancel your Gateway vacation package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your airline, hotel or car rental company may impose a charge. Looking for more information? Check out our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Things to do

Marco Island: 10,000 Islands Shelling Boat Tour

Marco Island: 10,000 Islands Shelling Boat Tour

CA $137
per adult
100% of travellers recommend
Marco Island: 10,000 Islands Shelling Boat Tour
Historic Walking Tour of Fort Myers

Historic Walking Tour of Fort Myers

CA $41
per adult
100% of travellers recommend
Historic Walking Tour of Fort Myers
Fort Myers: Guided Standup Paddleboarding or Kayaking Tour

Fort Myers Dolphin & Manatee Kayak or Paddleboard Tour

CA $98
per adult
80% of travellers recommend
Fort Myers Dolphin & Manatee Kayak or Paddleboard Tour
See all activities in Fort Myers
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.