Windward 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
Price found within the past 48 hours. Click for updated prices.
  • 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 18 hours ago
    Hyatt Vacation Club at Coconut Cove, Bonita Springs
  • View from room
    Jul 18 - Jul 25

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

    Vanderbilt Beach
    7 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 • Detroit (DTW) - Fort Myers (RSW)
    DTW - RSW • 1 stop RSW - DTW • 1 stop
    CA $3,683
    CA $2,036
    per traveller
    found 19 hours ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • 2 outdoor pools, cabanas (surcharge), pool umbrellas
    Aug 10 - Aug 21

    The Perry Hotel Naples + Flight

    Naples
    11 nights
    4.5 star property
    9.6/10 - Exceptional (827 reviews)
    "I come back again"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YYZ) - Miami (MIA)
    YYZ - MIA • Nonstop MIA - YYZ • Nonstop
    CA $2,282
    CA $1,371
    per traveller
    found 1 day ago
    The Perry Hotel Naples
  • 2 outdoor pools
    Aug 8 - Aug 15

    The Lighthouse Resort Inn & Suites + Flight

    Fort Myers Beach
    7 nights
    3.0 star property
    8.6/10 - Excellent (1,669 reviews)
    "The bathroom was poorly maintained, the sink was clogged, and the noise was very annoying. The terrace was right above the tiki bar, and the breakfast service included items different from what I ordered. They gave room keys to other people who entered while we were resting, which was a big mistake."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YYZ) - Fort Myers (RSW)
    YYZ - RSW • 1 stop RSW - YYZ • 1 stop
    CA $2,143
    CA $1,401
    per traveller
    found 1 day ago
    The Lighthouse Resort Inn & Suites
  • Exterior
    Jul 18 - Jul 25

    Shell Island Beach Club + Flight

    East End
    7 nights
    4.0 star property
    9.6/10 - Exceptional (23 reviews)
    "Very clean. Excellent location, close to beach, walkable to restaurants."
    Reviewed December 21, 2025
    Roundtrip • Detroit (DTW) - Fort Myers (RSW)
    DTW - RSW • 1 stop RSW - DTW • 1 stop
    CA $2,999
    CA $2,019
    per traveller
    found 19 hours ago
    Shell Island Beach Club

Where to stay in Windward

Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward
Famous lighthouse on ocean shore and expensive residential houses in island small town Boca Grande on Gasparilla Island in southwest Florida

Palm Island

1 out of top 10 points of interest in this area

While visiting Palm Island, you might make a stop by sights like Lemon Bay and Don Pedro Island Beach.

Find hotels in Palm Island

Windward Hotel Deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Jun 12 to Jun 13
CA $258
CA $359 total
Jun 12 - Jun 13
includes taxes & fees
9.2/10 Wonderful! (2,705 reviews)
"Great place to rest and relax. Amazing pools and restaurants. Staff super nice and helpful. Coming back for sure."

Reviewed on May 27, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Sleep Inn & Suites Port Charlotte - Punta Gorda

Sleep Inn & Suites Port Charlotte - Punta Gorda

2.5 out of 5
806 Kings Hwy Port Charlotte FL
Fully refundable
The price is CA $103 per night from Jun 9 to Jun 10
CA $103
CA $116 total
Jun 9 - Jun 10
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Couldn't beat the price the only negative was the jacuzzi in my room didn't work no water to fill it and my Door ti enter the room was very very lose meaning I had to use deadbolt lock to keep it shut"

Reviewed on May 23, 2026

Sleep Inn & Suites Port Charlotte - Punta Gorda
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
812 Kings Hwy Port Charlotte FL
Fully refundable
The price is CA $112 per night from Jun 21 to Jun 22
CA $112
CA $125 total
Jun 21 - Jun 22
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
"Very good. Clean room, staff friendly I really enjoyed my time there"

Reviewed on May 26, 2026

Comfort Inn & Suites
See all 6,133 properties in Windward
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 Windward vacation package cost?
Explore the best of Windward from just . Choose from a wonderful selection of flights, hotels and rental cars to suit your budget. Land even better deals when you add a couple of tours or activities to your vacation package.
How do I get a cheap travel package to Windward?
Creating your own Windward vacation package with Expedia is an easy way to save. We have access to more than 550 air carriers and 1,000,000 hotels globally. With such a fantastic range to pick from, you'll have no worries putting together your perfect adventure.
Where should I stay in Windward?
We recommend staying near the action. Many travelers like to book hotels in the vicinity of top sights, such as Little Gasparilla Island Beach, Gasparilla Marina and Don Pedro Island Beach.
How far in advance should I book my Windward vacation?
The earlier you book, the better. Air carriers typically release flights nearly 12 months ahead of departure, and this is an excellent opportunity to pick up some of the lowest prices. Boss just told you to use up your vacation time in a few weeks? Don't fret. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Windward travel package include?
That's up to you. You can select from a variety of Windward packages, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your dream Windward escape looks like, you'll save!
What should I know before booking a Windward travel package?
A travel package can be easier on the credit card than separately booking everything you need for your escape. For example, combine your hotels, flights and rental cars and save a packet. Whatever your vacation goals are, you'll find a package that matches your budget.
If I'm not able to travel, can I cancel my Windward vacation package?
Don't stress if you're rethinking your Windward vacation package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We understand your circumstances can suddenly change, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.

Discover the most popular places to visit in Windward

Don Pedro Island State Park

Commune with nature and explore the great outdoors at Don Pedro Island State Park during your travels in Placida. Wander the beautiful beaches in this relaxing area.

Don Pedro Island State Park

Gasparilla Marina

Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this family-friendly area.

Gasparilla Marina

Things to do

Wild dolphins on Charlotte Harbor!

Tropical Tides Scenic Day Cruise - Public

CA $81
per adult
Tropical Tides Scenic Day Cruise - Public
Sunset Tiki Boat Cruise

Sunset Tiki Boat Cruise (BYOB)

CA $94
per adult
Sunset Tiki Boat Cruise (BYOB)
See all activities in Placida
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.