Windward Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

Top Holiday Package Deals in Windward

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was CA $1,034, price is now CA $699 per person
CA $699
per person
Jun 30 - Jul 4
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,008 reviews)
This place is a gem!

Reviewed on Apr 6, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was CA $1,411, price is now CA $931 per person
CA $931
per person
May 15 - May 19
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.8/10 Exceptional! (1,146 reviews)
Absolute hidden Gem!! Loved it

Reviewed on Apr 7, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $2,866, price is now CA $1,892 per person
CA $1,892
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,002 reviews)
Excellent , more than what I expected

Reviewed on Apr 5, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,106, price is now CA $755 per person
CA $755
per person
Jun 27 - Jul 1
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (725 reviews)
Very beautiful hotel, everything in great condition

Reviewed on Apr 7, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $1,392, price is now CA $953 per person
CA $953
per person
Jun 30 - Jul 4
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (821 reviews)
Beautiful Grounds! Very comfortable rooms. The pool was a blast!

Reviewed on Apr 6, 2026

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 Don Pedro Island Beach and Lemon Bay.

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 $291 per night from May 7 to May 8
CA $291
CA $395 total
May 7 - May 8
includes taxes & fees
9.2/10 Wonderful! (2,360 reviews)
Great place

Reviewed on Apr 7, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda

3 out of 5
1941 Tamiami Trl Port Charlotte FL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from May 8 to May 9
CA $120
CA $135 total
May 8 - May 9
includes taxes & fees
7.8/10 Good! (1,010 reviews)
Old, smells

Reviewed on Apr 8, 2026

Days Inn by Wyndham Port Charlotte/Punta Gorda
Best Western Plus Ambassador Suites Venice

Best Western Plus Ambassador Suites Venice

2.5 out of 5
400 Commercial Ct Venice FL
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Apr 27 to Apr 28
CA $156
CA $176 total
Apr 27 - Apr 28
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
We booked this room for a single overnight stay. The hotel was very clean and the room was spacious. Highly recommend. The staff was very helpful and friendly.

Reviewed on Apr 6, 2026

Best Western Plus Ambassador Suites Venice
See all 6,116 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 CA $699. 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!

Charlotte Harbor: Dolphin Discovery Day Cruise

CA $81
per adult
Charlotte Harbor: Dolphin Discovery Day Cruise
Sunset Tiki Boat Cruise

Sunset Tiki Boat Cruise (BYOB)

CA $95
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.