
Windward Vacation Packages
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Top Holiday Package Deals in Windward
Price found within the past 48 hours. Click for updated prices.


LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was CA $4,381, price is now CA $1,984 per person
CA $1,984
per person
Nov 18 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
The lights are on, but nobody is home!
Staying in the older low-rise block was a thrill as we had stayed there over 30 years ago...and still the dolphins splashed in the shallows...as if on a schedule! The huge works going on made the tiki bar area a no-go zone, but the beach remains as lovely as ever. However, the hotel seems to think it is better than it is, as we had to send back a chicken main that was simply inedible, and very strangely presented. Unfortunately, things got worse when out toilet stopped functioning, and despite many calls and after a 5 hour wait with no action, we went to find someone and fortunately bumped into a maintenance worker who discovered that housekeeping had turned off the water valve! The total lack of interest, concern and action from the front desk in a way sums up their current operations...they have disengaged from satisfying the guest by seemingly putting their own self-importance ahead of genuine interest in their guests. Too bad...another potentially great property leaves our list of desirable future stays.
Reviewed on Sep 10, 2025

The Perry Hotel Naples
Price was CA $2,129, price is now CA $1,053 per person
CA $1,053
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
nice and very clean, comfortable room, quit at night around the pool feel good
Reviewed on Sep 8, 2025

Inn on Fifth
Old Naples
Price was CA $2,833, price is now CA $1,541 per person
CA $1,541
per person
Nov 18 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
Staff was very friendly and helpful. Pool was clean with bar and hot tub. Nice gym. Located right in the heart of old Naples. They have shuttle to the beach and offer chairs and umbrellas.
Reviewed on Sep 10, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club
Price was CA $4,610, price is now CA $2,625 per person
CA $2,625
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9.8/10 Exceptional! (285 reviews)
Beautiful apartment! Great city view on the balcony. Pool area was lovely.
Reviewed on Aug 27, 2025
Where to stay in Windward
Find the best Windward areas and neighborhoods for the activities you enjoy most. Learn more about Windward

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.
Windward Hotel Deals

Sunseeker Resort Charlotte Harbor
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Oct 2 to Oct 3
CA $188
CA $271 total
Oct 2 - Oct 3
includes taxes & fees
9.2/10 Wonderful! (1,463 reviews)
"Clean, very clean."
Reviewed on Sep. 9, 2025

Country Inn & Suites by Radisson, Port Charlotte, FL
24244 Corporate Ct, Port Charlotte, FL
Fully refundable
The price is CA $102 per night from Sep 21 to Sep 22
CA $102
CA $115 total
Sep 21 - Sep 22
includes taxes & fees
7.6/10 Good! (1,037 reviews)
"Good hotel!"
Reviewed on Sep. 9, 2025

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
North Captiva
9.4/10 Exceptional! (86 reviews)
So relaxing!
"Thank you for sharing your property with us! We had magnificent views—- including a full double rainbow 😍 the space was comfortable and clean and perfect for a long weekend getaway. We were able to easily access our boat to spend time on Cayo costa, lunch on cabbage key and a dip in the pool at ..."
Reviewed on Aug. 4, 2024
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.
Frequently asked questions
Discover the most popular places to visit in Windward
Gasparilla Marina
Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this relaxing area.
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.
Things to do
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.