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Windward Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Windward area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Windward to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Windward are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Windward hotel reviews by fellow wanderers

Baymont by Wyndham Punta Gorda/Port Charlotte

5 out of 5

Posted 4 hours ago

Travelocity Verified Review

"Closeness to the airport made for a restful stay. "

A verified traveler stayed at Baymont by Wyndham Punta Gorda/Port Charlotte

The Suites at Fishermen’s Village- 2 Bedroom Suites

5 out of 5

Posted 5 hours ago

Travelocity Verified Review

"Our stay at Fishermans Village was 10 out of 10. Unexpectedly, we added a third night because it was so enjoyable. From eating outside overlooking the water to having drinks by the tiki bar while watching the sunset, we could not have asked for anything more. Our room had a full harbor view with a private balcony. How beautiful it was to sit out on the balcony and watch the boats and be mesmerized by the water. The room was one of the cleanest in any hotel in which we have stayed. I cannot think of one negative, so hurry up and share in the joy we felt. "

A verified traveler stayed at The Suites at Fishermen’s Village- 2 Bedroom Suites

Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

1 out of 5

Posted 9 hours ago

Travelocity Verified Review

"When we turned on the light at night there were a dozen roaches. We killed many of them and left the lights on for the short few hours until dawn. We noted this to the front desk and showed photos. She promised a full refund. When I called to ask about the refund they told me the manager declined it. I also don’t like that they use traditional metal keys that could be duplicated. This is a serious security issue. "

A verified traveler stayed at Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda

3 out of 5

Posted 11 hours ago

Travelocity Verified Review

"Parking area is well lit; property is clean inside & out; staff very friendly & thourough. Availability of hot water was lacking; no additional amenities w/exception of hair dryer. Asked for fridge & rec'd within a couple hours. I may stay there again, but making sure to adjust for the issues stated above."

A verified traveler stayed at Microtel Inn & Suites by Wyndham Port Charlotte/Punta Gorda