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Top hotels in Windward

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
$250 nightly
The price is $280 total per night from Feb 1 to Feb 2
$280 total
Feb 1 - Feb 2
Total with taxes and fees
A marina and a restaurant are featured at this smoke-free condo resort. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking ...
Everything good

Reviewed on Jan 19, 2026

Opens in a new windowThe Suites at Fishermen’s Village- 2 Bedroom Suites
North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **

North Captiva FL
This vacation home featured laundry facilities and barbecue grills.
Our family had an amazing stay at this cute little house. It was perfect for us. We will be rebooking and coming back again! Adore the point house and feel it's the best house on the island if you are looking for some peace and quiet and privacy.

Reviewed on Dec 31, 2025

Opens in a new windowNorth Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
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
$182 nightly
The price is $204 total per night from Feb 16 to Feb 17
$204 total
Feb 16 - Feb 17
Total with taxes and fees
A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this resort. If you want to take your pet along, this pet-friendly property offers ...
Helpful staff, eager to make you feel welcomed. The hotel is new, clean, and modern. Will be back!

Reviewed on Jan 15, 2026

Opens in a new windowSunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
812 Kings Hwy Port Charlotte FL
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $121 total per night from Feb 1 to Feb 2
$121 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. ...
The room was clean but needs updating. The hotel is showing ware. Staff was very nice to work with...

Reviewed on Jan 16, 2026

Opens in a new windowComfort Inn & Suites
Motel 6 Venice, FL

Motel 6 Venice, FL

2 out of 5
281 US 41 Bypass North Venice FL
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $82 total per night from Jan 25 to Jan 26
$82 total
Jan 25 - Jan 26
Total with taxes and fees
This motel features 10 beach bars and an outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a snack bar/deli, ...
The rooms are exceptionally clean

Reviewed on Jan 20, 2026

Opens in a new windowMotel 6 Venice, FL
Baymont by Wyndham Punta Gorda/Port Charlotte

Baymont by Wyndham Punta Gorda/Port Charlotte

2.5 out of 5
9035 Mac Drive Punta Gorda FL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $130 total per night from Jan 23 to Jan 24
$130 total
Jan 23 - Jan 24
Total with taxes and fees
This motel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub ...
Easy

Reviewed on Jan 12, 2026

Opens in a new windowBaymont by Wyndham Punta Gorda/Port Charlotte
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
$110 nightly
The price is $123 total per night from Jan 25 to Jan 26
$123 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
Yes

Reviewed on Jan 17, 2026

Opens in a new windowSleep Inn & Suites Port Charlotte - Punta Gorda
Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

2.5 out of 5
24244 Corporate Ct Port Charlotte FL
Fully refundable
$103 nightly
The price is $115 total per night from Jan 25 to Jan 26
$115 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
The temp of the heated pool was perfect.

Reviewed on Jan 18, 2026

Opens in a new windowCountry Inn & Suites by Radisson, Port Charlotte, FL
Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway

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

2 out of 5
625 Tamiami Trail S Venice FL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $93 total per night from Jan 22 to Jan 23
$93 total
Jan 22 - Jan 23
Total with taxes and fees
A restaurant and an outdoor pool are featured at this motel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, ...
Great location. The rooms look a little rough around the edges but with traveling a lot those hotels always seem to be the best. I travel on a budget so this was the best price and location. Will 100% be back again. Also definitely go to their restaurant attached to it, you won’t be ...

Reviewed on Jan 18, 2026

Opens in a new windowIsland Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway
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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.

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

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