Windward Passage Resort puts you within a 10-minute drive of Key West Express and Estero Boulevard Beach. Guests can take a dip in the outdoor pool, and the hot tub makes for a relaxing end to the day.
Southwest Florida Intl. Airport (RSW) - 42 min drive
Restaurants
License to Chill Bar - 14 min walk
The Yucatan Beach Stand - 14 min walk
Doc Ford’s Rum Bar & Grille - 5 min drive
World Famous Lighthouse Tiki Bar - 15 min walk
The Whale - 17 min walk
About this property
Windward Passage Resort
Windward Passage Resort puts you within a 10-minute drive of Key West Express and Estero Boulevard Beach. Guests can take a dip in the outdoor pool, and the hot tub makes for a relaxing end to the day.
At a glance
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Hotel size
53 rooms
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Arriving/Leaving
Check-in time starts at 4:00 PM
Late check-in subject to availability
Minimum check-in age: 21
Check-out time is 10:00 AM
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Special check-in instructions
The front desk is open Monday - Friday (8:00 AM - 4:00 PM) and Saturday - Saturday (7:00 AM - 5:00 PM)
Front desk staff will greet guests on arrival at the property
If you are planning to arrive after 4:30 PM please contact the property in advance using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools
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Required at check-in
Credit card, debit card, or cash deposit required for incidental charges
Government-issued photo ID may be required
Minimum check-in age is 21
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Pets
Pets not allowed
WIFI
Internet
Free WiFi in public areas
Free WiFi in rooms (speed: 250+ Mbps (good for 3–5 people or up to 10 devices))
LOCAL_PARKING
Parking
Free uncovered onsite self parking
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Other information
Designated smoking areas
Property amenities
What to do
On the beach
Beach volleyball
Services
Laundry facilities
Free bicycle rentals
Beach sun loungers
Pool loungers
Pool umbrellas
Facilities
An outdoor pool
Hot tub
Accessibility
Elevator
Elevator door width (inches): 33
Wheelchair-accessible path to elevator
Well-lit path to entrance
Stair-free path to entrance
Room amenities
Home comfort
Climate-controlled air conditioning and heating
Iron/ironing board
Freshen up
Soap and shampoo
Hair dryer
Towels
Toilet paper
Stay connected
Laptop-friendly workspace
Free WiFi (speed of 250+ Mbps (good for 3–5 people or up to 10 devices))
Food and drink
Full-sized refrigerator/freezer
Microwave
Kitchen
Stovetop
Oven
Cookware, dishes, and utensils
Dishwasher
More
Guidebooks/recommendations
Fees & policies
Policies
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
This property accepts credit cards and debit cards. Cash is not accepted.
Credit cards accepted: Visa, Mastercard, American Express, Discover
Frequently asked questions
Is there a pool at Windward Passage Resort?
Yes, there's an outdoor pool.
Are pets allowed at Windward Passage Resort?
Sorry, pets aren't allowed.
Is parking offered on site at Windward Passage Resort?
Yes, there's free self parking.
What are the check-in and check-out times at Windward Passage Resort?
You can check in starting at 4:00 PM. Check-out time is 10:00 AM.
What is there to do at Windward Passage Resort and nearby?
Have fun with onsite activities like volleyball and cycling. Enjoy a relaxing soak in the hot tub and an invigorating swim in the outdoor pool.
Does Windward Passage Resort have self-catered rooms fitted with kitchens or kitchenettes?
Yes, a kitchen is available in every room, and also includes cookware, a refrigerator, and a microwave.
What's the area around Windward Passage Resort like?
Windward Passage Resort is a short 13-minute walk from Estero Boulevard Beach and 3 minutes' walk from Lynn Hall Memorial Park.
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Reviews
Windward Passage Resort Reviews
8.0
Very Good
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.More informationOpens in a new window
10
Cleanliness
7.0
Amenities
6.0
Staff & service
10
Property conditions & facilities
Reviews
Verified
10/10 Exceptional
May 2, 2026
We had an excellent stay, the entire staff was super friendly and helpful. We will definitely stay there again!
Jose A
Jose A, 3-night trip
Verified
6/10 Good
Apr 17, 2026
This is a Time-Share property and the view from my room was anything, but what it shows on the picture. I was placed in the end unit of the motel building in the parking lot with the only view of the gulf if I would walk thru the parking lot, under the main building to the beach. The whole area is still under construction. So, my room that was nice and recently remodeled faced the parking lot on one side, and a fence with construction behind it on the other side. It was almost as if I pissed someone off really bad. The pool is ok, the beach area is great. No service from staff at all. They expect you to do own laundry and take own garbage out. Beach chairs you need to have your own or take theirs and bring them back. Cushions are extra, but no one to get them from if after 4pm. Check in is no earlier than 3, the the office closes at 4. There are no signs for the property and office not visible from parking and no instructions are provided. You need to get to the lock box by the office, call after hours service who will provide a code to access lock box to get your key. Next day you can get the parking pass, extra key and instructions where to take your garbage.