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Your Seaside Retreat in Key West
The Key West Windward Pointe Resort sits next to the nearby ocean

Your Seaside Retreat in Key West

Sunset celebrations and warm, tropical breezes await you with this stay at Hyatt Vacation Club at Windward Pointe in Key West, FL. This exclusive offer includes a $50 Resort Certificate or 5,000 World of Hyatt Points.
Exterior view of Key West Windward Point
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Or Call 888-812-9682 to Book

Worry Free Booking, Take Up to 12 Months to Travel
* Price includes tax and resort fee; a surcharge of up to $200 may apply for high demand seasons. Attendance at a  120-minute timeshare sales presentation of the Hyatt Vacation Club Portfolio Program is required.
Details of Participation
  • GOLF
  • sunset sails
Resort Information
A tropical retreat overlooking the Atlantic Ocean, Windward Pointe captures the essence of Key West. The resort, located at the southeastern tip of the island’s southernmost point, boasts a freeform infinity-edge pool with a poolside restaurant, a hammock overlooking the ocean, and an array of games. Nearby, enjoy Smathers Beach and the iconic Southernmost Point landmark. On-site, get involved with Inspired Experiences for unforgettable moments together during your Key West stay.
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2-Bedroom Villa
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Full Kitchen
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Private Patio
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Washer & Dryer
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Kid Friendly
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On-Site Dining
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Resort Amenities

Whether you stay with the whole family or it’s just adults, there are so many ways to stay engaged, entertained, active, or relaxed at Windward Pointe.

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Woman in striped towel walks along a shimmering resort pool

Swimming Pool

 A rainbow-colored outdoor hammock at a seaside resort


Inspired Activities & Experiences

Discover rewarding things to do on your vacation in Key West. Our curated program helps you connect with the area — and each other — during your stay at our Key West, Florida resort. Take part in experiences from each of the program’s three pillars: Explore, Engage, and Express. From adventurous activities to mellow moments, this is vacation time well spent.
Women enjoying a group painting class
Canvas Art

Bring out your inner artist and showcase your creativity for some true vacation therapy.

Live Entertainment & Pool Games

Enjoy some great music, poolside games, fun socializing, and more with DJ Jimmy Jamz.

Vibrant pieces of green and aqua sea glass arranged in a heart shape
Sea Glass Art

Work with area artist Petra to create an amazing keepsake made of beautiful local sea glass.

Key West
Things to do
The Hemingway House in Key West, Florida

The Hemingway Home and Museum

Tour this historic 1851 home where famed author Ernest Hemingway lived from 1931 to 1939.

Aerial view of Mallory Square in Key West, Florida

Mallory Square

Explore the epicenter of Key West life since the 1820s — and don’t miss the daily Sunset Celebration.

Oil Lamp Inside the Harry Truman House

Harry S. Truman Little White House

Visit Florida’s only presidential museum, where Truman spent a total of 175 days during his presidency.

Colorful fish swim among a coral reef

Key West Aquarium

View, learn about, and interact with an exciting variety of marine life from the Florida Keys region.

See what guests are saying about Hyatt Vacation Club at Windward Pointe

Tripadvisor 5 bubble

Beautiful and clean!

"This hotel is beautiful. The room feels more like a condo than a hotel room. It’s spacious, clean, and comfortable. The pool area is beautiful with views of the ocean. I would definitely stay here again. We were a family of four, and the two bedroom was perfect for us."

Tripadvisor traveler review from June 2023

Tripadvisor 5 bubble

Beautiful view

"This resort is absolutely beautiful, the views are great, the rooms are very nice, staff great & accommodating! The food at the sandwich shop very tasty, I loved everything about this resort & would definitely stay again."

Tripadvisor traveler review from August 2022

Tripadvisor 5 bubble

This place is AMAZING!

"It was incredible. We almost didn’t want to leave the room, it was so luxurious. Will come to stay again and again. We booked the Ocean View suite and my oh my, we felt spoiled. This is the place to stay."

Tripadvisor traveler review from July 2022

Your Getaway Package

What’s included:
  • Enjoy your stay in a at Hyatt Vacation Club at Windward Pointe, Key West
Why you get it:
  • Resort Preview: You and your family will be our guests at a fun and friendly 120-minute timeshare sales presentation, where you’ll learn about the benefits of vacation ownership with Hyatt Vacation Club.
  • We want to welcome travelers like you to explore the natural beauty of the local area.
Details of Participation
Woman in the pool at Hyatt Vacation Club at Windward Pointe, Key West
Hammock near the water at Hyatt Vacation Club at Windward PointeTwo chairs on the beach at Hyatt Vacation Club at Windward Pointe, Key West
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