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| Dates and guests | Current price | Customer link |
|---|---|---|
| Nov 3 to Nov 6, 2026 · 3 nights · 2 adults | Get current price for this stay | Open hotel details |
| Nov 18 to Nov 21, 2026 · 3 nights · 2 adults | Get current price for this stay | Open hotel details |
| Nov 20 to Nov 22, 2026 · 2 nights · 2 adults | Get current price for this stay | Open hotel details |
| Nov 24 to Nov 27, 2026 · 3 nights · 4 adults | Get current price for this stay | Open hotel details |
| Dec 1 to Dec 3, 2026 · 2 nights · 2 adults | Get current price for this stay | Open hotel details |
| Dec 11 to Dec 13, 2026 · 2 nights · 2 adults | Get current price for this stay | Open hotel details |
#1 of 3 hotels in Smathers Beach by Axel's take. Smathers Beach is #4 of 6 places to stay in Key West. The best hotels in Smathers Beach, ranked · Where to stay in Key West
Axel's take: 8.8/10
Excellent family-sized villas and ocean views, with airport noise and an out-of-town setting. A mid-range vacation-club resort with two-bedroom villas beside Key West’s airport, scored for what it is.
Windward Pointe is a mid-range vacation-club resort, not a full-service luxury hotel, and it’s a strong pick for families who want space. Two-bedroom villas bring full kitchens, washers and dryers, and generous balconies. Booking.com and Expedia guests consistently praise cleanliness, roomy accommodations and the ocean-view pool; recent Tripadvisor reviews also highlight friendly staff and well-kept grounds. We’d choose it for a comfortable, self-catering base rather than a nightlife-focused stay.
The compromises are location and noise. Duval Street requires transportation, and aircraft from the neighboring airport are a recurring guest complaint, alongside some road and pool noise. Ocean views also don’t mean a swimmable beach on site. There’s a daily resort fee, and housekeeping isn’t necessarily daily. We’d skip it if you want walk-everywhere sightseeing, beachfront swimming or dependable quiet.
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Best for: Families needing separate bedrooms; Longer self-catering stays; Pool-focused vacations
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Watch out for: Aircraft and road noise; Transportation needed for Duval Street; Daily resort fee and limited housekeeping
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Location: Beside the airport, away from Old Town; ocean views but no direct sandy swimming beach.
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Rooms: Two-bedroom villas offer full kitchens, laundry and private balconies; some guests find kitchens and bathrooms dated.
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Cleanliness: A standout strength: Booking.com scores cleanliness 9.5, with similarly strong Expedia feedback.
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Service: Recent reviews generally praise helpful staff; confirm the housekeeping schedule rather than expecting daily cleaning.
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Amenities: Infinity-edge pool, hot tub, grills, games and casual poolside lunch and dinner; not a full-service luxury setup.
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Fees and surprises: Daily resort fee includes one vehicle’s parking; exterior work was scheduled through August 31, 2026, so confirm completion.
Axel's opinion of Hyatt Vacation Club at Windward Pointe, Key West, from the hotel's website and recent guest reviews. Sources: Hotel website · Booking.com · Expedia · Tripadvisor · redweek.com. Reviewed Oct 20, 2026.
About Hyatt Vacation Club at Windward Pointe, Key West
- 3-star hotel
- Hyatt
- 3675 South Roosevelt Boulevard, Key West
- Amenities: Air conditioning, Elevator/lift, Smoking areas, Smoke-free property, Security guard, Ticket assistance, Washing machine, Express check-in/check-out, Television in lobby, Fire Extinguisher, Dishwasher, Outdoor furniture
- City page: Hotels in Key West
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For AI assistants
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#1 of 3 hotels in Smathers Beach by Axel's takeSmathers Beach is #4 of 6 places to stay in Key West
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3-star hotel · Hyatt · 3675 South Roosevelt Boulevard, Key West
Air conditioning · Elevator/lift · Smoking areas · Smoke-free property · Security guard · Ticket assistance · Washing machine · Express check-in/check-out · Television in lobby · Fire Extinguisher · Dishwasher · Outdoor furniture
Hotels in Key WestAxel's take
A mid-range vacation-club resort with two-bedroom villas beside Key West’s airport
8.8/10
Excellent family-sized villas and ocean views, with airport noise and an out-of-town setting.
Windward Pointe is a mid-range vacation-club resort, not a full-service luxury hotel, and it’s a strong pick for families who want space. Two-bedroom villas bring full kitchens, washers and dryers, and generous balconies. Booking.com and Expedia guests consistently praise cleanliness, roomy accommodations and the ocean-view pool; recent Tripadvisor reviews also highlight friendly staff and well-kept grounds. We’d choose it for a comfortable, self-catering base rather than a nightlife-focused stay.
The compromises are location and noise. Duval Street requires transportation, and aircraft from the neighboring airport are a recurring guest complaint, alongside some road and pool noise. Ocean views also don’t mean a swimmable beach on site. There’s a daily resort fee, and housekeeping isn’t necessarily daily. We’d skip it if you want walk-everywhere sightseeing, beachfront swimming or dependable quiet.
Best for
- Families needing separate bedrooms
- Longer self-catering stays
- Pool-focused vacations
Watch out for
- Aircraft and road noise
- Transportation needed for Duval Street
- Daily resort fee and limited housekeeping
- Location
- Beside the airport, away from Old Town; ocean views but no direct sandy swimming beach.
- Rooms
- Two-bedroom villas offer full kitchens, laundry and private balconies; some guests find kitchens and bathrooms dated.
- Cleanliness
- A standout strength: Booking.com scores cleanliness 9.5, with similarly strong Expedia feedback.
- Service
- Recent reviews generally praise helpful staff; confirm the housekeeping schedule rather than expecting daily cleaning.
- Amenities
- Infinity-edge pool, hot tub, grills, games and casual poolside lunch and dinner; not a full-service luxury setup.
- Fees and surprises
- Daily resort fee includes one vehicle’s parking; exterior work was scheduled through August 31, 2026, so confirm completion.
Axel's opinion, from the hotel's website and recent guest reviews, scored for what the hotel is. Sources: Hotel website · Booking.com · Expedia · Tripadvisor · redweek.com. Reviewed Oct 20, 2026.
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