Avg. for October
Select dates to see prices and availability
Avg. for October
Nightly prices at Westwinds Inn average $162 in September, the cheapest month, and $446 in February, the most expensive, based on the last 12 months.
| Month | Average price |
|---|---|
| January | $351 |
| February | $446 |
| March | $375 |
| April | $325 |
| May | $293 |
| June | $212 |
| July | $200 |
| August | $183 |
| September | $162 |
| October | $230 |
| November | $255 |
| December | $259 |
Most expensive: February (~$446)
Cheapest: September (~$162)
Swimming pool
Non-Smoking Rooms
Tour Desk
Housekeeping
Garden
Scuba Diving
Sails To Rails Museum at Flagler Station (0.2 miles)
Key West Bight Marina (0.2 miles)
Donkey Milk House (0.3 miles)
Key West Historic Seaport (0.3 miles)
The Kite House (0.3 miles)
Schooner Western Union (0.3 miles)
5
Room details
Sleeps 2
200 ft²
9
Room details
Sleeps 2
200 ft²
5
Room details
Sleeps 2
250 ft²
6
Room details
Sleeps 2
300 ft²
4
Room details
Sleeps 4
325 ft²
8
Room details
Sleeps 2
11
Room details
Sleeps 4
400 ft²
7
Room details
Sleeps 4
275 ft²
9
Room details
Sleeps 2
250 ft²
Based on 1,336 verified reviews
AI-generated summary based on recent guest reviews
At Westwinds Inn, travelers praise the walkable Old Town location and charming garden setting with two small pools, plus friendly, helpful staff, while noting no on site parking and some small or dated rooms with occasional dampness and maintenance issues.
Read moreWas this helpful?
Vincent
4 weeks ago
·
Stayed 3 nights
Christina Schalde
Aug 29, 2026
·
Stayed 3 nights
Joy
Jul 25, 2026
·
Stayed 3 nights
Mark
Jul 22, 2026
·
Stayed 3 nights
Ernest
Jul 8, 2026
·
Stayed 4 nights
Nearby parking is available at a fee of USD 42 per night, located 499 feet away from the property.
A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM.
Check-in is from 3:00 PM to 7:00 PM, and check-out is at 11:00 AM. Early or late check-in/check-out may be available upon request and should be arranged in advance.
The property includes step-free entrances and wheelchair-accessible facilities in public areas. Specific details on room accessibility features are not provided.
The property is located in Key West's Historic District, within a 15-minute walk of Duval Street and Florida Keys Beaches. It is 0.8 miles from Mallory Square and 1.3 miles from the Southernmost Point.
Yes, the property features an outdoor heated pool. Operational hours are not specified.
Children 11 years old and younger are not permitted at this property.
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Average nightly price across deals, with taxes & fees.
Prices in USD for 2 guests, updated daily.