Westwinds Inn rates, Key West

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Dates and guests	Current price	Customer link
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

#8 of 9 hotels in Mallory Square & Historic Seaport by Axel's take. Mallory Square & Historic Seaport is #2 of 6 places to stay in Key West. The best hotels in Mallory Square & Historic Seaport, ranked · Where to stay in Key West

Axel's take: 8.3/10

A welcoming Old Town base with lovely pools, but check renovation status before booking. a small, historic 3-star inn in Old Town Key West, scored for what it is.

Westwinds Inn is a small, historic 3-star inn whose strongest selling points are its tropical grounds and walkable Old Town location. We'd pick it for a car-free couples' break: the seaport and Duval Street are within walking distance, and two pools, included continental breakfast and weekday happy hour add real appeal. Expedia and Booking.com guests repeatedly praise cleanliness, helpful staff and the garden setting.

The rooms are less consistent: some guests describe fresh renovations, while others report compact layouts and tired bathrooms. More importantly, Tripadvisor and Expedia guests report on-site construction, including stays in September and October 2026; confirm what work remains before committing. There's no on-site parking or elevator, and the hotel welcomes children only from age 12. We'd skip it for guaranteed quiet during renovations, step-free access without advance arrangements, or a full-service resort experience.

Best for: couples exploring Old Town; car-free sightseeing breaks; travelers who enjoy garden pools
Watch out for: on-site construction reported through October 2026; compact rooms and uneven bathroom condition; no on-site parking or elevator
Location: Walkable Historic Seaport District base near restaurants and Duval Street; not beachfront.
Rooms: Room sizes and condition vary; some recent renovations, but recurring bathroom maintenance comments.
Cleanliness: Strong overall cleanliness feedback across Booking.com and Expedia, despite occasional exceptions.
Service: Helpful staff earn frequent praise, though some Tripadvisor guests describe an indifferent reception.
Amenities: Two pools, one seasonally heated; free continental breakfast, weekday happy hour and Wi-Fi.
Fees and surprises: Hotel says no resort or credit-card processing fees; deposits and cancellation penalties apply, and construction completion is unconfirmed.

Axel's opinion of Westwinds Inn, from the hotel's website and recent guest reviews. Sources: Hotel website · Booking.com · Expedia · Tripadvisor. Reviewed Oct 20, 2026.

About Westwinds Inn

3-star hotel
914 Eaton St, Key West
Amenities: Air conditioning, Smoking areas, Smoke-free property, Newspapers, Ticket assistance, Garden, No elevators, Reception desk, Non-smoking rooms, Accessibility features, Laundry, Concierge services
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#8 of 9 hotels in Mallory Square & Historic Seaport by Axel's take Mallory Square & Historic Seaport is #2 of 6 places to stay in Key West

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3-star hotel · 914 Eaton St, Key West

Air conditioning · Smoking areas · Smoke-free property · Newspapers · Ticket assistance · Garden · No elevators · Reception desk · Non-smoking rooms · Accessibility features · Laundry · Concierge services

Hotels in Key West

Axel's take

a small, historic 3-star inn in Old Town Key West

8.3/10

A welcoming Old Town base with lovely pools, but check renovation status before booking.

Best for

couples exploring Old Town
car-free sightseeing breaks
travelers who enjoy garden pools

Watch out for

on-site construction reported through October 2026
compact rooms and uneven bathroom condition
no on-site parking or elevator

Location: Walkable Historic Seaport District base near restaurants and Duval Street; not beachfront.
Rooms: Room sizes and condition vary; some recent renovations, but recurring bathroom maintenance comments.
Cleanliness: Strong overall cleanliness feedback across Booking.com and Expedia, despite occasional exceptions.
Service: Helpful staff earn frequent praise, though some Tripadvisor guests describe an indifferent reception.
Amenities: Two pools, one seasonally heated; free continental breakfast, weekday happy hour and Wi-Fi.
Fees and surprises: Hotel says no resort or credit-card processing fees; deposits and cancellation penalties apply, and construction completion is unconfirmed.

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. Reviewed Oct 20, 2026.

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