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Southwinds Motel rates, Key West

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Dates and guestsCurrent priceCustomer link
Nov 18 to Nov 21, 2026 · 3 nights · 2 adultsGet current price for this stayOpen hotel details
Nov 20 to Nov 22, 2026 · 2 nights · 2 adultsGet current price for this stayOpen hotel details

#5 of 9 hotels in Southernmost Point & Casa Marina by Axel's take. Southernmost Point & Casa Marina is #3 of 6 places to stay in Key West. The best hotels in Southernmost Point & Casa Marina, ranked · Where to stay in Key West

Axel's take: 8.2/10

A friendly Old Town base with useful extras, but small rooms and added fees. a no-frills 2-star motel in Old Town Key West, scored for what it is.

Southwinds is a no-frills 2-star motel near the southern end of Duval Street, and a strong pick for travelers who prioritize exploring over room time. Recent Tripadvisor and Expedia guests repeatedly praise the helpful staff, clean rooms and walkable location. Two outdoor pools and the adjacent Tipsy Rooster bar give this simple property more appeal than a bed alone. We'd choose it for an unfussy Key West break, not a resort stay.

The trade-offs are dated interiors, some cramped rooms and bathrooms, and sound carrying between rooms. Light sleepers should request a room away from the bar, which has daily live music. Breakfast is continental, and the hotel's policies place it and beach-chair service within a mandatory daily amenity fee; parking costs extra. We'd skip it if spacious, modern rooms or dependable quiet matter most.

  • Best for: couples exploring Old Town; travelers happy with simple rooms; pool-and-bar downtime

  • Watch out for: Small, dated rooms and bathrooms; Thin walls and live music nearby; Mandatory amenity fee; parking extra

  • Location: Walkable to southern Duval Street and Southernmost Point; near the beach, not beachfront.

  • Rooms: Basic and often described as comfortable, but room size, storage and bathroom space can disappoint.

  • Cleanliness: Recent feedback is predominantly positive, with cleanliness stronger than the property's condition.

  • Service: Friendly, helpful staff are a consistent strength across Tripadvisor and Expedia.

  • Amenities: Two outdoor pools, continental breakfast, nearby beach-chair service and an adjacent bar; no gym.

  • Fees and surprises: Daily amenity fee and separate parking charge; redevelopment is proposed in city records, but an active-work schedule was not verified.

Axel's opinion of Southwinds Motel, from the hotel's website and recent guest reviews. Sources: Hotel website · Tripadvisor · Expedia · Booking.com · en.planetofhotels.com · keywest.legistar.com. Reviewed Oct 20, 2026.

About Southwinds Motel

  • 2-star hotel
  • 1321 Simonton Street, Key West
  • Amenities: Air conditioning, 24-hour reception, Smoking areas, Smoke-free property, Heating, Newspapers, Ticket assistance, Outdoor furniture, Non-smoking rooms, Room service, Fridge, Cable TV
  • City page: Hotels in Key West

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#5 of 9 hotels in Southernmost Point & Casa Marina by Axel's takeSouthernmost Point & Casa Marina is #3 of 6 places to stay in Key West

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Southwinds Motel

2-star hotel · 1321 Simonton Street, Key West

Air conditioning · 24-hour reception · Smoking areas · Smoke-free property · Heating · Newspapers · Ticket assistance · Outdoor furniture · Non-smoking rooms · Room service · Fridge · Cable TV

Hotels in Key West

Axel's take

a no-frills 2-star motel in Old Town Key West

8.2/10

A friendly Old Town base with useful extras, but small rooms and added fees.

Southwinds is a no-frills 2-star motel near the southern end of Duval Street, and a strong pick for travelers who prioritize exploring over room time. Recent Tripadvisor and Expedia guests repeatedly praise the helpful staff, clean rooms and walkable location. Two outdoor pools and the adjacent Tipsy Rooster bar give this simple property more appeal than a bed alone. We'd choose it for an unfussy Key West break, not a resort stay.

The trade-offs are dated interiors, some cramped rooms and bathrooms, and sound carrying between rooms. Light sleepers should request a room away from the bar, which has daily live music. Breakfast is continental, and the hotel's policies place it and beach-chair service within a mandatory daily amenity fee; parking costs extra. We'd skip it if spacious, modern rooms or dependable quiet matter most.

Best for

  • couples exploring Old Town
  • travelers happy with simple rooms
  • pool-and-bar downtime

Watch out for

  • Small, dated rooms and bathrooms
  • Thin walls and live music nearby
  • Mandatory amenity fee; parking extra
Location
Walkable to southern Duval Street and Southernmost Point; near the beach, not beachfront.
Rooms
Basic and often described as comfortable, but room size, storage and bathroom space can disappoint.
Cleanliness
Recent feedback is predominantly positive, with cleanliness stronger than the property's condition.
Service
Friendly, helpful staff are a consistent strength across Tripadvisor and Expedia.
Amenities
Two outdoor pools, continental breakfast, nearby beach-chair service and an adjacent bar; no gym.
Fees and surprises
Daily amenity fee and separate parking charge; redevelopment is proposed in city records, but an active-work schedule was not verified.

Axel's opinion, from the hotel's website and recent guest reviews, scored for what the hotel is. Sources: Hotel website · Tripadvisor · Expedia · Booking.com · en.planetofhotels.com · keywest.legistar.com. Reviewed Oct 20, 2026.

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