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Simonton Court Historic Inn & Cottages rates, Key West

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#1 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: 9.1/10

A standout Old Town inn for personal service, tropical gardens and quiet pool time. An adults-only historic boutique inn with cottages in Old Town Key West, scored for what it is.

Simonton Court is an adults-only historic boutique inn, not a basic two-star hotel. Its former cigar factory, cottages and garden paths give it genuine Key West character, while four small pools make staying put appealing. We'd strongly recommend it for couples who want to walk to Duval Street without sleeping amid the nightlife. Recent Tripadvisor and Expedia guests repeatedly praise the welcoming staff, clean rooms and surprisingly peaceful grounds; included breakfast adds to the appeal.

Choose your exact room carefully: layouts and sizes vary, some accommodation involves stairs, and older finishes occasionally draw criticism. This is characterful rather than uniformly polished lodging. Parking costs extra, spaces are limited and advance arrangements matter. We'd skip it for a standardized luxury experience or book only after confirming access needs.

  • Best for: Couples exploring Old Town on foot; Adults seeking quiet pool time; Travelers who prefer historic inns

  • Watch out for: Room sizes, layouts and finishes vary; Stairs to some rooms; no elevator; Limited paid parking requires advance arrangements

  • Location: The official address is 523 Eaton Street, near Duval Street and within easy walking distance of Old Town attractions.

  • Rooms: Individually configured rooms and cottages; check the specific unit's size, stairs and outdoor space before booking.

  • Cleanliness: Strong overall cleanliness ratings across Booking.com and Expedia; recent praise substantially outweighs isolated complaints.

  • Service: Warm, helpful staff are a consistent highlight across Tripadvisor, Booking.com and Expedia.

  • Amenities: The hotel advertises four pools, tropical gardens and complimentary breakfast; bicycle rentals are also listed.

  • Fees and surprises: Parking is charged separately, limited and must be arranged ahead; the property is adults-only.

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

About Simonton Court Historic Inn & Cottages

  • 2-star hotel
  • 320 Simonton St, Key West
  • Amenities: Air conditioning, 24-hour reception, Smoke-free property, Newspapers, Ticket assistance, Garden, Terrace, Outdoor furniture, Adults Only, No elevators, Non-smoking rooms, Room service
  • City page: Hotels in Key West

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#1 of 9 hotels in Mallory Square & Historic Seaport by Axel's takeMallory Square & Historic Seaport is #2 of 6 places to stay in Key West

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Simonton Court Historic Inn & Cottages

2-star hotel · 320 Simonton St, Key West

Air conditioning · 24-hour reception · Smoke-free property · Newspapers · Ticket assistance · Garden · Terrace · Outdoor furniture · Adults Only · No elevators · Non-smoking rooms · Room service

Hotels in Key West

Axel's take

An adults-only historic boutique inn with cottages in Old Town Key West

9.1/10

A standout Old Town inn for personal service, tropical gardens and quiet pool time.

Simonton Court is an adults-only historic boutique inn, not a basic two-star hotel. Its former cigar factory, cottages and garden paths give it genuine Key West character, while four small pools make staying put appealing. We'd strongly recommend it for couples who want to walk to Duval Street without sleeping amid the nightlife. Recent Tripadvisor and Expedia guests repeatedly praise the welcoming staff, clean rooms and surprisingly peaceful grounds; included breakfast adds to the appeal.

Choose your exact room carefully: layouts and sizes vary, some accommodation involves stairs, and older finishes occasionally draw criticism. This is characterful rather than uniformly polished lodging. Parking costs extra, spaces are limited and advance arrangements matter. We'd skip it for a standardized luxury experience or book only after confirming access needs.

Best for

  • Couples exploring Old Town on foot
  • Adults seeking quiet pool time
  • Travelers who prefer historic inns

Watch out for

  • Room sizes, layouts and finishes vary
  • Stairs to some rooms; no elevator
  • Limited paid parking requires advance arrangements
Location
The official address is 523 Eaton Street, near Duval Street and within easy walking distance of Old Town attractions.
Rooms
Individually configured rooms and cottages; check the specific unit's size, stairs and outdoor space before booking.
Cleanliness
Strong overall cleanliness ratings across Booking.com and Expedia; recent praise substantially outweighs isolated complaints.
Service
Warm, helpful staff are a consistent highlight across Tripadvisor, Booking.com and Expedia.
Amenities
The hotel advertises four pools, tropical gardens and complimentary breakfast; bicycle rentals are also listed.
Fees and surprises
Parking is charged separately, limited and must be arranged ahead; the property is adults-only.

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

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