Simonton Court Historic Inn & Cottages – Key West Resort Review
Last updated: August 28, 2026
Choose Simonton Court Historic Inn & Cottages if...
- You're a couple wanting a quiet historic retreat steps from Duval Street nightlife
- You're a history enthusiast drawn to restored Victorian and Conch architecture
- You want multiple pools in an intimate, non-resort setting
Skip Simonton Court Historic Inn & Cottages if...
- You're traveling with children — this is a strict adults-only property
- You want a modern full-service resort with concierge dining and spa
- You want beachfront access — this is an inland Old Town inn
AskTheKeys Traveler Match
How well does Simonton Court Historic Inn & Cottages fit your trip?
Before you book — the one trade-off
Simonton Court trades on-site dining and resort services for four pools and historic garden quiet just steps from Duval's nightlife.
AskTheKeys Decision SummarySimonton Court Historic Inn & Cottages is best for couples and solo travelers who want a quiet, historic boutique inn with four pools and lush gardens within walking distance of Duval Street — without the noise of staying on the strip itself. It is not ideal for families with children, guests who want a modern full-service resort, or travelers who need on-site dining beyond breakfast.
Simonton Court Historic Inn & Cottages is a 30-room adults-only historic inn on two acres at 320 Simonton Street in Old Town Key West. The property features Victorian and Conch-style architecture, four outdoor swimming pools, lush tropical gardens, complimentary continental breakfast served poolside, and free bicycle rentals. It sits just a short walk from Duval Street while maintaining a peaceful, garden-like atmosphere.
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Before You Book
The details that matter after you've narrowed down your options.
Best for
- Couples who want a quiet historic retreat steps from Duval Street nightlife
- Solo travelers seeking a peaceful adults-only boutique with garden ambiance
- History enthusiasts drawn to restored Victorian and Conch architecture
- Guests who value multiple pools in an intimate, non-resort setting
Not ideal for
- Families with children — this is a strict adults-only property
- Guests who expect a modern full-service resort with concierge dining and spa
Quick facts
| Address | 320 Simonton Street, Key West, FL 33040 |
|---|---|
| Phone | +13052946386 |
| Check-in / Out | 3:00 PM / 11:00 AM |
| Parking | $30/day (limited on-site, by request) |
| Pets | No |
| Beach access | No |
| Pool(s) | Yes |
| Spa | No |
| EV charging | Unknown |
Location & nearby
Simonton Court Historic Inn & Cottages is located in Old Town / Duval Street within Key West.
What's nearby
- Duval Street(0.1 mi, 2 min walk)
- Mallory Square(0.3 mi, 6 min walk)
- Key West First Legal Rum Distillery(0.1 mi, 3 min walk)
- Ernest Hemingway Home & Museum(0.4 mi, 8 min walk)
- Key West Lighthouse & Keeper's Quarters(0.4 mi, 8 min walk)
- Southernmost Point Buoy(0.5 mi, 10 min walk)
- Fort Zachary Taylor State Park & Beach(0.8 mi, 16 min walk)
- Key West Butterfly & Nature Conservatory(0.5 mi, 10 min walk)
Amenities overview
Property highlight features
- 4 outdoor swimming pools (some heated, open 24/7)
- 2-acre tropical gardens with Victorian architecture
- Complimentary continental breakfast served poolside
- Free bicycle rentals (direct bookings)
- Complimentary yoga sessions
- 30 individually decorated guestrooms & cottages
Pricing positioning
Typical nightly pricing tends to fall in the $$$ range, depending on season and room type.
mid-to-upper boutique historic inn
Compare current room availability and secure member-only pricing.
We handle our lodging checks through Expedia's network engine so you can lock in hidden seasonal discounts and stack your One Key™ rewards points across different island brands.
Independent Decision Engine
Florida Keys Resorts operates as a fully objective, crowdsourced review system. We do not accept paid placements from hotels to alter their scoring records. Instead, we use standardized API connections to provide transparent third-party rate checks for our community.
How Simonton Court Historic Inn & Cottages Compares to Other Key West Resorts
Simonton Court Historic Inn & Cottages vs Curry Mansion Inn
- Simonton Court Historic Inn & Cottages wins:quieter 2-acre garden compound with 4 pools and cottage-style rooms
- Curry Mansion Inn wins:grand Victorian mansion with museum-quality common areas and Duval frontage
Simonton Court Historic Inn & Cottages vs Island City House Hotel
- Simonton Court Historic Inn & Cottages wins:adults-only with 4 pools and Victorian compound on 2 acres
- Island City House Hotel wins:family-friendly historic trio of houses with tropical courtyard and suite-style rooms
Simonton Court Historic Inn & Cottages vs Hyatt Centric Key West Resort & Spa
- Simonton Court Historic Inn & Cottages wins:intimate historic boutique with garden atmosphere and poolside breakfast
- Hyatt Centric Key West Resort & Spa wins:full-service Hyatt with spa, modern rooms, and brand-backed amenities
Simonton Court Historic Inn & Cottages vs Ambrosia Key West
- Simonton Court Historic Inn & Cottages wins:historic inn compound on Simonton with multiple pool areas and cottage-style accommodations
- Ambrosia Key West wins:Fleming Street B&B with 3 heated pools and private-entrance rooms
Simonton Court Historic Inn & Cottages vs Weatherstation Inn
- Simonton Court Historic Inn & Cottages wins:larger historic compound with multiple pools, cottages, and expansive grounds
- Weatherstation Inn wins:compact quiet inn near the waterfront with refined atmosphere and intimate scale
FAQs
Is Simonton Court Historic Inn adults only?
Yes. Simonton Court is a strict adults-only property. No children are permitted. The inn caters to couples and solo travelers seeking a peaceful, mature atmosphere in Old Town Key West.
How many pools does Simonton Court have?
The inn has four outdoor swimming pools spread across the 2-acre property. Some pools are heated, and all are available 24 hours a day for guest use.
Is Simonton Court walkable to Duval Street?
Yes. Simonton Court is at 320 Simonton Street, about a 2-minute walk to Duval Street. Restaurants, bars, shopping, and nightlife are all easily accessible on foot, and no car is needed.
Does Simonton Court serve breakfast?
Yes. A complimentary continental breakfast is served poolside each morning. The setting in the tropical garden courtyard makes it a relaxing way to start the day.
Does Simonton Court have on-site parking?
Limited on-site parking is available at $30 per day by request. Since the inn is highly walkable to all Old Town attractions, many guests find a car unnecessary during their stay.
What style are the rooms at Simonton Court?
The inn has 30 individually decorated guestrooms and cottages set within restored Victorian and Conch-style buildings. Each room features unique furnishings, private bathrooms, and either a balcony or patio.
Does Simonton Court allow pets?
No. Simonton Court does not allow pets. The inn maintains a quiet, garden-focused atmosphere for adult guests.
Is Simonton Court good for couples?
Yes. The adults-only policy, historic architecture, four pools, tropical gardens, and proximity to Duval Street dining make Simonton Court a strong pick for couples who want a quieter boutique alternative to larger Key West resorts.