Westwinds Inn – Key West Resort Review
Last updated: August 28, 2026
Choose Westwinds Inn if...
- You want a classic Key West inn with a heated pool and included breakfast
- You're an adult traveler wanting a quiet Eaton Street base near Duval
- You value Riley Hotel Group service standards and historic architecture
Skip Westwinds Inn if...
- You're traveling with young children — the intimate inn is adult-oriented
- You want large resort amenities like a spa, gym, or multiple restaurants
- You want beachfront access or modern, contemporary design
AskTheKeys Traveler Match
How well does Westwinds Inn fit your trip?
Before you book — the one trade-off
Westwinds is an intimate inn without resort-scale facilities — you trade spa, gym, and beach access for a quiet historic pool courtyard a short walk from Duval.
AskTheKeys Decision SummaryWestwinds Inn is best for couples and adult travelers who want a classic Key West boutique inn with a heated pool, complimentary breakfast, and a quiet Eaton Street location within easy walking distance of Duval Street. It is not ideal for families with young children, guests seeking large resort amenities, or travelers who want direct beachfront access.
Westwinds Inn is a boutique inn at 914 Eaton Street in Old Town Key West, part of the Riley Hotel Group Key West Collection. The property features individually styled guest rooms in a restored historic Key West home, a heated pool surrounded by tropical gardens, and complimentary continental breakfast. Its location on Eaton Street — a quieter residential parallel to Duval — provides walkable access to Old Town dining, galleries, and nightlife while maintaining a relaxed neighborhood atmosphere. The Riley Hotel Group management ensures consistent service standards. The inn's classic Key West architecture, heated pool, and included breakfast position it as a solid mid-range boutique option in the Old Town corridor.
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Before You Book
The details that matter after you've narrowed down your options.
Best for
- Couples seeking a classic Key West inn with heated pool and included breakfast
- Adult travelers who want a quiet Eaton Street base within walkable Old Town
- Guests who value Riley Hotel Group collection standards and consistent service
- Travelers who appreciate restored historic Key West architecture and tropical gardens
Not ideal for
- Families with young children — the intimate inn atmosphere is adult-oriented
- Guests who want large resort amenities like spa, fitness center, or multiple restaurants
- Travelers seeking direct beachfront access — no beach on-site
- Those who prefer modern/contemporary design over classic Key West inn style
Quick facts
| Address | 914 Eaton Street, Key West, FL 33040 |
|---|---|
| Phone | (305) 296-4440 |
| Check-in / Out | 3:00 PM / 11:00 AM |
| Parking | No on-site parking; street and nearby garage available |
| Pets | No |
| Beach access | No |
| Pool(s) | Yes |
| Spa | No |
| EV charging | No |
Location & nearby
Westwinds Inn is located in Old Town / Eaton Street within Key West.
What's nearby
- Duval Street(0.2 mi, 4 min walk)
- Key West Historic Seaport(0.3 mi, 6 min walk)
- Mallory Square(0.5 mi, 10 min walk)
- Ernest Hemingway Home & Museum(0.5 mi, 10 min walk)
- Key West Lighthouse & Keeper's Quarters(0.3 mi, 6 min walk)
- Key West Cemetery(0.2 mi, 4 min walk)
- Southernmost Point Buoy(0.7 mi, 14 min walk)
- Fort Zachary Taylor State Park & Beach(0.6 mi, 12 min walk)
Amenities overview
Property highlight features
- Heated pool with tropical garden surroundings
- Complimentary continental breakfast daily
- Individually styled rooms in restored historic Key West home
- Classic Key West architectural character
- Part of Riley Hotel Group Key West Collection
- Quiet Eaton Street location — 4 minutes to Duval
Pricing positioning
Typical nightly pricing tends to fall in the $$ range, depending on season and room type.
mid-range classic Key West inn with pool and breakfast
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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 Westwinds Inn Compares to Other Key West Resorts
Westwinds Inn vs Island City House Hotel
- Westwinds Inn wins:single-building boutique inn with classic Key West character and intimate scale
- Island City House Hotel wins:multi-building historic compound with kitchenette suites, tropical gardens, and family-friendly options
Westwinds Inn vs The Mermaid & The Alligator
- Westwinds Inn wins:Riley-managed inn with consistent collection standards, heated pool, and Eaton Street quiet
- The Mermaid & The Alligator wins:independent garden B&B with tropical pool, gourmet breakfast, and quirky Old Town personality
Westwinds Inn vs Simonton Court Historic Inn & Cottages
- Westwinds Inn wins:compact single-building inn with classic Key West style and Riley collection backing
- Simonton Court Historic Inn & Cottages wins:sprawling adults-only compound with multiple pool areas, cottages, and larger property footprint
FAQs
Does Westwinds Inn have a pool?
Yes. Westwinds Inn has a heated pool surrounded by tropical gardens. The pool area provides a private courtyard retreat for guests and is open daily.
Is breakfast included at Westwinds Inn?
Yes. Complimentary continental breakfast is included daily, featuring pastries, fresh fruit, coffee, and juice.
How far is Westwinds Inn from Duval Street?
Westwinds Inn is located at 914 Eaton Street, approximately a 4-minute walk from Duval Street. Eaton Street runs parallel to Duval in a quieter residential section of Old Town, providing easy access to dining and nightlife while maintaining a relaxed atmosphere.
Is Westwinds Inn part of a hotel group?
Yes. Westwinds Inn is part of the Riley Hotel Group Key West Collection, which manages several boutique properties across Old Town Key West including The Mermaid & The Alligator, Coco Plum Inn, and Azul Key West. Each property is individually styled but shares consistent service standards.
Does Westwinds Inn have parking?
No on-site parking is available. Street parking and a nearby city parking garage are options. The property's central Eaton Street location makes most Old Town destinations walkable.
Is Westwinds Inn pet-friendly?
No. Westwinds Inn does not allow pets on the property.
What is the check-in time at Westwinds Inn?
Check-in is at 3:00 PM and check-out is at 11:00 AM. Early check-in or late check-out may be available upon request, subject to availability.
What is the architectural style of Westwinds Inn?
Westwinds Inn is set in a restored historic Key West home featuring classic Conch-style architecture with tropical garden surroundings. Rooms are individually styled to reflect the property's historic character while offering modern comforts.