1. Casa Marina Key West, Curio Collection by Hilton

311 guest rooms, including 63 suites. casamarinaresort.com

Key advantages
Here you will find the largest private beach in Key West and two ocean-front pools. Casa Marina was built in the 1920s and recently underwent major updates. With Casa Marina, you get more onsite amenities like pools, beach, spa, and restaurants which means you can spend more time “on-resort” if you like. Good for families or larger groups who want a consistent resort experience.

Potential trade-offs
Tend to cost more and less intimate than a small B&B or boutique guesthouse or more unique water stay.

2. Beachside Resort & Residences

222 guest rooms, including 129 suites with gourmet kitchens plus 93 standard king rooms. beachsidekeywest.com

Key advantages
Many accommodations are large condo-style suites with kitchens, multiple bedrooms and private balconies, which is a big plus for families or folks staying longer. Has a private beach and marina with water-access amenities. At Beachside Resort, you’ll have a pool, restaurant and beach access without necessarily being in a huge resort crowd. If you’re staying longer or want more space like a kitchen or separate living areas, this gives you more flexibility than a typical 1-bed hotel room.

Potential trade-offs
Location is a bit farther from “Old Town” walk-to restaurants/bars so you’ll need to have a way to get around town.

3. Opal Key Resort & Marina

This waterfront resort has 178 guest rooms and suites. Opal Key Resort

Key advantages
Opal Key Resort is just steps from the harbor, cruise-ship dock, near the heart of Old Town Key West, just off Duval Street — excellent for those who want easy access to the nightlife, dining and attractions. On-site marina with slip access, which is a unique feature among Key West hotels. Resort-level amenities with pool, bars, waterfront dining. The location and amenities make it easy to “walk and play” in Key West; less need for car/transport. Also good for water-activity opportunities.

Potential trade-offs
Being close to the cruise ship port can introduce more foot traffic/noise from docked ships or nearby public areas than you’ll find at more unique & intimate accommodation.

Large hotel/resort pros and cons…

Pros:

  • More amenities in one place – e.g., pools, spa, beach access, multiple dining and bar options, often room service.

  • Scale & choice – more room types (suites, multi-bedrooms), more flexibility for families/groups.

  • Facilities & service – often have on-site concierge, event staff, more consistent maintenance.

  • Location – many large resorts position themselves in prime locations (waterfront, easy walk to main attractions).

  • Convenience – If you prefer “everything at your fingertips,” a larger resort can give you that versus scattered smaller accommodations where you might need to commute for amenities or dining.

Cons:

  • Cost – Larger resorts often command premium pricing.

  • Atmosphere – They may feel more “corporate/resort-like” and less intimate than a boutique guesthouse or vacation rental.

  • Occupancy & crowd – More guests can mean busier pools, more foot traffic, less “quiet” feel.

  • Location trade-offs – Some large resorts might be a bit farther from the Old Town core (if they’ve built on slightly more remote land for size) or be adjacent to high-traffic areas (e.g., cruise ship docks) with associated noise.

  • Room type selection matters – In large properties there can be big variation in view/quality; choosing the right room (view, floor, facing away from traffic) is important.