Which area/resort would be best?

Question

First time to the Keys and it will be just my husband and I.

We want somewhere laid back, with the resort on the water. It would be nice if a couple of restaurants were within walking distance.

I know the Keys are not a beach destination, but even a resort with a small man made beach area would be nice. We will spend 1/2 of our time lounging by the pool, so a nice pool is a must.

We are resort people (I understand the fees and pricing) and like nicer places. Ideally under $600 a night. We aren’t looking for any certain activities or nightlife per se.

Little Palm Island and Sunset key cottages are a bit out of our budget.

Ideas that stick out are Bakers Cay, Cheeca Lodge, Hawks Cay, Pier House, Isla Bella.

Any thoughts or ideas are welcome, thanks!

Answer

Visiting the Florida Keys for the first time as a couple is a wonderful opportunity to relax in a beautiful, tropical setting. Since you’re looking for a laid-back resort experience with waterfront views, a nice pool, and some dining options within walking distance, here’s a breakdown of the resorts you mentioned and a few thoughts:

Resort Options:

Bakers Cay Resort, Key Largo: This is a lovely resort with a large waterfront pool, access to a small private beach area, and a tropical vibe. It’s laid-back and generally less crowded. Dining options are available on-site, and some local restaurants are walkable. Pricing often comes in under $600/night, making it a great first-time Keys option.
Cheeca Lodge, Islamorada: Cheeca Lodge is a classic, upscale resort with a beautiful pool, water access, and plenty of amenities. The on-site restaurants are good, and the grounds are serene. It can sometimes approach the top of your budget, but you may find deals depending on timing. The beach area is small but pleasant for lounging.
Hawks Cay, Duck Key: Known for its larger resort feel, Hawks Cay has multiple pools, a lagoon-style pool, and various water activities. It’s more family-oriented but still a good choice for couples. Dining options on-site are good, but walkability to off-property restaurants is limited, so a car is helpful here.
Pier House, Key West: Situated near Old Town Key West, Pier House offers oceanfront rooms and a small pool. It’s perfect if you want to combine a relaxing resort stay with the walkable dining, shopping, and casual nightlife of Key West. Pricing can fluctuate, sometimes above your $600/night range.
Isla Bella Beach Resort, Marathon: Isla Bella has a long beach area, multiple pools, and modern, comfortable rooms. Dining is available on-site, though off-site options require a short drive. The resort offers a more contemporary, upscale feel while remaining relaxed. Prices are often within your budget.

Recommendations:

If you want the most relaxing, tropical experience with waterfront lounging and a small beach, Bakers Cay or Isla Bella are excellent choices.
If you want a combination of resort relaxation and walkable dining/shopping, Pier House in Key West is ideal.
If you want classic luxury with more amenities and are okay spending near the top of your budget, Cheeca Lodge is a strong contender.
Hawks Cay is more resort-focused and family-oriented; it’s best if you enjoy lots of amenities and water activities but may be less intimate.

Overall, for a first-time, romantic, and laid-back Keys experience under $600/night, Bakers Cay and Isla Bella are probably your best bets. Pier House is a great option if you want more of the Key West experience with dining and local exploration.

Which area/resort would be best?

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