Islamorada Resorts

Question

We are treating our daughter to a 3 night stay in the Keys for a much needed break from PA school. We are wanting somewhere mid keys (islamorada) that has nice rooms, tropical pool, maybe a bar, and is somewhat peaceful .. preferably on the Gulfside … would love ideas!

Answer

Great idea to take a relaxing 3-night break in Islamorada — you’ve picked a charming spot in the Keys, and there are several lovely resorts that might fit the “tropical, peaceful, room to unwind” vibe you’re going for. Below are some top resort suggestions *plus insights and tips* to help you choose.

Here are several resort options in or around Islamorada that could suit your needs:

La Siesta Resort & Villas — Part of the Islamorada Resort Collection. La Siesta feels very lush and tropical, with walk-in private beaches, mature trees, and a relaxed, low-key atmosphere.
Amara Cay Resort — Also part of the Resort Collection. This is a boutique-style resort with luxe—but laid-back—spaces, great views (including Alligator Reef Lighthouse), and a really authentic Keys atmosphere.
Three Waters Resort & Marina — A Tribute Portfolio resort. It has a marina, contemporary rooms, pool, waterfront dining, and access to all the amenities of the Resort Collection.
The Islands of Islamorada — A very upscale, secluded resort with oceanfront pools, elegant villas and suites, more private beach / shore access, and concierge-level service.
Islander Resort Islamorada — Although technically on the bay side, it’s very peaceful, with a tropical pool, waterfront activities, cozy villas, and calm energy.
Sands of Islamorada — More modest and simpler, but very charming, family-owned, and “old-Florida” in style. It’s quieter, with a peaceful feel, a pool, and oceanfront spots.

Thinking specifically about your preferences (mid-Keys, peaceful, tropical pool, bar, Gulf-side feel):

If “peaceful” is top priority: La Siesta Resort & Villas or The Islands of Islamorada are excellent. La Siesta gives that leafy, laid-back Keys feeling, while The Islands offers luxury and seclusion.
For a resort with good on-site dining / bar + overall resort amenities: Three Waters Resort & Marina is a strong pick. It has several dining venues, a raw bar, and more “resort feel.”
If you want a resort that feels more boutique / “local island”: Amara Cay is ideal — it’s not huge, and it feels very Keys-authentic.
If you don’t mind being on the bay side rather than the Atlantic (Gulf-facing Keys are limited): Islander Resort gives a calm, bay-side feel with mangrove views, a quiet pool, and water-based activities.

Other things to keep in mind / tips for your 3-night stay on Islamorada:

Since you’re treating your daughter: ask about villa or suite options — some rooms will feel more like a little getaway than a standard hotel room.
Check for resort-hopping perks: The Islamorada Resort Collection (“Resort Hopper” package) allows access to multiple resort amenities, which can expand dining and activity choices.
Plan for downtime by the pool: Even if you want to do some local exploration, make sure to schedule “pool + chill” time — that’s the beauty of a Keys resort.
Bring / rent water-gear: Kayaks, paddleboards, or paddle-boating from the marina (at Three Waters or Islander) is a relaxing way to enjoy the water without big crowds.
For meals: Use the on-site restaurants, but also consider venturing out for local seafood / island-style dining. Having a resort base makes it easy to mix “relax day” meals with “exploration day” meals.
Book in advance: Mid-Keys resorts can fill up, especially for a 3-night stay, so locking in your rooms early is smart.

My recommendation: Based on what you said (a “much needed break,” relaxing, tropical pool, somewhat peaceful), I lean toward La Siesta Resort & Villas or Amara Cay. They feel more intimate and quiet compared to a big resort, but still have lovely rooms, greenery, and a very “Keys vacation” ambiance. If you want a little more resort dining and activity without feeling too busy, Three Waters Resort & Marina is a great balance.

Islamorada Resorts

More Islamorada Travel Questions

The attractions mentioned in this question

Popular Destinations

Popular Travel Questions