The 6 Best Luxury Resorts in Islamorada FL | Hand-Picked for 2025
We checked every option available and found the best luxury resorts in Islamorada FL that provide an upscale experience in one of the most beautiful natural settings in the world.
These properties, in a way, offer a kind of laid-back opulence that’s totally fitting for anyone chasing comfort, sunshine, and a bit of peace that’s hard to come by elsewhere.
That kind of barefoot elegance and breezy comfort doesn’t just happen by chance—it takes a special kind of resort to pull off both upscale and unfussy without trying too hard.
Therefore, these Islamorada luxury resorts each offer something a little different, but all of them provide the kind of setting where time slows down and indulgence feels natural.
Table of Contents
Methodology
To determine the best luxury resorts Islamorada offers, we spent time reading what actual guests had to say on sites like TripAdvisor, Google Reviews, and Expedia.
We looked for patterns—comments that, for instance, mentioned consistently warm hospitality, beach setups that were more or less effortless, or rooms that felt more like thoughtfully curated hideaways than just places to crash.
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The 6 Best Luxury Resorts in Islamorada FL for 2025
6. La Siesta Resort & Villas
Key Highlights:
- Spans across 6+ acres with tropical greenery and waterfront stretches
- Small beach with paddleboards, bikes, and kayaks included
- Updated multi-room villas that feel like coastal homes
La Siesta Resort & Villas, though relatively under the radar, is one of the most casually polished Islamorada luxury resorts you’ll stumble across.
The layout feels more like a quiet, leafy neighborhood than your usual crowded property, with paths that wind through palms and colorfully trimmed cottages that feel like a boutique property.
Suites, studios, and family-sized villas are available, many of which come with kitchenettes, breezy patios, and cozy living areas that make it pretty easy to settle in without fuss.
While the beachfront here isn’t massive, it’s quite peaceful—and actually, it might be that smaller scale that makes it feel more personal.
Guests, especially those bringing kids or small groups, love the extras like free kayak use and the convenient proximity to restaurants you can casually bike to in a few minutes.
In short, if you’re looking for luxury resorts in Islamorada FL that offer a more down-to-earth take on elegance, La Siesta kind of just gets it.
Reviews & Latest Price on TripAdvisor
5. Playa Largo Resort & Spa, Autograph Collection
Key Highlights:
- Set on nearly 15 acres of tropical waterfront
- Includes ceviche bar, seafood restaurant, and beach grill
- Ocean Spa and waterfront bungalows available
So technically, this retreat is not in Islamorada—it’s over in nearby Key Largo—but honestly, Playa Largo Resort & Spa is just too polished and well-reviewed to ignore.
Being part of Marriott’s Autograph Collection means it’s not your cookie-cutter chain experience, and the design here feels more like a boutique destination that’s been given the five-star treatment.
The rooms tend to be generously sized, with features like rainfall showers, plush mattresses, and outdoor seating that makes you want to stay out just a little longer at night.
For something a bit more exclusive, their waterfront bungalows are basically like renting your own beachfront cottage, complete with privacy and posh vibes.
Dining’s not a problem here either—with three different spots serving everything from fresh ceviche to grilled mahi and tropical cocktails you probably can’t pronounce but will definitely want to try.
For folks who don’t mind being a few miles up the road from Islamorada, this one’s a strong contender among Islamorada luxury resorts in terms of both comfort and coastal charm.
Reviews & Latest Price on TripAdvisor
4. Bungalows Key Largo
Key Highlights:
- Florida Keys’ only all-inclusive, adults-only luxury resort
- Private bungalows with soaking tubs and garden showers
- Full access to restaurants, pools, and yoga sessions
Alright, so this one’s also technically not in Islamorada—but Bungalows Key Largo is practically the definition of luxury dialed all the way up.
It’s all-inclusive, adults-only, and pretty much feels like you’ve stepped into a tropical wellness dream that’s wrapped in privacy and soft linens.
The private bungalows here aren’t just standard rooms—they’re standalone mini-residences, each with outdoor garden showers, spa-style bathrooms, and patios where you can kick back without seeing another soul.
Meals are included and surprisingly gourmet, with the kind of wine list and seafood options that suggest someone in the kitchen really, really cares.
There’s also an ocean-view spa, multiple bars, yoga by the water, and two pools that manage to feel serene instead of busy.
In a way, this property sort of sets the bar for what luxury resorts in Islamorada FL could be if they went all-in on privacy, exclusivity, and effortless relaxation.
Reviews & Latest Price on TripAdvisor
3. The Caribbean Resort
Key Highlights:
- Family-friendly cottages with multiple bedrooms and kitchens
- Private marina for boating and fishing access
- Quiet pool surrounded by lush greenery
The Caribbean Resort feels like someone took the comforts of a private vacation rental and paired them with the consistency and care of a boutique resort stay.
The vibe is quiet, low-key, and just a little bit nostalgic, which is kind of perfect for guests looking for something that isn’t trying too hard to impress—yet still manages to do just that.
The cottages and suites here are incredibly spacious, with full kitchens, living areas, and screened porches that face either the garden or the water.
The grounds themselves are covered in tropical vegetation, with pathways leading past the pool, hammocks, and a marina where fishing boats are often docked and ready to go.
It’s not the kind of place with five restaurants and DJs at night—but that’s exactly why so many return year after year.
When people mention Islamorada luxury resorts that actually feel like a local secret, this one, pretty often, is what they mean.
Reviews & Latest Price on TripAdvisor
2. Cheeca Lodge & Spa – Best-Seller
Key Highlights:
- 27 beachfront acres filled with activities
- Spa, 3 restaurants, golf, and paddle sports all on-site
- Overwater pier perfect for sunset walks or fishing
Cheeca Lodge & Spa is one of those rare Islamorada luxury resorts that’s been around for decades, yet somehow still feels like it’s kept up with the times without ditching its character.
Set on a sprawling piece of waterfront land, the resort offers pretty much every amenity you could want—golf, tennis, spa treatments, paddleboarding, and even a movie theater for rainy days.
Rooms and suites come in a few different styles, from recently upgraded oceanfront kings with rainfall showers to romantic bungalows tucked into quiet corners of the property.
The food is solid across the board, especially at Atlantic’s Edge, their upscale oceanfront dining space where seafood and steaks get the spotlight.
The beach, which is private and lined with shaded loungers, connects to a long wooden pier that’s popular for evening strolls or early-morning fishing.
Basically, if you want one of the most well-rounded luxury resorts in Islamorada FL that somehow balances full-service flair with local Keys soul, Cheeca delivers it in spades.
Reviews & Latest Price on TripAdvisor
1. The Islands of Islamorada – Best Overall
Key Highlights:
- Multi-bedroom villas with kitchens and waterfront views
- Infinity-edge pool with private cabanas
- Personal concierge service and boat dockage
The Islands of Islamorada tops the list as the best luxury resort in Islamorada.
This is a gated collection of high-end villas that, frankly, feel more like mini beach mansions than resort suites—complete with gourmet kitchens, spa bathrooms, and wraparound balconies made for slow mornings and salty breezes.
The infinity pool overlooks the ocean and never feels crowded, and there’s a low-key bar setup nearby for drinks when the sun starts to dip.
What stands out here is the sheer amount of space—both inside and out—which makes it popular with groups or extended families looking for a splashy but secluded place to stay.
In a way, it’s everything people mean when they say private luxury, but in a spot that still puts you near all the Islamorada action when you want it.
Reviews & Latest Price on TripAdvisor
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