The 8 Best 5-Star Resorts in Florida Keys

We looked through all the options to determine the best 5 star resorts Florida Keys has to offer so that you can plan your perfect upscale paradise getaway.

Surprisingly enough, genuine five-star accommodations are rather scarce in this part of the Sunshine State. There are plenty of fancy places to stay, yet only a handful actually meet that ultra-luxurious benchmark.

Now, for those looking to stay somewhere that oozes sophistication and first-class comfort, we’ve rounded up the best 5 star resorts Florida Keys has to offer and also put together a list of solid 4-star alternatives as well.

Table of Contents

Methodology

To put together this list of the best five star resorts in Florida Keys, we combed through an overwhelming number of guest reviews via Google Reviews and Expedia, and included industry rankings as well as firsthand experiences from people who actually know what high-end travel is all about.

Every resort featured here had to offer exceptional guest service, next-level amenities, and that hard-to-find blend of relaxation and indulgence that people expect when booking the best five star resorts Florida Keys has to offer. Now, in other words, we weren’t just looking at fancy lobbies and beachside pools—we wanted the whole package.

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Best 5-Star Resorts Florida Keys

3. Casa Marina Key West, Curio Collection by Hilton

Google Reviews Score: 3.6 out of 5.0

Now, for those who appreciate history mixed with a little bit of coastal glam, Casa Marina has that whole old-world-meets-modern vibe.

Built way back in the 1920s, this spot, in many ways, feels like stepping into another era—except with the perks of contemporary luxury. That’s not to say everything is perfect, but still, it has its own unique charm.

The resort boasts a rare private stretch of beach, which, frankly, isn’t something you find often in the Keys. The two ocean-facing pools offer a rather peaceful retreat, yet for those who crave a little more action, there are plenty of water sports to keep things interesting.

Meanwhile, the on-site spa is the kind of place where stress just kind of disappears.

Guests can choose from traditional rooms or more spacious suites, many of which have balconies that give an uninterrupted view of the Atlantic.

That said, the resort has undergone some renovations, and, to be honest, reactions have been mixed. Nevertheless, it remains a go-to for those who want an elegant yet laid-back stay.

Reviews & Latest Price on TripAdvisor

2. H2O Suites Hotel

Google Reviews Score: 4.7 out of 5.0

If privacy and tranquility top the list of must-haves, H2O Suites might just be the best bet. This is an adults-only escape and, unlike some of the larger resorts, this one leans into a sleek, contemporary look with a strong emphasis on personal space.

Each suite comes with its own little plunge pool, making it feel almost like a private oasis.

Meanwhile, the rooftop pool, reserved exclusively for guests, offers a rather impressive skyline view of Key West. Food-wise, there’s no on-site restaurant, but given the prime location, it’s not hard to find an incredible meal just a short walk away.

Service is, as expected, top-tier, with staff who actually seem to enjoy making guests feel welcome.

For couples seeking an ultra-relaxed atmosphere with modern surroundings, this place definitely delivers, making it the 2nd best 5 star resort in Florida Keys.

Reviews & Latest Price on TripAdvisor

1. Little Palm Island Resort & Spa

Google Reviews Score: 4.6 out of 5.0

When it comes to absolute, no-questions-asked luxury, Little Palm Island is pretty much in a league of its own.

That’s why we think it is the best 5 star resort in Florida Keys, period. As a matter of fact, it’s one of those places that feels more like a dream than an actual destination.

Accessible only by boat or seaplane, this secluded paradise is tailor-made for those who prefer their vacations with a hefty dose of exclusivity.

Thatched-roof bungalows, complete with outdoor showers and oceanfront views, set the tone for a stay that is completely off the grid—in the best possible way.

The resort actively encourages guests to unplug, meaning no TVs or distractions, just pure relaxation. The private beach is nothing short of breathtaking, with swaying palms and water that looks impossibly blue.

Fine dining here is an experience in itself, with gourmet dishes that showcase fresh, locally sourced ingredients. Meanwhile, the spa offers treatments that take relaxation to a whole new level.

For honeymoons, anniversaries, or just a splurge-worthy getaway, this is as good as it gets.

Reviews & Latest Price on TripAdvisor

Top 4-Star Resorts in the Florida Keys

Since there are only three true 5 star resorts Florida Keys has to offer, travelers looking for luxury will find that some high-end four-star alternatives can deliver an experience that’s nearly as refined.

These resorts offer upscale accommodations, top-tier dining, and premium amenities that come close to five-star standards.

5. Opal Key Resort & Marina

Google Reviews Score: 4.5 out of 5.0

Located right by Mallory Square, Opal Key has a front-row seat to Key West’s legendary sunsets. The resort, in many respects, is ideal for those who want to mix luxury with a lively atmosphere.

The waterfront pool is a prime spot for unwinding, while the marina location means easy access to boating excursions. The rooms, featuring modern yet cozy designs, offer either city or ocean views.

Reviews & Latest Price on TripAdvisor

4. Hyatt Vacation Club at Beach House, Key West

Google Reviews Score: 4.5 out of 5.0

For those who prefer extra space, Hyatt Vacation Club delivers with villa-style accommodations that feel more like private residences than hotel rooms. The full kitchens make it an excellent option for longer stays.

With a private beach and a lagoon-style pool, the resort offers a pretty relaxed atmosphere. While it doesn’t have the full-service feel of a five-star resort, the personalized touches make up for it.

Reviews & Latest Price on TripAdvisor

3. Ocean Key Resort & Spa

Google Reviews Score: 4.6 out of 5.0

Right at the end of Duval Street, Ocean Key blends upscale comfort with a vibrant atmosphere. The pool overlooks the Gulf, while the on-site spa specializes in island-inspired treatments.

Rooms are colorful and fun, with many offering balconies perfect for watching the sunset. It’s the perfect mix of high-end and lively.

Reviews & Latest Price on TripAdvisor

2. Tranquility Bay Beachfront Resort

Google Reviews Score: 4.6 out of 5.0

Located in Marathon, this resort offers townhome-style accommodations, making it a top choice for families and groups. The private beach and three pools create an ideal setting for relaxation.

With an on-site restaurant known for excellent seafood, plus plenty of space to spread out, it’s an easy pick for an upscale, stress-free escape.

Reviews & Latest Price on TripAdvisor

1. Marquesa Hotel

Google Reviews Score: 4.8 out of 5.0

More boutique than resort, Marquesa Hotel is all about charm and personal service. The historic conch-style houses have been transformed into a refined retreat.

With lush gardens, a peaceful pool area, and an award-winning restaurant, it’s ideal for those who prefer intimate, high-end accommodations.

Reviews & Latest Price on TripAdvisor