Name: Waterfront House with Boat Dock
Rating: 6

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Our top choices for Windley Key 4-star hotels

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo

Melissa

$384 nightly

May 19 - May 20

Total with taxes and fees

3 restaurants, breakfast, lunch, dinner served; American cuisine

Reefhouse Resort & Marina

Key Largo

Mayaprasannakumar

$319 nightly

May 3 - May 4

Total with taxes and fees

Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room

Amara Cay Resort

Matecumbe

David

$249 nightly

May 11 - May 12

Total with taxes and fees

Islander Resort

Matecumbe

DeShawn

$255 nightly

May 17 - May 18

Total with taxes and fees

In-room safe, individually decorated, individually furnished

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada

Joseph Ganino

$322 nightly

May 25 - May 26

Total with taxes and fees

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Kristie Howle

$408 nightly

May 17 - May 18

Total with taxes and fees

Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

La Siesta Resort & Villas

Matecumbe

Kathy

$259 nightly

May 13 - May 14

Total with taxes and fees

On the beach, sun loungers, beach umbrellas, beach towels

The Islands of Islamorada

Matecumbe

Michael

$634 nightly

May 6 - May 7

Total with taxes and fees

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Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Windley Key.

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

$312 nightly

$351 total

May 14 - May 15

Total with taxes and fees

9.2/10 Wonderful! (1,317 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Check out the local area in Windley Key as you venture to sights like Windley Key Fossil Reef Geological State Park.

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Top Windley Key Hotel Reviews

Islander Resort

8/10 Good

"Overall, we had a wonderful stay at the Islander Resort. Since we visited on a Sunday night, dining options on the property were somewhat limited. However, we highly recommend the Lorelei Restaurant just across the street—it offers excellent food and drinks, live music, and truly stunning sunset views that made our evening especially memorable."

Amara Cay Resort

10/10 Excellent

"We had the most amazing stay at Amara Cay in Islamorada for our honeymoon! From the moment we arrived, everything felt effortless, relaxing, and truly special. The property is absolutely beautiful—clean, modern, and perfectly captures that laid-back luxury island vibe. The rooms were comfortable and well-kept, with stunning views that made it hard to leave. The pool area and private beach were highlights for us—plenty of space to unwind, with crystal-clear water and the most peaceful atmosphere. It never felt overcrowded, which made it even more enjoyable. The staff was incredibly kind and attentive throughout our stay, always going out of their way to make sure we had everything we needed. You can tell they genuinely care about the guest experience. The location is also perfect—close to everything in Islamorada while still feeling like a private escape. Whether you're looking for a romantic getaway or just a relaxing trip, this place checks every box. We’ll absolutely be back and couldn’t recommend it more!"

Baker's Cay Resort Key Largo, Curio Collection by Hilton

8/10 Good

"Room was great! Didn't like the fact you could order food at their restaurant and take tour leftovers back but no way to warm them up unless you went to the front desk. Pool and hot tub were filthy with cups and fruit over the weekend and not cleaned til check out time Tuesday morning of course. The hour free with the kayaks or paddle boards was a really awesome perk. Restaurant was beautiful with nice seating, but prices weren't comparable to size or quality of some foods."

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Windley Key Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Windley Key, Islamorada are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Windley Key 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Windley Key. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Windley Key, Islamorada, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Windley Key hotels offer everything your heart desires.

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