Explore top 2026 4 Star Hotels in Windley Key

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Top Windley Key 4 Star hotels

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$273 nightly

$308 total

Jan 27 - Jan 28

Total with taxes and fees

A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...

8.8/10 Excellent! (1,263 reviews)

Amazing place to stay. Staff was great

Reviewed on Jan 16, 2026

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

97000 Overseas Hwy Key Largo FL

Fully refundableReserve now, pay when you stay

$388 nightly

$437 total

Jan 22 - Jan 23

Total with taxes and fees

A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

8.6/10 Excellent! (1,006 reviews)

The rooms were ok, they were outdated with non working A/C, ripped curtains, old furniture and electrical outlets that does not hold the plugs. Towels smelled bad. However the staff except for one lady in the front was all amazing. They smiled and tried to help with everything. The resort is on an ...

Reviewed on Jan 9, 2026

Playa Largo Resort & Spa, Autograph Collection

97450 Overseas Highway Key Largo FL

Fully refundableReserve now, pay when you stay

$488 nightly

$549 total

Feb 1 - Feb 2

Total with taxes and fees

This luxury resort features a full-service spa, a marina, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the ...

8.8/10 Excellent! (1,001 reviews)

My family and I loved every minute. I have two pre teen boys and we loved the fishing, pool, the staff was so fun and great. I would highly recommend this resort to anyone. The beach was amazing. All of it was lovely! We will be back!

Reviewed on Jan 14, 2026

Islander Resort

82100 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$380 nightly

$428 total

Jan 29 - Jan 30

Total with taxes and fees

A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...

9.2/10 Wonderful! (1,008 reviews)

Really liked this place! Had a few issues with hot water and the shower. They were definitely responsive about fixing but there were some language barriers which made that a little difficult. Some of the furniture around the pool needed some love. And there was a lot of empty space on the property ...

Reviewed on Jan 13, 2026

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL

Fully refundableReserve now, pay when you stay

$365 nightly

$411 total

Jan 21 - Jan 22

Total with taxes and fees

The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...

8.6/10 Excellent! (1,005 reviews)

The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well

Reviewed on Jan 12, 2026

The Islands of Islamorada

82779 Old Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

$602 nightly

$677 total

Jan 21 - Jan 22

Total with taxes and fees

2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach ...

9.6/10 Exceptional! (70 reviews)

Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on Nov 25, 2025

The Caribbean Resort Coconut Palm North

117 South Carroll Street Islamorada FL

A marina and an outdoor pool are featured at this smoke-free vacation home. Free self parking and a convenience store are also offered on site.

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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.

4 Star Hotels Windley Key

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Windley Key 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Windley Key will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Windley Key, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.