Explore top 2026 4 Star Hotels in Windley Key

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Top Windley Key 4 Star hotels

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

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

4 out of 5
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$352 nightly
The price is $396 total per night from Jun 2 to Jun 3
$396 total
Jun 2 - Jun 3
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! (1,056 reviews)
The name of this place should be Baker’s Cay FAMILY resort. While I totally understand this was not an adults only property, there were screaming kids everywhere. The biggest issue is no soundproofing in the rooms. We were woken in the middle of the night every night and early mornings by a crying ...

Reviewed on Apr 30, 2026

Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$319 nightly
The price is $354 total per night from May 3 to May 4
$354 total
May 3 - May 4
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Family-friendly ...
9.4/10 Exceptional! (1,410 reviews)
The Reef house is a beautiful place to stay. Good view, not crowded, super nice, friendly, helpful staff! the only negative thing was there was no microwave in the room. Highly recommend staying here!!!

Reviewed on May 1, 2026

Opens in a new windowReefhouse Resort & Marina
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$255 nightly
The price is $286 total per night from May 17 to May 18
$286 total
May 17 - May 18
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! (1,001 reviews)
Wonderful resort. Immaculate grounds. Just a very happy place.

Reviewed on Apr 30, 2026

Opens in a new windowIslander Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$251 nightly
The price is $283 total per night from May 18 to May 19
$283 total
May 18 - May 19
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)
Very expensive at Tiki Bar. Also disappointed with offer of late check then insulting $100 price tag.

Reviewed on May 1, 2026

Opens in a new windowAmara Cay Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$313 nightly
The price is $352 total per night from Jun 1 to Jun 2
$352 total
Jun 1 - Jun 2
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
9/10 Wonderful! (192 reviews)
Clean updated room, great view and balcony! Loved the property and amenities.

Reviewed on Apr 25, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
$392 nightly
The price is $441 total per night from May 31 to Jun 1
$441 total
May 31 - Jun 1
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! (1,005 reviews)
Excellent

Reviewed on May 1, 2026

Opens in a new windowPlaya Largo Resort & Spa, Autograph Collection
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $266 total per night from May 27 to May 28
$266 total
May 27 - May 28
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! (1,001 reviews)
It was simply stunning. Beautiful location, great facilities, spacious apartment and for a family of 5 the door key card being on the wristband is genius. Thank you for a wonderful stay

Reviewed on Apr 21, 2026

Opens in a new windowLa Siesta Resort & Villas
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$649 nightly
The price is $730 total per night from May 3 to May 4
$730 total
May 3 - May 4
Total with taxes and fees
A marina, 2 outdoor pools, and a 24-hour gym 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! (75 reviews)
The "suite" was a single room with a king and pullout sofa, there was no separation. So if you are traveling with children be aware that this is the same as a double queen at any other hotel room.

Reviewed on Apr 30, 2026

Opens in a new windowThe Islands of Islamorada
Condo in the Keys

Condo in the Keys

4 out of 5
500 Burton Dr Tavernier FL
The private beach and full-service spa are among the highlights at this apartment. There's fun for all ages with a playground and an arcade/game room, and families ...
8/10 Very Good! (14 reviews)
Nice kitchen. Great view.

Reviewed on Mar 27, 2026

Opens in a new windowCondo in the Keys
Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views

4 out of 5
Long Key FL
A marina and an outdoor pool are featured at this smoke-free apartment. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue ...
Opens in a new windowFlorida Keys Getaway w/ Stunning Ocean Views
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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.

Recent Windley Key hotel reviews by fellow wanderers

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