Explore top 2026 4 Star Hotels in Windley Key

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

This weekend
Next weekend

Top Windley Key 4 Star hotels

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$389 nightly
The price is $433 total per night from Mar 4 to Mar 5
$433 total
Mar 4 - Mar 5
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! (1,395 reviews)
Nice property. Clean and comfortable rooms, nice pool and beach area. Enjoyed many great restaurants in the area.

Reviewed on Mar 2, 2026

Opens in a new windowReefhouse Resort & Marina
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
$498 nightly
The price is $560 total per night from Mar 5 to Mar 6
$560 total
Mar 5 - Mar 6
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! (161 reviews)
i paid over 7 thousand dollars for 2 rooms for 4 nights..800 a night to get a view of a parking lot. i am a gold member of Marriott. The room was so small, no latch on door and the drawers were broken. HIGHLY DISAPPOINTED

Reviewed on Mar 2, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$389 nightly
The price is $438 total per night from Mar 8 to Mar 9
$438 total
Mar 8 - Mar 9
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! (1,259 reviews)
We enjoy the amenities but the rooms air-conditioned is not working, we call the front desk twice to get it fix.

Reviewed on Mar 2, 2026

Opens in a new windowAmara Cay Resort
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
$509 nightly
The price is $572 total per night from Mar 11 to Mar 12
$572 total
Mar 11 - Mar 12
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)
There was a major issue with the valet parking upon arrival. The attendant was overwhelmed, there were no bellhops available, I was prohibited from using the cart & the manager refused to speak with me when I asked to address the issue with her. If they are not going to have proper staffing and oversight, ...

Reviewed on Mar 2, 2026

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

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$502 nightly
The price is $565 total per night from Mar 26 to Mar 27
$565 total
Mar 26 - Mar 27
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! (1,009 reviews)
Great boutique type hotel with good amenities. Excellent landscaping, lighting and access to amenities.

Reviewed on Mar 2, 2026

Opens in a new windowIslander 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
$503 nightly
The price is $566 total per night from Mar 22 to Mar 23
$566 total
Mar 22 - Mar 23
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! (1,003 reviews)
The resort is very relaxing and beautiful. The welcome mojito set the vibe. We traveled with our 10 month old infant who had a wonderful time in the pool and beach. The rooms were large and clean. Requested a first floor patio and was assigned one. It really helped not having to do an elevator with ...

Reviewed on Feb 26, 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
$345 nightly
The price is $389 total per night from Mar 8 to Mar 9
$389 total
Mar 8 - Mar 9
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, ...
8.8/10 Excellent! (1,001 reviews)
Room was clean, had some wear and tear but overall a good room for 5 of us. Beds were comfy. This is a quiet resort, but we did like that we could go to the other resorts. Loved the amenties. My only complaint was I wish they were available past 4pm. We wanted to do some water activities after returning ...

Reviewed on Feb 28, 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
$1,028 nightly
The price is $1,157 total per night from Mar 10 to Mar 11
$1,157 total
Mar 10 - Mar 11
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 ...
9.8/10 Exceptional! (71 reviews)
This place exceeded my expectations. Such a beautiful and quiet setting. Don't want to leave, but I will definitely be backa a beautiful

Reviewed on Feb 27, 2026

Opens in a new windowThe Islands of Islamorada
Florida Keys Getaway w/ Stunning Ocean Views

Florida Keys Getaway w/ Stunning Ocean Views

4 out of 5
Long Key FL
$933 nightly
The price is $1,046 total per night from Mar 25 to Mar 26
$1,046 total
Mar 25 - Mar 26
Total with taxes and fees
A marina and an outdoor pool are featured at this smoke-free apartment. Business travelers can take advantage of the free WiFi in public areas. Free self parking ...
Opens in a new windowFlorida Keys Getaway w/ Stunning Ocean Views
 The Caribbean Resort Coconut Palm North

The Caribbean Resort Coconut Palm North

4 out of 5
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.
Opens in a new window The Caribbean Resort Coconut Palm North
Don't see what you're looking for?
See all available properties in Windley Key
View all properties
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

Explore More Ways to Travel with Travelocity