The Best 4 Star Hotels in Islamorada, FL from $249

Q: What are the best 4-star hotels in Islamorada?

Expedia travelers highly recommend Cheeca Lodge & Spa . From its handy amenities to its welcoming staff, every feature of this 4-star hotel in Islamorada is designed to offer an incredible vacation experience.

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Our top choices for Islamorada 4-star hotels

A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.

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

Key Largo

Damion

$312 nightly

Nov 29 - Nov 30

Total with taxes and fees

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

2. Islander Resort

Matecumbe

DEBORAH

$250 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

3. Amara Cay Resort

Matecumbe

Amir

$222 nightly

Nov 17 - Nov 18

Total with taxes and fees

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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

Islamorada

Liosbel

$272 nightly

Nov 29 - Nov 30

Total with taxes and fees

An aerial view of a resort with a large pool, palm trees, and a beach.

5. Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

Jorge

$312 nightly

Nov 29 - Nov 30

Total with taxes and fees

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

6. La Siesta Resort & Villas

Matecumbe

Brianne

$237 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden deck with a thatched-roof gazebo, overlooking a clear blue sea.

7. Condo in the Keys

Tavernier

Angela

8. Pineapple Beach by Florida Keys Luxury Rentals

Islamorada

9. The Sanctuary Islet by Florida Keys Luxury Rentals

Key Largo

10. Serenity by Florida Keys Luxury Rentals

Matecumbe

11. Turtle Nest Estate by Florida Keys Luxury Rentals

Matecumbe

12. Lime Key by Florida Keys Luxury Rentals

Buccaneer Point

13. Midnight Runner by Florida Keys Luxury Rentals

Tavernier

14. Bay Beach by Florida Keys Luxury Rentals

Key Largo

Top Islamorada Hotel Reviews

Islander Resort

Matecumbe

10/10 Excellent

Patrick

A beach resort with a calm pool, lounge chairs, and palm trees.

Reefhouse Resort & Marina

Key Largo

10/10 Excellent

Deb

Playa Largo Resort & Spa, Autograph Collection

Rock Harbor

10/10 Excellent

jose

Amara Cay Resort

Matecumbe

10/10 Excellent

Kasha

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

Key Largo

10/10 Excellent

The property is beautiful. Well maintained and the beach is gorgeous. Our room was clean but could use a coat of paint. The activities at the beach are wonderful. Kayaking and paddle boarding was fun. The hut at the beach for drinks is cute but it’s $20 for one drink with all the fees they add on. The food was meh. There are much better places to eat for the money. Also, there is a $49 a day resort charge that we were unaware of. With all the being said, we plan on going back. Just a little more...

Kathleen

A wooden deck with a pool and chairs overlooking a beach with palm trees.

Grassy Flats Resort & Beach Club

Marathon

10/10 Excellent

We stayed at this hotel several times. It is very nice, It’s nice that they have a separate area for adults. They also have 3 in house places to eat, a tiki bar for lunch, a roof top for breakfast and bar in the evening and a restaurant for dinner (didn’t go to this one though). They include free paddle boards and kayaks. The rooms could have better A/C, they added another portable fan and seem to be having issues with A/C, hopefully will be resolved soon. Also they don’t have room service...

Victoria

Find out more about Islamorada

The preparation of any vacation starts with picking a splendid spot. Islamorada is a popular choice with travelers because it offers so much. But, "location, location, location" applies to more than just your vacation destination. Now that you got a feel for the town, it is time you to learn a little more about your home for the next few nights.

Hotels as Stunning as the City

Islamorada saw its fair share of visitors last year. Expedia's comment section features reviews that can help you narrow down your choices. When you book a 4-star room you can breathe easy knowing that these properties strive to meet your wishes. You'll never need to search long for to keep up with your exercise schedule, a refreshing dip, or delectable dinner during your stay, thanks to everything these hotels offer. They work hard to make their facilities and grounds hospitable from the time you step onto the property and with each step throughout the hotel. Islamorada has several wonderful accommodations that make for the perfect escape.

Rooms have been furnished to keep you as comfortable as possible, with amenities like designer bathroom products, ultra-comfortable bedding, and in-room tea or coffee. So, sit back and unwind. Moreover, if you find yourself in need of anything else, you can rest assured the staff will work their best to ensure you stay pleased during your time. These properties are so nice that you'll regret the day you have to return home.

Book a 4-Star Hotel in Islamorada Today!

Your vacation to Islamorada should be one where you don't have to worry about the little things. Make sure to book soon. With so few accommodations, and so many people desiring to vacation in Islamorada, you may miss the chance to book the perfect place.

Frequently Asked Questions

What are the best 4-star hotels in Islamorada?

Expedia travelers highly recommend Cheeca Lodge & Spa. From its handy amenities to its welcoming staff, every feature of this 4-star hotel in Islamorada is designed to offer an incredible vacation experience.

How much does it cost to stay in a 4-star hotel in Islamorada?

To book a 4-star hotel in Islamorada that matches your budget, take advantage of Expedia's sort and search filters. Take a look at what's available during your vacation dates and use our pricing filter to set your limit. You can also sort your results by the most budget-friendly retreat first.

Search for the lowest price from $249

What's the difference between 5-star and 4-star hotels in Islamorada?

Treat yourself to luxury living during your Islamorada getaway by staying at a 4-star hotel. As well as featuring upmarket accommodations, these properties are usually filled with amenities such as bathrobes, large beds and plenty more. A 5-star hotel will go the extra mile to make your trip an even more lavish and unforgettable one. 24-hour concierge assistance, elegant furnishings and gourmet dining are just the start of the first-rate conveniences and services you'll likely get access to.

Does Islamorada have any 4-star all-inclusive resorts?

Enjoy a relaxing vacation experience where almost everything is included in the one upfront rate by using our "All inclusive" filter. Sticking to your budget is a cinch when your meals, accommodations and activities are already taken care of. After something a little different? Browse the offers on our standard 4-star hotels in and around Islamorada too.

Are there any 4-star casino hotels in Islamorada?

To find your ideal escape in Islamorada, simply use our filter tool to refine your search. Boasting resort-style amenities and a premium level of service, staying in a 4-star casino hotel is a sure bet for a good time.

What are the top 4-star hotels in downtown Islamorada?

Explore the city with ease when you vacation at Cheeca Lodge & Spa. Around 1 mi southwest from downtown Islamorada, this 4-star hotel is the ideal spot to see the most of this bustling city with the added convenience of a steam room and scooter rentals.

Find 4 Star Hotels in Islamorada, FL from $249

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

Our top choices for Islamorada 4-star hotels

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

2. Islander Resort

3. Amara Cay Resort

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

5. Playa Largo Resort & Spa, Autograph Collection

6. La Siesta Resort & Villas

7. Condo in the Keys

8. Pineapple Beach by Florida Keys Luxury Rentals

9. The Sanctuary Islet by Florida Keys Luxury Rentals

10. Serenity by Florida Keys Luxury Rentals

11. Turtle Nest Estate by Florida Keys Luxury Rentals

12. Lime Key by Florida Keys Luxury Rentals

13. Midnight Runner by Florida Keys Luxury Rentals

14. Bay Beach by Florida Keys Luxury Rentals

Top Islamorada Hotel Reviews

Islander Resort

10/10 Excellent

Find out more about Islamorada

Hotels as Stunning as the City

Book a 4-Star Hotel in Islamorada Today!

Frequently Asked Questions

What are the best 4-star hotels in Islamorada?

How much does it cost to stay in a 4-star hotel in Islamorada?

What's the difference between 5-star and 4-star hotels in Islamorada?

Does Islamorada have any 4-star all-inclusive resorts?

Are there any 4-star casino hotels in Islamorada?

What are the top 4-star hotels in downtown Islamorada?

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