A beach with white lounge chairs, a covered pavilion, and palm trees.

Find 4 Star Hotels in Islamorada, FL from $241

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Check availability on Islamorada 4 Star Hotels

Tonight
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Islamorada 4-star hotels

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Jessica
$214 nightly
$241 total
Aug 18 - Aug 19
Total with taxes and fees
Cheeca Lodge & Spa

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Rey
$203 nightly
$228 total
Aug 20 - Aug 21
Total with taxes and fees
Chesapeake Beach Resort

3. Islander Resort

Islander Resort
Matecumbe
United States
Chris
$295 nightly
$332 total
Sep 2 - Sep 3
Total with taxes and fees
Islander Resort

4. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Estefani
$224 nightly
$252 total
Aug 20 - Aug 21
Total with taxes and fees
Amara Cay Resort

5. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
United States
Isabel
$193 nightly
$217 total
Aug 18 - Aug 19
Total with taxes and fees
Pines & Palms Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Ana
$272 nightly
$306 total
Sep 7 - Sep 8
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
$237 nightly
$266 total
Aug 23 - Aug 24
Total with taxes and fees
La Siesta Resort & Villas

8. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
MARC
$158 nightly
$178 total
Aug 26 - Aug 27
Total with taxes and fees
Fisher Inn Resort & Marina

9. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
United States
RAIBEL
$138 nightly
$155 total
Sep 17 - Sep 18
Total with taxes and fees
Hadley Resort and Marina

10. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
United States
Lisa C
$149 nightly
$168 total
Aug 30 - Aug 31
Total with taxes and fees
Coconut Cove Resort and Marina

11. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
$409 nightly
$459 total
Sep 17 - Sep 18
Total with taxes and fees
The Islands of Islamorada

12. La Jolla Resort

La Jolla Resort
Matecumbe
United States
adrian
$144 nightly
$162 total
Aug 19 - Aug 20
Total with taxes and fees
La Jolla Resort

13. The Caribbean Resort

The Caribbean Resort
Matecumbe
United States
jose
The Caribbean Resort

14. Drop Anchor

Drop Anchor
Islamorada
United States
Marianela
$140 nightly
$153 total
Aug 18 - Aug 19
Total with taxes and fees
Drop Anchor

15. Casa Morada

Casa Morada
Matecumbe
United States
Lois
$160 nightly
$180 total
Aug 31 - Sep 1
Total with taxes and fees
Casa Morada

16. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
United States
Lauren
$152 nightly
$171 total
Sep 8 - Sep 9
Total with taxes and fees
Ragged Edge Resort & Marina

17. Sunset Inn

Sunset Inn
Matecumbe
United States
Jeanne
Sunset Inn

18. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
United States
beata
$263 nightly
$295 total
Aug 30 - Aug 31
Total with taxes and fees
Bayside Villas by Islander Resort

19. Matecumbe Resort

Matecumbe Resort
Matecumbe
United States
Kathleen
Matecumbe Resort

20. The Ocean View Inn & Pub

The Ocean View Inn & Pub
Islamorada
United States
Patrice
$191 nightly
$215 total
Sep 16 - Sep 17
Total with taxes and fees
The Ocean View Inn & Pub
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Islamorada.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
$214 nightly
$241 total
Aug 18 - Aug 19
Total with taxes and fees
9.2/10 Wonderful! (1,397 reviews)
Cheeca Lodge & Spa
Waterfront House with Boat Dock

Waterfront House with Boat Dock

213 Aberdeen Ct Tavernier FL
Get rates
6/10 (3 reviews)
Waterfront House with Boat Dock
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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.

Learn more about Islamorada

The turquoise waters between the Keys offer world-class fishing that even beginners can enjoy with knowledgeable local guides. Spend mornings snorkeling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

See all hotels in Islamorada
A wooden pier extending into calm waters with a covered seating area and a boat docked at the end.

Top Islamorada Hotel Reviews

La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Great Florida keys feeling. Staff was very helpful. Clark was at the front desk and offered some ideas for local dinning 👍"
wini 2-night trip
Posted 18 hours ago
La Siesta Resort & Villas
Islander Resort

Islander Resort

10/10 Excellent
"This property is beautiful. Each room has a patio that leads that has a scenic route that leads ti the pool. The staff was exceptional and I would recommend this resort for families with small children."
Aisha 1-night trip
Posted 20 hours ago
Islander Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"Stayed in build 7 and it had a great view restaurant was good the bars where nice and most of all I booked a fishing trip with Whiskey Throttle guide service and Sean put me on a dinosaur of a tarpon and boy was it a beast. If the fishing is slow grab Whiskey Throttle for a great water adventures."
Gary 1-night trip
Posted 3 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
The Islands of Islamorada

The Islands of Islamorada

10/10 Excellent
"Very helpful staff and all amenities are in excellent usable condition. The villas and the suites are very comfortable with beautiful comfortable bathrooms."
Lila 3-night trip
Posted 2 weeks ago
The Islands of Islamorada

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 $241
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.

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