TOP Recommended Islamorada Hotels with Swimming Pools for a Perfect Stay!

Latest Hotels Reviews for Islamorada

Ragged Edge Resort & Marina
4.5/561 Reviews
My husband and I stayed a week at the Ragged Edge Resort & Marina. We were delighted with the spacious apartment especially the two bathrooms. Our apartment had a well equipped kitchen, a counter for eating and a comfortable living area with a sofa and chairs. From the kitchen/living room window we had a beautiful view of the pier and ocean. The pool and pier area provided lots of space and lounge chairs for swimming, fishing and enjoying the sun. In the evening we used the resort's bicycles to tour the neighborhood. The staff at Ragged Edge were wonderful. They made sure we had everything we needed. There were many restaurants nearby but our favorite was ”Lazy Days”. We also took a day trip to Key West which was about 70 miles south of the resort.
Amara Cay Resort
4.2/5102 Reviews
Ameracay is a very nice resort. It's not too far and easily accessible. It gas a nice tiki brand beach as well as a very nice courtyard with game areas and firepits. The resort is in an area that has iguanas. These are harmless if left alone. Make sure yiu balcony door is shut so a curious iguana does not visit. You also should ve aware that in case of a cold snap, iguanas fall from trees. As long as they don't hit you in the head again they are harmless. Visited the outside bar fi a sandwich. Everything in the Keys cost more so prices are moderate. We shared a sandwich with no issues. The lobby area is very nice with suspended swinging chairs. Decorations are ”islandish” which is appropriate. There is a selfie wall which has keys mounted. There is also a wall mounted magnetic Scrapple game. There are nice restaurants within walking distance. Both Midway and Lazy Boys were busy. If you go out for dinner, expect moderate wait. Staff was exceptionally nice and helpful. The resort has a very snLl gift shop. Not much for men unless you need a bathing suit. The only problem was the entire area was having water issues. There was no hot water in the room. I would stay again. It's about half the cost of staying in Key West. There are places very close by if you want to plY in, on, or under the water. It may be possible to book a ride out to Alligator Reef Lighthouse via a service near by. Lots of places to hop on a fishing boat. The water off Islamadora is a nationally protected coral reef. Make sure you know what you can and can't do on the reef. The resort does not allow drone flying on property. You might be able to fly from a nearby bridge. I will probably visit again.
Chesapeake Beach Resort
4.3/5102 Reviews
Prior to arriving - we called the hotel and ask for a room that is for guests that have mobility issues. Same type but easily assessable. when we arrived, the reservation did not have us in a room that was accessible. the front desk attendant had no authority to fix the issue that we had fixed prior to arriving with another front desk person. He told us he moved us when in fact he had not done anything. Finally, we checked in and went to the room and it was the wrong room type - we reserved 2 queen beds that this one was 1 bed. We had to go back to the front desk and get a room with 2 queen beds - which was our original reservation type. The front desk was as accommodating as they could be because she had to wait for ”approval” from the mgr. Checking in took almost an hour. In my opinion - the worst check out experience ever. We were racing to get the kids dressed and backed - we were running 5-10 minutes behind check out time and no less then 4 hotel people came or banged or let themselves into our room to rush us out. Mind you their parking lot was completely empty, and they did not have some sort of waiting list to get into the rooms. It took them about an hour to check us into our room and they resorted to this type of behavior to hurry us out with 5-10 minutes after 11am check out time. In my opinion, the pool areas were nice - just the pool was a little dirty, with leaves or other debris in it. Kids did not seem to care. They enjoyed themselves. In my opinion - the worst check out experience ever. We were racing to get the kids dressed and backed - we were running 5-10 minutes behind check out time and no less then 4 hotel people came or banged or let themselves into our room to rush us out. Mind you their parking lot was completely empty, and they did not have some sort of waiting list to get into the rooms. It took them about an hour to check us into our room and they resorted to this type of behavior to hurry us out with 5-10 minutes after 11am check out time. I gave a 3 rating regarding this resort because the resort property is very nice. The rooms are super nice. The location is also very nice - if you don't have to interact with the staff then your stay may go smoother than ours. For us we will NEVER stay there again unless they get new management.
Islander Resort
4.3/5101 Reviews
5 Stars... it was great, and it all started with the extraordinary reception and welcoming by Dusti Rose 🌹 at the front desk. She was warm, friendly, personal, and extremely nice. She answered any and all questions and provided information on the hotel and Islamorada... just a great welcoming experience.. She was superb, to say the least. Thank you, Dusti and the Islander. We'll definitely be coming back.
Cheeca Lodge & Spa
4.4/5102 Reviews
Great trip! We enjoyed it a lot! Great service, we love our room (ocean front) the only issue that we had is that we didn’t have access to internet through wifi
Fisher Inn Resort & Marina
3.8/598 Reviews
The reception staff were lovely, so welcoming and helpful. Little heated pool and nice sun loungers, just missing some umbrellas to make it perfect. The outside grill was great to use and clean. Room didn’t get cleaned during our two night stay though… 🤷🏼♀️

Frequently Asked Questions

  • What promotions are available for hotels with Swimming Pools in Islamorada?

    Trip.com offers various promotions and discounts to its users throughout the year. You can check out the Promotions page to see what promotions Trip.com has going on.

  • What is the average room rate at Swimming Pools hotel in Islamorada?

    The average price for hotels in Swimming Pools in Islamorada is ₹ 44,681 on weekdays and ₹ 55,246 on weekends (Friday to Saturday).

  • What are the popular hotels with Swimming Pools in Islamorada?

    Whether you are traveling to Islamorada for business or tourism, Amara Cay Resort , Chesapeake Beach Resort and Cheeca Lodge & Spa are all preferred hotels.

Hotel Information for Travelers

Number of Hotels56
Number of Reviews1,826
Highest Price₹ 192,493
Lowest Price₹ 12,352
Average Price (Weekdays)₹ 44,681
Average Price (Weekends)₹ 55,246