Islamorada

Islamorada Hotels with Pools

Select your dates to find the best hotel with Swimming Pool in Islamorada.

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Top Hotels with Pools in Islamorada

Recommended Islamorada hotels with Swimming Pool for a perfect stay!
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Highest Rated
Amara Cay Resort
Amara Cay ResortAmara Cay Resort
Hotel near Islamorada
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and 13 minutes by foot from Indian Key Historic State Park. This beach resort is 1.4 mi (2.3 km) from Hurricane Monument and 1.6 mi (2.5 km) from Florida Keys Brewing Co.. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and a fitness center. This resort also features wireless internet access (surcharge), gift shops/newsstands, and wedding services. Getting to nearby attractions is a breeze with the complimentary area shuttle that operates within 4.00 mi. Grab a bite at ReelCatch, one of the resort's 2 restaurants, or stay in and take advantage of the room service (during limited hours). Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Cooked-to-order breakfasts are available daily from 6:00 AM to 11:00 AM for a fee. Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 110 air-conditioned rooms featuring flat-screen televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Wireless internet access (surcharge) is available to keep you connected. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers.

GGary McGinnis 2023.03.15
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.
Very Good
102 reviews
4.2/5
Price from
PHP 19,873
per night
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La Siesta Resort & Villas
La Siesta Resort & VillasLa Siesta Resort & Villas
Hotel near Islamorada
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. This beach resort is 1 mi (1.7 km) from Hurricane Monument and 1.3 mi (2.1 km) from Florida Keys Brewing Co.. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and bicycles to rent. Additional amenities at this resort include wireless internet access (surcharge), wedding services, and a picnic area. Guests can catch a ride to nearby destinations on the complimentary area shuttle. Take advantage of the resort's room service (during limited hours). Quench your thirst with your favorite drink at the poolside bar. Cooked-to-order breakfasts are available daily from 7:00 AM to 11:00 AM for a fee. Featured amenities include a 24-hour front desk and a water dispenser. Make yourself at home in one of the 55 individually decorated guestrooms, featuring kitchenettes with refrigerators and microwaves. Your pillowtop bed comes with Egyptian cotton sheets. Wireless internet access (surcharge) keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, as well as safes and desks.
Very Good
101 reviews
4.1/5
Price from
PHP 18,138
per night
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Cheeca Lodge & Spa
Cheeca Lodge & SpaCheeca Lodge & Spa
Hotel near Islamorada
The Cheeca Lodge & Spa provides a great place for travelers to relax after a busy day. The Cheeca Lodge & Spa offers a pleasant stay in Islamorada for those traveling for business or leisure. Famous local attractions Florida Keys Brewing Co, Gyotaku by Lisa Lee and Monroe County Public Library, can all be reached with a short walk. At the end of a busy day, travelers can unwind and relax in the hotel or go out and enjoy the city. This Islamorada hotel features parking on site. For guests traveling as a couple, this hotel is consistently one of the most popular choices.

LLuengoRUP 2023.09.26
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
Excellent
102 reviews
4.3/5
Price from
PHP 18,408
per night
Check Availability
Islamorada
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Islander Resort
Islander ResortIslander Resort
Hotel near Islamorada
The Islander Resort is an ideal spot for travelers wanting to discover the city. The Islander Resort is an ideal choice for travelers who want to take in the sights and sounds of Islamorada. The nearby area boasts an abundance of attractions including Hurricane Monument, Skins and Fins Charters and Islamorada Private Charters. This hotel makes a great place to kick back and relax after a long day of sightseeing. Guests of this Islamorada hotel can make use of the parking facilities.

2024.10.26
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.
Excellent
97 reviews
4.3/5
Price from
PHP 20,143
per night
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Hadley Resort and Marina
Hadley Resort and MarinaHadley Resort and Marina
Hotel near Islamorada
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum. This beach hotel is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1 mi (1.6 km) from Matecumbe United Methodist Church. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands. A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM. Featured amenities include express check-out, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 37 air-conditioned rooms featuring refrigerators. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers.
98 reviews
3.9/5
Price from
PHP 10,856
per night
Check Availability
The Islands of Islamorada
The Islands of IslamoradaThe Islands of Islamorada
Hotel near Islamorada
With a stay at The Islands of Islamorada in Islamorada (Matecumbe), you'll be within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. This beach villa is 0.8 mi (1.3 km) from Keys History & Discovery Center and 1.1 mi (1.8 km) from Matecumbe United Methodist Church. Dip into one of the 2 outdoor swimming pools or enjoy other recreational amenities including a 24-hour fitness center and a pickleball court. This villa also features complimentary wireless internet access, concierge services, and wedding services. Wrap up your day with a drink at the poolside bar. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have designer toiletries and hair dryers.
Outstanding
27 reviews
4.7/5
Price from
PHP 46,693
per night
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Fisher Inn Resort & Marina
Fisher Inn Resort & MarinaFisher Inn Resort & Marina
Hotel near Islamorada
The Fisher Inn Resort & Marina provides a great place for travelers to relax after a busy day. Visitors to Islamorada will find that the Fisher Inn Resort & Marina is a fantastic accommodation choice. With multiple attractions nearby including Freedom Boat Club, Capt. Easy Charters and LegaSea Charters, guests will find plenty to keep themselves occupied. When guests have some time on their hands they can make use of the onsite facilities. For those driving themselves, parking is provided on site. For guests traveling with groups of friends, this hotel is consistently one of the most popular choices.

GGuest User 2024.04.18
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… 🤷🏼♀️
101 reviews
3.8/5
Price from
PHP 12,678
per night
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio ResortThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Hotel near Islamorada
The Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort provides a great place for travelers to relax after a busy day. The Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is an ideal choice for travelers who want to take in the sights and sounds of Islamorada. This hotel is located near many of Islamorada's attractions including LegaSea Charters, Florida Keys Jetpacks and Snake Creek Marina / SD Marine Group. After a long day of sightseeing, guests can retire to the comfort of the hotel. This Islamorada hotel offers parking on site.
Very Good
100 reviews
4.0/5
Check Availability
Sunset Inn
Sunset InnSunset Inn
Hotel near Islamorada
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center. This hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.3 km) from History of Diving Museum. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite. Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and bidets. Conveniences include laptop-compatible safes and coffee/tea makers, and housekeeping is provided daily.

GGuest User 2025.01.16
Its decent but its not easy to find in the evening or night when its dark. Would help if it has a bright sign for the Inn. It has a pool at the back and you can hear the noise if people are partying out there but it seems to quiet down fortunately for us for the day we were there.
Excellent
101 reviews
4.4/5
Price from
PHP 11,373
per night
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Islander Bayside Villas & Boatslips
Islander Bayside Villas & BoatslipsIslander Bayside Villas & Boatslips
Hotel near Islamorada
With a stay at Islander Bayside Villas and Boatslips, you'll be centrally located in Islamorada, just a 4-minute walk from Hurricane Monument and 7 minutes by foot from Florida Keys Brewing Co.. This beach hotel is 0.4 mi (0.7 km) from MoradaWay Arts & Cultural District and 0.5 mi (0.9 km) from Matecumbe United Methodist Church. Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, a picnic area, and complimentary use of a nearby fitness facility. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 25 guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Your pillowtop bed comes with premium bedding, and all rooms are furnished with queen sofa beds. Rooms have private furnished balconies. 55-inch LCD televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected.
Excellent
63 reviews
4.3/5
Price from
PHP 32,264
per night
Check Availability
See All Hotels With Swimming Pool in Islamorada

Latest Reviews for Islamorada Hotels

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Read genuine traveler ratings & reviews to find your perfect stay.
4.6/5
Outstanding
GGuest UserMy 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.
Ragged Edge Resort & Marina

Ragged Edge Resort & Marina

Hotel near Islamorada
Price per night from:PHP 15,257
4.3/5
Excellent
Ffood4fun007Prior 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.
Chesapeake Beach Resort

Chesapeake Beach Resort

Hotel near Islamorada
Price per night from:PHP 17,835

Frequently Asked Questions

Where is the best place for a stay with Swimming Pools in Islamorada?

Whether you are traveling to Islamorada for business or fun, Amara Cay Resort , Breezy Palms Resort and Cheeca Lodge & Spa are all preferred hotels.

What’s the typical price for hotels with Swimming Pools in Islamorada?

For hotels with Swimming Pools in Islamorada, the average price on weekdays is PHP 31,251, and the average price on weekends (Friday–Saturday) is PHP 36,396.

What are some great hotel promotions for property with Swimming Pools in Islamorada?

Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see what promotions are available on Trip.com.

Islamorada Hotels with Swimming Pool Information

Total Properties56
Number of Reviews1,856
Highest PricePHP 111,412
Lowest PricePHP 10,870
Average Price (Weekdays)PHP 31,251
Average Price (Weekends)PHP 36,396