Hotels in Islamorada

Best Islamorada Hotels

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38 Best Hotels to Stay in Islamorada

Trip.com brings you a curated list of top accommodations in Islamorada, complete with reviews, price insights, and amenity highlights, making it easy to find the perfect place to stay.
Most Booked
Lowest price
Closest to downtown
Highest Rated
Amara Cay Resort Hotels in Islamorada
Amara Cay Resort Hotels in IslamoradaAmara Cay Resort Hotels in IslamoradaAmara Cay Resort Hotels in IslamoradaAmara Cay Resort Hotels in IslamoradaAmara Cay Resort Hotels in IslamoradaAmara Cay Resort Hotels in Islamorada
99+
Hotels in Islamorada
Outdoor swimming pool
Private beach area
Diving
+9
"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
101 reviews
8.5/10
1 night
From €252
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Cheeca Lodge & Spa Hotels in Islamorada
Cheeca Lodge & Spa Hotels in IslamoradaCheeca Lodge & Spa Hotels in IslamoradaCheeca Lodge & Spa Hotels in IslamoradaCheeca Lodge & Spa Hotels in IslamoradaCheeca Lodge & Spa Hotels in IslamoradaCheeca Lodge & Spa Hotels in Islamorada
99+
Hotels in Islamorada
Golf course
Outdoor swimming pool
Private beach area
+17
"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"
Very Good
108 reviews
8.9/10
1 night
From €458
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Sunset Inn Hotels in Islamorada
Sunset Inn Hotels in IslamoradaSunset Inn Hotels in IslamoradaSunset Inn Hotels in IslamoradaSunset Inn Hotels in IslamoradaSunset Inn Hotels in IslamoradaSunset Inn Hotels in Islamorada
64
Hotels in Islamorada
Outdoor swimming pool
Private parking
Wi-Fi in public areas
"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."
Very Good
100 reviews
8.7/10
1 night
From €184
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Islander Resort Hotels in Islamorada
Islander Resort Hotels in IslamoradaIslander Resort Hotels in IslamoradaIslander Resort Hotels in IslamoradaIslander Resort Hotels in IslamoradaIslander Resort Hotels in IslamoradaIslander Resort Hotels in Islamorada
99+
Hotels in Islamorada
Outdoor swimming pool
Private beach area
Beach volleyball
+10
"Nice hotel rooms that you can drive up to. Nice amount of space—although the bathroom is very small. Pool area is ok, not enough umbrellas. Didn’t get water everyday despite being told it was included with the resort fee. The access to the sea isn’t great. Yoga was fantastic."
Very Good
101 reviews
8.9/10
1 night
From €386
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Hotels in Islamorada
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Hotels in IslamoradaThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Hotels in IslamoradaThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Hotels in IslamoradaThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Hotels in IslamoradaThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Hotels in IslamoradaThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Hotels in Islamorada
99+
Hotels in Islamorada
Outdoor swimming pool
Private beach area
Diving
+9
"The resort was very beautiful and well maintained. The cottage we stayed in was spacious and we really liked the decor and how soft the beds were. The food was good but a little pricey. We were not impressed with the cabana rental. The cabana was not ready when we arrived. We had to wait for it to be cleaned and set up. The cabana was not labeled and we were confused on which cabana was ours as there were 2 next to each other. We asked when service would start and we were told 10am, then we asked again at 10:45, then went to the front office at 11:30 and when 12pm rolled around with no service we decided to leave and get our money back on the cabana. At that point all we paid for was a chair and towel which did not meet our expectation when spending $250.00 on a cabana for the day. I would recommend several things for the cabana. 1. Number the cabanas so you can clearly see the number. Telling us Cabana 2 does not help when they are beside each other. 2. Stock the min fridge with water. 3. Clearly explain on the cabana rental that food/service will not start until a certain time. We expected to at least get something to drink while in the cabana. 4. Install a call button or app that you can be in contact with someone when you need something. There was a significant delay on getting our refund. And we do appreciate the Manager helping us on Friday get that resolved before we checked out on Saturday morning. All in all, the resort was great. We loved the vibe and updates made to the property. The rooms were comfortable and fresh, and we loved the beds as they were very comfortable, and the sheets were so soft. Everyone was friendly and pleasant. We most enjoyed fish like a local with Patrick. We found that the pool in the middle of the property was less used and felt more quiet and more private therefore we spent our time with a good book. I would give the stay at 4.5 out of 5. Highly recommend trying out Three Waters Resort."
Very Good
79 reviews
8.7/10
1 night
From €376
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La Siesta Resort & Villas Hotels in Islamorada
La Siesta Resort & Villas Hotels in IslamoradaLa Siesta Resort & Villas Hotels in IslamoradaLa Siesta Resort & Villas Hotels in IslamoradaLa Siesta Resort & Villas Hotels in IslamoradaLa Siesta Resort & Villas Hotels in IslamoradaLa Siesta Resort & Villas Hotels in Islamorada
99+
Hotels in Islamorada
Outdoor swimming pool
Private beach area
Private parking
+2
"The hotel was very comfortable and was very comfortable."
Very Good
102 reviews
8.3/10
1 night
From €235
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Breezy Palms Resort Hotels in Islamorada
Breezy Palms Resort Hotels in IslamoradaBreezy Palms Resort Hotels in IslamoradaBreezy Palms Resort Hotels in IslamoradaBreezy Palms Resort Hotels in IslamoradaBreezy Palms Resort Hotels in IslamoradaBreezy Palms Resort Hotels in Islamorada
56
Hotels in Islamorada
Parking
Wi-Fi in public areas
Private beach area
+2
With a stay at Breezy Palms Resort in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park. This beach aparthotel is 1.4 mi (2.3 km) from Hurricane Monument and 1.6 mi (2.6 km) from Florida Keys Brewing Co.. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. This aparthotel also features complimentary wireless internet access, gift shops/newsstands, and tour/ticket assistance. Featured amenities include luggage storage, laundry facilities, and a safe deposit box at the front desk. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 40 guestrooms, featuring kitchens with full-sized refrigerators/freezers and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include separate sitting areas and coffee/tea makers, and housekeeping is provided weekly.
Very Good
100 reviews
8.6/10
1 night
From €136
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Chesapeake Beach Resort Hotels in Islamorada
Chesapeake Beach Resort Hotels in IslamoradaChesapeake Beach Resort Hotels in IslamoradaChesapeake Beach Resort Hotels in IslamoradaChesapeake Beach Resort Hotels in IslamoradaChesapeake Beach Resort Hotels in IslamoradaChesapeake Beach Resort Hotels in Islamorada
99+
Hotels in Islamorada
Private parking
Luggage storage
Wi-Fi in public areas
+1
"The place is beautiful and very clean. There were a couple of hiccups but the hotel was quick to fix it. The only part that is upsetting is using on the amenities: fish rod, it kept tangling up. But overall, we will be returning. The breakfast was like no other."
Very Good
104 reviews
8.8/10
1 night
From €359
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Hadley Resort and Marina Hotels in Islamorada
Hadley Resort and Marina Hotels in IslamoradaHadley Resort and Marina Hotels in IslamoradaHadley Resort and Marina Hotels in IslamoradaHadley Resort and Marina Hotels in IslamoradaHadley Resort and Marina Hotels in IslamoradaHadley Resort and Marina Hotels in Islamorada
96
Hotels in Islamorada
Outdoor swimming pool
Private beach area
Snorkeling
+6
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.
Good
100 reviews
7.8/10
1 night
From €172
Check availability
Caloosa Cove Resort by CoolVacay Hotels in Islamorada
Caloosa Cove Resort by CoolVacay Hotels in IslamoradaCaloosa Cove Resort by CoolVacay Hotels in IslamoradaCaloosa Cove Resort by CoolVacay Hotels in IslamoradaCaloosa Cove Resort by CoolVacay Hotels in IslamoradaCaloosa Cove Resort by CoolVacay Hotels in IslamoradaCaloosa Cove Resort by CoolVacay Hotels in Islamorada
99+
Hotels in Islamorada
Outdoor swimming pool
Private beach area
Private parking
+2
With a stay at Caloosa Cove Resort by CoolVacay in Islamorada (Matecumbe), you'll be a 3-minute walk from Sunset Drive Beach and 6 minutes by foot from Anne's Beach. This condo is 3.9 mi (6.2 km) from Robbie’s of Islamorada and 4.2 mi (6.8 km) from Fiesta Key. Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and a picnic area. At Caloosa Cove Resort by CoolVacay, enjoy a satisfying meal at the restaurant. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 30 air-conditioned rooms featuring kitchens. Rooms have private balconies. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, as well as separate sitting areas and coffee/tea makers.
Great
40 reviews
9.0/10
Check availability
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Trip.com's insights for hotels in Islamorada

Plan smarter with Trip.com’s data-backed insights on travel seasons so that you can book your Islamorada hotel at the right time!

Which month offers the lowest hotel rates in Islamorada?

September is the most affordable month to book a hotel in Islamorada, with average nightly rates around €186. Prices peak in February, when rates reach about €759 per night.
(Based on Trip.com data from April 7, 2025 to April 7, 2026.)
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Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar

What is the cheapest day of the week for hotels in Islamorada?

Hotel rates in Islamorada are typically lowest on Friday, with average nightly rates around €380. Wednesday tends to be the most expensive, averaging €753 per night.
(Based on Trip.com data from April 7, 2025 to April 7, 2026.)
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Find your unique stays in Islamorada

Immerse yourself in the vibrant atmosphere of Islamorada with our handpicked accommodation options

Most-booked Islamorada hotels

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Check out these top-booked hotels from the past 30 days!
Casa Morada Hotels in Islamorada
9.1/10
82 review

Casa Morada

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History & Discovery Center. This beach hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.9 mi (1.4 km) from Florida Keys Brewing Co.. Pamper yourself with onsite massages or enjoy recreation amenities such as an outdoor pool. Additional features at this hotel include complimentary wireless internet access and concierge services. Take advantage of the hotel's room service (during limited hours). A complimentary continental breakfast is served daily from 7 AM to 10:30 AM. 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 16 individually decorated guestrooms, featuring minibars and DVD players. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have designer toiletries and hair dryers.
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Fisher Inn Resort & Marina Hotels in Islamorada
7.3/10
102 review

Fisher Inn Resort & Marina

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, just a 3-minute walk from Windley Key Fossil Reef Geological State Park and within a 5-minute drive of Rain Barrel Village. This beach motel is 1.9 mi (3.1 km) from History of Diving Museum and 2 mi (3.2 km) from Founders Park. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool. Additional amenities at this Art Deco motel 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, luggage storage, and coffee/tea in a common area. Free self parking is available onsite. Make yourself at home in one of the 22 individually decorated guestrooms, featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and irons/ironing boards, and housekeeping is provided on request.
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Ragged Edge Resort & Marina Hotels in Islamorada
9.4/10
100 review

Ragged Edge Resort & Marina

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
When you stay at Ragged Edge Resort & Marina in Islamorada, you'll be near the beach, within a 10-minute walk of Rain Barrel Village and Founders Park. This guesthouse is 0.6 mi (0.9 km) from Islamorada County Park and 2.1 mi (3.4 km) from Windley Key Fossil Reef Geological State Park. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. Additional features at this guesthouse include complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include express check-in, express check-out, and laundry facilities. Free self parking is available onsite. Make yourself at home in one of the 14 guestrooms. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include ceiling fans, and housekeeping is provided daily.
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La Jolla Resort Hotels in Islamorada
8.8/10
102 review

La Jolla Resort

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery Center. This hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from History of Diving Museum. 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 a picnic area. The front desk is staffed during limited hours. Limited parking is available onsite. Make yourself at home in one of the 20 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with showers are provided. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
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Coconut Cove Resort & Marina Hotels in Islamorada
7.4/10
100 review

Coconut Cove Resort & Marina

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
With a stay at Coconut Cove Resort and Marina in Islamorada, you'll be on the waterfront, just steps from Windley Key Fossil Reef Geological State Park and a 3-minute drive from History of Diving Museum. This beach hotel is 2 mi (3.3 km) from Rain Barrel Village and 2.2 mi (3.5 km) from Founders Park. Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional features at this hotel include complimentary wireless internet access, wedding services, and a picnic area. A complimentary continental breakfast is served daily from 9:00 AM to 11:00 AM. Featured amenities include a business center and coffee/tea in a common area. Free self parking is available onsite. Make yourself at home in one of the 20 guestrooms featuring refrigerators and microwaves. Rooms have private patios. 24-inch LCD televisions are provided, with cable programming available. Bathrooms have complimentary toiletries and hair dryers.
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Sands of Islamorada Hotels in Islamorada
8.6/10
82 review

Sands of Islamorada

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
Located in Islamorada (Matecumbe), Sands of Islamorada is within a 5-minute drive of Bud n' Mary's Dive Center and History of Diving Museum. This hotel is 4.7 mi (7.5 km) from Windley Key Fossil Reef Geological State Park and 6.6 mi (10.6 km) from Anne's Beach. Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include laundry facilities and a safe deposit box at the front desk. Free self parking is available onsite. Make yourself at home in one of the 9 individually decorated guestrooms, featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include safes and microwaves, and housekeeping is provided daily.
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The Ocean View Inn Hotels in Islamorada
8.4/10
35 review

The Ocean View Inn

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
With a stay at The Ocean View Inn & Pub in Islamorada, you'll be steps from Windley Key Fossil Reef Geological State Park and a 2-minute drive from History of Diving Museum. This hotel is 2.1 mi (3.4 km) from Rain Barrel Village and 2.2 mi (3.6 km) from Founders Park. Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access. Enjoy a satisfying meal at The Ocean View Pub serving guests of The Ocean View Inn & Pub. Need to unwind? Take a break with a tasty beverage at one of the 2 bars/lounges. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 7 air-conditioned rooms featuring microwaves. Rooms have private patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers.
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Pines & Palms Resort Hotels in Islamorada
9.0/10
99 review

Pines & Palms Resort

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 5-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center. This beach hotel is 1 mi (1.6 km) from Hurricane Monument and 1.2 mi (1.9 km) from Florida Keys Brewing Co.. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and wedding services. Take advantage of the hotel's room service. Need to unwind? Take a break at the bar/lounge, the beach bar, or the poolside bar for a tasty beverage. Featured amenities include limo/town car service, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 26 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.
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The Islands of Islamorada Hotels in Islamorada
9.4/10
39 review

The Islands of Islamorada

Hotel near Islamorada
A popular choice among guests booking hotels in 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 pools or enjoy other recreational amenities including a 24-hour fitness center and 2 outdoor pickleball courts. This villa also features complimentary wireless internet access, concierge services, and wedding services. Wrap up your day with a drink at the poolside bar. Cooked-to-order breakfasts are available daily from 9:00 AM to 11:00 AM for a fee. 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 feature showers with rainfall showerheads and designer toiletries.
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Bayside Villas by Islander Resort Hotels in Islamorada
8.7/10
70 review

Bayside Villas by Islander Resort

Hotel near Islamorada
A popular choice among guests booking hotels in Islamorada
With a stay at Bayside Villas by Islander Resort, 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 barbecue grills. Getting to nearby attractions is a breeze with the complimentary area shuttle that operates within 1.5 miles. Satisfy your appetite at Tides Beachside Bar, one of the hotel's 3 restaurants. Quench your thirst with your favorite drink at the bar/lounge. 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.
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Handpicked budget hotels in Islamorada

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Affordable stays in Islamorada, selected for value, comfort, and convenient locations.
Villa Located on the WaterFree Marina, and Trailer Parking. Hotels in Islamorada
9.6/10
0 review

Villa Located on the WaterFree Marina, and Trailer Parking.

Hotel near Islamorada

Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare), the villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with night lights, power and water.

The villa itself comes with a fully-equipped kitchen, washer and dryer, linens, queen and king beds, Cable TV, VCR, and a Florida room for dining. Windows in the living room and bedroom cover two thirds of the wall giving the feeling of the outdoors being in during the day and easy open/close window coverings provide privacy at night. This is a small house, near the water, no high-rise, no canal, and no density of people problem. This is a laid-back atmosphere for those who desire it.

Located on Upper Matecumbe Key, the "downtown" area of Islamorada, the property is quiet and hidden. Boats up to 25' are secure in our protected marina. Most trailers are able to launch from the property but a few extra-wide may have to use nearby launching places. There is trailer parking on the property as well as two parking places per unit. There are seven units on the property.


Free use of the village park(tennis, pickle ball, beach, pool, and dog park) is provided to guests. There are three state parks in the Islamorada area and the owner will provide passes. You are within walking distance to the best restaurants, shopping, and attractions. Free electric "taxis" are able to take you anywhere in town. Grocery, fishing and boating supplies are conveniently close.

Islamorada proudly calls itself the 'Fishing Capital of the World' and fishermen love us!
Located close to the best backcountry fishing on the edge of the Everglades, we are also able to easily access reef and blue water fishing. Our immediate bay provides fun catching tarpon and easy fishing on our seawall at night is a guest favorite. Owner has names of boat rental places and guides for all types of fishing and snorkeling. Next door to us is Back Country Cowboy. They rent kayaks, canoes, paddle boards, as well as bicycles. our bay is the perfect, protected area for all water activities. Oceanside, we have some of the best snorkeling and scuba areas in the Keys!

There's never a dull moment at our marina. We have an Osprey nest nearby. If you clean fish, you'll have lots of bird friends. Other visitors are manatees, octopi, and nurse sharks.
This property is treasured by guests and owners alike. The privacy is wonderful, the property peaceful, and the villas kept clean and updated. Most of our guests come year after year. Some have met friends one year and make the same dates together the next year. The size of the property is perfect- not too big, just right.

Three or four years ago, Fox News had a "US Best Sunsets" contest. Someone submitted one of our guest's pictures and we recognized it! "Our sunset" won over thousands submitted. Come and enjoy the best The Keys has to offer. Best location, best property, best fishing, and the best sunsets.



About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit 2 pets total).Under 60 lbs. Absent owner, pet crated..About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 3-17.Walk in water area, fishing on seawall at night..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
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Drop Anchor Resort & Marina Hotels in Islamorada
8.8/10
100 review

Drop Anchor Resort & Marina

Hotel near Islamorada
With a stay at Drop Anchor in Islamorada, you'll be on the waterfront, a 4-minute walk from Windley Key Fossil Reef Geological State Park and a 3-minute drive from Rain Barrel Village. This hotel is 1.9 mi (3 km) from Founders Park and 1.9 mi (3 km) from Islamorada County Park. 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. This Art Deco hotel also features complimentary wireless internet access, wedding services, and a picnic area. Featured amenities include a business center, a safe deposit box at the front desk, and coffee/tea in a common area. Free self parking is available onsite. Make yourself at home in one of the 18 air-conditioned rooms featuring 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 hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
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The Caribbean Resort Hotels in Islamorada
9.7/10
36 review

The Caribbean Resort

Hotel near Islamorada
A stay at The Caribbean Resort places you in the heart of Islamorada, within a 5-minute drive of Hurricane Monument and History of Diving Museum. This family-friendly hotel is 2.3 mi (3.7 km) from Bud n' Mary's Dive Center and 5.2 mi (8.4 km) from Founders Park. Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional amenities at this hotel include wedding services, a picnic area, and barbecue grills. Featured amenities include laundry facilities and an elevator. Make yourself at home in one of the 14 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. Rooms have private balconies or patios. LED televisions are provided for your entertainment. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.
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Welcome to Your Island Escape! Min 28-Day Reservation Required Hotels in Islamorada

Welcome to Your Island Escape! Min 28-Day Reservation Required

Hotel near Islamorada
Imagine waking up to warm ocean breezes, the gentle sway of palm trees, and the first golden light of the sun rising over the Atlantic. This is not just another day in paradise – this is your new way of living, breathing, and unwinding in the world-famous Florida Keys, known as the Sport Fishing Capital of the World. Whether your dream vacation includes world-class fishing excursions, snorkeling through coral reefs, paddling across turquoise waters, or simply relaxing in a private island oasis, your stay at our luxury resort-style 2-bedroom, 2-bath Seabreeze home promises an unforgettable experience. NO PETS ALLOWED.

Perfect for Monthly Stays & Extended Retreats
This property requires a minimum stay of 28 nights, making it perfect for:

* Remote workers seeking serenity with high-speed internet

* Retirees looking for extended winter escapes

* Families wanting more than a vacation—those craving island living

* Adventurers who want the Florida Keys lifestyle at their doorstep

Pet-friendly units are available upon request (please contact the resort for availability and approval).

ABOUT THE HOME

This 1,230 sq. ft. Seabreeze model has been intelligently designed to offer both privacy and connection, style and function, coastal elegance and home-like warmth. It’s not just a rental—it’s your very own island residence.

Key Features:

2 Bedrooms / 2 Full Bathrooms – One bedroom is located on the first floor (ideal for convenience), and the second is upstairs for ultimate privacy. Both living spaces offer sleeper sofas to accommodate the whole family.

Loft Lounge & Wet Bar – The second-floor lounge features a sleeper sofa, wet bar, entertainment area, and opens to your private deck with spectacular Resort and Atlantic Ocean views.

Fully Furnished, Coastal Inspired Décor – With a light, breezy tropical theme, each unit is individually decorated by its private owner, ensuring charm and uniqueness.

Sleeps 6 Comfortably – Perfect for couples, families, or a group of friends.

In-Unit Washer & Dryer – Convenience at your fingertips.

Fully Equipped Kitchen – Stainless steel appliances, quartz countertops, farm sink, barn door pantry access, cookware, dishes, utensils, small appliances, and more.

Private Balcony – Sip your morning coffee or evening cocktail while watching palm trees sway in the breeze and boats pass by on the horizon.

Minimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 2:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
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Wake up Every Day to the Sunrise from the Deck of This Waterfront Home 2Bed Home Hotels in Islamorada
10/10
0 review

Wake up Every Day to the Sunrise from the Deck of This Waterfront Home 2Bed Home

Hotel near Islamorada
This lovely home has 2 bedrooms and 2 baths. The home is completely furnished, just bring you sunscreen, flip flops and fishing rods!

While here, you will have full access to all of the Islamorada resort amenities and activities. Including a heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.

Islamorada is the fishing capitol of the world, and you will easily find plenty of nice dining locally. Founders park is directly across the street for those that wish to walk over and have a day at the beach, or just play some pickle ball.
A min of 28 nights is required for these homes. Boat slips may be booked for an additional fee.About pets:Pets allowed: dogs and cats (limit 2 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 2:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:Events allowed: family gatherings and birthday parties.Maximum event attendees: 6.
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Capt Craig's 2 Bedroom/1 bath  Apartment in Tavernier, Florida Keys Hotels in Islamorada
9.8/10
17 review

Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys

Hotel near Islamorada
Capt. Craig’s Guest Quarters

The Dolphin Suite is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities.

Freshly remodeled with the traveler in mind, enjoy our little piece of paradise-minutes from all that the Upper Keys has to offer.About pets:Pets allowed: dogs and cats (limit 1 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
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Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip Hotels in Islamorada
9.8/10
0 review

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

Hotel near Islamorada
Boat slip #13 is included in this rental.
Ocean view property in the Village of Islamorada located in the Florida Keys at Mile Marker 85. The property is in a gated community filled with quaint streets and walking paths throughout the perfectly manicured grounds. A heated/cooled pool cascading over a 52' beach front property overlooking the Atlantic Ocean. Enjoy the convenience of having your private dock for a 31' boat with electricity and water included. Boat slip #13 is just steps away from a refreshing dip in the pool.

This home features high ceilings both upstairs and down and an open floor plan on the first floor. The kitchen is well-equipped with granite counters, stainless steel appliances and adjoins a comfortable dining area and living room. The dining area includes bar seating for two and a dining table for four and the living room is equipped with a sectional sofa with a pull-out-bed, an accent chair, coffee table and a flat screen. Hardwood floors throughout.

The master suite upstairs features a king size bed, flat screen tv and a private bathroom with a walk-in shower. Additionally, the master suite has a private balcony. The guest suite features one queen bed, a pull-out sofa, closet, private bathroom with walk-in-shower and a private balcony. A stacked washer and dryer are located on the second floor for the guest's convenience.


Note: I also have a 4-bedroom rental home with a boat dock included on the front row just across from the pool with a full view of the ocean. VRBO Listing 359378About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 6.
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FAQs About Islamorada Hotels

What is the average price of a hotel in Islamorada for this weekend?

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Islamorada this weekend is €513 per night. For a 4-star hotel, the average cost is €686 per night. If you're looking for a luxury experience, 5-star hotels in Islamorada this weekend typically cost €797 per night.

How much do hotels in Islamorada cost per night during weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Islamorada during weekdays is €413 per night. For a 4-star hotel, you can expect to pay around €576 per night. If you're looking for a luxury stay, 5-star hotels in Islamorada generally cost €564 per night on weekdays.

What are the best places to stay in Islamorada?

Some of the best places to stay in Islamorada are near popular attractions like History of Diving Museum, Theater of the Sea and Founders Park Soccer Fields, offering easy access to key sights and amenities.

What are the best family-friendly hotels in Islamorada?

Families visiting Islamorada often prefer hotels like Drop Anchor Resort & Marina (from €238), which are well-known for their family-friendly features of spacious family rooms and child-friendly services.

What are the top hotels in Islamorada near History of Diving Museum?

Some of the top hotels in Islamorada near History of Diving Museum include Chesapeake Beach Resort (from €224), Sunset Inn (from €190) and Casa Morada (from €365), all offering easy access to History of Diving Museum, making them ideal for visitors looking to explore the area.

Which hotels are the best hotels to stay at in Islamorada?

Islamorada has many popular hotels. Whether you're looking for a business stay or a vacation hotel, Cheeca Lodge & Spa (from €208), Amara Cay Resort (from €245) and Sunset Inn (from €190) are best choices.

What are the best hotels with a spa in Islamorada?

Plan a peaceful trip? Spa can be a wonderful experience when traveling. Cheeca Lodge & Spa (from €208) provides highly rated spa services.

What hotels in Islamorada provide swimming pools?

Cheeca Lodge & Spa (from €208), Amara Cay Resort (from €245) and Sunset Inn (from €190) are hotels with swimming pools. Book now and enjoy your swimming pool!

Which hotels in Islamorada have the best breakfast?

What hotel deals are available in Islamorada?

Trip.com offers multiple promotions and discounts all year round for both new users and loyal customers . Please check the promotions page to see what promotions are available now on Trip.com.

Islamorada Hotels Info

Number of reviews
2,172
Total properties
38
Weekday Avg. Price
€421
Weekend Avg. Price
€515
Trending hotel
Cheeca Lodge & Spa