A stunning beachside village located in the epic Florida Keys – Islamorada is a bucket list travel destination you NEED to visit. If you’re looking to soak up the sun then this is the place to be as the region attracts rays pretty much all year round meaning you can leave those warm clothes at home. Not only does Islamorada have epic sunny weather, it also is home to beautiful hotspots and a variety of entertaining activities including gorgeous cream-colored beaches, spectacular coves, awesome waterparks, and incredible snorkeling trips.
Despite its relatively small size, Isla Morada is actually a collection of multiple islands which means you need to choose wisely when picking your accommodation! That’s why we’ve created the ultimate guide on ‘Where to Stay in Islamorada’ where we’ve broken down three of the best neighborhoods to stay in along with giving you top tips on things you can do nearby.
Quick Tips – Where to Stay in Islamorada?
- Best Neighborhood in Islamorada to be close to everything – Upper Matecumbe Key
- Where to stay in Islamorada on a budget – Plantation Key
- Where to stay in Islamorada for families – Lower Matecumbe Key
Where to Stay in Islamorada
Angler’s Reef Resort is located in the laid-back Lower Matecumbe Key neighborhood and has a lavish yet relaxed atmosphere perfect for those who want a chilled-out place to stay when visiting Islamorada. The hotel is southernly located away from the busy streets and boasts amazing facilities making guests not want to leave the resort including awesome jetties, an outdoor swimming pool, a beautiful garden, and a private beach.
Chesapeake Beach Resort
- Private beach area
- Windley Key Fossil Reef Geological State Park is 3.2 km away.
- History of Diving Museum (3 minutes’ walk) or see a show at the Theater of the Sea (4 minutes’ drive).
Chesapeake Beach Resort
- Private beach area
- Windley Key Fossil Reef Geological State Park is 3.2 km away.
- History of Diving Museum (3 minutes’ walk) or see a show at the Theater of the Sea (4 minutes’ drive).
Chesapeake Beach Resort is the perfect destination for those who fancy a bit of luxury but don’t want to fork out the prices for an exclusive five-star resort. Located in the popular neighborhood of Upper Matecumbe Key the resort is nearby top sites including Windley Key Fossil Reef Geological State Park, Cheeca Rocks, and Library Beach Park. The hotel also has great facilities including uniquely designed outdoor pools and a private beach area equipped with plenty of sun loungers.
Ragged Edge Resort & Marina
- 1 swimming pool
- 10-minute walk from the beach. Located in Islamorada.
- 3.1 km from Windley Key, Ragged Edge Resort & Marina features barbecue facilities and views of the pool.
Ragged Edge Resort & Marina
- 1 swimming pool
- 10-minute walk from the beach. Located in Islamorada.
- 3.1 km from Windley Key, Ragged Edge Resort & Marina features barbecue facilities and views of the pool.
Located just a ten-minute walk from the nearest beach along with a short distance from Windley Key, the Ragged Edge Resort & Marina is an awesome place to stay in Matecumbe Key if you want a great location whilst still being on a budget. The hostel also offers great on-site amenities including a refreshing outdoor pool perfect for cooling off in along with an awesome BBQ area where you can whip up a tasty and budget-friendly dinner.
Here are our overall top recommendations for places to stay in Islamorada
Islamorada’s 3 Best Neighborhoods to Stay in
Neigborhood#1 – Upper Matecumbe Key
Best Neighborhood in Islamorada to be close to everything
- COOLEST thing to do in Upper Matecumbe Key – Have a BBQ Library Beach Park
- BEST place to visit in Upper Matecumbe Key – The Keys History & Discover Centre
Situated bang in the middle of the long stretch of Isla Morada, guests who choose to stay in Upper Matecumbe Key will be surrounded by things to do which makes it the perfect place to stay for those who want to be close to everything. Here you will find the greatest selection of cafes, restaurants, and bars along with key landmarks meaning you won’t have to trek too far to grab a bite to eat or perhaps have a drink or two overlooking the waterfront.
This neighborhood has a vibrant atmosphere in comparison to the rest of Islamorada, however, the nature of the region is still relaxed and chilled so you can expect to spend your days exploring the area’s natural beauty in peace. We HAVE to recommend you visit a restaurant which overlooks the water at least once if you’re staying in Upper Matecumbe Key as it’s a truly amazing experience.
- Have a sunset meal at Islamorada fish company
- Take a boat trip to nearby islands
- Visit Isla Morada brewery and distillery
- Go snorkelling at Cheeca Rocks
Best Budget Hotel in Upper Matecumbe Key
Pines & Palms Resort
A beautiful resort with budget-friendly prices the Pines & Palms Resort is situated near the stunning Alligator Reef right on the waterfront. The hotel also features amazing facilities including a private beach, freshwater swimming pool, and Tiki Bar – we can assure you you won’t find much better budget-friendly options with such good facilities in Islamorada.
Best Mid-Range Hotel in Upper Matecumbe Key
Chesapeake Beach Resort
Chesapeake Beach Resort provides luxurious rooms on a private beachfront property which boasts a sense of tranquility with its secluded and peaceful atmosphere. The hotel is equipped with many areas which have epic views including an outdoor pool, decking area, and multiple balconies. If you’re looking to explore Windley Key Fossil Reef Geological State Park then you’re in luck as the hotel is located less than two miles away.
Best Luxury Hotel in Upper Matecumbe Key
Islander Resort
If you’re looking to splash the cash on a lavish resort in the Upper Matecumbe Key neighborhood, then the Islander Resort is definitely the place to stay! The hotel offers beautiful views from fully furnished private porches, two incredible outdoor pools along with tasty dining options at its on-site Beachside Bar. You can also experience plenty of underwater activities from the hotel including snorkeling and scuba diving around the nearby reefs.
Neigborhood#2 – Plantation Key
Where to Stay in Islamorada on a Budget
- COOLEST thing to do in Plantation Key – Go swimming at Marlin Beach Park
- BEST place to visit in Plantation Key – Toilet Seat Cut
Plantation Key is the largest neighborhood to stay in Islamorada which means there are plenty of places to stay for all types of travelers including those who are on a budget! There are also plenty of things to do in Plantation Key including taking an epic snorkeling trip off the coastline to Davis and Crocker Reef, dining along Whale Harbor Marina along with visiting the fascinating Windley key Fossil Site
You also have the two interesting areas of Rain Barrel Village and Windley Key on your doorstep both of which offer unique experiences for visitors including art galleries, waterparks, and fancy boutiques.
When staying in Plantation key you have to visit arguably the most unique spot in Islamorada – Toilet Seat Cut. Here you will find a collection of toilet seats suspended above the sea, it might sounds weird but its actually a really cool experience.
- Have a bit to eat at Habanas Oceanfront Dining
- Visit Whale Harbor Marina
- Take a snorkelling trip to Davis and Crocker Reef
- Visit the Windley Key Fossil Site
Best Budget Hotel in Plantation Key
Ragged Edge Resort & Marina
Located just a ten-minute walk from the nearest beach along with a short distance from Windley Key, the Ragged Edge Resort & Marina is an awesome place to stay in Matecumbe Key if you want a great location whilst still being on a budget. The hostel also offers great on-site amenities including a refreshing outdoor pool perfect for cooling off in along with an awesome BBQ area where you can whip up a tasty and budget-friendly dinner.
Best Mid-Range Hotel in Plantation Key
Atlantic Bay Resort
The Atlantic Bay Resort provides the lavish facilities of a luxury hotel without the high-end prices! On site, the resort offers spacious and luxurious rooms along with a great selection of communal facilities including a beautiful beachfront area which is even more spectacular at sunset, a lovely outdoor pool along with a private pier where guests can go snorkeling from.
Best Luxury Hotel in Plantation Key
Pineapple Beach by Florida Keys Luxury Rentals
This private home-style resort is perfect for large groups with a huge five bedroom house available with a stunning interior and even more spectacular views looking over Pineapple Beach. On site, you will also find a unique rocky style pool along with an awesome jetty which is best enjoyed at sunset. The property is also located in a secluded yet safe area making it perfect for guests who fancy a bit of privacy on their trip to Islamorada.
Neigborhood#3 – Lower Matecumbe Key
Where to Stay in Islamorada for Couples
- COOLEST thing to do in Lower Matecumbe Key – Visit Old Road Gallery
- BEST place to visit in Lower Matecumbe Key – Anne’s Beach
The neighborhood of Lower Matecumbe Key epitomizes Islamorada’s relaxed and peaceful atmosphere with a lovely selection of chilled beachfront bars, laid-back surf shacks along with gorgeous white sandy beaches. The area is also full of beautiful resorts which are perfect for a romantic getaway making it perfect for couples visiting the region.
Lower Matecumbe Key is arguably the area with the most raw natural beauty with stunning hotspots including Sandy’s Cove, Gulf View and Anne’s Beach all of these places will leave you amazed with how picturesque they’re.
- Soak up the sun at Sandy’s Cove
- Take in the views at Gulf View
- Visit Caloosa Cove Marina
Best Budget Hotel in Lower Matecumbe Key
Caloosa Cover Resort & Marina
The Caloosa Cover Resort & Marina provides a great selection of accommodation options for guests staying in Lower Matecumbe Key all of which are brightly decorated and beautifully furnished. The property is just a ten-minute walk to the nearest beach if you fancy taking a dip in the ocean and it also has a refreshing outdoor pool if you don’t fancy making the trek for your swim. If you fancy keeping active then the resort also offers a great outdoor tennis court!
Best Mid-Range Hotel in Lower Matecumbe Key
Topsider Resort by Capital Vacations
The Topsider Resort is one of the most popular places to stay in Islamorada with hundreds of top-class reviews raving about its incredible on-site facilities available for a steal of a price. These incredible facilities include spa baths, hot tubs, an outdoor swimming pool along with a beautiful outdoor garden and terrace area. Nearby the property you have the beautiful Sea Oats Beach as well as being just a short drive from arguably the most picturesque beach in the neighborhood- Anne’s Beach.
Best Luxury Hotel in Lower Matecumbe Key
Angler’s Reef Resort
Awesomely located on the southern tip of Lower Matecumbe Key, Angler’s Reef Resort is an idyllic destination if you want a peaceful getaway away from the hustle and bustle. Here you are just a stone’s throw away from a beautiful beach that is epic for snorkeling along with a small private marina with a selection of boats available for rent. Guests also have access to a private garden, sparkling outdoor swimming pool, and grill area.
Final Thoughts on the Best Places to Stay in Islamorada Key
So that is the stunning village of Islamorada an epic destination for those who want to soak up the sun whilst experiencing a relaxed atmosphere by the ocean. We hope this guide has helped you decide where to stay in Islamorada depending on what you want from your travel experience. Despite its small size it is good to look in detail at this guide on where to stay in Islamorada, as each neighborhood offers something unique, and where you locate yourself will definitely impact your experience.
So what are you waiting for? Get booking, this Idyllic beachside getaway is waiting for you!
If you end up booking any of these epic hotels we have listed above be sure to let us know, we love hearing about your experiences.
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