The Florida Keys are a sprawling 125 mile long chain of islands off the southern tip of Florida. The Keys are made up of 44 islands, with 42 bridges chaining the larger islands together via The Overseas Highway (US Route 1). If you are interested in a Florida Keys vacation rental but are overwhelmed by trying to decide on which island, this guide will attempt to make that decision easier. Many people picture the Florida Keys as just Key West, but that couldn’t be farther from the truth.
This guide will start on the northernmost island of the Florida Keys and make our way south, ending at Key West. We won’t cover every single island in the Keys, instead focusing on the more popular ones. Feel free to use the table of contents below to skip around, this guide is extremely large. Alright, enough talk, here is the most comprehensive guide to Florida Keys vacation rentals on the internet:
Key Largo is the northernmost island of the Florida Keys, about an hour from Miami and 2 hours from Key West. Much like how Key West and Key Largo are at opposite ends of The Keys, the culture and vibe of the islands are opposite as well. You are much more likely to find a dive shop than a dive bar in Key Largo. The laid back and more spread out vibe of Key Largo lends itself well to families who enjoy being on the water.
Much of the activity in Key Largo focuses on watersports. The snorkeling and diving around the island’s John Pennekamp Coral Reef State Park are the best in the Florida Keys. The more spread out nature of Key Largo means that this is definitely a “rental car required” vacation destination. You will notice Key Largo feels like less of a touristy island than the Southern Keys, with more of a small town local feel. Mrs. Mac’s Kitchen (Mrs. Mac’s on Tripadvisor) is a local restaurant that epitomizes this local feel and can’t be missed on a trip here. Their Key Lime Pie shakes are to die for!
The inventory of Key Largo vacation rentals are a good mix of houses and small condo complexes. Some of the best values can be found here, compared to the overall average nightly rates of Florida Keys vacation rentals. Unfortunately, Monroe County laws prohibit Key Largo house rentals that are less than 28 days. Condos and townhomes do not have this restriction and are happy to accept weekly rentals. If you are in the market for a monthly house rental in Key Largo, these restrictions have lowered demand to the point where you can get a really good deal. Most of our readers are more interested in weekly rentals so here is our favorite Key Largo condo rental: Casa Azul, a 2BR Key Largo Vacation Rental-VRBO Listing
Plantation Key (Islamorada)
Plantation Key is the start of the chain of islands known as Islamorada. You’ve probably heard of Islamorada, but probably not the individual islands that make up Islamorada. Plantation Key is about 6 miles long and much narrower than Key Largo. This means almost all Plantation Key vacation rentals are waterfront. It is also far less commercially developed.
Being less developed has its perks but also its downsides. If you are looking for a bunch of stuff to do this island probably isn’t for you. What it is good for though, is having a central home base to explore the rest of the Upper Florida Keys. The dining options are somewhat limited on the island, with the standout being Marker 88 (https://marker88.info/), a sprawling beach bar and grill with incredible water and sunset views. It’s a can’t miss on the island.
There are some incredible vacation rentals on Plantation Key, and this house is one of our favorites: Beachfront Islamorada House Rental with Private Dock-VRBO
Upper Matecumbe Key (Islamorada)
Heading further down the Keys, we come to Upper Matecumbe Key. When you hear about or see pictures of Islamorada, more than likely this is the island you picture. Upper Matecumbe is the unofficial “headquarters” of Islamorada, with an abundance of things to do and places to stay. Some of the most beautiful and biggest Islamorada house rentals are located on Upper Matecumbe Key, but there is an abundance of awesome resorts as well.
Known as the “Sport Fishing Capital of the World”, Islamorada and Upper Matecumbe Key are a seafood lovers paradise. Even if you aren’t into fishing, the seafood here is world class. There is an astounding number of beachfront and dockside seafood restaurants on this island. Lazy Daze is our favorite (check the Tripadvisor reviews: Lazy Daze) but Mangrove Mike’s and Morada Bay are can’t miss restaurants as well. There is also two great breweries on the island, Florida Keys Brewing Co. (https://floridakeysbrewingco.com/) and Islamorada Brewery and Distilling (https://islamoradabreweryanddistillery.com/).
The number of vacation rentals available of Upper Matecumbe Key is vast for the relatively small size of the island. You can rent everything from massive sprawling estates to quaint 1 bedroom cottages on the sand. Our favorite rental is going to be a house that is probably way too big for just a single couple, but an incredible opportunity to take the whole family on the trip of a lifetime. Even if this beachfront mansion isn’t in your budget, it’s worth a look at the pictures: 9BR/9BA Islamorada Beachfront Mansion with Private Chef-VRBO Listing
Long Key (and the town of Layton which sits on it) is definitely smaller than the islands before it, but it is unique enough it deserves a mention. Most of the island is actually Long Key State Park, which is a sprawling preserve. You won’t find much in the way of restaurants on the island itself, but this can be a great spot to make a home base for exploring The Keys. There is an awesome small resort here as well that we definitely recommend, Lime Tree Bay Resort (Check Lime Tree Bay Resort Availability and Rates).
Long Key vacation rentals are pretty scarce, but if you can find availability, this is one of the best areas to get a true white sand beachfront rental. The beach areas on the keys can be rather limited, so this is a unique area. Our favorite VRBO rental on Long Key is a 2BR duplex located directly on the beach with its own dock. The views from the deck are incredible, and its a great value to boot. Check this unit for availability: 2BR Long Key Vacation Rental on the Beach-VRBO Listing
Vaca Key and Key Colony Beach
Vaca Key and Key Colony Beach are generally just called part of the larger island of Marathon, but they are in fact different keys. These islands are great if you want to be close to the hustle and bustle of Marathon, without the crowds. Being just a few minutes drive from Marathon gives you access to a multitude of restaurants and things to do, but far enough away to be a bit more relaxing.
Unlike Long Key, there are a ton of Vaca Key and Key Colony Beach vacation rentals available. You will notice Key Colony Beach is mainly condos and smaller houses on canals with ocean access, while Vaca Key has many larger houses available for rent. Our top rental here is an absolute stunner, a magnificent 3BR waterfront house that you just have to see to believe. This is definitely a luxury choice (and is priced accordingly), but this is simply one of the most beautiful rentals in The Keys. The pictures and reviews speak for themselves: Gulf Front 3BR Luxury Florida Keys Vacation Rental-VRBO Listing
Marathon is one of the most popular and developed islands in the Keys. The city of Marathon is made up of 13 islands, inc Vaca Key and Key Colony Beach that we covered above. The large main island of Marathon that everyone thinks of when you picture Marathon is what we are referring to in this section. This island has a wide variety of attractions, lots of restaurants, and plenty of places to stay. In our opinion, this is one of the most commercialized islands in the Keys. The advantage to that commercialization is that there is TONS of stuff to do; with the downside that it does lose some of that small beach town feel.
As far as places to stay go, there is just about every end of the spectrum in Marathon. From small family owned resort to big houses on the beach, there’s a Marathon vacation rental for every budget or group size. Our favorite budget Marathon resort is Captain Pips Hideaway (Captain Pips Rates and Availability), it’s a no frills resort that is clean, comfortable, on the water, and won’t break the bank. The best bigger Marathon resort is Tranquility Bay Resort (Tranquility Bay Resort Rates and Availability). Tranquility Bay is an absolutely gorgeous property, with panoramic ocean views and a beautiful beachfront pool.
Our favorite Marathon house rental is a 2 bedroom waterfront house called Coco Plum Paradise. This house has a huge pool and is a mere 10 steps from the oceans. The VRBO reviews speak for themselves, check it out: Coco Plum Paradise, a Marathon Oceanfront Beach House Rental-VRBO Listing
Little Torch Key
Moving about 20 miles Southwest from Marathon, we come to Little Torch Key (sometimes referred to as Little Palm Island). This small island is the polar opposite of Marathon. To some that might be boring, to others it’s very relaxing. There’s no fancy restaurants, just laid back beach bar and grills. Little Torch Key resorts are small and laid back. The dress code on this small Florida Keys island is shorts and flip flops 365 days a year. Kiki’s Sandbar Beach Bar and Grill (Kiki’s Tripadvisor Reviews) is the quintessential Florida Keys beach restaurant, laid back with great food, cold drinks, and beautiful views on the sand.
There are several large canal systems on Little Torch Key, giving almost all the houses access to the ocean if you bring or rent a boat. There are only a couple resorts on Little Torch Key, but Parmer’s Beach Resort (Check Rates and Availability) is a great value. It’s nothing fancy, but on the water, clean and cozy. Little Torch Key is one of those islands where we recommend skipping a resort and going with one of the awesome Florida Keys vacation rentals available on the island. Our favorite Little Torch Key vacation rental is called Barry’s Beach, and it includes a main house and guest house. This Keys oceanfront rental includes a total of 8 bedrooms and 5 bathrooms between the 2 houses, and is rated to sleep 20 people. With a 200 foot dock and heated pool overlooking the ocean, there is plenty to do for large groups. Barry’s Beach, a 8BR Oceanfront Florida Keys House Rental-VRBO Listing
Moving farther South down the Overseas Highway towards Key West, we arrive at Ramrod Key. To be honest, there isn’t a whole lot going on here. There is one restaurant, the Boondocks Grille and Draft House. The reason we like Ramrod Key is because it is perfectly located between Key West and Marathon. This location let’s you enjoy the multitude of attractions at both popular islands. If you stay on Marathon, you probably won’t make the drive to Key West and vice versa. Ramrod Key makes both accessible, making it a relaxing home base for exploring the lower Keys.
There are a bunch of really good Keys vacation rentals on Ramrod Key, but there is one definite standout. Island View, is a 3BR oceanfront Florida Keys estate rental that sits on a massive triple lot. The private heated pool is one of the largest in the lower Keys. Right off the pool is a huge covered Tiki bar overlooking the pool and the ocean. This private estate feels really close to a Caribbean resort with this fun setup. The reviews are a perfect 5.0/5.0 average review score with 50 verified reviews from guests. This is an awesome house that we can’t recommend enough. Island View, a 3BR Ramrod Key Beachfront Estate-VRBO Listing
Getting closer to Key West, Cudjoe Key is 19 miles from the final stop on the Overseas Highway. There is a bunch of great seafood restaurants in Cudjoe Key. The best reviewed and our overall favorite is The Square Grouper (Tripadvisor Reviews). Surprisingly, there aren’t any resorts on Cudjoe Key that we would recommend. The reviews are really varied and no quality resort stands out. Luckily, there are many Cudjoe Key vacation rentals that are much better options than any of the resorts on the island.
Our overall top Cudjoe Key vacation rental is a 2BR house located in the Sunrise Beach Resort. This Florida Keys resort is a little different than you would expect. Sunrise Beach Resort is made up of 10 individual beachfront houses with shared use of a beautiful beach, huge dock system and big heated pool. This house rental comes with 4 kayaks you can launch right off the beach in calm, crystal clear water. There are also 4 bikes included as well. There are many shops and restaurants located within walking or riding distance from the house. With so many added amenities at this property, it’s easy to see why it gets such a high review score. Check for yourself here: 2BR Cudjoe Key House Rental in Sunrise Beach Resort-VRBO Listing
Our next area is both the Upper and Lower Sugarloaf Keys. These islands are some of the bigger islands in the lower Florida Keys, but are largely undeveloped. This is a beautiful area for nature lovers. Sugarloaf Key is a perfect location for anyone wanting to be a few minutes from the action of Key West and Boca Chica, but still in a secluded and quiet area. Upper Sugarloaf Key is home to one of our favorite seafood restaurants in the Florida Keys, South of the Seven. They offer some of the most creative and interesting seafood dishes in the Keys. They use local fresh caught seafood and are constantly changing their menu based on what’s in season. Check their Facebook page for the latest specials and menu updates: https://m.facebook.com/Southoftheseven/
Sugarloaf Key is unique because most of the vacation rentals here are beachfront mansions. This is definitely one of the most expensive places to find a Florida Keys house rental, but they are really, really nice. Most Sugarloaf Key rentals are on the water. The overall top rental in our opinion is a 4BR, 5BA rental called Villa of the Setting Sun. It would be a challenge to find a more elegant rental. The property is extremely private and secluded, offering picture perfect views. It’s pricey for sure, but it is definitely awesome. Check it out: 4BR Villa of the Setting Sun-VRBO Listing
Boca Chica Area
Most of this area surrounding Boca Chica Key is a Naval military base, there are very few house or condo rentals on the island. Most of the housing is homes for the soldiers working at the military base. There are few restaurants and fewer reasons to stay on this island. Skip it and head to our next island instead.
We’ve made it to Stock Island, the last stop before Key West. This island is full of great restaurants, hotels and resorts. The vibe here isn’t as relaxed as some of the smaller islands in the lower Keys, but isn’t nearly as wild as Key West. You can’t miss making a stop at The Hogfish Bar and Grill (http://www.hogfishbar.com/). Their specialty is a fried Hogfish sandwich that is to die for. If you’ve never had Hogfish, it’s a fish local to the Keys with a white flaky meat that has a taste similar to scallops.
If we had to pick, our favorite Stock Island Resort would be Oceans Edge Resort and Marina (Oceans Edge Resort Rates and Availability). This beautiful Florida Keys resort is on the water, has awesome food and beverage options, and a great oceanfront pool. Our favorite Stock Island vacation rental is actually right outside the Oceans Edge Resort.This 3 bedroom condo is part of the small Oceans Edge condo complex. The complex has its own pool and amenities from the resort, yet you can still walk down and eat at the resorts restaurants. This is a great option for longer term stays and for bigger groups. Check out the rates and availability here: 3BR Oceans Edge Condo-VRBO Listing