Beachfront Properties and Vacation Rentals in Key West, Islamorada, Key Largo, and More
The Florida Keys offer a romantic and beautiful destination for couples who want to get away for awhile. From Key West to Key Largo, the Florida Keys offer no shortage of beautiful beachfront vacation rentals, unique Airbnbs, and Key West style beach houses. The area is filled with activities that couples can enjoy together, including water sports, romantic restaurants, and fun filled adventures. Each unique Florida Key has its own personality and character. There is also a diverse range of places to stay, from charming hotels to luxurious villas and posh apartments. Many vacation rentals have private pools, while others are beachfront or right in the heart of downtown Key West.
Jump to: Key West
| Lower Keys
| Marathon Key
| Key Largo
Key West, Florida - Airbnbs & Vacation Rentals
For many visitors, Key West is the place to stay in the Florida Keys. If you're looking to be at the center of the action, then Key West can't be beat. There are countless delicious restaurants, an endless supply of lively bars, and all kinds of activities including the quintessential Florida Keys sunset cruises. The town also has a fascinating history and some interesting sights that are worth exploring. Popular sights include The Oldest House
, which dates back to the 1820’s, Higgs Beach African Graves, which has a tragic but poignant story, and the Harry S. Truman Little White House. Also make sure you visit the Southernmost Point as well as the Ernest Hemingway Home and Museum. If you plan to get out on the water – and you should because this is the Florida Keys – there is no shortage of options. The area has excellent kayaking, snorkeling, diving, and fishing.
For the perfect date night, head to Mallory Square at sunset. There are street performers, musicians, and plenty of things to see and do. Key West also has the best nightlife in the area, so you can enjoy some wine or beer under the stars, whatever your style.
It's easy to fly into Key West Airport but you can also expect to pay a bit more than a flight to Miami International Airport. It will save you the time of driving the 3.5 hours from Miami (granted, it's a pretty spectacular drive).
Key West is the most pedestrian friendly town in the Florida Keys. Even so, you'll want a car to explore everything that the islands have to offer (check car rental prices here
Key West has a number of nice hotels. The prices are a bit more than elsewhere in the Keys, but that's the cost of being near all of the action. Most of the properties are smaller condos or hotel rooms, but what's lost in space is often made up for in convenience.
Romantic Key West Airbnb with a Pool
This charming cottage is the perfect romantic retreat with a pool and a private spa. It has a kitchenette, a cozy bed, and a nice bathroom.
The Lower Florida Keys - Airbnbs & Vacation Rentals
If you're looking for a more natural and peaceful get away, then the Lower Keys are an excellent option. They start at the famous Seven Mile Bridge and include popular places such as Big Pine Key, Little Duck Key, Summerland Key, Big Torch and Little Torch Keys, Cudjoe Key, Sugarloaf Key, Big Coppitt Key, and Stock Island. Nearby you'll find wildlife refuges, a national marine sanctuary and a state park. This is also the most likely area for spotting key deer, so keep your eyes peeled.
For a unique and eclectic spot, head to Stock Island, which is an artists retreat. There are a number of nice art studios as well as a nice waterfront area with bars and restaurants. This area is also the main base for the fishing industry in the Florida Keys, so you'll enjoy delicious fresh seafood and a number of nearby marinas.
This area has all of the typical outdoor activities including snorkeling, diving, kayaking, paddle boarding, and more. It's a great place to get out on the water and enjoy everything that the Florida Keys have to offer.
There are a range of rental properties available in the area. Luxury homes and upscale properties make the perfect romantic getaway, but if you're looking for affordability and something a little more basic, there are a number of RV's available for rent as well.
Little Torch Cottages - Waterfront Florida Keys Airbnb
2 Bedroom, 2.5 Bathrooms, Pool
This townhouse is part of a quiet complex in a great location. You can use the pool, fitness center, and it's on the water, too. With a very modern and new kitchen, along with luxury bathrooms and a relaxing bed, anyone would be comfortable here. This is a great romantic retreat right on the waterfront.
Marathon Key, Florida - Airbnbs & Vacation Rentals
Marathon is located right in the middle of the Keys, so it makes a great base for exploring the entire area. It's just over an hour from both Key West and Key Largo.
For couples that want a quiet beach setting, then this is a great place to stay. Bahia Honda State Park
and Sombrero Beach are both excellent places to spend the day. Both areas have nature trails and Bahia Honda also offers camping, but you'll need to reserve your spot well in advance.
Marathon has a number of fun attractions to visit. The Dolphin Research Center
is an excellent place to spend some time if you love marine life. It's a nonprofit organization, not a marine theme park, so you can feel good about the price of admission benefiting the animals. It's also a great place to swim with dolphins. The Turtle Hospital
is another popular place to visit for animal lovers, as is Crane Point Nature Museum.
Prices for vacation rentals in Marathon range from about $150 for a small bungalow or apartment rental to $900 for luxury villas with private pools. There are a number of luxury and high end options, and even the smaller, more affordable rentals are generally high quality.
Marathon Key Beachfront Airbnb
The location of this condo can't be beat. It's right by the beach and is a quiet retreat for a couple. Luxury meets comfort here, and you can just enjoy the sea views all day long. The fully-equipped kitchen will let you cook all of your meals. You also have access to the pool of the complex. And the balcony overlooks the beach!
Beachfront Marathon Key Airbnb with Private Pool
This spacious rental is a great price with a pool
and a convenient location. It’s not far from the beach and everything in town. It also has a dock on the canal where you can bring your own boat, or use the included kayaks
to explore the water.
Islamorada, Florida - Airbnbs & Vacation Rentals
Another great base for exploring the entire Florida Keys is Islamorada. It's part of the middle keys and is about 1.5 to 2 hours from Key West and just half an hour to 45 minutes from Key Largo. Islamorada is a village made up of five keys including Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key.
This village is a little less commercialized than some other parts of the Keys so it makes a peaceful and relaxing place to visit. You might need to drive to Marathon though for a wider variety of restaurants.
There are a number of great activities for couples around Islamorada. You can enjoy live music at the ICE Amphitheater at Founders Park. They host a number of concerts and live performances. You could also head to Theater of the Sea for a classic Florida Keys experience. It's a Florida Keys staple, and they have entertaining dolphin and sea lion shows that are fun for all ages. There are also a number of state parks in the area including Indian Key Historic State Park, Long Key State Park, and Indian Key Historic State Park. For beer lovers, Islamorada is where you'll find the only production brewery in the Florida Keys. The Florida Keys Brewing Company is a small micro brewery with an eclectic style that feels like a quintessential part of the Florida Keys.
Like elsewhere in the Florida Keys, you'll find plenty of vacation rentals in Islamorada. Prices are a bit more expensive than Key Largo and you can expect to pay anywhere from $250 a night for a simple bungalow to upwards of $1000 a night for a luxurious beachfront villa.
Affordable Islamorada Airbnb Apartment
This is an affordable apartment for a couple who wants to escape to paradise. It's a quiet retreat that's clean and comfortable.
Flakey's Islamorada Airbnb
And here’s a cozy place to stay that's convenient to everything, including the live music at the bar, plenty of restaurants, and beaches, too.
Key Largo, Florida - Airbnbs & Vacation Rentals
Key Largo is the northernmost island of the Florida Keys and it's just a one-hour drive from Miami. This is the place to stay if you're looking for some of the best diving and snorkeling in the Florida Keys. Much of the surrounding waters are protected by marine parks, so you'll see a variety of marine life and coral. The most popular dive spots are found in John Pennekamp Coral Reef State Park, the Mosquito Bank or Sea Gardens, Molasses Reef, and the Grecian Rocks.
Key Largo has a friendly community vibe. There are plenty of water activities available and some fun local hangouts in the town. As the northernmost key, the water is blue, but not yet the striking blue that the Florida Keys are most known for. You'll find as you head further south the water takes on a more tropical quality. .
There are a number of vacation rentals available in Key Largo. Prices are slightly more affordable than you'll find elsewhere in the Florida Keys. You can expect to pay anything from $150 a night for something small and simple to $300 a night for a house or bungalow.
Key Largo Waterfront Airbnb
The outdoor space really makes this house special. It has a dock on a canal, beaches nearby, and access to the nearby mangroves. Also included is a full kitchen, comfortable living room area with a TV, a grill, and kayaks to explore the area.
Conch Life Haven - Key Largo Airbnb
This is a really cute house that's very clean and comfortable. It’s fully stocked, includes admission to the nearby state parks, includes bikes, and has a washer and dryer. The beaches are nearby, as are the canals for boating and water sports.