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Florida Keys Vacation Home Rentals Oceanfront

The Best Beachfront Rentals In The Florida Keys

Buying a Vacation Rental, Florida Keys

Are you looking for amazing beachfront rentals in the Florida Keys? Perfect!

The keys are one of the most beautiful places in the sunshine state and an epic winter destination on the East Coast. If you want to make the best of your Florida vacation, staying in a beachfront vacation rental in the Florida Keys is ideal!

Key West is the most popular place to stay in the keys however, if you are after a beach holiday, you may want to consider other places like Marathon or Islamorada.

In this article, you will discover the best beachfront cottages in the Florida Keys but also beach houses for families, condos and cheaper options for couples.

Weve included a selection of vacation rentals including VRBO and others. That way, you will be sure to find your perfect beachfront rental in the keys!

Disclosure: This post may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no extra cost for you!

Top Rental Accommodation Types In Florida Keys


Pro Tip: RentByOwner makes it easy to compare the best listings on RBO homes from online vacation rental OTAs, including and more. Use the Advanced Filter feature at the top to easily flip between RBO homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Florida Keys.

Welcome Home To Florida Keys Oceanfront Rentals

The magic of the area provides plenty of opportunities to get out and explore, which is why youll be so pleased to return to your vacation rental that features a beach view. Sometimes the pressure of seeing it all can overtake your getaway, making you feel like youre missing out by opting for a quiet moment in the comfort of your own space. No more. Wake up slow, listening to the crashing waves as you blissfully soak in the peaceful morning minutes that youre tucked between luxury linens atop a quality mattress.

With our wide selection of beach view rentals, were confident we can find the perfect Floriday keys oceanfront rental homes for you and your guests. Whether youre traveling with that special someone or are looking for a large place to accommodate your entire group, weve got just the place. Youve simply got to decide if you want a full vacation home all your own, or would you prefer more of a condo setting complete with all the amenities?

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Florida Keys Vacation Home Rentals


  • The Florida Keys have some of the best weather in the world, offering sunny skies throughout the year and warm temperatures no matter the season.
  • As a renter of The Florida Keys vacation rentals by owner can be sure to enjoy the outstanding water-sports, boat dock and other activities on the ocean.
  • Activities such as swimming, snorkelling, diving, boating, watching dolphins, eco tours and especially the world class sport fishing that helped to make the Florida Keys world famous.
  • These islands of the Sunshine State Key Largo, Islamorada, Marathon, Big Pine, the Lower Keys, and Key West, have numerous and wide ranging attractions that are sure to please visitors and residents regardless of their interests, passions, or hobbies.
  • The southern tip of Key West is just 90 miles from Cuba. The Florida Keys are in the subtropics.
  • Most of the land areas in Monroe County, but a small portion extends into Miami-Dade County.
  • The Florida Keys population is 73,090, most of the population is concentrated areas like the city of Key West, which has 32% of the entire population of the Keys.

Florida Keys vacation home rentalsKey Largo vacation rentals

Casa De Ivy A 5br Key Largo Beachfront House Rental

Florida Keys Luxury Vacation Rentals

Casa de Ivy is a beautiful 5 bedroom Key Largo beachfront vacation rental home. This house has an infinity pool overlooking the white sand beach, a newly built dock, and sand volleyball court off the beach. Key Largo is the first island off of the Florida mainland, and is actually closer to Miami than Key West. This is nice if you are flying into Miami International Airport. Key Largo is also the largest island in the Keys.

This Florida Keys rental house is rated to sleep 12 people, with plenty of outdoor entertaining space for large groups. The views from the covered 2nd story patio are hard to beat, and most rooms in the home have views of the ocean. The calm water of Blackwater Sound is perfect for swimming, snorkeling or kayaking right off your own beach. You can even bring your own boat or rent one to utilize the large dock on the property. Casa de Ivy is extremely popular and it can be difficult to find openings, but if you are lucky enough to find an open time you wont be disappointed. Find more pictures and check the availability of this house here:Casa de Ivy-VRBO Listing

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Things To Do Around Our Florida Keys Vacation Rentals

  • Get out on the water. Getting out on the open water is the heart and soul of the Keys. Sign up for a scuba class, hit the seas with parasailing, or snorkel in Key Largo. Head out with fishing gear to catch something for dinner, or admire the surf and watch for dolphins.
  • Adventure on land. Little Conch Key’s laid-back attitude, and the sea turtle hospital in Marathon are just a taste of your Florida Keys options. Swing by the preserved mango swamps of Marathon or visit dolphins at the Dolphin Research Center. Head to the Key West Butterfly and Nature Conservatory in between beach trips for more wonder and wildlife.
  • Heading to our Florida Keys vacation rentals is an ideal choice for someone looking to get away from the daily grind. After a few days in your Florida Keys beach house rental, you’ll wish you could stay forever.

Sun Beaches And Nature Are Yours With A Florida Keys Vacation Rental

The Keys are an Archipelago in the southeast end of mainland Florida. There are in total more than 1,700 islands, and less than 5% of those are inhabited. The islands have unique flora and fauna and a warm climate throughout the year. It is a destination for travelers who wish to surround themselves with nature, enjoy the white sandy beaches of the islands or enjoy water sports. Florida Keys vacation rentals are a great way to discover and enjoy everything this perfect destination offers.

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The 10 Best Beaches In The Florida Keys

1. Bahia Honda State Park: A 2.5-mile long beach with white sand, shallow turquoise water, and palm trees.

2. Sombrero Beach: This beach is situated on Marathon and offers white sands, amenities, a playground, and grassy lawns.

3. Harry Harris Park: A man-made beach that has sand shipped in when required. The nearby jetty provides protection, making this a safe place for children to swim.

4. John Pennekamp Coral Reef State Park: A small beach where you can easily swim to the reef from the beach and snorkel in the calm water.

5. Coco Plum Beach: This natural beach is a nesting site for endangered turtle species.

6. Higgs Beach: Here you’ll find white sand, shallow water, and a number of activities such as volleyball.

7. Sandspur Beach: A small public beach with good snorkeling sites.

8. Smathers Beach: This beach has good launch sites kayakers.

9. Fort Zachary Taylor Beach: A popular beach for families as it has the safest swimming area in the Keys.

10. Dog Beach: The only beach in the Keys that allows unleashed dogs.

Magic Everywhere You Turn

Sunrise Getaway House Vacation Rental, 1580 73rd Street Ocean, Marathon, Florida Keys

When youre visiting a magical place like the islands located just west of Tampa, FL, the desire to see and do everything is real. To start, the beaches are like none youve ever seen before. There are miles and miles of white sand, offering the perfect warm haven for your feet to sink into. Youll find each island offers a unique vibe and beach experience, so we recommend you try them all.

Anna Maria Island offers great facilities like changing cabanas, showers, lifeguards on duty, walk/bike paths, and even cafes providing food, ice cream, and cocktails throughout the day. Alternatively, Longboat Key is known for its resort setting and upscale golf course on the waterfront.

Lido Key, on the other hand, while also known for their shopping, beaches, and restaurants, also offers a unique look at the natural habitat of the Florida Key wildlife and ecosystem. Quick Point Nature Preserve, at the bordering southeast tip of Longboat Key, provides an up close look at the mangrove habitat. This man-made tidal lagoon and natural lagoon area provide you a special opportunity to observe where animals of the air, sea, and land all come together. Another favorite destination in this area is the Mote Marine Laboratory and Aquarium, where you can get a firsthand encounter with dolphins, sharks, otters, stingrays, squids, and countless varieties of fish species that you wont otherwise encounter in the wild on your own.

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Things To Do In Key Largo

Barefeet Rentals is here to help you plan your Key Largo activities. Charter a boat to snorkel our exotic coral reefs or dive our incredible shipwrecks . Swim with the dolphins. Experience the thrill of the catch and release of the big one on a deep-sea fishing excursion. Take an airboat tour of the Everglades National Park for a cherished experience.A cant-miss tour is Garls Coastal Kayaking for a unique and unforgettable eco-adventure through the Florida Keys and Everglades. See the one-of-a-kind manatee in its natural habitat! Stop in at The Florida Keys Wild Bird Sanctuary, visit an alligator farm close by, take a glass-bottom boat ride and witness the amazing 9 bronze statue of Christ in its unusual setting beneath the ocean at Key Largo Dry Rocks. Created by the artist to symbolize peace of mankind and to inspire all who explored and loved the sea.As the evening wanes, set sail on a sunset cruise or, just go native dig your toes in the sand and relax watching the most gorgeous sunsets in the world ending your evening while listening to live entertainment offered at many of our restaurants and pubs.

Sunset Key Cottages In Downtown Key West

The sunset key cottages are the ultimate Key West experience!

They are ideally located downtown which is perfect to go explore Key West. You will get direct access to the beautiful beach and other amenities.

There are an amazing pool, spa center and tennis court! If you are a foodie, you will also enjoy a meal at the restaurant.

The cottages themselves are stunning. The decor is very modern and pretty.

Its the perfect place to stay in the Florida keys for couples.

Photo credit: Vrbo. See more photos.

If you are looking for a fantastic house away from the crowds but not too far from Key West, this beach house is for you!

Its a typical 2-floor Floridan house with 3 bedrooms, 3 bathrooms and a spacious balcony. Its located on the beach which means that its as close as it can ever get!

You will feel like on a private island! If you are travelling with kids, its the perfect place to stay! Its also only 30 minutes away from Key west which means you can easily go there for an afternoon.

Its also worth mentioning that the house was fully renovated and is very modern.

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Toddlers School Age Or Teenagers: Activities For All Ages

Visitors that are coming to stay in a Florida key vacation rental with kids will have many options for family-friendly activities. There are options for kids of all ages, from toddlers to teens.

The little ones will enjoy spending time at the Sheriff’s Animal Farm, home to some unusual inhabitants including lemurs, emus and alligators. For younger or older teens, the Dolphin Research Center runs week-long camps based on their age range, where they can be introduced to dolphins and learn to about their behavior.

At the Key West Aquarium, guests can interact and feed marine life at the ‘Touch Tank’ or take a guided tour through the Turtle Hospital to learn how to help rescued marine life. However, the best way to see all the beautiful sealife the Keys has to offer is to hire a snorkle and take to the ocean.

Whether you choose to relax and enjoy the incredible surroundings, or take the family on a new adventure every day, staying in your Florida Keys vacation home creates a comfortable, more private experience for the entire family.

The 5 Biggest Florida Keys Beach House Rentals

dawnowendesignsinc: Florida Keys Vacation Home Rentals ...

Ryan BellinoFlorida Atlantic Coast Islands, Florida Gulf Coast Islands0

With year-round beautiful warm weather and crystal clear water, its easy to see why the Florida Keys have been one of the most popular vacation destinations in the United States for decades. The Florida Keys stretch over 100 miles long and contain hundreds of islands. Each of the bigger islands has a unique identity, some more laid back, others more party oriented. Most of the islands that make up the Florida Keys are extremely narrow, so massive lots and properties are rare. This list contains the biggest Florida Keys Beach house rentals available at the time of writing. While some of these Keys vacation rentals seem extremely expensive at first, they are almost always a better value than booking multiple hotel rooms for a large group. Breaking the overall cost down on a per bedroom basis is a good way to compare prices. Now lets get on to our list of the biggest Florida Keys beachfront rentals!

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Our Featured Florida Keys Vacation Rentals

Beautiful & Brand New

260 13th StreetKey Colony Beach, FL 33051

This spacious 3 bedroom, 3 full bathrooms, 2 half bath custom built home has everything you could desire.

Private Pool & 40 ft dock!

100 Ave EMarathon, FL 33050

Open concept meets modern elegance in this stunning canal-front pool home located in the heart of the Florida Keys.

Private Pool & large dock!

This brand new home is perfectly appointed in a beautiful, up and coming Gulf-side neighborhood.

Private Pool & 70 ft dock!

A Secluded 4br Islamorada Estate On The Beach

This 4 bedroom beachfront Islamorada estate is the smallest on our list, but it still is rated to sleep 10. Islamorada is made up of several islands, and this rental is located on the island called Lower Matecumbe Key. This area is full of restaurants and attractions and is a great location for families. Right down the road at Robbies Marina and Restaurant you can do the famous hand feeding of giant Tarpon or rent kayaks or jet skis.

The pool at this estate is one of the most beautiful on our list. The pool area is directly off the beach and also has a connected hot tub. The kitchen is equipped with high end commercial appliances, making it easy to have a relaxing dinner at the house. Jim, the owner of this property, takes a ton of pride in making sure every guest has a wonderful experience. This is evident by the fact that with over 50 verified reviews, they have not received anything other than 5.0/5.0 from every single guest. This is extremely rare, and tells you how amazing this Keys rental home really is. Find more pictures and check the availability of this house here:Islamorada 4BR Estate-VRBO Listing

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About Florida Keys Oceanfront Rental On Rent By Owner

With more than 142 oceanfront rentals in or near Florida Keys, Rent By Owner features many wonderful beachfront places to stay. Are you traveling with groups, families, friends, or as a couple to Florida Keys? RBO vacation homes will give you maximum comfort and essential amenities such as full kitchens, Wi-Fi, hot tubs, outdoor pools, recreation and theater rooms, laundry facilities, and more for your comfort.

Looking for a beach or oceanfront rental in Florida Keys, Florida with a pool? Rent By Owner has a large selection of villas, condos, cabins, and cottages. There are rentals for both large and small travel groups. RBO vacation homes can assist you in finding the perfect accommodation in Florida Keys that meets your travel budget, giving you the option to find direct access to the stunning beaches and ocean views, Rent by Owner has plenty of room for an extended family or small family, whether you are looking for a luxury villa, resort, furnished home, cozy condo with breathtaking views with private bedrooms and baths near Florida Keys, find an oceanfront rental with an amazing view.

A Luxury 5br Marathon Beachfront House With A Dock And Private Beach

Vacation Rental Property at 1792 109th St. in Marathon, Florida Keys

Although this beachfront Marathon rental house isnt the biggest on our list, the location and outdoor amenities are our favorites. Off of the beautiful private beach there is a peninsula that extends out into the ocean. On this peninsula there is an awesome covered tiki hut with seating and a TV. There isnt a better place to relax in the Keys. The saltwater pool lies between the house and the putting/chipping green off the beach. Yes, you can brush up on your golf game right off your own beach. The dock has space for 3 boats, including 1 space that can accommodate a 100 ft boat.

This 5 bedroom, 4 bath rental is rated to sleep 16, plenty of space for large families or multiple families. The Sub Zero commercial appliances complete the beautiful custom kitchen. The panoramic ocean views from both the 1st and 2nd floor will make it hard to leave. This property barely misses the perfect 5.0/5.0 average review score after over 40 verified reviews, coming in at 4.9/5.0. If fantastic outdoor amenities are big on your priority list, this Keys vacation rental is tough to beat. Find more pictures and check the availability of this house here:5BR Marathon Beach House-VRBO Listing

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