Pet Friendly Florida Keys Vacation Rentals

Key Colony Half Duplex on Canal. Pool Club too! 320 Side
Florida Keys > Marathon Area > Key Colony Beach
House , Bedroom(s): 2 , Sleeps: 5
This side of the duplex is a 2 bedroom, 2 bathroom and sits on a canal with 30 feet of dock space. Other side available too!!
From $900 /Week
Keys Livin' Large
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 5 , Sleeps: 12
5 Bedroom 4 Bath With Pool/ And Tiki Bar/TV, and Kayaks on Gulfside
From $570 /Night
Amazing Marathon Property! Turtle Cove - Pool and Hot Tub, Quick Atlantic Access!
Amazing Marathon Property! Turtle Cove - Pool and Hot Tub, Quick Atlantic Access!
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 3 , Sleeps: 8
Escape to the Keys ~ Located in Marathon, waterfront, pool & hot tub, single family home. 3 bed / 2 bath, dockage with quick ocean access.
From $236 /Night
Keys Living
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 4 , Sleeps: 8
3 BR 2BA With Private Pool, Tiki Bar/ Ground Floor Apt available for fee for guests renting entire house
From $321 /Night
4BR2BA, Pool with Spa, Tiki, Quick Atlantic access!
4BR2BA, Pool with Spa, Tiki, Quick Atlantic access!
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 4 , Sleeps: 10
Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on a canal with private pool, hot tub & tiki! Kayak and Paddleboard included!
From $229 /Night
Keys Dreaming
Keys Dreaming
Florida Keys > Marathon Area > Marathon
House , Bedroom(s): 4 , Sleeps: 10
Spectacular 4BR/3BA home on canal near Sombrero Beach, fishing, and shopping
From $428 /Night

OFFER Fall in Love with Marathon, Florida! Any Week in Sept-Nov 2021- $2499. Rental Rate! Book Directly with Owners Save $$$

Special offer period: Sep 1, 2021 - Nov 30, 2021

Breeze Swept - Florida Keys Monthly Rental By Owner - Pet Friendly
Florida Keys > Lower Keys Area > Big Pine Key
House , Bedroom(s): 3 , Sleeps: 6
Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This rental is a monthly rental only!
From $6,200 /Month
Florida Keys > Islamorada Area > Islamorada
House , Bedroom(s): 4 , Sleeps: 12
House, 4 Bedrooms, 3 Baths, (Sleeps 2-12), Heated salt water pool. 70+ ft deep water dock, Screened in upper porch, lower outside bar with tv and bbq.
From $400 /Night
Island Chalet - Little Torch Key Monthly Rental with Dock
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 3 , Sleeps: 6
Located on Little Torch Key with awesome boat access to Big Pine channel! This rental is a monthly rental only.
From $4,100 /Month
Margarita Villa - Little Torch Key Monthly Rental with Dock
Florida Keys > Lower Keys Area > Little Torch Key
Villa , Bedroom(s): 3 , Sleeps: 6
Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!
From $4,300 /Month
Palm Villa- Little Torch Key Monthly Vacation Rental with Dock
Florida Keys > Lower Keys Area > Little Torch Key
Villa , Bedroom(s): 3 , Sleeps: 6
This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything! This rental is a monthly rental.
From $5,900 /Month
Buccaneer Boathouse - Florida Keys Monthly Rental
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 2 , Sleeps: 4
Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys! Monthly rental.
From $3,300 /Month
5 Pirates Hideaway Canal Front Home wPrivate Pool and Seawall for your boat
Florida Keys > Lower Keys Area > Little Torch Key
House , Bedroom(s): 3 , Sleeps: 8
House 3 Bed/3 bath (Sleeps 6 adults) This is a 28 day minimum rental
From $200 /Night
Barbados Landing- Florida Keys Waterfront Monthly Rental
Florida Keys > Lower Keys Area > Ramrod Key
House , Bedroom(s): 2 , Sleeps: 4
Come stay at this charming tropical style House. This rental is a monthly rental only! Snowbirds Welcome!
From $3,400 /Month
Sunkissed - Florida Keys Monthly Rental
Florida Keys > Lower Keys Area > Ramrod Key
House , Bedroom(s): 2 , Sleeps: 4
Sun Kissed you will be during your stay at this wonderful home on Ramrod Key! Monthly rental only!
From $3,300 /Month
St. Croix - Florida Keys Monthly Vacation Rental with Dock
Florida Keys > Lower Keys Area > Ramrod Key
House , Bedroom(s): 2 , Sleeps: 4
This Ramrod Key rental is a great spot for your next Florida Keys vacation!This vacation rental is a monthly rental and must be rented for 28 days or greater.
From $2,800 /Month
Coral House - Florida Keys Monthly Rental with Pool and Dock
Florida Keys > Lower Keys Area > Ramrod Key
House , Bedroom(s): 3 , Sleeps: 6
NEW swimming pool!This rental is a monthly rental only and must be rented for 28 days or greater.
From $4,900 /Month
Sunset Paradise
Florida Keys > Lower Keys Area > Summerland Key
House , Bedroom(s): 3 , Sleeps: 8
Billion dollar view, 3 bed 3 bath and deep water dock
From $364 /Night
Hawkins Heaven - Florida Keys Waterfront Monthly Rental with Dock
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 2 , Sleeps: 4
Come stay at this heavenly oasis!This rental is a monthly rental only
From $4,200 /Month
Key Largo Ocean Front Villa with Dock and Incredible views
Florida Keys > Key Largo Area > Key Largo
Villa , Bedroom(s): 2 , Sleeps: 6
2 bedroom Ocean Front Villa in Key Largo
From $400 /Night
Aloe House - Affordable Cudjoe Key Monthly Rental with Dock
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 3 , Sleeps: 6
You're only a short distance from fabulous Looe Key, one of the best diving and snorkeling sites in the Lower Florida Keys! Monthly rental
From $5,000 /Month
Blue Palms Retreat Vacation Rental
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 3 , Sleeps: 9
3 bed/2 bath Ocean Front Home with Heated Pool
From $457 /Night
Family Retreat Florida Keys - Perfect for Large Groups - Private Beach and Pool!
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 6 , Sleeps: 14
House, 6 Bedrooms + Sunroom, 4 Baths, (Sleeps 12-16)
Fandango - 5 Bedroom Florida Keys Beach House Rental
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 5 , Sleeps: 12
House, 5 Bedrooms, 3 Baths, (Sleeps 10+)
From $572 /Night
Tropical Paradise - Cudjoe Key Rental
Florida Keys > Lower Keys Area > Cudjoe Key
House , Bedroom(s): 2 , Sleeps: 6
House, 2 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 8)
From $500 /Night

Florida Keys Vacation Rentals Guide  

Located some 120 miles from the southernmost tip off the mainland Florida, the Florida Keys form a coral archipelago between the Gulf of Mexico and the Atlantic Ocean. There are over 1700 islands in the Keys that entice visitors from across the world to explore these tropical islands on land or under water. 

The Florida Keys provide the perfect destination for a tropical getaway, offering no shortage of adventures on land or sea. These islands cater to a wide variety of interests, whether you are looking for a night on the town or fun family activities. For land-lovers, the Keys offer quality-dining, artisanal and mainstream shopping, wildlife tours, music events, and even walking routes to get to know the island's history. Those looking for an oceanside experience can find many beautiful beaches for snorkelling, diving, jet skiing, boating, surfing, and more! 

Each island offers a unique experience for any type of getaway, for all ages to create special memories to bring home with them. The Florida Keys have an abundance of beautiful vacation rentals to choose from that dot the island and its waterfront. These owners take pride in their homes and provide a comfortable and affordable experience for those looking to enjoy the best of what the Florida Keys have to offer. 

The Florida Keys 

The Islands of the Florida Keys 

Most of the Keys' islands are largely uncharted and only more than thirty are inhabited. They are divided into the Upper Keys, Middle Keys, Lower Keys, and outlying islands.This archipelago extends as a 125 mile-long chain of islands and the Overseas Highway connects the mainland to Key West through a series of 42 bridges. Each island caters to different interests making the planning process of your trip a breeze, whether it be a romantic getaway or family vacay. The following are just a few of the many unique islands in the Keys where you can find fun activities to do on land or sea:

Key West 

America's most southern point, Key West is a charming and tropical island with a rich history and culture. Even the great Ernest Hemingway and Tennessee Williams wrote some of their best works while on the island. You can visit Hemingway's home or visit the Mel Fisher Maritime Museum, which boasts an extensive collection of 17th century shipwreck artifacts. Mallory Square is a must-visit spot in Key West for local shops, tasty Floridian food, and various events year-round. Grab a cold drink at the Sunset Pier to see the popular Sunset Celebration while live music plays. Key West has many options for water activities, such as Danger Charters excursions that tour the lush mangroves in kayaks.


Known as the world's hub for sport-fishing, Islamorada is about a 90-minute drive south from Miami. For a shoreline getaway, Islamorada is perfect for its wide variety of water-sports and activities. Islamorada's islands have beautiful beaches to relax on the powdery sand or take a dive in the crystal waters. Anne's Beach, one of Islamorada's popular beaches, is a touristic spot perfect for those looking to sunbathe, picnic by the sea, swim, or even do some catamaran sailing. If you're looking to get away from the crowd, Islamorada Library Beach and Park is a tourist-free spot great for its seclusion and caters to families with its playground. 

Key Largo 

Key Largo is worth exploring on land, but its true wonders are under the ocean's surface. This island calls itself the 'diving capital of the world' and with reason! Covering 70 nautical square miles, explore the marine-life in the John Pennekamp Coral Reef State Park from a glass-bottom boat, or by scuba-diving and snorkelling. For advanced divers, tour the 2002 USS Spiegel Grove shipwreck which lies in 130 feet of water. 

Highlights of the Florida Keys

  • Take a trip to Marathon's Turtle Hospital to learn about the rehabilitation process for injured sea turtles. The hospital provides an up-close experience during their educational tours, which last about 90 minutes. 
  • Accessible by boat or seaplane, Dry Tortuga's National Park is a stunning attraction that boasts Fort Jefferson, a mighty 19th century fortification. Snorkelers and divers can explore the shipwrecks, coral, and seagrass around Fort Jefferson's moat wall. 
  • The Butterfly and Nature Conservatory in Key West features 50-60 different butterfly species and more than 20 exotic bird species in a glass-enclosed conservatory. This immersive tour provides a tropical learning experience for everyone. 
  • Visit Key West's extravagant Fantasy Fest event, a 10-day long festival in October. Fantasy Fest is filled with costumed parties, marches, fairs, balls, and even a parade! 

Things to Do in the Florida Keys

The Florida Keys all have something special to offer for everyone's idea of a getaway. Here are some of our suggestions for fun activities to add to your vacation's itinerary: 

  • Visit the beautiful beaches: Harry Harris Park, Sombrero Beach, and Calusa Beach are highly recommended  
  • Visit the many aquariums and marine-life research centers, such as the Dolphin Research Center in Grassy Key.
  • Pub-crawl in Key West to see the best of island night life  
  • Biking around the island  
  • Take the kids to Truman Waterfront Park 
  • Fishing. There are many companies who offer fishing tours or you can venture out yourself!   
  • Boating. You can even book a tour in a glass-bottom ship! 
  • Go on a historic walking tour! There is a lot of rich culture to learn about on each island 
  • Parasailing 
  • Scuba diving 
  • Local boutique shopping 
  • Fine dining and casual restaurants 
  • Jet-skiing 
  • Kayaking


There are plenty of gorgeous vacation rentals to choose from in the Florida Keys through the Florida Rental By Owners website. We cater exclusively to travelers looking to communicate and book directly with the owner. There are no traveler fees for using Florida Rental By Owners website, and all owners are verified for ownership. All transactions occur directly between you and the owner. You can also read online reviews and guest experiences to ensure your vacation rental will meet (or exceed!) your travel goals.    

Do you have questions about the Florida Keys area? 

Join our  Local Facebook Travel   Group and ask one of the local experts.  

Statistics about the Florida Keys

There are currently 83 properties listed in the Florida Keys area. Of these, there are 14 budget-friendly properties available for rent on various islands in the Keys. 34 rental homes provide access to a pool, the perfect place to cool off after a day at the beach. For snowbirds looking for a long-term rental, we have 14 listings that are perfect, and some are even waterfront properties! If you would like a further breakdown of the statistics, use the search filters on Florida Rental By Owners website to look for accommodations meeting your criteria.

Vacation Rental Price Information pertaining to the Florida Keys

Prices for rentals per night range from $150 to $691. Per week, listing costs range from $800 to $4750. Finally, rental home prices vary from $2900 to $19,000 per month. You can expect to see these prices fluctuate depending on the season. Be sure to enter your dates in the filter bar for an accurate cost calculation. 

Accommodation Types in the Florida Keys

There is a wide variety of vacation rental home types that cater to all travellers: 

  • 68 rentals are listed as 'houses'.
  • rentals are listed as 'condos'. 
  • rental is listed as a 'bungalow'.
  • rental is listed as a 'house boat'. 

When to Visit the Florida Keys

Overall, the Keys' tropical atmosphere make it the perfect place for a getaway year-round. However, it is important to plan around the different seasons to curate your ideal trip. Peak season is from mid-December to April, due to holiday patterns and school breaks. Many tourists travel throughout these months, so expect some traffic. Off-season occurs from late April to early June and November to mid-December. These times offer the least expensive rental costs and the quietest times of the year on the islands. For those looking to relax on the beach, it would be best to book during the off-season months. Although this means fewer activities will be available, you'll still be able to enjoy hot weather with fewer tourists. If you need activities for kids, then you'll be more likely to find unique events during peak seasons, though events run throughout the year.    

Traveling to the Florida Keys

There are several modes of transportation to reach your destination in the Keys, including plane, ferry, bus, car, and even sea plane! Most of the airports listed below are international for those travelling from outside of the United States. The following list provides you with a few transportation options: 


The Key West International Airport has four major carriers, those being: American Airlines, Delta Air Lines, Silver Airways, and United Express. EYW flies non-stop to 14 destinations, mostly across the east of the United States. Travelers should note that the furthest west any plane flies from this airport is Dallas, Texas.  


KMTH currently does not service any passenger airline flights, instead it offers a charter service. A flight can be arranged on a request basis. 


The Miami Airport is about an hour drive to Key Largo, the gateway island to the Florida Keys. MIA is the third-busiest airport for international passengers in America. Miami Airport services ten carrier airlines, such as American Eagle, Delta Airlines, and United Airlines. 

Weather Statistics for the Florida Keys

Since the Florida Keys cover a large area, it's hard to pinpoint specific high and low temperatures for the seasons. But, the best months to visit are late April to early June, when the weather is nice and warm. If you prefer hotter temperatures, we suggest you visit during August. But it's important to know that peak hurricane season arrives in August. Another option is to visit during November to mid-December when the weather is cool, but you can beat the tourist traffic! 

Food and Drinks in the Florida Keys

Each island in the Florida Keys offers local restaurants that provide a unique take on delicious Floridian-fusion food to enjoy. Most popular amongst these restaurants is seafood and Caribbean-inspired dishes. But don't worry if these aren't to your liking, you can still eat like an islander with plenty more to choose from! The Keys has a great selection of restaurants that satisfy everyone's palates from local seafood to to fresh tacos and farm to table options. Some favourite restaurants include:

  • Key Largo's The Fish House is known for its inviting atmosphere where families and friends can enjoy a dish of Florida's best fresh and local seafood. 
  • Relax by Duck Key's waters in Angler and Ale's dockside restaurant and try Floridian style dishes. We recommend having one of their many cocktail and beer choices. They even have a 'hook and cook' option!  
  • Blue Heaven in Key West is just that... heavenly. The property is playfully decorated with bright colours and eclectic knick knacks. The restaurant attracts many for its delicious breakfast, lunch, and dinner options. 
  • Looking for something other than seafood? Islamorada's Ciao Hound offers yummy Italian eats to enjoy indoors or on their beautiful patio.  

Florida Keys FAQ's 

What types of property can I rent in the Florida Keys?

Florida Rental By Owners (FLARBO) is full of a wide variety of vacation rentals in Florida including condos, cottages, town-homes, duplexes, villas, holiday, and private homes. Our property selection features several homes and condos in the Florida Keys. We recommend selecting a property based on your needs such as proximity to beach areas, waterfront docks, parking, wheelchair accessibility, nearby attractions, and whether or not the property is pet-friendly or boat-friendly.

Should I rent a House in the Florida Keys? 

Absolutely! Florida Keys' accommodations include houses which often offer a larger space for family vacations, or larger groups looking to share a private property amongst themselves. 

Are the Florida Keys a good place for Snowbirds looking for monthly rentals? 

Yes, there are many homes and condos that rent on a monthly basis in the Florida Keys' islands that are perfect for long-term guests. Don't forget to adjust your search in FLARBO's filter bar when looking for a long-term rental.

Will I pay any fees to book a property on Florida Rental By Owners?

Never! We never charge any fees to book a property on Florida Rental By Owners. And we never take a commission from an owner. If you are looking for a VRBO or Airbnb type rental or lodging accommodation, why pay the extra fees? Use! We put you in direct contact with the owner or manager of the property rental on your chosen Florida Keys' island so you always get the best price.

I am a Vacation Rental Property Owner Can I List My Home for Rent on Florida Rental By Owners?

Yes! We have a multitude of subscription levels to advertise your vacation rental for any budget. Our Book Direct, No Commission Fee Subscription Model suits the majority of short term owners. You can view the details located on our List Your Property page here.

Click the photo below to search the Florida Keys area.

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