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Florida Keys Investment and Vacation Rental Properties
As a popular vacation destination, the Florida Keys offers a multitude of unique real estate investment opportunities, whether it is as a primary home, second home, a new business, or an income producing vacation rental home, with varying Returns on Investment.
There are many options for investment properties for sale in the Florida Keys, and buying a vacation rental or multi-family home that allows legal 7 day or less rentals, or even 28 day minimum rentals for snowbirds, provides a great chance to live in this beautiful tropical destination in the Florida Keys. Our rental season runs year round, so high occupancy rates are the norm. Single family homes, condos, townhomes, half duplexes, duplexes, triplexes, condotels, or multi family houses are some of the many alternatives that will also allow you to find a great deal.
The Florida Keys has it all, whether you prefer the nightlife and excitement of living and playing in Key West, having easy access to Miami and the mainland in Key Largo, or choosing an investment property in any of the beautiful waterfront communities in between. Some of the better known Islands being Islamorada, Marathon, and Big Pine Keys, just to name a few.
There are many types of properties available for you to see right now. Let us help you find the perfect property to suit your home or investment needs using our local knowledge and expertise. Be sure to call us for a quick and easy conversation to determine the specifics of what you are looking for, especially if you are an out of town buyer. We will be the eyes and ears for you, pre-screening the appropriate properties that suit your financial and other needs.
Contact us for a personalized and extensive list of investment properties in the Florida Keys. We will provide detailed information regarding vacation rental or investment opportunities in each of the Keys, create pro forma's for individual properties, and negotiate the best price
Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!
Considering selling or refinancing your home? Contact us today to find out how we can be of assistance to you! Or check out our Useful Information Page!
Properties For Sale Allowing Short Term Rentals
HANDYMAN SPECIAL - Priced to Sell! Opportunity knocks with this 2-bedroom, 1-bath RV park model featuring a permitted screened addition and a spacious outdoor entertainm...
- 2 Beds
- 1 Baths
- 621747 MLS
Amazing opportunity at an affordable price to own your first home in The Florida Keys with daily rentals to offset your cost. This property is one of the largest parcels...
- 2 Beds
- 1 Baths
- 621655 MLS
Remodeled Kawama townhome w/ 3 night rentals allowed. Gated community on the ocean side mile marker 99. The community offers full resort amenities such as a salt-water ...
- 2 Beds
- 3 Baths
- 621404 MLS
3 bedroom 2.5 bath 3 Story Townhome at Townhomes of Sister's Creek in Marathon.
- 3 Beds
- 3 Baths
- 621343 MLS
RARELY AVAILABLE AT FUTURA YACHT CLUB! This beautifully remodeled end-unit townhome offers an exceptional Florida Keys lifestyle, complete with two side-by-side deeded bo...
- 2 Beds
- 3 Baths
- 621264 MLS
Perfect Florida Keys townhouse with proven Rental Income! Located in resort style Mariners Club Key Largo - gated community, unit offers a unique opportunity to rent as a...
- 4 Beds
- 4 Baths
- 621241 MLS
Bonefish Yacht Club Townhomes, a Middle Keys premiere boating community cloistered around the 50 slip Bonefish Marina. Resort style living in this sought after oceanfront...
- 2 Beds
- 3 Baths
- 621219 MLS
THE LOWEST-PRICED UNIT CURRENTLY ON THE MARKET AT INDIGO REEF, OFFERED UNDER $1 MILLION! WOW! An incredible opportunity to own in one of Marathon's most sought-after Gulf...
- 3 Beds
- 3 Baths
- 621097 MLS
Experience waterfront living at its finest in this beautifully remodeled 2-bedroom, 2.5-bath condominium in the highly sought-after Gulfpointe I Condominiums. One of the ...
- 2 Beds
- 3 Baths
- 620886 MLS
DUCK KEY - Experience the ultimate Florida Keys lifestyle in this stunning 3-bedroom, 3-bath Villa located in the world-renowned Hawks Cay Resort. Perfectly positioned to...
- 3 Beds
- 3 Baths
- 620817 MLS
Welcome to your Florida Keys retreat at the desirable Kawama Yacht Club in Key Largo! One of the few properties in Key Largo that allows nightly Rentals.This beautifully ...
- 2 Beds
- 3 Baths
- 620813 MLS
Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living spac...
- 1 Beds
- 1 Baths
- 620746 MLS
Exceptional investment opportunity in the exclusive Bonefish Yacht Club -- one of the few Florida Keys communities permitted for lucrative short-term 7-day vacation renta...
- 2 Beds
- 3 Baths
- 620715 MLS
Experience the best of the Florida Keys in this beautifully appointed 3-bedroom, 2.5-bath waterfront townhome in the desirable Bonefish Townhomes community. Offering pano...
- 3 Beds
- 3 Baths
- 620681 MLS
Rarely available end-unit townhome in the highly coveted, gated community of Indigo Reef! Because Unit 26 is a premium end-unit, it is bathed in abundant natural light...
- 3 Beds
- 3 Baths
- 620657 MLS
Charming two-story townhome with cheerful tropical touches that brighten every stay in the Florida Keys. The home features a open-concept first floor plan which includes ...
- 2 Beds
- 3 Baths
- 620630 MLS
KAWAMA YACHT CLUB BEAUTIFULLY RENOVATED 2 Bedrooms - 2 Full Bathrooms Unit E5, CBS Block Townhome located on a beautiful Saltwater Lagoon in an Oceanfront Manned Gated Co...
- 2 Beds
- 3 Baths
- 620527 MLS
Introducing an exquisite POOLSIDE retreat at Tranquility Bay Beachfront Resort in the heart of the Florida Keys--a pinnacle of refined island sophistication and world-cla...
- 3 Beds
- 2 Baths
- 620221 MLS
Fabulous opportunity to live in the heart of the Keys in Marathon, Florida. This 3-bedroom, 2.5-bath townhome is located in the desirable gated community of Sisters Creek...
- 3 Beds
- 3 Baths
- 620207 MLS
Classic Keys Beach House Vibe with Proven Rental Income! Discover the ultimate Florida Keys getaway and investment opportunity with this 2-bedroom, 2.5-bathroom beachf...
- 2 Beds
- 3 Baths
- 620168 MLS
🌴💦 BIG NEWS FOR THE FLORIDA KEYS! 💦🌴 The largest waterpark in the Florida Keys is coming to Hawks Cay Resort in 2026! 🎉 Now is t...
- 2 Beds
- 2 Baths
- 620093 MLS
Oceanfront Paradise Awaits at The Cay! 50K Price Reduction - Priced to Sell! Experience the ultimate Keys lifestyle in this pristine, never-before-rented 2-bedroom,...
- 2 Beds
- 3 Baths
- 620070 MLS
This Beautiful Half duplex has a New Addition added to a well-maintained townhouse-style half duplex. In addition to the 3 bedrooms, there is a family room/ den upstairs...
- 3 Beds
- 4 Baths
- 619746 MLS
**Stunning Marathon Florida Waterfront Home Allowing Weekly Rentals With IMMEDIATE Income ** Welcome to your dream coastal escape! This exceptional 3-bedroom, 3-bath, FUR...
- 3 Beds
- 3 Baths
- 618887 MLS
Great opportunity at this little house, seems larger than it looks. Screen porch can be used for a second bedroom. Full size kitchen with a beautiful gas stove and full-s...
- 1 Beds
- 1 Baths
- 618791 MLS
Reduced Quarterly Dues! Own a piece of paradise perfectly situated at the southern point in Key Colony Beach. This turnkey property not only offers comfort with tropical ...
- 3 Beds
- 3 Baths
- 613852 MLS
Live the Florida Keys Lifestyle in Sunset Village! This unique 2-bedroom, 2.5-bath townhouse offers something you don't see often, ocean views from both the front and the...
- 2 Beds
- 2 Baths
- 617967 MLS
Imagine arriving in the Keys, dropping your bags and heading straight out on the boat. That's the beauty of life at Coral Lagoon, where the NEW DOCKS ARE COMPLETE and you...
- 3 Beds
- 3 Baths
- 614760 MLS
Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal ...
- 2 Beds
- 1 Baths
- 618228 MLS
Recently updated throughout, featuring a completely renovated spa/jacuzzi installation, brand new tile flooring throughout the entire unit, and freshly painted interior a...
- 2 Beds
- 3 Baths
- 618452 MLS
World-class resort living meets effortless, low-maintenance ownership in this beautifully refined CANAL-FRONT TOWNHOME in the Florida Keys. Designed for those who value b...
- 2 Beds
- 2 Baths
- 618643 MLS
35ft Slip #106 few steps away included in Sale* An exceptional opportunity to own a two-bedroom Conch-style villa in the desirable Lake Lucille area of Hawks Cay Resort. ...
- 2 Beds
- 2 Baths
- 617869 MLS
43' DOCK! FRESHLY UPDATED INTERIOR! This tastefully furnished half duplex townhome features 4 generous bedrooms, 3 full bathrooms, a laundry room and a dream kitchen! ...
- 4 Beds
- 3 Baths
- 613547 MLS
An exceptional opportunity to own a two-bedroom, one full bath and one half bath villa in a prime location along Sunset Village Drive, just steps from the Sunset Pool. Ha...
- 2 Beds
- 2 Baths
- 617875 MLS
This elegant villa is perfectly situated just steps from the Sunset Pool, offering breathtaking water views. As an end unit, it enjoys an abundance of natural light, brig...
- 2 Beds
- 2 Baths
- 611959 MLS
LUXURIOUS townhome in desirable INDIGO REEF located in Marathon! One of the most beautiful units in this upper end development with immaculate interior finishes and spect...
- 3 Beds
- 3 Baths
- 610221 MLS
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