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Inspired Real Estate in America's Tropical Paradise

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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, 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 consultation 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 formas 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!

Properties For Sale Allowing Short Term Rentals

1 Clara Boulevard, Key Colony image
1 Clara Boulevard, Key Colony $1,500,000

Home is on Lot 9, lot 10 is a vacant buildable lotmust be sold together as package, owner will not separate. Home has been refreshed with interior painting & new carpetin...

  • 2 Beds
  • 2 Baths
  • 601625 MLS
321 9th Street, Key Colony image
321 9th Street, Key Colony $1,279,000

Beautiful gem in the highly sought after Key Colony Beach! This rare large half duplex is ready to be a vacation rental or permanent residence for new buyers! This proper...

  • 2 Beds
  • 3 Baths
  • 601627 MLS
171 3rd Street, Key Colony image
171 3rd Street, Key Colony $1,299,000

Light and airy coastal chic half-duplex just waiting for you to start living the Keys Life. Nothing to be done here, everything has been updated! Two Bedroom/Two Bath in ...

  • 2 Beds
  • 2 Baths
  • 601592 MLS
59 W Kyle Way, Marathon image
59 W Kyle Way, Marathon $3,995,000

Located at the southern end of Marathon near the base of the world-famous Historic 7 Mile Bridge is this beautiful vacation home. From the moment you arrive at the grand ...

  • 4 Beds
  • 2 Baths
  • 601588 MLS
701 Spanish Main Drive Unit #649, Cudjoe image
701 Spanish Main Drive Unit #649, Cudjoe $298,000

A Golden opportunity that's priced to sell to a buyer looking for a great investment or a permanent resident that wants to enjoy the great amenities that Venture Out offe...

  • 1 Beds
  • 1 Baths
  • 601582 MLS
58704 Overseas Highway, Marathon image
58704 Overseas Highway, Marathon $950,000

Peace, serenity, and a little bit of Florida Keys history found in Paradise! Nestled on a half an acre of artistically cleared land in Grassy Key, this cozy 1948 built F...

  • 2 Beds
  • 1 Baths
  • 601578 MLS
601 W Ocean Unit #208C, Key Colony image
601 W Ocean Unit #208C, Key Colony $675,000

Come be a part of the Cay Condo community beloved for its beautiful oceanfront setting with private white sand beach, immaculately maintained tropical grounds, heated poo...

  • 2 Beds
  • 3 Baths
  • 601571 MLS
202 Southard Street Unit #4, Key West image
202 Southard Street Unit #4, Key West $932,000

This ground floor, two- bedroom, one bath condo features tile floors, granite kitchen counter tops and updated bath with shower. French doors open to the large rear deck ...

  • 2 Beds
  • 1 Baths
  • 601570 MLS
7004 Harbor Village Drive, Duck image
7004 Harbor Village Drive, Duck $715,000

This Immaculate updated 2-bedroom, 2 bath Villa overlooks the crystal blue canal waters of Duck Key. Enjoy the serenity offered by your private patio with your own spa po...

  • 2 Beds
  • 2 Baths
  • 601565 MLS
480 Margate Drive, Marathon image
480 Margate Drive, Marathon $799,000

This charming 2 bedroom 2 bath home is located in one of Marathon's most sought after neighborhoods. Built in 2019, this home is equipped with an all home 22KW generator...

  • 2 Beds
  • 2 Baths
  • 601563 MLS
7003 Harbor Village Drive, Duck image
7003 Harbor Village Drive, Duck $715,000

This Updated Spa Villa is located steps away from the fishing dock in the heart of Harbor Village. The unit features a remodeled kitchen, bathrooms, flooring on first lev...

  • 2 Beds
  • 2 Baths
  • 601557 MLS
11490 2nd Avenue Ocean, Marathon image
11490 2nd Avenue Ocean, Marathon $599,000

Contractor special, 60 ft dock, New Commercial grade aluminum roof, Impact windows, East facing for cool evening on the dock, weekly rentals allowed, and large 1435 sf fl...

  • 2 Beds
  • 2 Baths
  • 601556 MLS
11243 3rd Avenue Gulf, Marathon image
11243 3rd Avenue Gulf, Marathon $1,850,000

Your Next Vacation Airbnb/VRBO rental Property in the Florida Keys. Flood insurance is assumable $737 yearly, see all detailed information in the document section. The se...

  • 5 Beds
  • 4 Baths
  • 601546 MLS
570 Sombrero Beach Road, Marathon image
570 Sombrero Beach Road, Marathon $1,899,000

Beautiful 4/3 home on Sombrero Beach Road waiting for you! This home has 2 beds & 2 baths upstairs and 2 beds & 1 bath downstairs. The large backyard is perfect for a poo...

  • 4 Beds
  • 3 Baths
  • 601530 MLS
205 & 321 26th Street Ocean, Marathon image
205 & 321 26th Street Ocean, Marathon $849,000

For those with a vision - opportunities abound with this legal duplex situated on a deep water canal that leads to Boot Key Harbor, one of the premier sailing and boating...

  • 4 Beds
  • 2 Baths
  • 601525 MLS
2600 Overseas Highway Unit #70, Marathon image
2600 Overseas Highway Unit #70, Marathon $910,000

Excellent Rental Income Property that offers Gulf views from your 3 bedroom Beach house at Tranquility Bay Beach House Resort Resort. Enjoy the stunning tropical pools, p...

  • 3 Beds
  • 3 Baths
  • 601513 MLS
701 Spanish Main Drive Unit #481, Cudjoe image
701 Spanish Main Drive Unit #481, Cudjoe $799,000

Gorgeous open water home with 2 bedrooms and 2 bathrooms complete with a 35 foot seawall and stunning sunrise views! This beautifully appointed home comes furnished with ...

  • 2 Beds
  • 2 Baths
  • 601512 MLS
11600 1st Avenue Gulf Unit #15, Marathon image
11600 1st Avenue Gulf Unit #15, Marathon $1,295,000

Fully furnished 3-bedroom townhouse with great waterfront and sunset views. Private dock for up to 31' boat just steps from the back terrace. Weekly rentals allowed, whic...

  • 3 Beds
  • 3 Baths
  • 601506 MLS
546 Porter Lane, Key West image
546 Porter Lane, Key West $1,295,000

Truly charming townhome in the award winning Truman Annex located in the heart of Old Town. This lovely home features two bedrooms with ensuite bathrooms plus a powder ro...

  • 2 Beds
  • 3 Baths
  • 601505 MLS
180 8th Street, Key Colony image
180 8th Street, Key Colony $765,000

Concrete Home Built in 2002, Above flood, Flood policy in place for buyer to assume, East facing for cool evenings on your back porch with concrete pad and very private w...

  • 4 Beds
  • 2 Baths
  • 601504 MLS
2040 Dolphin Drive, Marathon image
2040 Dolphin Drive, Marathon $1,200,000

Lazy days beckon in a relaxing neighborhood close to all of Marathon's many conveniences and with quick access to Gulf and Atlantic waters. Outside you'll find a generous...

  • 3 Beds
  • 2 Baths
  • 601500 MLS
581 10th Street, Key Colony image
581 10th Street, Key Colony $3,150,000

Oasis in KCB, Legal Duplex, with 75 ft of concrete seawall, Gorgeous Aqua Blue pool with splash pad surrounded by beautiful Travertine pavers, 3beds and 2baths on each le...

  • 6 Beds
  • 4 Baths
  • 601492 MLS
7984 Tuna Drive, Marathon image
7984 Tuna Drive, Marathon $584,900

Amazing opportunity to live the Keys Life! 3 bedroom, 2 bathroom one story home on an oversized lot. Easy access to the community boat ramp right around the corner. Tiled...

  • 3 Beds
  • 2 Baths
  • 601489 MLS
2600 Overseas Highway Unit #66, Marathon image
2600 Overseas Highway Unit #66, Marathon $810,000

Buy your own beach house at this laid back beach resort in the Florida Keys! Perfect as an investment and vacation home, owners have up to 5 weeks use per year and proper...

  • 3 Beds
  • 4 Baths
  • 601486 MLS
22 7th Street, Key Colony image
22 7th Street, Key Colony $849,000

Key Colony Beach Causeway location with superior boat dockage, finger pier and direct access to both the ocean and bay. Beautifully updated and immaculate in condition. O...

  • 2 Beds
  • 2 Baths
  • 601482 MLS
125 Key Heights Drive, Islamorada image
125 Key Heights Drive, Islamorada $869,000

This is the perfect family Keys home in desirable Key Heights, Islamorada! This home has recently been renovated and also expanded its living space in 2020. The owners ...

  • 3 Beds
  • 3 Baths
  • 601471 MLS
241 9th Street, Key Colony image
241 9th Street, Key Colony $815,000

Renowned Key Colony Beach location, west facing canal front half duplex featuring two-bedrooms, two-bathrooms, ~1000 sqft. & 37.5 ft concrete seawall with step-down exten...

  • 2 Beds
  • 2 Baths
  • 601470 MLS
1250 27th Street, Marathon image
1250 27th Street, Marathon $850,000

Luxury is an experience, not a price point. For those looking for endless views, this property exudes that (and more) at a price point. Offering a lovely two bedroom, two...

  • 2 Beds
  • 2 Baths
  • 601468 MLS
109 Avenue D Avenue Unit #305, Marathon image
109 Avenue D Avenue Unit #305, Marathon $379,000

Great weekend get-a-way unit. Boat ramp pool, boat slip, tennis court, trailer parking area. I has a screened porch/ Linai with some water view. It is a short boat ride t...

  • 1 Beds
  • 2 Baths
  • 601469 MLS
2002 109th Street Gulf Street, Marathon image
2002 109th Street Gulf Street, Marathon $2,400,000

Home has been in the family since it was built in 1962. It has great bones and has a fantastic open water view with year round sunrises and beautiful back burn sunsets. T...

  • 3 Beds
  • 2 Baths
  • 601451 MLS
500 Burton Drive Unit #4208, Tavernier image
500 Burton Drive Unit #4208, Tavernier $699,500

D model with TWO oceanfront balconies comes with this updated 2/2 Oceanfront Condo. Being sold fully furnished with a housewares package too. Impact windows & doors. Huge...

  • 2 Beds
  • 2 Baths
  • 601446 MLS
620 Thomas Street Unit #186, Key West image
620 Thomas Street Unit #186, Key West $959,000

First floor Shipyard condominium features 2 bedrooms and 1 bath. Updated kitchen with stainless steel appliances, granite countertop, and updated bath with shower. Large ...

  • 2 Beds
  • 1 Baths
  • 601443 MLS
2600 Overseas Highway Unit #25, Marathon image
2600 Overseas Highway Unit #25, Marathon $825,000 ▼

Spacious, 3 bedroom, 3.5 bath, Tranquility Bay Resort Beach House. Turnkey, furnished in Coastal style, granite counter tops and stainless steel appliances. 2 balconies o...

  • 3 Beds
  • 4 Baths
  • 601442 MLS
311 25th Street, Marathon image
311 25th Street, Marathon $524,900

Newer Built Stilted Townhome with 3beds, 2.5baths, + extra den/dining room on main floor. Eat in kitchen, 2 balconies, Tile throughout except carpet on bedrooms and hallw...

  • 3 Beds
  • 3 Baths
  • 601425 MLS
500 Burton Drive Unit #4209, Tavernier image
500 Burton Drive Unit #4209, Tavernier $719,000

Ocean Pointe condo in desirable building IV with gorgeous views of the Atlantic Ocean from living area, kitchen and master bedroom! Offering a two bedroom, two bath condo...

  • 2 Beds
  • 2 Baths
  • 601417 MLS
233 Sombrero Beach Road, Marathon image
233 Sombrero Beach Road, Marathon $3,200,000

NEW CONSTRUCTION-MARATHON- CANAL FRONT home with modern design and an open floor plan. No association fees and weekly rentals make this home a gem. Walk or bike to famo...

  • 3 Beds
  • 3 Baths
  • 601405 MLS
240 10th Street, Key Colony image
240 10th Street, Key Colony $949,000

Distinctly coveted Key Colony Beach location, East facing stilted waterfront half duplex featuring two-bedrooms, two-bathrooms, nearly 1,300 square feet inside, and 37.5 ...

  • 2 Beds
  • 2 Baths
  • 601402 MLS
201 E Ocean Drive Unit #1-210, Key Colony image
201 E Ocean Drive Unit #1-210, Key Colony $525,000

BEACH FRONT CONDO LIVING IN KEY COLONY ..LOCATED IN THE GEM OF THE KEYS! This 2 bedroom 2 bath condo has an open floor plan great for entertaining. Spacious kitchen with ...

  • 2 Beds
  • 2 Baths
  • 601400 MLS
1401 Simonton Street Unit #6, Key West image
1401 Simonton Street Unit #6, Key West $1,100,000

This is a rare opportunity to have your own transient licensed condo at the beautiful Santa Maria Suites resort in Old Town Key West! Revel in the tranquil setting of th...

  • 2 Beds
  • 2 Baths
  • 601394 MLS
1361 Overseas Highway Unit ##G-11, Marathon image
1361 Overseas Highway Unit ##G-11, Marathon $210,000

Galway Bay is a 55+ LAND LEASE community. This nicely maintained, 3/2 home is cozy, inviting and warm, offers a spacious floor plan, full kitchen ready for your cooking....

  • 3 Beds
  • 2 Baths
  • 601389 MLS
1300 W 75th Street, Marathon image
1300 W 75th Street, Marathon $2,699,000

Beautiful new construction in the Heart of Marathon! Wake up to delightful ocean views and end the day with gorgeous sunsets. This stunning property has lush landscaping ...

  • 4 Beds
  • 3 Baths
  • 601387 MLS
133 Key Heights Drive, Tavernier image
133 Key Heights Drive, Tavernier $1,075,000

Private location on double lot with mature landscaping providing a tropical oasis. 2 Bedroom/ 2 bath upstairs with a 1 bedroom/1 Bath apartment downstairs. Large Tiki Hut...

  • 3 Beds
  • 3 Baths
  • 601379 MLS
1 Sadowski Cswy, Key Colony image
1 Sadowski Cswy, Key Colony $1,998,000 ▼

Absolutely Gorgeous 4 bedroom/2.5 bath single family home with open water views, TWO 30 foot boat slips, 20,000 lb. boat lift plus its just minutes from the ocean via the...

  • 4 Beds
  • 3 Baths
  • 601366 MLS
1800 Atlantic Boulevard Unit #C219, Key West image
1800 Atlantic Boulevard Unit #C219, Key West $1,357,000

Your search is over for the perfect home to enjoy beach front Key West Living. Just a short bicycle ride from Old town Key West. This corner floor plan condo is professio...

  • 2 Beds
  • 2 Baths
  • 601365 MLS
302A N Anglers Drive, Marathon image
302A N Anglers Drive, Marathon $999,750

This completely renovated canal front, stilted home has so much to offer: 50 feet of canal frontage, deep water dockage, and a private, full-size pool and heated spa - al...

  • 2 Beds
  • 2 Baths
  • 601360 MLS
581 E Ocean Drive Unit #14, Key Colony image
581 E Ocean Drive Unit #14, Key Colony $599,000

Florida Keys living at it's best! Well-appointed condo in Sunset Beach Community in prestigious Key Colony with pool and ocean views. Featuring a bright open 1,200 sq. f...

  • 2 Beds
  • 2 Baths
  • 601357 MLS
57681 Morton Street, Marathon image
57681 Morton Street, Marathon $5,995,000

Custom built, modern masterpiece with pool situated on over 3 private acres of tropical paradise with Open Water views. Over 4,600 sq. ft. of living space on two levels w...

  • 3 Beds
  • 4 Baths
  • 601344 MLS
235 Sombrero Beach Road Unit #2, Marathon image
235 Sombrero Beach Road Unit #2, Marathon $1,599,900

Sunny weather and sandy beaches await you in Marathon! This beautiful waterfront villa is located in the heart of Marathon and located just down the street from Sombrero...

  • 4 Beds
  • 3 Baths
  • 601308 MLS
500 Burton Drive Unit #1415, Tavernier image
500 Burton Drive Unit #1415, Tavernier $689,000

Fantastic updated TOP FLOOR condo with beautiful OCEAN VIEWS from your porch and living room! This unit offers two bedrooms and two baths and is being sold furnished. Imp...

  • 2 Beds
  • 2 Baths
  • 601318 MLS
390 9th Street, Key Colony image
390 9th Street, Key Colony $795,000

Spacious half duplex with 37.5 ft of dockage! Two bedroom/two bath with plenty of living space. Kitchen is open to the dining area. All with beautiful canal views through...

  • 2 Beds
  • 2 Baths
  • 601313 MLS
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Ewa and Peter Schwarz, Realtors® 
Proud Islamorada Residents
TheKeysLifestyle@gmail.com

305.781.5704  |  305.394.5171 
LoKation Real Estate, Pompano Beach, FL 
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