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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

property image
11710 5th Avenue Ocean, Marathon $695,000

Cute conch cottage completely updated and redone! No detail spared! All impact windows, stainless steel Kitchen-Aide appliances, corner lot, garage, off-street parking sp...

  • 2 Beds
  • 2 Baths
  • 594324 MLS
1140 E 92nd Street, Marathon image
1140 E 92nd Street, Marathon $1,300,000

Wake with the Dolphins! New Construction with two stories, 3 porch/decks, pool and dock. This home has open water views with two decks on front, and a few hundred feet to...

  • 3 Beds
  • 4 Baths
  • 594323 MLS
5105 Sunset Village Drive, Duck image
5105 Sunset Village Drive, Duck $439,000

A stunning villa located in a very desirable ocean side location at Hawks Cay Resort, just steps from a private sandy beach. This villa has a remodeled kitchen, new furni...

  • 2 Beds
  • 2 Baths
  • 594325 MLS
340 5th St, Key Colony image
340 5th St, Key Colony $1,300,000

~~~ Attention Buyers ~~~ ''New Construction'' Single family home on 5th Street Key Colony Beach. Eastern exposure 3 bedroom, 2 bathroom pool home with 60 feet of seawal...

  • 3 Beds
  • 2 Baths
  • 594321 MLS
335 Sombrero Beach Road, Marathon image
335 Sombrero Beach Road, Marathon $624,900

2/2 stilted canal front home with approximately 45 feet of wood dockage and attached garage leaving plenty of room for storage. Home has a spacious deck and both open/cov...

  • 2 Beds
  • 2 Baths
  • 594320 MLS
717 White Street, Key West image
717 White Street, Key West $875,000

Surrounded by lush trees sits this beautifully updated Meadows property. Landscaped with three outdoor seating areas this home is indoor outdoor living at its best. This ...

  • 3 Beds
  • 2 Baths
  • 594318 MLS
311 Calzada De Bougainville, Marathon image
311 Calzada De Bougainville, Marathon $1,197,000

Beautiful Home just a 5 minute walk from Sombrero Beach. Strong vacation rental history! All one floor living and an open floor plan. There are two master bedroom suites,...

  • 3 Beds
  • 3 Baths
  • 594310 MLS
701 Spanish Main Drive Unit #614, Cudjoe image
701 Spanish Main Drive Unit #614, Cudjoe $299,000

Pride of ownership with this adorable 2 bedroom 2 bathroom home with open concept living! Dedicated dining room, large family room and roomy kitchen with plenty of stora...

  • 2 Beds
  • 2 Baths
  • 594308 MLS
1500 Ocean Bay Drive Unit #D2, Key Largo image
1500 Ocean Bay Drive Unit #D2, Key Largo $429,900

Kawama townhouse cute bungalow style. Great location with a private walkway to unit and lagoon. Full bath downstairs. 2 bedrooms with private patios and a full bath upsta...

  • 2 Beds
  • 2 Baths
  • 594301 MLS
201 7th Street Unit #9, Key Colony image
201 7th Street Unit #9, Key Colony $210,000

Truly Unique Refurbished Condo in the center of Key Colony Beach. High ceilings, nicely decorated, renovated kitchen, spacious bedroom, surrounded by parks, golf course, ...

  • 1 Beds
  • 1 Baths
  • 594300 MLS
88747 Old Hwy Highway, Islamorada image
88747 Old Hwy Highway, Islamorada $2,999,000

Exceptional Property On Millionaires Row! The home is located on 1.47 acres offering 3 bedrooms & 2.1 bathrooms, screened porch, dockage with a boat lift, roof top deck,...

  • 3 Beds
  • 3 Baths
  • 594295 MLS
716 26th Street Ocean, Marathon image
716 26th Street Ocean, Marathon $574,300

This adorable canal front home has been completely updated and meticulously maintained and is waiting for you to make it your private escape to the Keys. Enjoy all the c...

  • 3 Beds
  • 3 Baths
  • 594293 MLS
701 Spanish Main Drive Unit #26, Cudjoe image
701 Spanish Main Drive Unit #26, Cudjoe $299,000

This custom home shows beautifully and was designed for entertaining family and friends with a large kitchen that opens to the living and dining room. The guest bedroom...

  • 2 Beds
  • 1 Baths
  • 594287 MLS
1500 Ocean Bay Drive Unit #B8, Key Largo image
1500 Ocean Bay Drive Unit #B8, Key Largo $435,000

Turn key 2/2 corner townhouse in one of the best locations in Kawama, just steps to salt water lagoon, pool and chickee hut. 2/1 up and a full bathroom on first floor, b...

  • 2 Beds
  • 2 Baths
  • 594286 MLS
329 63rd Court Gulf, Marathon image
329 63rd Court Gulf, Marathon $425,000

Up and down duplex convenient to everything. Large lot on a dead end street. 1st floor unit has covered parking. 2nd floor unit has a large open porch.

  • 2 Beds
  • 2 Baths
  • 594271 MLS
11267 5th Avenue Gulf, Marathon image
11267 5th Avenue Gulf, Marathon $1,260,000

This perfect Keys home is solid CBS construction and stilted with 3 bedrooms and 2 baths upstairs and a legal downstairs guest suite/office with full bath downstairs. The...

  • 4 Beds
  • 3 Baths
  • 594270 MLS
701 Spanish Main Drive Unit #253, Cudjoe image
701 Spanish Main Drive Unit #253, Cudjoe $399,900

Open Water Views 35' DockageSparkling Clean 2Bd/2Ba Vacation Home!THIS IS ONE OF THE NICEST UNITS IN ALL OF VENTURE OUT!!! THE HOME HAS BEEN COMPLETELY RENOVATED TOP TO B...

  • 2 Beds
  • 1 Baths
  • 594263 MLS
261 11th Street, Key Colony image
261 11th Street, Key Colony $1,250,000

Attention buyers! You've been looking for that home that's totally renovated and move-in ready? You found it with this 4 bedroom, 3 bath waterfront home in desirable Key ...

  • 4 Beds
  • 3 Baths
  • 594249 MLS
389 N Anglers Drive Unit #202, Marathon image
389 N Anglers Drive Unit #202, Marathon $315,000

Sombrero Beach condo at Coral Club. Two bedroom, two bath second floor unit with great views of the canal. Large master bedroom closet and vanity area. Windows on the ...

  • 2 Beds
  • 2 Baths
  • 594246 MLS
2000 Coco Plum Drive Unit #1102, Marathon image
2000 Coco Plum Drive Unit #1102, Marathon $369,000

Units on this floor rarely make it to open market. Most are sold before they get to MLS. Main Balcony faces East for shaded evenings and the most beautiful Sunrises. We h...

  • 1 Beds
  • 2 Baths
  • 594234 MLS
58078 Morton Street, Marathon image
58078 Morton Street, Marathon $450,000

Located on two 75 X 120 lots. Cedar siding, cathedral ceilings. Free standing fireplace.Home needs TLC in and out.

  • 2 Beds
  • 3 Baths
  • 594229 MLS
2600 Overseas Highway Unit #26, Marathon image
2600 Overseas Highway Unit #26, Marathon $382,000

Looking for an income property that you can enjoy from time to time as well? I guarantee you won't find a better producing property at this price point than Tranquility B...

  • 2 Beds
  • 3 Baths
  • 594226 MLS
315 E Ocean Drive, Key Colony image
315 E Ocean Drive, Key Colony $697,000

Move in Ready! Waterfront Beautifully Renovated Half Duplex with a view of the ocean. Across the Street from the Glunz Resort a block walking distance to The Cabana Club....

  • 3 Beds
  • 3 Baths
  • 594223 MLS
95 Coco Plum Drive Unit #5C, Marathon image
95 Coco Plum Drive Unit #5C, Marathon $575,000

Bonefish Yacht Club Townhomes. A wonderful location and a wonderful community. This three bedroom and three bathroom townhome has views of Bonefish Marina, Key Colony Cha...

  • 3 Beds
  • 3 Baths
  • 594220 MLS
101 Gulfview Drive Unit #202, Islamorada image
101 Gulfview Drive Unit #202, Islamorada $765,000

Nice two bedroom, two and one half-bathroom Bay Harbour unit with 30' deeded boat slip closer towards the inside of the lagoon. Light rental history, excellent location! ...

  • 2 Beds
  • 2 Baths
  • 594216 MLS
312 Calzada De Bougainville, Marathon image
312 Calzada De Bougainville, Marathon $585,000

Single Family 3 bedroom 2 bath stilted modular home built in 2014 located in the desirable Sombrero area neighborhood and within minutes of walking distance to the beach!...

  • 3 Beds
  • 2 Baths
  • 594215 MLS
189 Carroll Street, Islamorada image
189 Carroll Street, Islamorada $829,900

Featuring tile and bamboo flooring throughout, with partial ocean views from the upstairs patio. The spacious master bedroom offers a large walk-in closet. Other features...

  • 3 Beds
  • 3 Baths
  • 594201 MLS
191 Carroll Street, Islamorada image
191 Carroll Street, Islamorada $849,990

Featuring tile flooring throughout, with partial ocean views from the upstairs patio. The spacious master bedroom offers a large walk-in closet. Other features include cu...

  • 3 Beds
  • 2 Baths
  • 594200 MLS
1500 Ocean Bay Drive Unit #R4, Key Largo image
1500 Ocean Bay Drive Unit #R4, Key Largo $499,000

Fully furnished 3 bedroom, 3 bathroom townhome in Kawama just steps away from the pool. Just bring your toothbrush and enjoy or carry on with the 80%+ rental occupancy. ...

  • 3 Beds
  • 3 Baths
  • 594199 MLS
1220 Newton Street Unit #1, Key West image
1220 Newton Street Unit #1, Key West $232,800

Quaint studio condo with loft in the heart of The Meadows. This condo is located in a building among only four other units. Unit #1 in on the main level and has high ceil...

  • 1 Baths
  • 594191 MLS
101 E Ocean Seapointe Condo Drive Unit #303, Key Colony image
101 E Ocean Seapointe Condo Drive Unit #303, Key Colony $1,695,000

Luxury awaits in this direct oceanfront condo, heated swimming pool and hot tub, boat slip with 16,000 lb boat lift, fishing pier, Electronic Blinds in the living room an...

  • 4 Beds
  • 3 Baths
  • 594189 MLS
1309 Albury Street, Key West image
1309 Albury Street, Key West $1,175,000

This Conch House has it all! 2 bedrooms, 2 1/2 baths, large open floor plan featuring vaulted ceilings with beautiful wooden beams and disappearing doors to a relaxing po...

  • 2 Beds
  • 3 Baths
  • 594187 MLS
630 107th St Ocean, Marathon image
630 107th St Ocean, Marathon $199,000

AS IS duplex building shell with a building right - two bedroom one bathroom and one bedroom one bathroom. Structure is hurricane damaged. Price reflects the current cond...

  • 3 Beds
  • 2 Baths
  • 594179 MLS
630 107th St Ocean, Marathon image
630 107th St Ocean, Marathon $129,000

Existing Structure is hurricane damaged. Price reflects the current condition of the building. This property is located within the only designated Economic Opportunity Z...

  • 3 Beds
  • 2 Baths
  • 594178 MLS
770 107th Street Ocean, Marathon image
770 107th Street Ocean, Marathon $1,595,000

Oceanfront property with 1 building right! Currently there is a hurricane damaged oceanfront single family residence with four bedrooms plus a guest house with 1 bedroom....

  • 4 Beds
  • 3 Baths
  • 594175 MLS
701 Spanish Main Drive Unit #659, Cudjoe image
701 Spanish Main Drive Unit #659, Cudjoe $345,000

Best Priced full stilt property in Venture Out! Unit 659 is a Premier location, close to the gate & close to the pool, store, sports courts, mail room and community cent...

  • 2 Beds
  • 2 Baths
  • 594174 MLS
701 Spanish Main Drive Unit #417, Cudjoe image
701 Spanish Main Drive Unit #417, Cudjoe $379,000

Perfect Keys Getaway - bring the boat, & bait & start enjoy life on the water in the Fabulous Florida Keys. This spot has it all starting w/a 35' concrete dock, large doc...

  • 2 Beds
  • 2 Baths
  • 594146 MLS
270 11th Street, Key Colony image
270 11th Street, Key Colony $749,000

Hurry while it lasts! Gorgeous 3 bedroom, 3 bath home that is updated and ready to move in. The exterior has a beautifully landscaped and fenced in yard, plenty of stor...

  • 3 Beds
  • 3 Baths
  • 594139 MLS
701 Spanish Main Drive Unit #249, Cudjoe image
701 Spanish Main Drive Unit #249, Cudjoe $348,000

Amazing waterfront property! Open Water views looking down a 60' wide canal to endless open water from this furnished 2Bd/1Ba vacation rental property. Features 17' doc...

  • 2 Beds
  • 1 Baths
  • 594135 MLS
172 Columbus Drive, Islamorada image
172 Columbus Drive, Islamorada $925,000

Fantastic location in Islamorada on Lower Matecumbe Key with exceptional boating access to both the Atlantic Ocean & Florida Bay. Enjoy partial ocean views from this sol...

  • 3 Beds
  • 3 Baths
  • 594132 MLS
1133 W Ocean Drive Unit #8, Key Colony image
1133 W Ocean Drive Unit #8, Key Colony $769,000

Luxurious Oceanfront Tri-Level Townhouse with SPECTAULAR Views. 3 Bedroom 3 Baths with 2,176 sq. ft. Open floor plan featuring travertine marble, stainless steel applianc...

  • 3 Beds
  • 3 Baths
  • 594114 MLS
1010 95th Street, Marathon image
1010 95th Street, Marathon $1,300,000

Panoramic Ocean Views from this Fabulous Water Front Stilted Home! Just Remodeled from Top to Bottom by Design Center. Home Features 3 bedrooms and 2.5 bathrooms. Top Flo...

  • 3 Beds
  • 3 Baths
  • 594107 MLS
500 Burton Drive Unit #2313, Tavernier image
500 Burton Drive Unit #2313, Tavernier $329,000

Well kept 1/1 with great Ocean views. This Condo grossed $53,756.99 in 2019. This Condo is being sold fully furnished, Impact sliders and front Door, Tankless hot water h...

  • 1 Beds
  • 1 Baths
  • 594095 MLS
651-655 49th Street Ocean Street, Marathon image
651-655 49th Street Ocean Street, Marathon $599,000

Cute ground level duplex, 2 bedroom, 1 bathroom on one side, and 1 bedroom 1 bathroom on the other side. Deep water dockage, beautiful outdoor space with Pergola, 2 sheds...

  • 3 Beds
  • 2 Baths
  • 594092 MLS
977 W 79th Street Ocean Street, Marathon image
977 W 79th Street Ocean Street, Marathon $548,000

Spacious 3 bedroom 2 bath single family home with room for a pool, RV, boats, wave runners, and much much more. The home has marble flooring in the main living area with ...

  • 3 Beds
  • 2 Baths
  • 594076 MLS
265 15th Circle, Key Colony image
265 15th Circle, Key Colony $2,990,000 ▼

Beautiful wide Open Ocean views in the day, beautiful sunsets, and twinkling lights in the evening. This is one of the selected Oceanfront single family properties in Ke...

  • 5 Beds
  • 3 Baths
  • 594056 MLS
325 Calusa Street Unit #497, Key Largo image
325 Calusa Street Unit #497, Key Largo $199,999

This lot is on the high side of the community backing to the boat storage. Sellers are very motivated. Great family oriented community, great for family with kids. Lots o...

  • 2 Beds
  • 1 Baths
  • 594063 MLS
115 Front Street Unit #103, Key West image
115 Front Street Unit #103, Key West $2,630,000

Wonderful waterfront condo in the Truman Annex! Enjoy spectacular sunsets from this 1st floor floor unit with 2 BD/ 2 BA and over 2,000 sq. ft. of living space. With an o...

  • 2 Beds
  • 2 Baths
  • 594058 MLS
151 Ave G, Marathon image
151 Ave G, Marathon $1,749,000

East facing 3 bedrooms 3 baths plus legally permitted room with a full bath downstairs, travertine marble floors, High ceilings 9.5 to 11' thru-out. Chef' kitchen high e...

  • 3 Beds
  • 3 Baths
  • 594055 MLS
5106 Sunset Village Drive, Duck image
5106 Sunset Village Drive, Duck $499,000

Outstanding Conch Villa offering 2 bedrooms and 2.5 baths on a very unique section of Sunset Village that offers breathtaking open water views, and a private sandy beach ...

  • 2 Beds
  • 3 Baths
  • 594044 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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