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Key Largo, Tavernier, Islamorada Properties Allowing Short Term Rentals
The Upper Keys have limited opportunities for properties that legally allow short term vacation rentals less than 28 days. This is an exclusive list of properties in Key Largo, Tavernier (Plantation Key), and Islamorada that allow rentals from 1, 3 7, or 14 days, maximizing the return on your investment.*
Some purchase these types of homes strictly for the ROI or as real estate investments. Most owners are either snowbirds, staying for a month or two or three in their own piece of paradise, or they may come in the glorious summer months to enjoy the spectacular water. Fishing, scuba diving, snorkeling, and boating are just a few ways that you can enjoy playing on the water. Or relax on a nearby beach, or at your pool, if that is your style!
Below you will find a list of homes currently for sale that allow short term rentals. Contact us to set up your own personalized search using our local knowledge to help you narrow down the perfect place for you to call home while having regular income as part of your investment. Get alerts for the instant a new property comes on the market, or choose daily, weekly or monthly alerts.
*Each property must be individually confirmed that they legally allow short term vacation rentals through Monroe County or the Village of Islamorada. Various by-laws apply that may impact the ability to apply for and receive a vacation rental license.
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Upper Keys Properties Allowing Short Term Rentals
UNIQUE! Completely remodeled with a reworked floorplan to optimize space & functionality, this townhome is the crown jewel of the building! Welcome to Holiday by the Sea ...
- 2 Beds
- 3 Baths
- 619255 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
ROGO EXEMPT LETTER IN HAND Completely renovated and rehabbed mobile home located on a prime high elevation and fenced lot. Plenty of parking for multiple vehicles and a...
- 2 Beds
- 2 Baths
- 620583 MLS
SELLER FINANCING AVAILABLE! Discover your perfect retreat in this charming and attractive mobile home, thoughtfully remodeled to offer a blend of comfort and style provid...
- 2 Beds
- 2 Baths
- 618047 MLS
BEAUTIFUL CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000! LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY IN THE HIGHLY DESIRABLE PLANTATION BY THE SEA ON THE OCE...
- 2 Beds
- 2 Baths
- 616280 MLS
WELCOME TO PARADISE BY THE SEA! THIS SPACIOUS CONDO LOCATED IN HIGHLY DESIRED PLANTATION KEY/SLAMORADA ON MILLIONAIRE'S ROW. THIS OCEANFRONT BUILDING OFFERS THE PERFECT B...
- 2 Beds
- 2 Baths
- 617381 MLS
Renovated Waterfront Home - Marina Resort Living! Motivated Seller! Own one of the largest lots in this exclusive 35-acre marina resort! Recently remodeled 2 bedroom 2 b...
- 2 Beds
- 2 Baths
- 616102 MLS
Price reduced and owner ready for an offer! Updated and charming mobile home located close to homeowners park in Key Largo. Being offered fully furnished, this wonderful...
- 2 Beds
- 2 Baths
- 619116 MLS
key Largo everything update in this beautiful Manufacture home 3/2 this home is located in key Largo MM101 in the bayside with two homeowners boat ramp, beach and pi...
- 3 Beds
- 2 Baths
- 620257 MLS
Experience the laid-back Florida Keys lifestyle in this beautifully maintained waterfront mobile home located at Mile Marker 103 bayside in one of Key Largo's most desira...
- 2 Beds
- 2 Baths
- 620571 MLS
Set in the very center of Islamorada's vibrant island community, this 2BD/2.5BA townhouse style condo in Sand Pebbles offers privacy, comfort, and convenience. The ground...
- 2 Beds
- 3 Baths
- 618784 MLS
Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. ...
- 2 Beds
- 2 Baths
- 620393 MLS
Beautiful updated Mobile Home Located In Key Largo with two private homeowners park with two boat ramp beach and picnic area 3 bedroom 2 bath walking closet beautif...
- 3 Beds
- 2 Baths
- 620087 MLS
Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft fo...
- 2 Beds
- 2 Baths
- 617971 MLS
Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setti...
- 3 Beds
- 3 Baths
- 619364 MLS
This island resort style unit offers stations for dockage up to 25-foot boats, trailer storage and boat ramp. There is a pool for the development, pickle ball and tenn...
- 2 Beds
- 2 Baths
- 619328 MLS
A versatile multi-unit opportunity in the heart of Tavernier. Offering three separate residences with a combined total of 5 bedrooms and 4 bathrooms, this property is wel...
- 5 Beds
- 4 Baths
- 619887 MLS
Welcome to your waterfront Keys escape in Key Largo! Nestled on a wide canal with no bridges to the bay, this boater-friendly property offers quick and easy access to ope...
- 3 Beds
- 2 Baths
- 619260 MLS
Fully furnished turn key townhome in Islamorada at Las Maravillas is available, one of only 10 private residences on the bayside on Lower Matecumbe in the Village. Docka...
- 2 Beds
- 2 Baths
- 619594 MLS
All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has...
- 3 Beds
- 2 Baths
- 613083 MLS
REDUCED !!!!! GREAT DEAL!!! Welcome to Unit H5 at Kawama Yacht Club -- a beautifully updated 2-story, 2 bed / 2 bath townhouse offering 918 sq ft of turnkey living spac...
- 2 Beds
- 2 Baths
- 616611 MLS
Ready to go rental unit! Nightly rentals are permitted. New furniture, newer appliances, ready for your renters. Step into the kitchen, a culinary haven boasting modern a...
- 2 Beds
- 2 Baths
- 619210 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
- 2 Baths
- 620527 MLS
Welcome to Port of Call--an intimate oceanfront enclave on Plantation Key where refined coastal living meets the effortless rhythm of the Florida Keys. Tucked within t...
- 2 Beds
- 3 Baths
- 619965 MLS
Live like you're on vacation! Welcome to the resort style living you've been dreaming of--complete with Deeded Boat Slip #3 and an 8,000 lb boat lift just steps from the ...
- 3 Beds
- 3 Baths
- 615524 MLS
Tropical Island Getaway l Exceptional Waterfront Living with Private Dock. Enjoy effortless Florida Keys living from this beautifully remodeled 2-bedroom, 2.5-bat...
- 2 Beds
- 3 Baths
- 619984 MLS
Discover this amazing marina property at Buttonwood Bay's D2, a 2-bedroom, 1.5 bathrooms townhouse overlooking the Florida bay and and a step away from a private beach on...
- 2 Beds
- 2 Baths
- 620333 MLS
Welcome to Waterfront Living at Buttonwood Bay in Key Largo! Experience stunning sunsets and the ultimate boater's paradise from this beautifully situated residence in th...
- 2 Beds
- 3 Baths
- 619228 MLS
This is the only end-unit town home located on the island area of the prestigious Buttonwood Bay Club. This fully furnished, beautifully updated home has granite countert...
- 2 Beds
- 3 Baths
- 618285 MLS
Discover the ultimate in waterfront living at Buttonwood Bay in south Key Largo--a gated, resort-style community built around a deep-water coral rock harbor with direct F...
- 2 Beds
- 3 Baths
- 617633 MLS
Exclusive and seldom available offering in the gated community of Key Largo Yacht Club. Completely remolded turn key 3 Bedroom 3 Bath 2 Car garage with ocean views from a...
- 3 Beds
- 3 Baths
- 620283 MLS
Luxury Ocean Front End Unit. The best views from the complex in this townhome with 50 ft deeded slip and boat lift. Indulge in the vibrant ocean colors of turquois...
- 3 Beds
- 2 Baths
- 612867 MLS
Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across f...
- 3 Beds
- 3 Baths
- 620704 MLS
Welcome to Tranquility, an exceptional three-bedroom oceanfront residence at Playa Largo Ocean Residences, an intimate and private luxury waterfront enclave in the heart ...
- 3 Beds
- 3 Baths
- 619005 MLS
Welcome to ''Sea-Esta''an exceptional, premiere 3-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in the heart...
- 3 Beds
- 3 Baths
- 618322 MLS
Welcome to ''Coral Breeze'', an exceptional premiere four-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in t...
- 4 Beds
- 5 Baths
- 618328 MLS
Welcome to ''The Lookout', a premiere four-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in the heart of Key...
- 4 Beds
- 5 Baths
- 618319 MLS
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