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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
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
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
Affordable Florida Keys Getaway - Perfect for Your First Home or Investment! An amazing opportunity to own your own piece of paradise in the Florida Keys at an afforda...
- 2 Beds
- 1 Baths
- 621655 MLS
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- 3 Beds
- 2 Baths
- 621512 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
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
Take a look at this newly upgraded trailer, with a concrete exterior, this two-bedroom property looks like a little house with concrete on the outside and partial concret...
- 2 Beds
- 2 Baths
- 621369 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
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
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
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
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
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
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
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
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
Discover easy bayfront living in this beautifully updated townhome at Executive Bay Club, where breathtaking views of Florida Bay take center stage. The open living area ...
- 3 Beds
- 2 Baths
- 621074 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
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
BAYFRONT OPPORTUNITY | Sunset Hammock, Unit 1D Direct bayfront living with a 28-foot boat slip! Rarely available, Unit 1D at Sunset Hammock offers a special opportunity...
- 2 Beds
- 3 Baths
- 621711 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
Hidden gem with 50 ft boat slip. Luxury Oceanfront End Unit in Exclusive Key Largo Yacht Club Discover one of Key Largo's best-kept secrets. Nestled within the priva...
- 3 Beds
- 2 Baths
- 620798 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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