Upper Keys Vacation Rentals
16 matching rentals.Most Popular
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Islamorada
Pelican Landing A 2-bedroom/2bath home, this hidden gem is located on Lower Matecumbe near mile marker 75. Step out the back of this house and enjoy the quiet serenity of this Lagoon front home. Need dockage? No problem...
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per night
2 beds
2 baths
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Key Largo
$200 discount on Romantic Keys Cottage On Canal With Private Slip. If You Want A Fun, Affordable, Romantic Getaway.(Call 305-304-1902) Park your boat at your private dock on a deep water canal right in your back yard. S...
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per night
2 beds
1 bath
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Islamorada
This great 2 bedroom 2 bath home has a wonderful ocean view from the decks plus protected dockage. Located in Lower Matacumbe on the ocean side of the island. A wonderful private home that is affordable. Perfect for you...
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per night
2 beds
2 baths
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Listings
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Kawama Yacht Club
Located one hour from Miami, Florida. the Kawama Yacht Club is your escape route to the Florida Keys. Situated at mile marker 100 on the Atlantic Ocean, this gated community offers all you need for a relaxing vacation o...
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per night
2 beds
2 baths
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Islamorada
Private heated pool (80-82 degrees) partially shaded, chiki bar with mini fridge next to the pool, outdoor shower, complete with deep sea canal and immediate access to the ocean & bay. Located on the peaceful, northern ...
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per night
2 beds
2 baths
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Tavernier
Tropical elegance in the Fabulous Florida Keys! - Ocean Pointe is an all-suite resort located in a 60 acre protected mangrove preserve directly on the Atlantic Ocean. It is entered through a private gatehouse and has fi...
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per night
2 beds
2 baths
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Islamorada
Total seclusion in 10 unit oceanfront complex along millionaires row on Plantation Key, Islamorada, the Sport Fishing Capital of the World. Off old highway, away from all the noise and traffic, yet walking distance from...
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per night
2 beds
2 baths
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Islamorada
This great 2 bedroom 2 bath home has a wonderful ocean view from the decks plus protected dockage. Located in Lower Matacumbe on the ocean side of the island. A wonderful private home that is affordable. Perfect for you...
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per night
2 beds
2 baths
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Islamorada
Pelican Landing A 2-bedroom/2bath home, this hidden gem is located on Lower Matecumbe near mile marker 75. Step out the back of this house and enjoy the quiet serenity of this Lagoon front home. Need dockage? No problem...
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per night
2 beds
2 baths
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Key Largo
A 24-hour guarded gate protects Key largo's secluded Kawama Yacht Club. This two-story villa overlooks a lake and offers views across natural nature preserves. Minutes to all of the Keys best entertainment and restauran...
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per night
2 beds
1 bath
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Key Largo
$200 discount on Romantic Keys Cottage On Canal With Private Slip. If You Want A Fun, Affordable, Romantic Getaway.(Call 305-304-1902) Park your boat at your private dock on a deep water canal right in your back yard. S...
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per night
2 beds
1 bath
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Islamorada
Minimum Weekly Rentals Only
License RE# 00417442-003300
Save $$$$$$ End Of Season Specials! Call or email for availability If you plan to Vacation in the next week or two - you may save Hundreds of Dollars due to last...
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per night
2 beds
2 baths
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Moon Bay
Penthouse Beauty. Free Boat Slip With Special Rates:
All Amenities Included. Regular Rates From $1,200.TO $1.500 WK.
Great Discount For 'penthouse'.
Pristine, Spacious, Private.
Each room is delicately well appointe...
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per night
2 beds
1.5 baths
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Key Largo
Location: Key Largo, Florida, USA (One hour drive from Miami International Airport)
Accommodations: House - 2 Bedrooms + Other (See Description) - 2 Baths - (Sleeps 4-6)
This beautifully appointed home is located on fi...
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per night
2 beds
2 baths
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Key Largo
This two bedroom, two bath ground level home with patio overlooking the open water with a sandy beach also has a 100ft dock with Free dockage and great for fishing and relaxing. An outdoor hot tub is surrounded with a l...
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per night
2 beds
2 baths
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Key Largo
Full size Kitchen Dining Room Entertainment Area Cable Electric Water Telephone (Local Calls) Washer & Dryer Patio with storage Front Porch 2 bedrooms 1 bathroom Private Entrance Marina Restaurant Pool Tennis Courts Bas...
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per night
2 beds
1 bath
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Key Largo
Relax and enjoy the open water breeze in this 2 bedroom 1 bathroomocean front home on one acre of secluded private proerty located at mile marker98.This home offers plenty of dockage tiki hut, kayaks foruse and is close...
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per night
2 beds
1 bath
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Islamorada
Total seclusion in 10 unit oceanfront complex along millionaires row on Plantation Key, Islamorada, the Sport Fishing Capital of the World. Off the old highway, away from all the noise and traffic, yet walking distance ...
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per night
2 beds
2.5 baths
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Tavernier
Excellent Location! Located right off Tavernier Creek, Oceanside. 1 minute to open ocean or bayside! (located at Mile Marker 90, Just South of Tavernier Creek Bridge) You can fish, snorkel, and scuba dive the renowned r...
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per night
2 beds
1 bath
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Blog Posts
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March 18, 2013
Key Largo is the first of the Florida Keys, as well as the largest. It is the northmost key, not far south of the famous Everglades National Park. If you fly into Florida, it is only about an hour dri...
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October 25, 2012
His Internet investigations lead him to the fact that The African Queen is now located in Key Largo, Florida around mile marker 100. It has been lovingly brought back to life by Captain Lance Holmquis...
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October 17, 2012
Key Largo: We had an early morning walkie, then went to the Blue Cow Cafe for breakfast, where we saw my new friend Bentley. Everyone who walked by admired me and petted me....
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September 04, 2012
Today, the guys made plans to go jet skiing for an hour in Islamorada, about 30 minutes north, so us girls took Travis to Theater of the Sea to see an assortment of shows. While there, we took a ride...
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August 03, 2012
On a recent trip, my favorite slice came from Ma's on Islamorada, one of the upper Keys. Ma's isn't a fancy restaurant; officially it's a fish camp but don't let that distract you. Ma's serves the pi...
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July 24, 2012
Last week, my teacher friends and I decided to take an impromptu trip to the Tiki Bar in Islamorada (Holiday Isle) near the Middle Keys. We were surprised by the fact that this was no longer a "public...
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July 17, 2012
On Tuesday, July 10, 2012, I ate dinner at the Pilot House located at 13 Seagate Boulevard Key Largo, FL 33037. The service was great and friendly, our waitress was Michelle. The restaurant was on the...
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July 14, 2012
On Tuesday, July 10, 2012, I ate lunch at Ma's Fish Camp located at 105 Palm Avenue, Islamorada, FL 33036. The place was, as my mom says, "Keysey". It had nice paintings for sale by local artists hang...
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June 26, 2012
I am not an artist; the closest I come is through photography. However, I recently found myself in Key Largo and was offered a painting class with Pasta. Hmm. My thoughts ran to my grandkids and tho...
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June 14, 2012
Father's day is Sunday! My son and i are taking daddy to Anna Maria Saturday followed by a seafood feast! If we play our cards right we may shuttling off from Anna Maria to Shell Key, now that is a...
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