Make a Florida Upper Keys vacation rental your home away from home in the Florida Keys.

Guests of Islamadora vacation rentals will find great fishing and diving opportunities here. Highlights for guests of Islamadora vacation rentals include hiking along the nature trails at Long Key State Recreation Area and visiting the Windley Key Quarry Fossil Reef State Geologic Site. The Theater of the Sea, on Windley Key, features shows starring dolphins and other sea creatures.

The northernmost island in the Florida Keys, Key Largo is just an hour’s drive south of Miami. Guests of Key Largo vacation rentals will find a number of local operators offering snorkeling and diving trips, as well as plenty of fishing charters. Other attractions for guests of Key Largo vacation rentals include kayaking and bird watching in the nearby Everglades. Tavernier vacation rentals are also a popular choice in the Upper Keys.

You're sure to find the perfect Upper Florida Keys vacation rental for a fabulous Florida vacation. Reserve your Upper Florida Keys vacation rental today!

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Sanibel Island rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.

While you're here, discover more about the Florida Keys in our vacation ideas section, which includes info on top beaches and topics like long-term rentals in Key Largo.

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Upper Florida Keys: Houses, Condos & More(887)

887 Results
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#43751vb
(89)
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#172415
(29)
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
#260920vb
(38)
3 - 13 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
#911472
(18)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
#404942vb
(28)
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
#452120vb
(12)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
#484134vb
(10)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
#491200vb
(9)
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#508249vb
(7)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
#151910
(10)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
#507954vb
(6)
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
#175223
(32)
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
#168455
(12)
30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
#254452vb
(6)
5 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
#497364vb
(5)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
#326184
(29)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
#513264vb
2 Reviews
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
#495162vb
1 Review
4 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
#191399
(143)
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
#3642442
1 Review
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
#330045
(29)
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#265117
(25)
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
#314828
(11)
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#107982
(6)
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
#225990
(3)
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
#312507
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#450084vb
(20)
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
#328833
(6)
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
#338691
(39)