Reach Higher Vacation Ground and Visit the Upper Florida Keys

Visiting Florida’s Upper Keys is like finding bliss on a faraway island without traveling to the ends of the earth. Whichever isle you choose will bring a sense of escape and relief, so pick one and let the quality vacationing begin.


Key Largo is the largest of these coral-constructed Keys and is also known as the The Diving Capital of the World. Thirty three miles long and nestled just off the coast of Florida, this will be a good fit for ecotourists and adventurers alike. And, if you just want a pleasant place to frolic on the beach or relax in the shade of an umbrella this isn’t a bad choice either.


The same goes for Islamorada, a collection of a few smaller Keys. Skip back and forth from one to the next, relishing the small-town atmosphere and engaging peace and quiet. Sport fishing is popular here, as are snorkeling, windsurfing and sailing.


No matter which of the islands ends up capturing your attention, you’ll surely have the chance to sample some conch chowder, Key Lime Pie and plenty of tropical drinks as you take in a sunset from your private lanai. Choosing to stay in a condo or beach house will make the most of the Florida Keys and allow plenty of moments like this to naturally arise.


If the idea of discovering the Caribbean experience that exists just off the coast of the peninsula sounds appealing, then it sounds like you’ll soon be opening the door to a soothing and restorative vacation.

Destination: Search

Vacation Rentals in Upper Florida Keys

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Welcome to Key Largo and Enjoy the Beautiful Blue Ocean – Property 314711

  • Upper Florida Keys rental - townhome, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, beach, near the ocean, accept credit card
  • $900 - $1,200/week
  • Calendar Last Updated On: Jul 19, 2008
Kawama Yacht Club is an oceanfront beach residential community located in MM 99 in Key Largo, Florida, only about 1 hour drive from Miami International...

Kawama Oceanside Townhouse 2bed/2bath – Property 218285

  • Upper Florida Keys rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, accept credit card
  • $1,095 - $1,150/week
  • Calendar Last Updated On: Jul 19, 2008
Kawama Yacht Club is a private gated community offering swimming pools (heated), tennis courts, children's playground, a beach and marina.

Kawama Yacht Club Townhouse II – Property 218301

  • Upper Florida Keys rental - townhome, 3 bedrooms, sleeps 8, 3 bathrooms, beach, near the ocean, accept credit card
  • $1,395 - $1,475/week
  • Calendar Last Updated On: Jul 19, 2008
This tri-level townhouse in located in Kawama Yacht Club at mile-marker 100 -- on the ocean side of Key Largo. This lushly-landscaped community is gated, and has...

Boat, Fish, Swim from Your Own Dock! – Property 158981

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 8, 1 bathroom, near the ocean, waterfront, accept credit card
  • Calendar Last Updated On: Jul 19, 2008
Come Play! Your 70-foot dock provides instant access to fun – whether boating, fishing, swimming or relaxing under the shady, palm-roof “Chickee.” Enjoy your privacy...

Oceanfront Condo - Ocean Views - Pool, Beach, Marina & Tennis – Property 311664

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $750 - $1,475/week
  • Calendar Last Updated On: Jul 18, 2008
We are offering for rent our beautiful, 2Bdrm/2BA condominium located directly on the ocean in Key Largo (Tavernier), Florida.

Well Appointed : Kawama Yacht Club Condo, Pool, Quiet, away from US1 – Property 129969

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, beach, waterfront, swimming pool
  • $1,000 - $1,400/week
  • Calendar Last Updated On: Jul 17, 2008
The fully air conditioned accommodation at Kawama is all on one level. Queen in the master, 2 x full doubles in the second bedroom, sleeping six guests, with the...

Key Largo Beach House! Sunsets on the Bay! – Property 107982

  • Upper Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $1,050 - $1,500/week
  • Calendar Last Updated On: Jul 17, 2008
A beautiful house on 3 acres of privately-owned gulfside property in Key Largo. Inside, the home is tastefully decorated with nautical-style decor and artwork.

Your new property advertisement – Property 190220

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 10, 3 bathrooms, air-conditioning, washing machine
  • $1,400 - $1,800/week
  • Calendar Last Updated On: Jul 17, 2008
Enjoy island breezes as you lie in the hammock on the huge, screen-enclosed porch, idly watching the constant parade of boats passing by on the waterway called...

Bayview Canal front home with Tiki Hut – Property 195059

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, waterfront, washing machine
  • Calendar Last Updated On: Jul 17, 2008
This 2 story home is extremely clean, and has been updated and decorated in Keys style. It is located bayside at MM98 on a very wide canal that gets lots of manatees...

Beautiful Islamorada Boater's Paradise home in the Florida Keys – Property 192446

  • Upper Florida Keys rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, beach, near the ocean, swimming pool
  • $2,100 - $2,400/week
  • Calendar Last Updated On: Jul 17, 2008
Boater's paradise is a beautiful canal front home with swimming pool, 4 bedroom/2 bathrooms, sleeps 8 in the famous Florida Keys.

Beautiful Captain's Cove – Property 218650

  • Upper Florida Keys rental - villa, 3 bedrooms, sleeps 8, 2 bathrooms, beach, waterfront, air-conditioning
  • Calendar Last Updated On: Jul 17, 2008
Relax and enjoy a peaceful get-away in beautiful Islamorada. This unique, upscale, three-bedroom/two-bath home is nestled on a bay overlooking the ocean.

Penthouse Condo Fabulous Sunsets in Key Largo – Property 69815

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, air-conditioning
  • $895 - $1,995/week
  • Calendar Last Updated On: Jul 17, 2008
Located one hour from Miami, Kawama Yacht Club Tower is your escape route to the Florida Keys. Situated at mile marker 100 on the Atlantic Ocean, this gated...

Tropical Paradise for Family and Boaters – Property 168455

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, air-conditioning
  • $2,000/week
  • Calendar Last Updated On: Jul 16, 2008
This oceanside, centrally located tropical paradise is perfect for a family or couples. Ideal for your boat, there is a new 70 feet (20 m) boat dock with 30/50 amp...

Our Kozy Key - Ocean Side - Off the beaten path – Property 177656

  • Upper Florida Keys rental - townhome, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, beach, near the ocean, swimming pool
  • $700 - $800/week
  • Calendar Last Updated On: Jul 17, 2008
2 bedroom 2 story townhouse is located in the tropical resort of Kawama Yacht Club, Key Largo FL. Located at mile marker 100, an hour's drive from the Miami...

Charming Key Largo Bayfront Home - Dock/Spa/Views – Property 147221

  • Upper Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, waterfront, accept credit card
  • $1,675 - $2,275/week
  • Calendar Last Updated On: Jul 15, 2008
Our Key Largo Villa, located in desirable Buccaneer Pointe, offers luxurious accommodations for up to six guests. Surrounding palms offer welcome shade from the hot...

Immaculate Fully Furnished 2/2 With Breathtaking Ocean Views – Property 167594

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • $1,110 - $1,250/week
  • Calendar Last Updated On: Jul 17, 2008
Immaculate 2 bedroom, 2 bathroom condo with breathtaking views of the Atlantic Ocean from the living room balcony. This condo boasts jacuzzi tubs in both bathrooms,...

Bonefish Bay: Islamorada Luxury Home with Resort Amenities – Property 152005

  • Upper Florida Keys rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, 1 half bath, beach, waterfront, swimming pool
  • $5,000 - $6,000/week
  • Calendar Last Updated On: Jul 14, 2008
Gorgeous home in the premier gated community in Islamorada. Bonefish Bay, an enclave of 12 Key West-style homes with all the amenities of a large resort.

Secluded Ocean Side Getaway on Deep Water Canal – Property 193601

  • Upper Florida Keys rental - , 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, air-conditioning, washing machine
  • Calendar Last Updated On: Jul 16, 2008
Come Relax in our tranquil, beautifully landscaped setting, just seconds from the Atlantic Ocean, at MM 93, in Tavernier. The house is very bright with an open...
SPECIAL OFFER! $100 OFF per Week Fall Special!! July 12 - November 1

Luxurious Oceanfront Resort-ENDLESS OCEAN VIEWS FROM INSIDE & OUT – Property 190239

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $850 - $1,995/week
  • Calendar Last Updated On: Jul 13, 2008
Luxurious 4th floor condominium offers spectacular panoramic views of the ocean, marina & sunsets. Enjoy the beautiful turquoise waters the Keys are famous for from...
SPECIAL OFFER! Fantastic Summer / Fall Special!!! Call! July 17 - December 20

New Oceanfront w/ Breathtaking views - 5 Star Resort – Property 129473

  • Upper Florida Keys rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, resort, waterfront, accept credit card
  • $1,796 - $3,495/week
  • Calendar Last Updated On: Jul 11, 2008
Ocean front (Atlantic) dream home, just a 15 ft from porch 2 ocean with magnificent views and phenomenal sunrises. Luxury condo with multi room entertainment...
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