When It Comes to the Keys, Lower is Better

Everyone knows that taking a trip to the Florida Keys is like escaping the country without going through the trouble of visiting a foreign land. You might as well venture as far offshore as possible by visiting the Lower Keys, where the sound of the real world is but a distant and ignorable hum.


Hundreds of enchanting islands make up this lazy archipelago, but the farther south you go the easier it is to settle into a vacation state of mind. Big Pine Key, Summerland Key, Sugarloaf Key and of course Key West are places that make it pretty easy to slow your pace and put your feet up. The inviting condos, cottages, town homes and beach houses spread throughout the region go even farther in inviting you to kick off your shoes and forget about alarm clocks and deadlines.


Free-spirited sunset celebrations, Ernest Hemingway’s house, vibrant Duval Street and the town motto of “One Human Family” are just a few of the reasons that Key West attracts people who like to do things a little differently. November through April is the dry season, so expect warm temperatures and little rainfall, while the remaining months are wetter, with summer temperatures hovering in the 80’s.


Fishing, kayaking, scuba diving and snorkeling can satisfy the urge to connect with nature in any of the Keys, which are actually made from the fossilized remnants of coral reefs. A National Marine Sanctuary surrounds the islands, and when you add in a few national parks and lots of exotic wildlife, like crocodiles and Key deer, it’s clear that this is much more exotic than the average beach destination.


Within the space of a few miles are lots of Keys and lots of diversions, so put the mainland at your back and prepare for an adventure in the wild fringes of Florida.

Destination: Search

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Vacation Rentals in Lower Florida Keys

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Paradise manor with private pool and patio – Property 208558

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 9, 2 bathrooms, near the ocean, garden
  • Calendar Last Updated On: Nov 8, 2009
Beautiful and spacious house with private pool in quiet neighborhood. The house has a living room with TV, DVD, VCR, CD/radio, dinning room, fully equipped kitchen...

Sunset Villa with gorgeous Open Water views and sunsets – Property 224210

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 10, 2 bathrooms, near the ocean, waterfront, pets considered
  • Calendar Last Updated On: Nov 8, 2009
Why stay at a hotel when you can enjoy beautiful open water views with extreme quiet and peacefulness at this end-of-the-road home.

Size Does Matter! Biggest Luxury Vacation Home on the Island – Property 265312

  • Lower Florida Keys rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, near the ocean, pool
  • Calendar Last Updated On: Nov 8, 2009
This is a brand new build, that has never been lived in. Built by a British designer with no attention to detail left out. European style molding's throughout the...

(Quiet) House with Guest Cottage – Property 232130

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, beach, near the ocean, pool
  • Calendar Last Updated On: Nov 7, 2009
This is a newly renovated and furnished property. Let the outdoors in and the indoors out at Casa Louisa. Four sets of French doors open up off the tastefully...

Beautiful Duval St. Condo, Location, Location!!!! – Property 156723

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, balcony
  • $1,000 - $1,400/week
  • Calendar Last Updated On: Nov 7, 2009
Location, Location, Location!!! You can't find a better location than Duval St. One of only three unique units. This Condo is above and behind Antonia's...

To-Lu HideAway -- Best Keys Getaway on Open Water – Property 237303

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 12, 3 bathrooms, near the ocean, waterfront, jacuzzi
  • $2,500 - $3,500/week
  • Calendar Last Updated On: Nov 7, 2009
It doesn’t get more tropical than this!! There’s a palm tree in the middle of the house! Tropical bamboo interior throughout continually reminds you are in...

Verandah – Property 7013694

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, beach, DVD
  • Calendar Last Updated On: Nov 7, 2009
VERANDAH - Tucked away on Historic Frances Street lies your island escape… Verandah is a stunning two bedroom two bath home with a private pool and plenty of space...

Ann Street Cottage – Property 20878

  • Lower Florida Keys rental - condo, 1 bedroom, sleeps 2, 1 bathroom, non smoking only, outlet shopping
  • $1,050 - $1,960/week
  • Calendar Last Updated On: Nov 7, 2009
This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.

Egret – Property 40076

  • Lower Florida Keys rental - house, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • $500 - $2,370/week
  • Calendar Last Updated On: Nov 7, 2009
Egret. The Colony Suites is a charming Historic Key West Style Conch Cottages nestled in the heart of Historic Old Town Key West, just three blocks from famous...

Casa Louisa – Property 72847

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, adventure, beach
  • $1,200 - $4,625/week
  • Calendar Last Updated On: Nov 7, 2009
CASA LOUISA – Is an authentic cigar makers cottage and located a hop, skip and a jump (just 1/2 block) from famous Duval Street.

Linger Longer – Property 82030

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 5, 1 bathroom, 1 half bath, adventure, beach
  • $720 - $2,520/week
  • Calendar Last Updated On: Nov 7, 2009
Linger Longer Enjoy an easy vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome located in the President's Walk of the Truman Annex.

Sunny Days – Property 88164

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 4, 1 bathroom, adventure, air-conditioning
  • Calendar Last Updated On: Nov 7, 2009
SUNNY DAYS - This cottage is beautifully maintained while retaining its original style and structure. Dade County pine is throughout the property adding a feel of...

Casa Atlantica One Bedroom – Property 20895

  • Lower Florida Keys rental - condo, 1 bedroom, sleeps 2, 1 bathroom, adventure, beach
  • $1,120 - $1,960/week
  • Calendar Last Updated On: Nov 7, 2009
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest.

Bamboo Key – Property 40025

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • $1,100 - $5,220/week
  • Calendar Last Updated On: Nov 7, 2009
Bamboo Key - Style is supreme in this two bedroom two bath condo in the Harbor Place neighborhood of the Truman Annex. This property has a beautiful view of both...

Heron – Property 40078

  • Lower Florida Keys rental - house, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • $500 - $2,370/week
  • Calendar Last Updated On: Nov 7, 2009
Heron. These cottages are some of several cottages located at the Colony cottages, formerly the Colony Guest House. These one bedroom one bath accommodations have a...

My Dream Home Can Be Yours Too!! – Property 150899

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, waterfront, balcony
  • Calendar Last Updated On: Nov 7, 2009
Brand new, beautiful two bedroom, two bathroom, stilt waterfront home. Sleeps six. Screened entry leads to french doors. The master suite has an oversized roman...

Banana Key – Property 40031

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • $800 - $3,850/week
  • Calendar Last Updated On: Nov 7, 2009
Banana Key Style is supreme in this two bedroom two bath condo in the Truman Annex with a beautiful view of the gulf. Bedding: K/2T<br /> <br /> $2600 per week...

Tropical Vineyard – Property 40036

  • Lower Florida Keys rental - condo, 1 bedroom, sleeps 2, 1 bathroom, adventure, air-conditioning
  • $500 - $2,030/week
  • Calendar Last Updated On: Nov 7, 2009
Tropical Vineyard - Is an upstairs one bedroom one bath Shipyard condominium located in the Truman Annex. Living area extends out, through French doors, to a very...

Nantucket South – Property 40023

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • $600 - $3,080/week
  • Calendar Last Updated On: Nov 7, 2009
Nantucket South - Beautiful and spacious 2 bedroom 2 bath single family home. Nantucket South is the only stand alone home in the Shipyard complex.

Island Time – Property 7028685

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, adventure, beach
  • Calendar Last Updated On: Nov 7, 2009
ISLAND TIME - Located in Old Town Key West near the famous Casa Marina, You are welcome home even before you walk in the door.
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