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

Vacation Rentals in Lower Florida Keys

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Casa Amor - 3BR Residence 2 Blocks from Duval Street – Property 233509

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, town, swimming pool
  • $2,100 - $6,000/week
  • Calendar Last Updated On: Jul 5, 2009
Welcome to Casa Amor, our love nest for ten years has been converted into a vacation rental for you. We are located just two blocks from upper Duval Street…home to a...

Ann Street Studio – Property 20876

  • Lower Florida Keys rental - house, 1 bedroom, sleeps 2, 1 bathroom, pets not allowed, communal pool
  • $1,190 - $1,967/week
  • Calendar Last Updated On: Jul 5, 2009
Perfect for two, this cute studio cottage has it all and is walking distance to everything. Located just one half block off Duval Street and right behind The Curry...

Ocean Front Home With Heated Pool & Dock – Property 179840

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, waterfront, swimming pool
  • Calendar Last Updated On: Jul 4, 2009
Adjust your attitude by adjusting your latitude! Just over a year old, 'Latitude Adjustment' is located on the open water on Ramrod Key.

Casa Margarita – Property 56463

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, children welcome, pets not allowed
  • $3,010 - $5,530/week
  • Calendar Last Updated On: Jul 4, 2009
Fantastic location combined with casual elegance makes this Key West cottage a great retreat to experience! And the historic seaport is just steps away with many...

Sunny Days – Property 88164

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 4, 1 bathroom, children welcome, pets not allowed
  • Calendar Last Updated On: Jul 4, 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...

Key West By Beach & Duval Street Old Town – Property 241481

  • Lower Florida Keys rental - house, 5 bedrooms, sleeps 12, 4 bathrooms, downtown, near the ocean, accept credit card
  • $5,700 - $6,700/week
  • Calendar Last Updated On: Jul 3, 2009
Prime Old Town Walking Location. Across the Street from Southernmost on the Beach, and down the Street from the Southernmost Point.

Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals) – Property 112032

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, accept credit card
  • $1,670 - $2,488/week
  • Calendar Last Updated On: Jul 3, 2009
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft private balcony accessible from the living and...

Key West ocean front luxury 3 bedroom vacation condo rental in the Truman Annex – Property 209190

  • Lower Florida Keys rental - condo, 3 bedrooms, sleeps 6, 3 bathrooms, downtown, waterfront, accept credit card
  • $3,000 - $4,500/week
  • Calendar Last Updated On: Jul 3, 2009
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This beautiful luxurious Harbor Place ocean front condo is within the...

Ocean Front Pool Home w/Pool & Dock available for monthly rental – Property 174010

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, waterfront, swimming pool
  • Calendar Last Updated On: Jul 3, 2009
Breezeswept Villa, a magnificent brand-new 3 Bedroom estate located on a tropical coastal community of waterfront homes just minutes to the magic of Key West.

Island Spice – Property 7013690

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, children welcome, pets not allowed
  • $990 - $3,190/week
  • Calendar Last Updated On: Jul 3, 2009
Island Spice is a lovely 2 bed, 2.5 bath townhome, located in the historic Foundry District of the prestigious Truman Annex community.<br /> The brick exterior, and...

Luxury Waterfront at the Galleon Resort in Old Town – Property 161268

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, resort, waterfront, accept credit card
  • $2,350 - $3,850/week
  • Calendar Last Updated On: Jul 3, 2009
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, fully equipped kitchen, breakfast area, dining...

On a Deep Water Canal with Open Water Views! - A Gift From the Sea - Big Pine – Property 407393

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, waterfront, air-conditioning
  • $1,000 - $1,200/week
  • Calendar Last Updated On: Jul 5, 2009
Escape the stress and cares of your daily life. Located on a boater-friendly canal in Pine Channel Estates three lots from open water.

Duval Roost – Property 20887

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, 1 half bath, pets not allowed, broadband access
  • $2,660 - $4,900/week
  • Calendar Last Updated On: Jul 3, 2009
You would never know that you are one half block from Duval Street in the heart of old town tucked away on a private lane.<br /> <br /> You enter the property down a...

Grinnell Getaway – Property 76143

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, children welcome, pets not allowed
  • $1,820 - $2,940/week
  • Calendar Last Updated On: Jul 3, 2009
Peaceful retreat in the historic district awaits you. This charming Old Town home is located opposite our historic cemetery, just 5 blocks from Duval Street.

Louisa House – Property 20885

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, pets, pets not allowed
  • $3,150 - $5,600/week
  • Calendar Last Updated On: Jul 3, 2009
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point.

Whitehead House – Property 20879

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, pets, heated pool
  • $2,240 - $3,990/week
  • Calendar Last Updated On: Jul 3, 2009
Unique two story, three bedroom, two bathroom home nested beside the Audubon House in Old Town Key West. Hidden behind the most photographed "Prohibition fence" in...

Key West Ocean Side Luxury w/ High Speed Internet – Property 174861

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, swimming pool
  • Calendar Last Updated On: Jul 2, 2009
Be our guest at one of the best that 1800 Atlantic Condominiums has to offer. With a wonderful tropical setting on the Atlantic Ocean & Smathers Beach, this...

Best Deal in Truman Annex - Cead Mile Failte – Property 241645

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, beach, downtown, accept credit card
  • $1,100 - $1,750/week
  • Calendar Last Updated On: Jul 2, 2009
Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from,...

Contemporary Condo @ Truman Annex-Walk to Beach/Duval St. - $1222/wk total Aug – Property 203228

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 5, 1 bathroom, beach, downtown, accept credit card
  • $1,100 - $1,600/week
  • Calendar Last Updated On: Jul 2, 2009
REDUCED RATE AUGUST & SEPTEMBER 2009 -- $900/WEEK RENT. Decorated in casual contemporary style, our second floor condo is newly-renovated, and centrally located in...

Truman Annex 2bed/1bath condo, premier downtown Key West location and amenities – Property 156587

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, swimming pool
  • $1,200 - $1,800/week
  • Calendar Last Updated On: Jul 2, 2009
Our 2bed/1 bath condo in the lovely gated community of Truman Annex provides the perfect way to experience Key West- like a local.
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