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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Beautiful Waterfront Single Family Home - 5 miles from Key West – Property 322888

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, near the ocean, waterfront, balcony
  • $875 - $1,050/week
  • Calendar Last Updated On: Nov 21, 2009
This is a beautiful Spanish style home on a clean swimming canal 9 miles from Duval Street, Key West. Our home is just 4 houses from the end of the canal and the...

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, pool
  • $3,000 - $4,500/week
  • Calendar Last Updated On: Nov 21, 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...

Spectacular,1 from OPEN water, Best Fish, Dive, Snorkel, views – Property 187539

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, near the ocean, waterfront, garden
  • $1,650/week
  • Calendar Last Updated On: Nov 21, 2009
Beautifully renovated in/out large home. One in from Open water on canal, awesome views, unique cut in boat SLIP under the house!

Luxury Key West Condo -All New Plus So Much More---- 7 Bikes Included Free! – Property 223545

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, pool
  • $1,100 - $1,400/week
  • Calendar Last Updated On: Nov 21, 2009
Condo located less than 1/2 mile outside of Key West in new gated community in Stock Island. 1100 sq. ft, beautifully decorated in Key West style.

Villa Soleil – Property 72842

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, adventure, balcony
  • $500 - $3,500/week
  • Calendar Last Updated On: Nov 21, 2009
VILLA SOLEIL is located in the historic Foundry section of Truman Annex, a beautiful gated community in the heart of Old Key West.

Aquamarine – Property 40043

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, adventure, air-conditioning
  • $500 - $2,240/week
  • Calendar Last Updated On: Nov 21, 2009
Newly remodeled condominium located in the Truman Annex Complex, which is 2 blocks from Duval Street and all of the Old Town Key West attractions.

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 21, 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...

# 175 - Venture Out – Property 7028244

  • Lower Florida Keys rental - house, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • $850 - $900/week
  • Calendar Last Updated On: Nov 21, 2009
This is a boater's paradise! This one bedroom/one bathroom home has a 35' concrete dock/seawall, with custom, padded aluminum dock posts, and a concrete...

Casa Atlantica One Bedroom – Property 20895

  • Lower Florida Keys rental - condo, 1 bedroom, sleeps 2, 1 bathroom, adventure, beach
  • $1,120 - $1,820/week
  • Calendar Last Updated On: Nov 21, 2009
Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest.

'CONCH CASA GRANDE' @ Truman Annex: 11' Ceilings, Private Pool & 6 Master Suites – Property 177191

  • Lower Florida Keys rental - house, 7 bedrooms, sleeps 12, 7 bathrooms, downtown, near the ocean, balcony
  • $7,000 - $15,000/week
  • Calendar Last Updated On: Nov 20, 2009
Conch Casa Grande might well be the largest home available for vacation rental in the Truman Annex, which is appealing to anyone who wants to have some elbow room...

'HIDDEN TREASURE' @ Casa East: Luxury 3BR's, Baby Grand Piano, Huge Private Pool – Property 177317

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, beach, near the ocean, pool
  • Calendar Last Updated On: Nov 20, 2009
On a quiet lane just 3 blocks from Smathers Beach is a very special home, hidden behind a sheltered front entrance with a five foot high louvered fence.

“FALLING WATER” @ Old Town: Breathtaking 5BR Private Compound with Private Pool – Property 180171

  • Lower Florida Keys rental - house, 5 bedrooms, sleeps 12, 4 bathrooms, 1 half bath, downtown, near the ocean, pool
  • Calendar Last Updated On: Nov 20, 2009
You would never guess what lies beyond the front gate: a dazzling residential compound of 3 custom-designed buildings around a pool with a continuous sheet of...

'COLORFUL CONCH' @ the Sanctuary: Decorator Home with 4BR/3BA & Private Pool – Property 189356

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 6, 3 bathrooms, beach, resort
  • Calendar Last Updated On: Nov 20, 2009
This beautiful private home has everything you could want in a vacation home. It has been meticulously furnished and maintained inside and out, and is located in...

'SOUTHERN STAR' @ William Street: Luxurious 3BR/3BA Historic Old Town Home – Property 193075

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, village, waterfront, pool
  • Calendar Last Updated On: Nov 20, 2009
Half a block from the Historic Seaport on William Street is a home that was recently recognized by the Historic Florida Key Foundation for excellence in...

“SOUTHWINDS” @ Key West Beach Club: 2 BR Beachfront Condo, Panoramic Ocean Views – Property 204250

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, pool
  • Calendar Last Updated On: Nov 20, 2009
On the south shore of Key West is a home with the best of both worlds: it is less than a mile from Old Town Key West, yet it is right on the beach, with commanding...

'SIMPLY IRRESISTIBLE' @ The Pool: 2BR 2.5BA Luxurious Poolside Townhome – Property 206279

  • Lower Florida Keys rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Simply Irresistible' is a private two-story town home nestled in the lush tropical landscaping that surrounds the gorgeous resort-style private pool in the Key West...

'SOUTHERNMOST BELLE' @ The Annex: 7 Bedrooms, Huge Porches & Large Private Pool – Property 225064

  • Lower Florida Keys rental - house, 7 bedrooms, sleeps 14, 5 bathrooms, downtown, resort, pool
  • $6,500 - $14,000/week
  • Calendar Last Updated On: Nov 20, 2009
'Southernmost Belle' is unique among vacation homes in Key West. First of all, is the location: This lavish mansion is located at one of Key West's most exclusive...

'GEORGIA PEACH' in Old Town: 4BR Luxury Home @ the Meadows – Property 225229

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, 1 half bath, downtown, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
On Georgia Street in 'the Meadows' of Key West is a house that is truly a peach among vacation homes. As soon as you walk onto the deep front porch and see the...

'TURTLE CAY SPA' @ the Sanctuary: Walled Yard & 2 Master Suites – Property 226088

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Turtle Cay Spa' is a bright and airy private home located in The Sanctuary, a quiet gated enclave set within the already gated grounds of the Key West Golf...

“PENNY'S POMPEI” @ Key West Golf Club: Elegant 2BR/1.5BA Townhome – Property 229104

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
'Penny's Pompei” is an elegant two-story town home located at the Key West Golf Club, directly across the street from the community's large resort style pool.
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