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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CUDJOE KEY Tropical Paradise, Gated Resort, KEY WEST 19 Miles – Property 193289

  • Lower Florida Keys rental - cottage, 2 bedrooms, sleeps 6, 2 bathrooms, resort, waterfront, swimming pool
  • $700/week
  • Calendar Last Updated On: Jan 7, 2009
For a TROPICAL VACATION come to our beautiful designer furnished cottage/mobile home at Venture Out Resort on Cudjoe Key. We provide two bicycles for your...

January Cancellation Special- REDUCED FOR JANUARY- CALL NOW! – Property 192107

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 12, 2 bathrooms, near the ocean, waterfront, accept credit card
  • $1,900/week
  • Calendar Last Updated On: Jan 7, 2009
The Cabana del Sol is ½ acre spacious property with swimming pool and sun deck on 150ft of waterfront property. Cute and comfortable waterfront bungalow with a very...

Overlook- Waterfront Pool Home - Private & a Nature lovers dream-Key Deer! – Property 309489

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 10, 2 bathrooms, beach, near the ocean, accept credit card
  • $1,900/week
  • Calendar Last Updated On: Jan 7, 2009
'The Overlook' at Big Pine Key is an exclusive private waterfront home located next to the Blue Heron and Key Deer Wildlife Refuges.

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

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, accept credit card
  • $1,000 - $1,500/week
  • Calendar Last Updated On: Jan 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...

Charming and Private – Property 169213

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, waterfront, swimming pool
  • Calendar Last Updated On: Jan 7, 2009
20 Miles from Key West and mini golf, private pool & hot tub, deluxe outdoor kitchen, outdoor shower, screened in porch all around, commercial ice maker & bait...

Enjoy open water views & excellent fishing & snorkeling right from your backyard – Property 213724

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, beach, waterfront, air-conditioning
  • Calendar Last Updated On: Jan 7, 2009
Best location in the lower keys - Everything you need to enjoy a perfect keys vacation: superb boating location, 60 foot concrete dock, outdoor shower (hot and cold...

Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex – Property 220630

  • Lower Florida Keys rental - townhome, 4 bedrooms, sleeps 8, 3 bathrooms, downtown, near the ocean, accept credit card
  • $2,700 - $4,500/week
  • Calendar Last Updated On: Jan 7, 2009
Enjoy all the charm Key West has to offer in this beautiful, newly renovated 4 bedroom/3 full bath house with private heated pool in the heart of Old Town.

Hemingway Hideaway in the Heart of Key West--Tasteful, Charming – Property 127835

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, downtown, swimming pool
  • Calendar Last Updated On: Jan 7, 2009
Historic charmer, one block from Ernest Hemingway's home, great location, and off street parking for two cars. There is historic context to Ernest Hemingway with...

Grand Reopening Ocean View Studio! Beach 30ft Away! See Atlantic Ocean from King – Property 311616

  • Lower Florida Keys rental - studio, sleeps 2, 1 bathroom, beach, downtown, air-conditioning
  • $900 - $1,800/week
  • Calendar Last Updated On: Jan 7, 2009
GOT BEACH? Reply to this listing WITH PROMO CODE 1YESFUN55 w/your phone number THE BEST stay in key west that has an oceanview..

Villa Soleil, Elegant Truman Annex condo in Old Town Key West – Property 188516

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 1 bathroom, downtown, near the ocean, accept credit card
  • $1,200 - $2,000/week
  • Calendar Last Updated On: Jan 6, 2009
Villa Soleil is a newly redecorated condominium in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former...

Waterfront- Private Boat Dock- Excellent fishing at the Lodge*Summer Savings** – Property 166614

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 1 bathroom, near the ocean, waterfront, accept credit card
  • $875 - $995/week
  • Calendar Last Updated On: Jan 7, 2009
The Lodge is a very comfortable, 2 bedroom 1 bath home on the water in a quiet, desirable Big Pine Key neighborhood. It is well decorated and equipped, and has...

Retreat at BPK - Waterfront Pool Home Ocean Access & Stunning Views – Property 162258

  • Lower Florida Keys rental - house, 6 bedrooms, sleeps 18, 4 bathrooms, beach, waterfront, accept credit card
  • $2,900 - $7,950/week
  • Calendar Last Updated On: Jan 7, 2009
You’ll love this house! It has 6 Bedrooms 4 baths, can accommodate up to 18 people in beds. Thirty foot pool surrounded by tropical fruits & plants, 150 foot boat...

The Cottage at Big Pine Key- Hot Tub & Tiki Hut *Private boat dock – Property 315042

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 8, 2 bathrooms, near the ocean, waterfront, accept credit card
  • $975/week
  • Calendar Last Updated On: Jan 7, 2009
The Cottage at Big Pine Key is located in the Doctor's Arm subdivision and just off Bogie Channel. The Cottage is Cape Cod style with an open floor plan.

Gilligan's Island Private Oasis - Florida Keys Vacation Rental – Property 223496

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 9, 3 bathrooms, near the ocean, waterfront, accept credit card
  • $2,500/week
  • Calendar Last Updated On: Jan 6, 2009
Gilligan’s Island Vacation Rental You won’t want to be rescued from this island oasis. You will enjoy the peace and quiet, relaxing by the pool, or taking your...

Designer Decorated Oceanfront Acre Private Home, Private Heated Pool – Property 317093

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 10, 2 bathrooms, beach, waterfront, accept credit card
  • Calendar Last Updated On: Jan 7, 2009
Cudjoe Key (15 minutes from Key West OR Bahia Honda State Park) 3 bedroom, 2 bath new home with master suite having a double sink, handmade tiles, wicker love seat...

2/2 Canalfront & Dockage Keys Getaway – Property 103696

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, waterfront, air-conditioning
  • $1,300/week
  • Calendar Last Updated On: Jan 5, 2009
In the heart of the Key Deer Preservation on deep water canal with 50 foot concrete dock and large breezy terrace. Located just 30 miles from Key West and minutes to...

Key West - Poolside Conch Paradise at Key West Golf Club – Property 164920

  • Lower Florida Keys rental - townhome, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, beach, near the ocean, swimming pool
  • $1,250 - $2,450/week
  • Calendar Last Updated On: Jan 5, 2009
This cute and airy, 2 bedroom bungalow style home, has been tastefully decorated and freshly painted to make your stay comfortable and relaxing.

Beautiful Retreat in Key West Area – Property 188664

  • Lower Florida Keys rental - house, 6 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, beach, waterfront, accept credit card
  • $3,500/week
  • Calendar Last Updated On: Jan 5, 2009
Our beautiful home is located on the bayside in Big Coppitt Key. Wake up in the morning to stunning views of the bay. The house is located in over 2 1/2 acre lot...

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
  • $1,650/week
  • Calendar Last Updated On: Jan 7, 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...

3 story home off the Canal, boat dock, pool, jacuzzi, breathtaking sunsets! – Property 155204

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, near the ocean, waterfront, accept credit card
  • $2,700 - $3,500/week
  • Calendar Last Updated On: Jan 5, 2009
Keyora..a jewel in the crown of Summerland Cove Isle. Located in a quiet, serene neighborhood. You are spoilt for view ..open water, canal, ocean view.
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