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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VO# 586 - 2 BR/ 2 BA in a 5 Star Resort with Ocean View – Property 294042

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, Near The Ocean, Waterfront, Communal Pool
  • Calendar Last Updated On: Jun 18, 2013
This is a beautiful sparkling clean house located just 19 miles from Key West in a guarded community. Park your boat right behind the house.

Island Sunrise Resort- 3 acre estate with open water sunrises. – Property 922434

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 7, 2 bathrooms, accept credit card, Near The Ocean, Waterfront
  • $2,200 - $2,900/week
  • Calendar Last Updated On: Jun 18, 2013
Island Sunrise Resort is a 3 acre estate with two houses to choose from. The whole property is only rented exclusively to the same party of people.

Villa Soleil-Enjoy America's Caribbean with Style and Comfort – Property 141421

  • Lower Florida Keys rental - townhome, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, accept credit card, Near The Ocean, Town
  • $1,600/week
  • Calendar Last Updated On: Jun 18, 2013
Villa Soleil is an elegant townhouse located in the Truman Annex section of Old Town, close to the ocean and great sunset views.

Walk to the beach! – Property 392129

  • Lower Florida Keys rental - studio, 1 bedroom, sleeps 2, 1 bathroom, Beach, Downtown, Near The Ocean, Air Conditioning
  • Calendar Last Updated On: Jun 18, 2013
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this studio apartment is minutes...

Ocean Retreat – Property 327107

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 5, 2 bathrooms, 1 half bath, accept credit card, Near The Ocean
  • Calendar Last Updated On: Jun 18, 2013
Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high...

Coral Hammock - Beautiful Poolside Home (28) – Property 994631

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, accept credit card, Communal Pool
  • $1,400 - $2,000/week
  • Calendar Last Updated On: Jun 18, 2013
This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for...

Simonton Studio, an Old Town get-away for 2. New Pricing – Property 332511

  • Lower Florida Keys rental - studio, sleeps 2, 1 bathroom, accept credit card, Near The Ocean
  • $750 - $1,500/week
  • Calendar Last Updated On: Jun 18, 2013
This Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West.

Ocean Paradise – Property 327109

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 8, 4 bathrooms, Beach, Near The Ocean, Private Pool
  • Calendar Last Updated On: Jun 18, 2013
Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third...

'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo.. – Property 390177

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, accept credit card, Downtown, Near The Ocean, Town, Village, Waterfront
  • $3,300 - $5,500/week
  • Calendar Last Updated On: Jun 18, 2013
Directly facing the Gulf of Mexico right next to Mallory Square, this beautiful penthouse condo is the perfect place to spend your stay in Key West.

'SWEET CAROLINE'S SANCTUARY @ THE SEAPORT': Cozy 1BR/1BA Condo + Pool, Spa... – Property 390174

  • Lower Florida Keys rental - condo, 1 bedroom, sleeps 4, 1 bathroom, accept credit card, wheelchair accessible
  • Calendar Last Updated On: Jun 18, 2013
This charming condo is located in the exclusive Old Town Key West neighborhood of the Historic Seaport, just steps from both the treasures of the Seaport shopping...

Private Luxury in Prestigious Casa Marina Neighborhood – Property 298674

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 7, 3 bathrooms, 1 half bath, Downtown, Near The Ocean, Private Pool
  • Calendar Last Updated On: Jun 18, 2013
Please call us to be sure you get the best booking experience in Key West. The Casa Marina neighborhood is one of the most coveted residential areas in Historic Old...

Paradise Manor with private pool available fall 2013 – Property 208558

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 9, 2 bathrooms, accept credit card, Beach, Near The Ocean
  • $1,790 - $1,990/week
  • Calendar Last Updated On: Jun 18, 2013
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...

'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo... – Property 904145

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, 1 half bath, accept credit card, Downtown, Near The Ocean, Waterfront
  • $2,950 - $5,000/week
  • Calendar Last Updated On: Jun 18, 2013
This beautiful penthouse condo is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby.

Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West – Property 3567100

  • Lower Florida Keys rental - bungalow, 2 bedrooms, sleeps 6, 1 bathroom, Communal Pool, Air Conditioning
  • Calendar Last Updated On: Jun 18, 2013
Just 3 houses down from the open water, with a 35' concrete dock/seawall complete, swim ladder and fishing table - perfect for cleaning that 'catch of the day', and...

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West – Property 3579706

  • Lower Florida Keys rental - bungalow, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, Communal Pool
  • Calendar Last Updated On: Jun 18, 2013
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. Located on the open water, with a 52'...

Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West – Property 315267

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, Resort
  • $975 - $1,600/week
  • Calendar Last Updated On: Jun 18, 2013
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. Located on the open water, with a 52'...

Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean – Property 972748

  • Lower Florida Keys rental - bungalow, 1 bedroom, sleeps 2, 1 bathroom, accept credit card, Tennis Court
  • Calendar Last Updated On: Jun 18, 2013
For nearly 15 years now guests have been delighted to discover the Beach Bungalow-Key West. Nestled among palm trees, hibuscus, and boganvillas, the Beach Bungalow...

Atlantic Mansion-Estate on Private Paradise Penisula – Property 297619

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, limited accessibility, wheelchair accessible
  • Calendar Last Updated On: Jun 18, 2013
A Paradise treasure can be your vacation dream home! The dream of vacationing on the water on a tropical island has now come together in this spectacular ocean...

Large private home in the heart of Old Town Key West! – Property 3004586

  • Lower Florida Keys rental - house, 5 bedrooms, sleeps 8, 5 bathrooms, accept credit card, Downtown, Near The Ocean
  • Calendar Last Updated On: Jun 18, 2013
Step into the luxury Key West lifestyle by staying in this magnificent home. Conveniently located just 2 blocks from Duval Street, and 4 blocks to the Sunset...

Rose Lane Villa - VISTA 1 bedroom, 1/2 block off Duval – Property 299234

  • Lower Florida Keys rental - villa, 1 bedroom, sleeps 4, 1 bathroom, accept credit card, Downtown, Near The Ocean
  • Calendar Last Updated On: Jun 18, 2013
Voted 'Best Value Hotel' in the Florida Keys by the Miami Herald. Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the...
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