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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A Touch of Bermuda at Truman Annex – Property 102572

  • Lower Florida Keys rental - cottage, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, town, swimming pool
  • $1,800 - $2,100/week
  • Calendar Last Updated On: Jul 19, 2008
Envision yourself relaxing in a wood framed conch cottage with sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no...

Blue Aqua – Property 181611

  • Lower Florida Keys rental - house, 5 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, waterfront, washing machine
  • $4,000 - $4,500/week
  • Calendar Last Updated On: Jul 18, 2008
This 4100+ square foot house has 5 bedrooms 4 bathrooms house is situated on open water on Summerland Key. There is also a small apartment that can be included as...

Captain Ron's Tropical Vacation Hide Away – Property 149014

  • Lower Florida Keys rental - house, 2 bedrooms, sleeps 4, 1 bathroom, 1 half bath, near the ocean, waterfront, accept credit card
  • Calendar Last Updated On: Jul 18, 2008
On the Water Stilt home on boating canal 1/4 mile from the open water. Fully furnished, central air conditioned, decorated in Nautical and tropical motif.

Luxury Truman Annex Home - Classic Key West Charm – Property 164696

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, beach, resort, swimming pool
  • Calendar Last Updated On: Jul 17, 2008
Classic Key West charm and great location within the Truman Annex gated community make this home of distinction an ideal place for that tropical getaway that you...

Little Torch Key Tropical Paradise – Property 176318

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, near the ocean, waterfront, air-conditioning
  • Calendar Last Updated On: Jul 17, 2008
Little Torch Key, Oceanside at mile marker 28 feels like paradise. This truly unique, delightful tropical paradise is only a 25 minute short scenic drive to...

The Perfect Get-away in Paradise – Property 185263

  • Lower Florida Keys rental - condo, sleeps 4, 1 bathroom, near the ocean, town, accept credit card
  • Calendar Last Updated On: Jul 18, 2008
The Galleria Condominiums, a wonderful retreat for a fun-filled or relaxing get-away! Each unit bears the name of a renowned artist, in salute to the artistic...

The White House Key West's Finest Monthly Rental/4 BR – Property 187082

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, town, swimming pool
  • Calendar Last Updated On: Jul 16, 2008
The White House is an address and house of distinction! Finely detailed with unparalleled amenities, this the the perfect vacation home for the discriminating guest...

****Fall Discounts****The Retreat at BPK - Waterfront Pool Home with Ocean Views – Property 162258

  • Lower Florida Keys rental - house, 6 bedrooms, sleeps 18, 4 bathrooms, beach, waterfront, accept credit card
  • $2,900/week
  • Calendar Last Updated On: Jul 16, 2008
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...

MINI SEASON *The Lodge - Private boat dock- Waterfront – 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: Jul 16, 2008
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...

MINI SEASON- Waterfront Cabana with pool-Summer Specials!! – Property 192107

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 12, 2 bathrooms, near the ocean, waterfront, accept credit card
  • $1,600 - $1,900/week
  • Calendar Last Updated On: Jul 16, 2008
The Cabana del Sol is ½ acre spacious property with swimming pool and sun deck on 150ft of waterfront property. The Cabana del Sol is a cute and comfortable...

The Overlook at Big Pine Key - Waterfront Pool Home FALL SPECIALS – 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: Jul 16, 2008
'The Overlook' at Big Pine Key is an exclusive private waterfront home located next to the Blue Heron and Key Deer Wildlife Refuges.

**Fall Discount**The Cottage at Big Pine Key - Waterfront, Hot Tub & Tiki Hut – 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: Jul 16, 2008
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.

Truman Annex (Gated 4BR's/4Bath's-private Pool) – Property 146133

  • Lower Florida Keys rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, downtown, resort, swimming pool
  • Calendar Last Updated On: Jul 16, 2008
Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block away from Duval and Mallory Square.

Oceanfront Seclusion – Property 194747

  • Lower Florida Keys rental - villa, 3 bedrooms, sleeps 6, 2 bathrooms, beach, waterfront, swimming pool
  • Calendar Last Updated On: Jul 15, 2008
Located on the open water on the south side of Cudjoe Key, this home is that special place where you can get away from it all.

The Beach House (Ocean Front) in Big Pine Key, FL-Amazing Ocean Views! – Property 147325

  • Lower Florida Keys rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, beach, waterfront, accept credit card
  • $2,100/week
  • Calendar Last Updated On: Jul 19, 2008
Fantastic Direct Beach Front House! If you are a nature lover, this is the house to rent in the Lower Keys. Long Beach Estates is an exclusive, private, nature...

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
  • Calendar Last Updated On: Jul 15, 2008
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...
SPECIAL OFFER! $2,150/week - August & September August 1 - October 3

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
  • $2,750 - $3,850/week
  • Calendar Last Updated On: Jul 19, 2008
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...

Waterfront Luxury in Old Town Key West – Property 166032

  • Lower Florida Keys rental - condo, 1 bedroom, sleeps 5, 1 bathroom, resort, waterfront, accept credit card
  • $1,450 - $2,420/week
  • Calendar Last Updated On: Jul 19, 2008
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a fantastic, fully equipped kitchen,...

Henry's Piece Of Paradise On The Ocean In Key West (nightly / weekly) – Property 103905

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, waterfront, accept credit card
  • Calendar Last Updated On: Jul 14, 2008
1350 sq ft of fabulous living space located on the 2nd floor, with garden and partial ocean views from a 38 ft private balcony accessible from the living and both...

Gorgeous Waterfront Condominium With Stunning Views! – Property 163420

  • Lower Florida Keys rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, beach, waterfront, accept credit card
  • $2,100/week
  • Calendar Last Updated On: Jul 14, 2008
Luxurious! Comfortable! Unforgettable! Located on the Atlantic Ocean with magnificent views, this beautifully decorated tropical island condo offers everything you...
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