Search for vacation rental homes on the Florida Keys

Have a Fling in the Florida Keys

The Florida Keys are a little wilder, a little bit beyond the typical Florida scene and perhaps a little closer to what you’re looking for in a romantic - yet not too distant - escape. You don’t have to worry about passports or language barriers down here; these islands may feel far away but they have a way of feeling like home, too. Thanks to the abundance of Florida Keys vacation rentals scattered about like so many conch shells, you can truly have it all as you finally treat yourself to a getaway built for two.


In Islamorada, Key Largo, Marathon and Key West (that’s just for starters) there are beach houses, condos, villas and cottages for everyone. You and your partner in crime (not that it should be deemed illegal to steal a long weekend and just enjoy yourselves) can take your pick from among luxury digs and modest love nests alike; head for a stretch of shoreline hopping with clubs and tiki bars or hide away on your own little island – literally.


Weigh your options, talk it over with your lucky companion and see how the scenario develops. Activities will range from diving and snorkeling to drinking and dancing, nodding off on the beach to nodding off next to your private pool…you set the schedule and itinerary as you please. You won’t be able to control the time of the sunset – or your amazement at its brilliance – but other than that the strings are yours to pull.


A popular place for weddings, honeymoons and lovey-dovey rendezvous, you’ll soon feel the good vibes for yourself. Maybe it’s the island culture, maybe it’s the chance to have the whole house to yourself; the point is, this trip will be good for you both.

  1. Cabana del Sol - Waterfront Pool home-Private boat dock-Ocean Access — Property 192107

    Vacation House rental in Florida Keys area
    • House
    • 3 bedrooms , sleeps 12
    • 2 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Rates (shown in USD)
    $1600 - $1900 per property per week
  2. Relax and Getaway in This Completely Refinished Quiet Home — Property 205196

    Vacation House rental in Key West area
    • House
    • 3 bedrooms , sleeps 10
    • 2 bathrooms
    • beach, near the ocean
    • accept credit card
    Rates (shown in USD)
    $1200 per property per week
  3. Summerland Key Oceanfront Retreat — Property 142751

    Vacation House rental in Summerland Key area
    • House
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
  4. Key Largo Mar-a-Villa, Kawama Yacht Club — Property 200310

    Vacation Villa rental in Key Largo area
    • Villa
    • 3 bedrooms , sleeps 9
    • 3 bathrooms
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
  5. Oceanfront Private Retreat! — Property 220145

    Vacation House rental in Tavernier area
    • House
    • 3 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
  6. Designer Decorated Oceanfront Acre Private Home, Private Heated Pool — Property 317093

    Vacation House rental in Cudjoe Key area
    • House
    • 3 bedrooms , sleeps 10
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
  7. Luxury pool home with great view~ $995 on all remaining 2008 dates — Property 218899

    Vacation House rental in Marathon area
    • House
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $1995 - $3495 per property per week
  8. Your new property advertisement — Property 190220

    Vacation House rental in Key Largo area
    • House
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • air-conditioning
    • washing machine
    Rates (shown in USD)
    $1400 - $1800 per property per week
  9. Tropical Breezes I Oceanside 1/2 Duplex — Property 307668

    Vacation House rental in Key Colony Beach area
    • House
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • near the ocean, waterfront
    • accept credit card
    Rates (shown in USD)
  10. Gated Oceanfront Estate - Tropical Paradise - Pool & Boat Dock — Property 207734

    Vacation Hotel rental in Sugarloaf Key area
    • Hotel
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • beach, waterfront
    • swimming pool
    Rates (shown in USD)
    $3750 - $4950 per property per week

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