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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.

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  1. Amazing Beach Home In Paradise!!!!!! — Property 208420

    Vacation House rental in Florida Keys area
    • House
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • beach, near the ocean
    • terrace
    Blow-Out Special In November & December!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1600 - $1800 per property per week

  2. 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
    • garden
    Special Weeks 11/28 & 12/5 $1300 Each
    S P E C I A L    O F F E R
    Rates (shown in USD)

  3. Breezeswept Villa
    Ocean Front Home w/Heated Pool, Dock, & WiFi available for monthly rental — Property 174010

    Vacation House rental in Ramrod Key area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • waterfront
    • pool
    January 2010 is still available !!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $750 - $1625 per property per week

  4. Weekly Oceanfront Bungalow, Private Dock, Deep Channel, 80' Pool, Tenn — Property 315267

    Vacation House rental in Cudjoe Key area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • resort, waterfront
    • tennis court
    Special last minute $700 week rate!
    S P E C I A L    O F F E R
    Rates (shown in USD)

  5. Executive Ocean Front Florida Keys House with Pool — Property 168177

    Vacation House rental in Marathon area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • pool
    Thanksgiving Special Just $2975
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2750 - $4500 per property per week

  6. Sunsets on the open Gulf. Private Dock , Free extra night if stay week. — Property 230930

    Vacation House rental in Marathon area
    • House
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, waterfront
    • garden
    Stay one week , get EXTRA NIGHT FREE!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $895 per property per week

  7. Bayside Beauity
    Bayside Beauty in Sugarloaf Key — Property 257918

    Vacation House rental in Sugarloaf Key area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • near the ocean, waterfront
    • garden
    Rates (shown in USD)
    $1800 - $2900 per property per week

  8. Lovely Anglers Reef Home
    Charming cottage style home on quiet street — Property 254609

    Vacation House rental in Islamorada area
    • House
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • pool
    Rates (shown in USD)
    $1450 - $1700 per property per week

  9. Waterfront Duplex - Key Colony Beach (MA382) — Property 114729

    Vacation House rental in Key Colony Beach area
    • House
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • near the ocean, waterfront
    • pets considered
    Rates (shown in USD)
    $1175 per property per week

  10. Old Town Retreat
    Tropical Retreat. — Property 207517

    Vacation House rental in Key West area
    • House
    • 4 bedrooms , sleeps 7
    • 3 bathrooms
    • downtown
    • pool
    Rates (shown in USD)
    $1175 - $1875 per property per week

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