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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. Key West Conch Cottage, 'Casa Louisa'' — Property 135603

    Vacation Cottage rental in Florida Keys area
    • Cottage
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, town
    • pool
    Rates (shown in USD)

  2. Gated Bayfront Paradise, Caribbean Cottage in a Tropical Oasis — Property 145869

    Vacation Cottage rental in Key Largo area
    • Cottage
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, waterfront
    • garden
    Rates (shown in USD)
    $1600 per property per week

  3. Cudjoe Key--VENTURE OUT - Tropical Paradise Gated Resort, Key West 19 Miles — Property 193289

    Vacation Cottage rental in Cudjoe Key area
    • Cottage
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • resort, waterfront
    • pool
    Rates (shown in USD)
    $750 per property per week

  4. Fran's Place on the Water - Christmas OPEN — Property 241937

    Vacation Cottage rental in Key Colony Beach area
    • Cottage
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • near the ocean, waterfront
    • air-conditioning
    Rates (shown in USD)
    $850 - $1000 per property per week

  5. Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay — Property 231642

    Vacation Cottage rental in Islamorada area
    • Cottage
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, near the ocean
    • pets considered
    Rates (shown in USD)
    $1095 - $1295 per property per week

  6. Waterfront Cottage - DISCOUNTS . .Quiet, Single-family House! Boat Dock. — Property 301744

    Vacation Cottage rental in Key Colony Beach area
    • Cottage
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, waterfront
    • pool
    Rates (shown in USD)
    $1000 - $1875 per property per week

  7. A Touch of Bermuda at Truman Annex — Property 102572

    Vacation Cottage rental in Key West area
    • Cottage
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, town
    • pool
    Rates (shown in USD)
    $1800 - $2100 per property per week

  8. The Golden Hibiscus — Property 207969

    Vacation Cottage rental in Cudjoe Key area
    • Cottage
    • 1 bedroom , sleeps 6
    • 1 bathroom
    • near the ocean, resort
    • pool
    Rates (shown in USD)
    $600 per property per week

  9. Tree Top Resort
    3 BR/2bth Home , beach, hot tub, pool & boating access with dock. — Property 139917

    Vacation Cottage rental in Big Pine Key area
    • Cottage
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • balcony
    Rates (shown in USD)
    $1800 - $1900 per property per week

  10. 2009 Special Pricing Hemingway Like Cottage/Tropical Pool — Property 224554

    Vacation Cottage rental in Key West area
    • Cottage
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, town
    • pool
    Rates (shown in USD)
    $1500 - $2250 per property per week

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