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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.

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  1. Designer Decorated Oceanfront Acre Private Home, Private Heated Pool — Property 317093

    Vacation House rental in Florida Keys 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)

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

    Vacation House rental in Florida Keys area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • resort, waterfront
    • tennis court
    Special Weeks Of 11/28 & 12/5 $850 Each
    S P E C I A L    O F F E R
    Rates (shown in USD)

  3. ~La Casa Habana~Paradise in a private retreat on Grassy Key. — Property 176323

    Vacation House rental in Grassy Key area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • village, waterfront
    • pool
    10% DISCOUNT
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1900 - $3200 per property per week

  4. 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

  5. Paradise manor with private pool and patio — Property 208558

    Vacation House rental in Key West area
    • House
    • 4 bedrooms , sleeps 9
    • 2 bathrooms
    • near the ocean
    • garden
    Rates (shown in USD)
    $700 per property per week

  6. Size Does Matter! Biggest Luxury Vacation Home on the Island — Property 265312

    Vacation House rental in Key West area
    • House
    • 5 bedrooms , sleeps 10
    • 4 bathrooms
    • near the ocean
    • pool
    Rates (shown in USD)

  7. (Quiet) House with Guest Cottage — Property 232130

    Vacation House rental in Key West area
    • House
    • 3 bedrooms , sleeps 8
    • 3 bathrooms
    • 1 half bathroom
    • beach, near the ocean
    • pool
    Rates (shown in USD)
    $1375 - $2475 per property per week

  8. Casa Mar Azul - Luxurious
    Casa Mar Azul - Wifi - Cabana Club & Pool, Golf - 38' Dock - Fall Sale 1,095 — Property 242066

    Vacation House rental in Key Colony Beach area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • near the ocean, waterfront
    • pool
    Rates (shown in USD)
    $995 - $1795 per property per week

  9. Beautiful Islamorada Boater's Paradise home in the Florida Keys — Property 192446

    Vacation House rental in Islamorada area
    • House
    • 4 bedrooms , sleeps 8
    • 2 bathrooms
    • near the ocean, waterfront
    • balcony
    Rates (shown in USD)
    $2100 per property per week

  10. 87 Tingler Lane - Ocean — Property 85650

    Vacation House rental in Marathon area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $2320 - $3100 per house per week

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